Kissimmee Vacation Rentals

(219 rentals)
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Kissimmee House
7 BR | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 4.5 bathrooms
16 reviews

Distance to park: 3 miles to Disney World Parks

$237

avg/night

$237
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

This spacious vacation rental home in Orlando is ideal for large families, accommodating up to 14 guests. The property features 7 bedrooms and 4.5 bathrooms, including two King Master Suites—one located on each floor. The first-floor suite includes a walk-in shower and a separate garden tub for ...

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Property Type

Kissimmee House

Featured review

"Kissimmee Stay"

My husband and I were able to stay the month of January and February at a home in Windsor Palms that is managed by Epic FloridaRentals. We had an amazing stay and we’re so impressed with how prompt the ...

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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
28 reviews

$149

avg/night

$149
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Indian Creek Disney Retreat is a beautiful 1800SF, well maintained home in the Indian Creek subdivision which is literally on Disney's doorstep and your home away from home. Indian Creek is not a gated community but has a lot of community amenities.In the 1st section of Indian Creek you will ...

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Property Type

Kissimmee Villa

Featured review

"Florida Vacation! ️"

My family and I retuned back to Lisa’s beautiful home the week of Thanksgiving for a week long trip. This is our 2nd time staying in her house and we absolutely loved it! The house was so clean from top ...

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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
4 reviews

$204

avg/night

$204
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Palm Tree Villa Florida, is tucked away in the much sought after location of Doral Woods. This large 4 Bedroom, 3 Bathroom villa, is ideal for making the perfect vacation.This is our own holiday home, so the furnishings are to a high standard, as you can see from the pictures and video. Fully Air ...

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Property Type

Kissimmee Villa

Featured review

"Lovely Villa with a lot of extras !"

Beautiful place for a relaxing holiday or just 15 minutes away from the Disney and Resorts area . The home was perfect and the welcome package was great. Andy was great and checked in on us during our stay. ...

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Kissimmee Villa
5 BR | 4 BA | Sleeps 11 | Quick View
Sleeps 11, 5 bedrooms, 4 bathrooms
4 reviews

$280

avg/night

$280
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

After. *** Location Location Location*** It’s all about. ‘The View’The uninterrupted view of the 14 acre lake and bird island, takes unwinding by the pool to a new level! Relax on a sun bed, or perhaps get wrinkly in the spa whilst ...

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Property Type

Kissimmee Villa

Featured review

"What a view"

In July 2023 we stayed at Winter Haven a fantastic villa in Lake Berkley which had enough room for 8 of us comfortably. The guys partially liked the games room/pool room, and we all loved to pool and jacuzzi, ...

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Kissimmee House
5 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 5 bathrooms
2 reviews

$302

avg/night

$302
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Booking is available from the website in Owner info.Modern architecture, state-of-the-art furnishings, and hip-to-the-minute décor make this 5 bedroom, 5 bath getaway in Storey Lake a bonafide safe haven for luxury and comfort. This home is brimming with amenities, from an action-packed game ...

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Property Type

Kissimmee House

Featured review

"Great place, nice price!"

The themed kids' rooms and game room are topping on this rental a club house with so much going on for everyone, including pickup/drop off service to and from the club house. Heated pool and gas grill. ...

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Kissimmee Villa
Studio | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 0 bedrooms, 4.5 bathrooms

$362

avg/night

$362
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

7 bedroom 4.5 bath waterfront home located in the highly desired Emerald Island resort close to Disney and Universal Studios. The ground floor of this villa is an open concept with a living area featuring a 65" Smart 4k tv. The granite countertop kitchen boasts all new 2022 stainless appliances. ...

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Property Type

Kissimmee Villa

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Kissimmee House
4 BR | 2.5 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 2.5 bathrooms
12 reviews

Distance to park: 6 miles to Disneyworld

$137

avg/night

$137
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Our villa is modern style furnished, has everything you would expect in a holiday home, 4 bedrooms, 2 with king-size beds, 1 with single bed´s, 1 with triple bunk bed all with private TV. 2 bathrooms, 1 guest toilet, fully equipped kitchen, etc. with ceran stove, fridge, oven, microwave, coffee ...

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Property Type

Kissimmee House

Featured review

"The way to go"

Very nice house. Pool heat price could be about 10 $ The extra cost hurts. Always need hangers.towels and a extra fridge in garage would be handy. Location close to shopping and restaurants Not good ...

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Kissimmee Townhome
3 BR | 3 BA | Sleeps 9 | Quick View
Sleeps 9, 3 bedrooms, 3 bathrooms
11 reviews

Distance to park: 5 miles to Animal Kingdom Lodge

$184

avg/night

$184
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

**The private pool is not heated unless requested by the guest. Pool heating is available for an additional fee of $10.00 per day. Pool heating must be arranged and paid for prior to arrival.***No long-term rentals - 14 nights maximum *Minimum rental age is 25 years old (exception for married couples ...

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Property Type

Kissimmee Townhome

Featured review

"FANTASTIC property!"

This is the place to stay! This rental truly felt like a home away from home. It was a short drive to countless restaurants and shopping...location is perfect! If you're going to Disney, you'll only ...

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Kissimmee House
6 BR | 5.5 BA | Sleeps 18 | Quick View
Sleeps 18, 6 bedrooms, 5.5 bathrooms
57 reviews

Distance to park: 4 miles to Animal Kingdom

$160

avg/night

$160
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Some of the best features of this house from Guest Reviews • Beautiful Vinyl Plank Flooring in all bedrooms, halls and on the steps • Less than a 4-mile drive to Disney World’s Animal Kingdom Theme Park • Two leather couches with a total of 4 power reclining seats • Privacy ...

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Property Type

Kissimmee House

Featured review

"Spacious, well-appointed house in a great location close to the Disney Parks."

The owner provided very detailed and helpful information regarding the house, the Orlando area and the Disney parks before we arrived. The house was very clean and tidy and all the rooms were as described. ...

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Kissimmee House
8 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 6 bathrooms
2 reviews
owner special
Owner special: Book 7 nights or more and enjoy a SWEET 15% off your stay! Offer not valid with any other discounts!

$396

avg/night

$396
avg per night
Owner special:
Book 7 nights or more and enjoy a SWEET 15% off your stay! Offer not valid with any other discounts!

View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Enjoy a whimsical getaway when you book a stay at this sleek, refreshing, 8-bedroom, 6-bathroom vacation rental home. Take a dip in the private pool, fix up something tasty in the fully equipped kitchen, play a game of pool in the game room, or head to the community fitness center for a quick workout. ...

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Property Type

Kissimmee House

Featured review

"Kissimmee Home/Windsor"

My family & I enjoyed our stay at this lovely home during the summer time. This house gave us an enjoyable experience that we will all remember. We didnt have any problems with the house and we hope to ...

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Kissimmee House
6 BR | 4 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 4 bathrooms
4 reviews

$311

avg/night

$311
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to your ultimate themed vacation experience in the heart of Kissimmee, Florida! Prepare to embark on an extraordinary journey as you step into this spectacular 6-bedroom, 4-bathroom house in the prestigious Windsor Hills community. This newly listed paradise has been meticulously designed to immerse ...

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Property Type

Kissimmee House

Featured review

"Amazing"

This was an amazing experience for my kids and I. I would definitely choose again!!!!!!!!!!!!!!!!!!!

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Kissimmee Villa
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
13 reviews

Distance to park: 12 miles to All Disney Theme Park

$109

avg/night

$109
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

If you will be visiting Orlando Florida for all of the great attractions including Walt Disney World, Universal Studios, Sea World theme parks, and all of the other major attractions? You can stay in our beautifully decorated 3 bedroom private villa, which boasts it's own private pool for less than ...

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Property Type

Kissimmee Villa

Featured review

"New Years Getaway"

Stayed month of January..Villa was very well equipped and very comfortable.Location was fantastic being so close to all attractions. Would highly recommend for anybody to stay..

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Kissimmee House
5 BR | 4.5 BA | Sleeps 15 | Quick View
Sleeps 15, 5 bedrooms, 4.5 bathrooms
1 review

$245

avg/night

$245
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to our luxurious and spacious vacation home situated in the stunning gated community of Windsor at Westside. This magnificent 5-bedroom, 4.5-bathroom villa boasts everything you need for an unforgettable vacation with your family and friends, Close to theme parks, shopping mall outlets, restaurants ...

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Property Type

Kissimmee House

Featured review

"CLEAN & COMFORTABLE, PERFECT RENTAL!"

The location is perfect! It's situated in a sweet little area thats quiet and clean. Yet it's not far from anywhere to drive. Walmart and target are just around the corner as well as a gas station and other ...

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Kissimmee Villa
5 BR | 3 BA | Sleeps 14 | Quick View
Sleeps 14, 5 bedrooms, 3 bathrooms

$157

avg/night

$157
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to our magical Disney-themed retreat! Nestled in the heart of the Westside at Windsor Resort, our cozy and charming home is the perfect place for you and your loved ones to experience all the wonders of the happiest place on earth. Whether you're planning a family vacation or a romantic getaway, ...

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Property Type

Kissimmee Villa

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Kissimmee House
6 BR | 4.5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4.5 bathrooms
9 reviews

$157

avg/night

$157
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Moran Disney Rentals would love to welcome you to our Luxury 6 bedroom house which is perfectly located on the exclusive Emerald Island Resort community less than 3 miles from the Walt Disney a world Parks in Florida. This property has 6 bedrooms two of which are master bedrooms with a further two and ...

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Property Type

Kissimmee House

Featured review

"22 Days of Bliss"

We spent the Christmas period at Katrina’s Florida home and it was absolutely delightful. A huge and spacious villa was the perfect way to unwind after a busy day in the parks..Katrina was fantastic ...

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Kissimmee Villa
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Distance to park: 4 miles to Disney

$220

avg/night

$220
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Magic Village Views, part of Trademark Collection by Wyndham. "Boutique style 3BDR very spacious Town house, ideally located in Magic Village community……right next to Disney’s parks like Magic Kingdom. All Units have unique furnishings, complete kitchens with gas range, ...

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Property Type

Kissimmee Villa

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Kissimmee Townhome
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms
1 review

$118

avg/night

$118
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

You have arrived in the "Vacation Capital of the World" and you're going to love staying in our luxury, 3 bedroom, 2.5 bath, fully equipped vacation townhouse rental situated near DisneyWorld and all other theme park attractions. The property rental is located within the resort community ...

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Property Type

Kissimmee Townhome

Featured review

"Beautiful Condo! Exactly as shown!"

We are a retired couple who stayed for 3 months from Jan to March. Beautiful Condo, exactly as pictured. Furniture is very comfy. Close to all attractions. We felt very safe. Publix and Walmart are ...

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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$273

avg/night

$273
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Experience the tranquility and relaxation of M&M Dream Villa! This quiet and relaxing four-bedroom villa is located just three miles Disney World. It features brand new Star Wars-themed kids' rooms with incredible Millennium Falcon beds, a-themed kids' bedroom, and marine life and Mickey-themed ...

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Property Type

Kissimmee Villa

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Kissimmee Villa
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2.5 bathrooms
1 review

Distance to park: 3 miles to Disneys Animal Kingdom

$201

avg/night

$201
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Our Home Features are 4 bedrooms consisting of 1 Master suit with en-suite bathroom located on the main level. 1 Queen and 2 twin rooms,1 twin room is themed Winnie the Poo,on the upper level, these bedrooms share the upper bathroom all bedrooms are equipped with TV and DVD player. There is a further ...

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Property Type

Kissimmee Villa

Featured review

"Tolles Haus"

Hallo, Wir haben hier mit der Familie Urlaub gemacht. Das Haus ist groß genug für acht Personen. Es ist super ausgestattet mit tollem Blick und schönem Pool. Der Vermieter ist sehr um eine tolle Atmosphäre ...

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Kissimmee Villa
4 BR | 3 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 3 bathrooms

$206

avg/night

$206
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Immerse yourself in luxury at our Kissimmee villa, perfectly located minutes from Disney and Universal. Nestled in a secure gated community, our home boasts a private pool and spa, a fully-equipped modern kitchen, and comfortable bedrooms including a master suite with a king bed. Exclusive amenities include ...

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Property Type

Kissimmee Villa

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Kissimmee Bungalow
4 BR | 3 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 3 bathrooms
6 reviews

$119

avg/night

$119
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Luxury Villa near Universal Studios and 15 Minutes from Disney with Large Private Pool, Game Room and Free Wifi. LCD TVs and Game Room in the villa complement the upscale furnishings and large pool included in the villa. There is plenty of space to spread out with 4 bedrooms and 3 bathrooms.Welcome ...

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Property Type

Kissimmee Bungalow

Featured review

"The house was fantastic and a great location."

The house was very easy to find, quiet neighborhood and Walmart was 2 minutes away. The was neat and tidy with all kitchen amenities needed to prepare a home cook meal. The Air conditioner was the best, ...

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Kissimmee Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Distance to park: 1 miles to Disney Animal Kingdom

$97

avg/night

$97
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Come and enjoy your vacation in this comfortable condo, right by Disney. Yes Enjoy Three large screen TV's, DVD and free Wi-FI.Yes Beautiful/alluring condo, 1 mile from Disney world and minutes from other attractions, Such as sea world and Universal studio. In Celebration area Florida. Walking ...

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Property Type

Kissimmee Condo

Featured review

"Great location, clean and comfortable."

We had everything we needed. Excellent communication. Perfect location. Close to the parks as well as restaurants, etc! We will be back.Thanks

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Kissimmee House
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
3 reviews

Distance to park: 7 miles to Disney Hollywood Studio

$156

avg/night

$156
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Beautiful, clean and spacious 5 bedroom and 4 bath house in the most sought after community near Disney! 10 minutes drive to Disney and you can hear the Disney fireworks at night. Close to stores, restaurants and tons of shops. The house was renovated and professionally designed recently. The house has ...

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Property Type

Kissimmee House

Featured review

"Perfect for golf trip"

Perfect house for the 8 of us on our golf trip. Close to restaurants and golf. House was clean and well appointed. Plenty of room for 8 guys aged 35-75.

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Kissimmee Villa
4 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4 bathrooms
2 reviews

$295

avg/night

$295
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Name Of Home: Walking on Sunshine VillaLocation: Windsor Hills Resort (24/7 guard gated community - Disney World only mins away!)Home Highlights: Recently Renovated Home - Incredible Air Conditioned 80s Game Room - Private South Facing Pool/Spa - Bunk Bedroom with PS5Property Type: Single ...

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Property Type

Kissimmee Villa

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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
17 reviews

Distance to park: 3 miles to Mgm

$125

avg/night

$125
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Beautiful 4 bedroom /3 bath private villa only 3 miles to Disney and other parks. Including heated pool/jacuzzi and game room. Free wifi and phone use in USA and Canada and PR. Fully furnished with all kitchen needs . Greatest location to shopping , all major restaurants and stores including supermarkets ...

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Property Type

Kissimmee Villa

Featured review

"Top class accommodation"

We couldn't fault our accommodation at all. Everything you needed was on hand. Lovely beds and a awesome view of the lakes in front of our pool.

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Kissimmee House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
15 reviews

Distance to park: 4 miles to Disney

$141

avg/night

$141
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Magical Dreams come true in our elegant private 4 bedroom villa, 3 bathroom, all located on one floor, Quiet upgraded comforts of home and luxuries of an exceptionally rated vacation resort/hotel. Newly resurfaced and freshly painted pool and spa is sure to impress. There will be no waiting in line ...

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Property Type

Kissimmee House

Featured review

"Perfect rental for all of our needs!"

This was a Christmas vacation never to be forgotten! We had the time of our lives! My children, grandchildren and I enjoyed the comforts and privacy of a home where we could take in all the theme parks ...

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Kissimmee Townhome
4 BR | 3.5 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3.5 bathrooms
12 reviews

Distance to park: 5 miles to Animal Kingdom

$116

avg/night

$116
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy Orlando, Florida, home to Disney World, Sea World, Universal Studios, and Islands of Adventure, in style. Our home is within minutes of all the Orlando attractions, golf courses, shopping, and exciting night life. Our richly appointed vacation Townhouse will give you luxurious living and a vacation ...

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Property Type

Kissimmee Townhome

Featured review

"Cozy stay at townhouse"

My wife, son and I stayed for the month of April. The resort property is well maintained. Garbage is picked up daily and each home has a bin right in front of the home.The condo was very clean upon ...

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Kissimmee House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

Distance to park: 4 miles to Disney

$221

avg/night

$221
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

You will love it here in our Boutique styled Condos featuring contemporary interiors, located in Magic Village gated community only 5 minutes away from Disney’s Animal Kingdom. Step into your private villa and discover a chic and contemporary yet invitingly cozy sanctuary. All three bedrooms are ...

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Property Type

Kissimmee House

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Kissimmee House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
18 reviews

$199

avg/night

$199
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

ASK ABOUT SPECIAL REDUCED NIGHTLY RATE REMAINING WINTER AND SUMMER 2025 DATES!Luxury 4 BR / 3 Bath Villa with Private Pool and Spa in Guarded Gated Resort Close to DisneyWelcome to the Disney Getaway Villa, located in the beautiful and luxurious Emerald Island Resort. This villa is “the ...

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Property Type

Kissimmee House

Featured review

"Fantastic Villa!"

We so enjoyed our stay at the villa! The games room and pool were awesome, community was peaceful and villa was spacious and lovely. Having laundry available to us (as a family with small children) and ...

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Kissimmee House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms

$202

avg/night

$202
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Luxury vacation homes accommodations feature contemporary interiors, located in Magic Village gated community only 5 minutes away from Disney’s Animal Kingdom. Step into your private villa at Magic Village Yards and discover a chic and contemporary yet invitingly cozy sanctuary. All Bedrooms are ...

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Property Type

Kissimmee House

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Kissimmee Villa
7 BR | 6 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 6 bathrooms
4 reviews

$308

avg/night

$308
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Introducing 101 Happy Memories Florida Villa, your gateway to unforgettable vacations in the heart of Formosa Gardens, just minutes from the enchantment of Disney World!Step into luxury with our private heated pool and spa, perfect for unwinding after a day of adventure. Thrill-seekers will love our ...

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Property Type

Kissimmee Villa

Featured review

"2nd time still a charm"

We enjoyed a stay here 3 years ago and we lucky enough to find it available again in 2024. We can't say enough except that the property was somehow even an improvement over the 1st time. This is a great ...

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Kissimmee House
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
9 reviews

$235

avg/night

$235
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

*** For smaller groups we offer the opportunity to rent the main house. This area has 4 Bedrooms and 3 Bathrooms Please contact us and ask for a quote ***Newly painted throughout Nov 2024Our beautiful 3000sq 5 Bed, 4 Bathroom home is located on a generous corner plot. With a south facing ...

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Property Type

Kissimmee House

Featured review

"Excitement Place at Christmas time was Incredible!"

Knowing at the beginning of 2024 that we were going to take a family vacation to Disney World with all of our children and grandchildren over the Christmas 2024 Holiday, we would need accommodations for ...

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Kissimmee House
7 BR | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 4.5 bathrooms

$437

avg/night

$437
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Perfect Family Destination Best lania/pool Minutes to Disney/Attractions/Conveniences Fun/Clean/ComfortableThis is a fantastic house for family getaways! Enjoy the Food and Wine Festivals. Mickey's Not So Scary Halloween Party, Unforgettable Disney Christmas celebration, and everything else ...

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Property Type

Kissimmee House

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Kissimmee House
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2 bathrooms
21 reviews

$172

avg/night

$172
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Sunset Lakes is ideally situated, just 4 miles from Disney World and a short drive from other popular attractions like Universal Studios, Sea World, and more. The proximity to Orlando and other destinations makes it a prime choice for travelers. The gated community offers various amenities such as a community ...

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Property Type

Kissimmee House

Featured review

"Vacation retreat/$15 Uber to Disney/ HGTV looking retreat"

We are completing our stay in the morning at this beautiful vacation retreat! We brought the family all seven of us ranging from age in two years old to 60 years old. The pool and patio is incredibly maintained, ...

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Kissimmee House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

Distance to park: 4 miles to Disney

$238

avg/night

$238
avg per night
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Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

"Boutique style very spacious Town house, ideally located in Magic Village community……right next to Disney’s parks like Magic Kingdom. All Units have unique furnishings, complete kitchens with gas range, living, and dining rooms with vaulted ceilings. Full size laundry room, extra ...

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Kissimmee House

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Kissimmee Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
3 reviews

Distance to park: 5 miles to Disneyworld and Disney Springs

$97

avg/night

$97
avg per night
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Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

You have arrived in the "Vacation Capital of the World" and you're going to love staying in our luxury, three bedroom, two bath, fully equipped vacation condo rental situated near DisneyWorld and all other theme park attractions. The property rental is located within the resort community ...

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Property Type

Kissimmee Condo

Featured review

"Holiday season in Kisimmee"

Excellent vacation in Florida Sunsations. Condo is close to main attractions , restaurants and airport. Excellent communication with owner Barry Paulus. Will return next year.

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Kissimmee House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Want to enjoy a stay at a vacation home for you and your family? Our house offers a direct escape to a vacation paradise just for you! It offers 4 bedrooms and 2 bathrooms, and accommodates with a cozy living room. In the garage, there is also a game room for you or children to relax and have some fun. ...

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Kissimmee House

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Kissimmee House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
9 reviews

Distance to park: 4 miles to Disney World

$152

avg/night

$152
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to La Casita on the Island (The Little House on the Island) "Our house, our casita" If you want a place to relax and enjoy the beautiful weather of Florida, I invite you to see the "encanto" (charm) that you can experience during your stay at La Casita on the Island.Enjoy ...

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Property Type

Kissimmee House

Featured review

"Great Villa"

Had a fantastic stay in the villa. Would definitely stay again and highly recommend. It was extremely clean and in a great location near shops, resturaunts and 192 and Disney. Would highly recommend and ...

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Kissimmee House
4 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 4 bedrooms, 3 bathrooms
17 reviews

$127

avg/night

$127
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Close to the Attractions but away from the crowds. 4 bedroom/3 bath single story home on "lake". Ducks, Sandhill Cranes, sometimes a falcon, turtles. King, king, and 4 twin beds, TV in all bedrooms, WiFi, FREE US, Canada and US Territory phone calls. Fully furnished. Not suitable for ...

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Property Type

Kissimmee House

Featured review

"Unreal stay"

We had a great week and it was everything they said it was. Stayed in the location before and we will definitely book again.

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Kissimmee House
4 BR | 3 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 3 bathrooms
5 reviews

Distance to park: 3 miles to Disney

$185

avg/night

$185
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

The Magic Emerald Island Villa invites you to experience an elegant escape near Disney World and Universal Studios. Our 4-bedroom, 3-bathroom villa accommodates up to 9 guests in comfort and style: • The main master bedroom features a king-size bed, a private en suite bathroom with a garden tub, ...

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Property Type

Kissimmee House

Featured review

"5*+ Magic Emerald Island Villa"

Excellent villa wonderful host.From the very first enquiry about renting Yelena’s Magic Emerald Island villa she was fantastic, guiding me through the booking and rental period until we left. Yelena ...

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Kissimmee House
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms
3 reviews
last minute deal
LAST MINUTE DEAL 4/15 - 4/30: Discounted April & May Deals, message for a quote.

Distance to park: 5 miles to Disney's Animal Kingdom

$300

avg/night

$300
avg per night
Offer for: Apr 15 - Apr 30:
Discounted April & May Deals, message for a quote.

View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Imagine coming home at the end of an exhilarating day at the parks... You grab a refreshing drink, relax in the poolside living area and reminisce about all you did that day.Memories made, job done!Serendipity offers all the comforts you dreamed of putting on your wish List:★ Pool & ...

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Property Type

Kissimmee House

Featured review

"Our Very Magical Thanksgiving"

From the moment we inquired about booking until the day we checked out communication was extremely easy and quick responses. Upon arrival everything was so clean. Pictures don’t do it justice. We had ...

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DEAL
Kissimmee House
7 BR | 5.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 5.5 bathrooms
2 reviews

Distance to park: 5 miles to Disney World

$207

avg/night

$207
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Excellent Private Detached Family Vacation home/Villa located in the Prestigious Man Gated Vacation Resort of EMERALD ISLAND RESORTS. SPECIAL DISCOUNTS FOR LONGER STAYS !!! . Monthly bookings during January to April at special rates._________________________________________________________________ This ...

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Property Type

Kissimmee House

Featured review

"Amazing 7 Bed rooms Villa Near Disney"

Our stay with Family and friens were superb. Cost is just a fraction of what otherwise with any Hotels. VEry large House with 7 Bedrooms and 6 Wash rooms. Own private pool and lanai . Bbq grill was provided ...

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Kissimmee Villa
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Distance to park: 4 miles to Disney Theme Parks

$223

avg/night

$223
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Magic Village Views, part of Trademark Collection by Wyndham. This 4 Bedroom 4.5 Bath Luxury Townhouse Villas is a must stay. located in an ideally located gated community……right next to Disney’s parks. All Units are En-Suites with unique furnishings, complete kitchens, ...

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Property Type

Kissimmee Villa

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Kissimmee Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
17 reviews

$142

avg/night

$142
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This Disney Villa is a fully furnished home and is one of the best kept turnkey properties you will find in Indian Creek ! Has an airy open floor plan, lots of light. Enjoy the crystal clear South facing pool and the covered lanai on your sunny and warm Florida holidays.This luxurious private home ...

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Property Type

Kissimmee Villa

Featured review

"Four Corners Indian Creek"

We stayed for one week and had a wonderful time. The house was perfect and the kids had a great time in the pool.

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Kissimmee Villa
8 BR | 6 BA | Sleeps 18 | Quick View
Sleeps 18, 8 bedrooms, 6 bathrooms
6 reviews

$540

avg/night

$540
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Big R‘s Villa, a luxurious 8-bedroom vacation home in the exclusive gated Windsor at Westside Resort located near Disney, Universal, and Orlando’s top attractions. Designed for comfort, fun, and relaxation, this spacious retreat accommodates up to 16 adults or 18 guests with children, ...

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Kissimmee Villa

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Kissimmee House
7 BR | 5.5 BA | Sleeps 16 | Quick View
Sleeps 16, 7 bedrooms, 5.5 bathrooms
1 review

Distance to park: 5 miles to Animal Kingdom

$275

avg/night

$275
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Peaceful Private Getaway – Private Pool, Hot Tub & Welcome to Islands of Magic @ , a spacious and family-friendly vacation home just 5 miles from Walt Disney World! Perfect for large families, group getaways, or multi-family trips, this beautifully designed home offers 7 bedrooms, a private ...

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Property Type

Kissimmee House

Featured review

"Best Vacation Home"

Renting this beautiful house was a breeze!! We were very happy that after checking out at least a dozen houses, we all agreed on this one!! We wanted a big house with lots of bedrooms/bathrooms! We got ...

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Kissimmee House
8 BR | 4.5 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 4.5 bathrooms
26 reviews
owner special
Owner special: Merry Month of May Special! Stay any 7 days this May and receive a 20% discount off nightly rate!

Distance to park: 3 miles to Disney's Animal Kingdom

$273

avg/night

$273
avg per night
Owner special:
Merry Month of May Special! Stay any 7 days this May and receive a 20% discount off nightly rate!

View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Mickey's Mansion for is the perfect vacation getaway! Our 8-bedroom, 4.5-bath home is conveniently located in the Four Corners area of Kissimmee, just minutes from Disney. Whether you’re looking for excitement or relaxation, Mickey's Mansion offers the best of both worlds, with a lively ...

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Property Type

Kissimmee House

Featured review

"Home Sweet Home"

Look no further for the perfect vacation home! This home has it all, great location, very clean and well appointed! It has all the amenities - a well maintained pool and spa, wonderful outdoor space with ...

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Kissimmee Villa
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Distance to park: 4 miles to Disney World

$226

avg/night

$226
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Magic Village Views, part of Trademark Collection by Wyndham. With a stay in a luxury condominium in an ideally located community, you won’t run out of exciting things to do and thoughtful amenities to enjoy. The hotel’s ideal location is right next to Disney’s parks. You’ll ...

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Property Type

Kissimmee Villa

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Kissimmee Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Distance to park: 2 miles to Disney

$140

avg/night

$140
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Our exquisite, tastefully decorated and perfectly maintained 2-bedroom and 2 full bath condo is perfect for your family and friends up to 6 people. We are on the top floor, and you will hear no noise from above! There are two double beds in the Master Bedroom with a walk-in closet and ensuite. The ...

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Property Type

Kissimmee Condo

Featured review

"5 star"

Super clean and tidy with lots to do around the property. Definitely Woukd stay again , beautiful layout of pool area

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Kissimmee Villa
6 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4 bathrooms

$323

avg/night

$323
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Forget your worries in this spacious and serene space. Plenty of room for all your traveling members! Disney getaway? Or just want a fun in the sun getaway? Then this is the house! Beautiful lake views while relaxing in the pool and spa! Discover your perfect getaway in this stunning 6-bedroom, 4-bathroom ...

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Property Type

Kissimmee Villa

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Kissimmee Vacation Rentals

Kissimmee Weather

 | 

7222°  489°
JANUARY
7323°  499°
FEBRUARY
7725°  5312°
MARCH
8228°  5814°
APRIL
8731°  6418°
MAY
9032°  7021°
JUNE
9233°  7222°
JULY
9233°  7222°
AUGUST
9032°  7122°
SEPTEMBER
8429°  6518°
OCTOBER
7926°  5714°
NOVEMBER
7323°  5010°
DECEMBER

Soak up the Sun on Your Next Trip to Kissimmee Vacation Rentals


There’s nothing quite like a vacation to sunny Florida, a unique and inviting state with a huge variety of distinctive cities and natural areas to explore. One popular vacation destination in Florida is Kissimmee, a charming city with plenty to see and do just south of the Orlando metropolitan area. 

Kissimmee has a lot more to offer visitors than just excellent weather year-round. With a huge variety of scenic nature, shopping opportunities, and outdoor activities, Kissimmee itself has lots to offer every member of the family, not to mention its extremely close proximity to some of Orlando’s biggest amusement parks. 

You could stay in a busy hotel during your trip to Kissimmee, but then you wouldn’t be able to get a truly immersive experience of local city life. Kissimmee vacation rentals allow you to enjoy Kissimmee from inside its authentic residential neighborhoods. Additionally, having your own home to live in rather than a jam-packed hotel will provide some much-needed peace and quiet during your vacation. It will also offer plenty of space for the whole family to spread out.  

Top Tips for Traveling to Kissimmee Rentals


Like most other Florida cities, Kissimmee enjoys sunshine and clear skies throughout the majority of the year. However, the tropical climate of the state means that bouts of rain can occur throughout the seasons, particularly during the summer months, peaking in August. 

In addition to a higher likelihood of rain, the summer season in Kissimmee tends to be the most humid time of year. That’s why most vacationers choose mid to late spring or early autumn to make their trip to the city. At those times of the year, vacationers can enjoy great weather and lots of outdoor activities. 

Though the Kissimmee Gateway Airport is located centrally within the city, most vacationers taking commercial flights will fly into Orlando International Airport. It is located roughly 17 miles northeast of the city center, about halfway between Kissimmee and Orlando. Vacationers coming in from elsewhere in Florida can access Kissimmee by road using U.S. Route 192 and U.S. Route 441.

Things to Do Nearby Kissimmee House Rentals


Some of the most popular natural areas around Kissimmee are the swamps, which are located in major local bodies of water like Lake Tohopekaliga (known around town as Lake Toho). At Boggy Creek Airboat Adventures, you can experience the swamps from the water and get the thrill of a lifetime on an airboat driven by a local wetlands expert. Get up-close views of gator ponds, discover precious gemstones, and then grab a delicious lunch with the family at Boggy Bottom BBQ! 

Looking to explore a piece of history during your trip to Kissimmee? Medieval Times Dinner & Tournament allows visitors to step into the 11th century for an evening of authentic feasting, jousting, and sword fighting in true medieval style! Enjoy a delicious four-course meal, incredible performances, and a truly unforgettable experience for the entire family.
 
Any vacation to Kissimmee isn’t complete without a trip or two to Old Town, a popular outdoor attraction with opportunities for shopping, dining, and family fun. Old Town is made up of an 18-acre stretch of classic city attractions, including the Old Town Ferris Wheel, the Great Magic Hall, and Mortem Manor, a year-round haunted house that is open for visitors to explore.

Kissimmee Annual Events


Kissimmee is a vibrant area with lots of annual festivals and events to enjoy in and around the city throughout the year. Kissimmee locals and visitors alike flock to the Ford Cuban Sandwich Festival each May near downtown Kissimmee, which celebrates the colorful history of Cuban cuisine in the area. Watch as local dining professionals attempt to build the world’s biggest Cuban sandwich during the event!
 
The Ford Taste of Latino Festival is another local opportunity to celebrate and experience the best in authentic Latin cuisines in Kissimmee. The event features a contest to find the Top Latino Chef as well as plenty of live music and dance performances to enjoy as you taste a variety of Latin dishes. 

Not sure if you’ll be in town for any of Kissimmee’s larger annual events? You can enjoy Show Car Saturday Nights every Saturday night in the city on Margaritaville Boulevard. Check out the city’s best classic cars from a variety of eras and enjoy the plethora of delicious eateries and exciting shops located along the boulevard.

Wining and Dining in Kissimmee  


Between your outdoor activities and trips to local amusement parks while in Kissimmee, you’re sure to need some satisfying food and refreshing drinks to complete your perfect day. Luckily, Kissimmee is home to some of the best restaurants that Florida has to offer, combining authentic local flavors with worldly cuisine. 

To start your day off right with a delicious and hearty breakfast, look no further than Woodsby’s Countryside Café. This spot has authentic, cozy diner vibes to spare, not to mention a stacked menu of classic breakfast favorites, coffee bar items, and unique dishes you won’t want to miss out on. 

Tarantino’s Italian Restaurant is a great choice for a vacation date night or simply a nice dinner out with the family. A hearty Italian meal is a great way to finish a fun day of activities, and you’re sure to get that and more at Tarantino’s. If you bring the family along, you can take advantage of the takeout dinner special, which feeds four and includes a massive entrée, salad, and garlic bread.


FAQ

How many vacation rentals are there in/around Kissimmee?

There are 219 Kissimmee vacation rentals available on FloridaRentals.com. From villa rentals to house rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Kissimmee?

There are vacation rentals available in Kissimmee for as low as $59 per night with an average price per night of $175.

Can I rent a house in Kissimmee?

Yes, you can find house rentals in Kissimmee close to Lakefront Park, Monument of States, and Old Town. Don't forget to stop in to Shingle Creek Park or the nearby theme parks!

Do any vacation rentals in Kissimmee have a pool?

Yes, there are 170 vacation rentals in Kissimmee with a pool on FloridaRentals.com. Search using our filters and book one for your next vacation!