Kissimmee Vacation Rentals

(224 rentals)
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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
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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 Villa
4 BR | 3 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 3 bathrooms

$180

avg/night

$180
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 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 House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$208

avg/night

$208
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to your dream vacation home! Nestled in the heart of the exclusive Storey Lake resort, this modern 4-bedroom townhouse is the perfect retreat for your Disney World or Universal Orlando getaway. With its unbeatable location, luxurious amenities, and a private pool, your vacation experience will ...

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Property Type

Kissimmee House

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

$311

avg/night

$311
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

$350

avg/night

$350
avg per night
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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 Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to park: 3 miles to Disney World

$143

avg/night

$143
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to Surrounded in Magic!Current 2025 availability: Apr 09-13/2025 at 20% OFF Apr 20-June 10/2025 June 24-Dec 31/2025 Email us for a quote.Kids of all ages will love this magical, bright and spacious Disney & Universal Studios themed (1400 sq ft), 3-bedroom, 2-bath, 1st floor condo. ...

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Property Type

Kissimmee Condo

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

$128

avg/night

$128
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This is a NON SMOKING condo *Community: Sweetwater Club VillasFloors: First Floor CondoPets: THIS IS NOT A PET FRIENDLY CONDORooms: 3 Bedrooms, 2 Bath rooms. En-suite in Master bedroom.Bed Configuration: King bed (1) Queen bed (1), Full Bed (1). Sleeps 6.Flooring: Tile throughout ...

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Property Type

Kissimmee Condo

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

$129

avg/night

$129
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 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 Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$120

avg/night

$120
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to our charming condo in the heart of Kissimmee, Florida! Nestled in the sought-after Villa Island Club, our inviting three-bedroom, two-bathroom retreat is the perfect spot for your next vacation. Located just off HWY 192, you’ll be less than 15 minutes from the magical gates of Walt Disney ...

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Property Type

Kissimmee Condo

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

$318

avg/night

$318
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 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 Condo
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms

$270

avg/night

$270
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This is a NON SMOKING condo *Community: Regal Palms Floors: Second Floor Condo Pets: Small Pets are ok, $150 pet feeRooms: 2 Bed rooms, 2 Bath rooms.Bed Configuration: King Bed (1) Bunk Beds 1 Full 1 TwinFlooring: Hard wood throughout with tile in bath and kitchen.General: Wi-fi, ...

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Property Type

Kissimmee Condo

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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

$216

avg/night

$216
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 Villa
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms
7 reviews

$160

avg/night

$160
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Your villa is located on the gated 5 Star Lake Berkley Resort in Kissimmee. 5 Beds, 3 Bath home that is beautifully furnished throughout (Big TV/Games Room/Heated Pool/Free Internet). Our villa is furnished to a very high standard and being all one level is ideal for one or two families. The villa ...

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Property Type

Kissimmee Villa

Featured review

"Excellent location"

Just returned from our holiday after 2 weeks at this lovely villa. Perfectly located 15mins from all the Disney parks and a stones throw from Walmart and our favourite Chick-a-fille. Set in a quiet, secure ...

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

$142

avg/night

$142
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 Townhome
4 BR | 3 BA | Sleeps 11 | Quick View
Sleeps 11, 4 bedrooms, 3 bathrooms
1 review

$203

avg/night

$203
avg per night
View Details

Key Amenities

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

About this property

New 4-bedroom, 3-baths townhouse with a private pool. Nestled in the peaceful Preserve Area of Storey Lake Resort, this property can accommodate up to 11 guests.It's totally equipped: - Kitchen has everything you need to cook - Towels & linen - Wifi - Basic cable and TVs - Enough free ...

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Property Type

Kissimmee Townhome

Featured review

"Excelente lugar para vacacional y pasar un tiempo en familia."

Nuestra estancia fue excelente desde la reservacion, el host muy atento, accesible y comunicador. La propiedad la encontramos en excelentes condiciones como así la vimos en las imágenes. Todo muy bonito, ...

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Kissimmee House
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms
3 reviews
owner special
Owner special: Discounted spring & summer rates. Message for a quote.

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

$299

avg/night

$299
avg per night
Owner special:
Discounted spring & summer rates. 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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Kissimmee Villa
5 BR | 5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 5 bathrooms

$215

avg/night

$215
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Embark on an enchanting journey with our exquisite 5-bedroom home nestled in the prestigious Windsor Hills community. Ideal for families or groups, this charming retreat promises a perfect blend of luxury and proximity to the magic.Key Features:Bedroom Retreats:2 King Beds 1 Queen Bed 5 ...

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Property Type

Kissimmee Villa

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

$178

avg/night

$178
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

If you’re searching for Orlando vacation rentals that will have plenty of room for your entire family, look no further than Windsor Palms with private pool. This incredible home can fit up to 10 guests between its 4 bedrooms and 3 bathrooms. You’ll find another incredible amenity around every ...

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Property Type

Kissimmee House

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

$193

avg/night

$193
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 Townhome
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
4 reviews

$225

avg/night

$225
avg per night
View Details

Key Amenities

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

About this property

A fabulous home-base for your trip to Orlando! Just Minutes to Theme Parks.Home Features:* 3 Bedrooms* 1 King, 1 Queen, 2 Full, 1 Twin (Sleeps 7-8) * All New Mattresses * TV's in every bedroom * USBs & Outlets convenient for charging* 3 Bathrooms* All En-Suite * ...

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Property Type

Kissimmee Townhome

Featured review

"Loved it."

Beautiful House, and a wonderful experience from start to finish! Cant wait to go back! The home was spacious and beautifully decorated and Lisa was a Pleasure to work with, and very helpful.

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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

$108

avg/night

$108
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
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
9 reviews

$240

avg/night

$240
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 ***Our beautiful 3000sq 5 Bed, 4 Bathroom home is located on a generous corner plot. With a south facing Pool and stunning views over the second ...

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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
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms

$281

avg/night

$281
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to our charming townhome in Bella Vida Resort, just a short 8 mile drive from the entrance to Walt Disney World! Make your vacation truly magical with the comfort and convenience of our delightful home. Also, do add to the convenience there is a Walmart Superstore around the corner and many, many ...

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Property Type

Kissimmee House

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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

$223

avg/night

$223
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 House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms

$201

avg/night

$201
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
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
3 reviews

$214

avg/night

$214
avg per night
View Details

Key Amenities

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

About this property

RECENTLY REFURBISHEDLuxurious Windsor Palms with an extra wide cul de sac lot and with a pool that is not overlooked. Our guests enjoy terrific privacy in one of the premier resorts in the Disney vicinity. We have a south facing pool with kiddy pool and stand alone hot tub. Numerous child friendly ...

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Property Type

Kissimmee Villa

Featured review

"Awesome vacation"

Everything was perfect from start to finish. House was better than we expected, owner was great to deal with and will for sure book this house again and have already referred friends to book this property ...

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

Distance to park: 6 miles to Disneyworld

$133

avg/night

$133
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

"Looking for a great vacation rental for the kids? This is it!!"

What a nice house! It has everything you could want in a vacation home. A very nice pool, patio and attached BBQ area with gas grill, literally a ton of DVD's to keep everyone entertained in the evening, ...

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

$155

avg/night

$155
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

4 Bedroom villa with 4 ensuite bathrooms.This exquisite villa is an ideal destination for a family holiday, offering a prime location.Situated within walking distance of the resort clubhouse and pool.Hi speed WiFi and air con throughout the villa.Set against a backdrop of serene ...

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Property Type

Kissimmee Villa

Featured review

"Modern and clean villa"

We had a wonderful time in this villa. We always love coming to the Bellavida resort. Our favorite location near the Disney parks. The villa is modern and was clean and has lots of privacy. We had a problem ...

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

Distance to park: 3 miles to Disney World Parks

$241

avg/night

$241
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

"Were Dreams really come true- AMAZING"

Marisela made our booking experience exceptional. She was very responsive and outstanding hosts. The home is absolutely beautiful and meticulously maintained! It is located in a secure gated community and ...

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

$345

avg/night

$345
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
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$198

avg/night

$198
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

Are you looking for a private home in Kissimmee for your next Florida vacation? Rolling Hills 7965 is just the place! This home is suited for up to 8 guests and features 4 bedrooms and 3 bathrooms. When you step inside, you’ll notice that the décor is upscale and tasteful to suit the style ...

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Property Type

Kissimmee House

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Kissimmee House
6 BR | 3.5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 3.5 bathrooms
1 review

$143

avg/night

$143
avg per night
View Details

Key Amenities

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

About this property

Step into sheer Luxury and experience gated resort style vacationing at its finest. at our Windsor Palms, 6 bedroom pool home, the special touches will leave every family member with a smile. This gorgeous home has two king bedrooms, two queen bedrooms and two rooms with 2 twin beds. With 4 bathrooms ...

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Property Type

Kissimmee House

Featured review

"Caaa vacasional"

Hola estoy muy interesado en rentar su casa de vacaciones la fecha es junio 26a julio 10 con mi familia somos 12

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Kissimmee Townhome
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
5 reviews

$95

avg/night

$95
avg per night
View Details

Key Amenities

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

About this property

FLAT SCREEN TV in Living Room! NEW MATTRESSES in all bed rooms NEW LAMINATE FLOORS in all bed rooms! Bed Room Configuration: 1 QUEEN Master Suite with balcony overlooking conservation area and private bath 1 bedroom with a double bed 1 bedroom with two twin beds. TV's in all Rooms! This ...

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Property Type

Kissimmee Townhome

Featured review

"Perfect location near attractions"

Loved our stay close to Disney and other attractions.Townhome was clean and had everything we needed for our stay. The owner was quick to respond to any questions. We would definitely stay here again.

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

Distance to park: 4 miles to Animal Kingdom

$163

avg/night

$163
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 and a recliner with a total of 5 power reclining seats • ...

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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
7 BR | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 4.5 bathrooms
1 review

$433

avg/night

$433
avg per night
View Details

Key Amenities

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

About this property

5 star property! Reviews say it all!You will be delighted by the great combination of lux comfort and Disney theming for the whole family! Located in the upscale Emerald Island Resort gated community, our newly remodeled home is a welcome oasis to return to after a long day enjoying the parks. Relax ...

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Property Type

Kissimmee House

Featured review

"Where to even start!!!"

Whenever we travel, I read reviews. Some reviews you wonder about because no two people seem to see it the same way. However with this house everyone seemed to love it and after staying there I can see ...

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

$128

avg/night

$128
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

"Relaxing"

I just wanted to say thank you to Diane for helping us in renting this house to me. My husband and I enjoyed every minute here. It was close to all the attractions and restaurants. Diane even but the ...

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

$230

avg/night

$230
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This is a NON SMOKING HOME *Community: Calabay Parc Floors: 2 Floor, 5 Bedrooms, master downstairs and 4 bedrooms up. Pets: Please ask about our pet policyRooms: 5 Bedrooms, 3.5 Bath rooms.Bed Configuration: Bedroom 1: King size bed with En-suite Bedroom 2: Queen size bed with shared bathroom. Bedroom ...

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Property Type

Kissimmee House

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Kissimmee House
8 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 6 bathrooms
2 reviews

$415

avg/night

$415
avg per night
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
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
9 reviews

Distance to park: 3 miles to Disney World

$145

avg/night

$145
avg per night
View Details

Key Amenities

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

About this property

4 Bedroom (2 master suites) 3 full baths, separate living and family rooms, will sleep up to 10 people. Decor in this house is Timeless!! Pool is newly resurfaced!The game room includes an 8 foot pool table and foosball table,. The private pool deck provides a distant view of the nightly DisneyWorld ...

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Property Type

Kissimmee House

Featured review

"Wonderful home!"

My family and I stayed here for a week and would definitely return. The home was spacious and clean. because it sat high, the back was private and did not look into another yard. The owner was very responsive ...

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

$174

avg/night

$174
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

$216

avg/night

$216
avg per night
View Details

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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Property Type

Kissimmee House

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

$312

avg/night

$312
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 House
9 BR | 8 BA | Sleeps 18 | Quick View
Sleeps 18, 9 bedrooms, 8 bathrooms
13 reviews

Distance to park: 3 miles to Disney Animal Kingdom

$692

avg/night

$692
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Mickey's Oyster is a luxurious oasis designed to make your Disney World vacation unforgettable. Nestled in a prestigious, gated community just minutes away from the magic, this freshly remodeled and renovated home offers an enchanting escape with all the comforts of a five-star resort. Luxurious ...

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Property Type

Kissimmee House

Featured review

"Hartley House family gathering"

We have just returned from a great family holiday in Florida we took all our family away for our fiftieth wedding anniversary ,three years late .We stayed at Hartley House ,we have never stayed in a american ...

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Kissimmee House
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms
12 reviews

Distance to park: 6 miles to Disney - Animal Kingdom

$119

avg/night

$119
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

This private, lakefront with nature reserve, pool home offers a fusion of luxury, comfort, and convenience. This spacious 3 bedroom and 2 bath home has cathedral ceilings and an open floorplan, with a living room, breakfast nook, and formal dining area. The kitchen is fully outfitted with all the appliances ...

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Property Type

Kissimmee House

Featured review

"Great Area"

Location was quiet. Home was beautiful and well maintained. My only comment would be to have a casserole dish to be able to bake something in the oven. Also a pizza pan. Besides these items it is well stocked. ...

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

$250

avg/night

$250
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This is a NON SMOKING condo *Community: Sweetwater Club VillasFloors: First Floor CondoPets: PLEASE ASK ABOUT OUR PET POLICY.Rooms: 3 Bedrooms, 2 Bath rooms. En-suite in Master bedroom.Bed Configuration: King bed (1) Queen bed (1), Two Twin Beds (2). Sleeps 6.Flooring: Ceramic ...

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Property Type

Kissimmee Condo

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Kissimmee Villa
9 BR | 10 BA | Sleeps 26 | Quick View
Sleeps 26, 9 bedrooms, 10 bathrooms
17 reviews

$965

avg/night

$965
avg per night
View Details

Key Amenities

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

About this property

Imagine a vacation like no other spent in a 9 bedroom, 10 bath custom luxury lakefront pool villa. The Formosa Grand is located in the exclusive gated community of Formosa Gardens Estates and one of the closest communities to Disney (less than 10 minutes!!) No expense was spared in the gorgeous estate ...

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Property Type

Kissimmee Villa

Featured review

"A Christmas To Remember"

My Family and I So Enjoyed This Beautiful Mansion For The Week Of Christmas. The Entry/Foyer was decorated with a beautiful tall Christmas Tree. As well as Christmas Decor around the house. Which was an ...

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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 224 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 $63 per night with an average price per night of $172.

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!