Kissimmee Vacation Rentals

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

$969

avg/night

$969
avg per night
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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 House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms

$202

avg/night

$202
avg per night
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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 House
7 BR | 5.5 BA | Sleeps 16 | Quick View
Sleeps 16, 7 bedrooms, 5.5 bathrooms
1 review
last minute deal
LAST MINUTE DEAL 4/26 - 4/30: Scoop up 4 nights & heated pool and spa Apr 26–30 for $999—your Disney retreat awaits!

Distance to park: 5 miles to Animal Kingdom

$277

avg/night

$277
avg per night
Offer for: Apr 26 - Apr 30:
Scoop up 4 nights & heated pool and spa Apr 26–30 for $999—your Disney retreat awaits!

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

$205

avg/night

$205
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 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 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 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
7 BR | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 4.5 bathrooms

$436

avg/night

$436
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 Villa
8 BR | 4 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 4 bathrooms
12 reviews

Distance to park: 6 miles to Disney

$380

avg/night

$380
avg per night
View Details

Key Amenities

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

About this property

AMAZING Pool Deck Extension cira 2023! Its the BIGGEST pool deck at the resort! Plus JAW DROPPING, Fancy, Fun, Fountain Jets w/ LED lighting, high-end glass tile & a Mickey Mosaic giving you an ULTIMATE luxury pool experience. This SALT WATER POOL/SPA will leave your skin feeling soft w/ no eye-sting ...

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Property Type

Kissimmee Villa

Featured review

"Amazing house"

We had an amazing time and the house had everything we needed and wanted for our vacation in Florida. If you are going to Florida we recommend this house. It's has a great pool and patio and can accommodate ...

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Kissimmee Villa
8 BR | 6 BA | Sleeps 17 | Quick View
Sleeps 17, 8 bedrooms, 6 bathrooms
1 review

$350

avg/night

$350
avg per night
View Details

Key Amenities

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

About this property

Disney Wood Wonderland*** 7 miles from Disney popular attractions Disney's Animal Kingdom Theme Park and Epcot. Walt Disney World and Magic Kingdom Park.

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Property Type

Kissimmee Villa

Featured review

"Couples retreat"

The house was well accommodated for the amount of guests. It was very specious, well maintained. We were satisfied with our stay.

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

Distance to park: 3 miles to Disney Parks

$132

avg/night

$132
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This home is thoughtfully furnished. Recently upgraded with a Tempur-Pedic contour supreme king size mattress, LED TV in every bedroom, Frozen themed and Mickey themed twin rooms. This four bedroom luxury home is specifically set up for vacationing guests. The house, just three miles from Disney, is located ...

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Property Type

Kissimmee House

Featured review

"Great vacation home"

We had the opportunity of spending 12 days at this beautiful palm breeze villa. This home came with everything we needed. Very close to all attractions and short distance to shopping. Our host made all ...

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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

$147

avg/night

$147
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 House
4 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 4 bedrooms, 2 bathrooms
11 reviews

$123

avg/night

$123
avg per night
View Details

Key Amenities

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

About this property

CHEERY AND BRIGHT. Just what a vacation home should be. 4 bedrooms, 2 bathrooms, great views and just minutes from all the fun. Fully furnished , just bring personal items or things you cannot live without. Located in Eagle Pointe, a well sought-after vacation home community. Just minutes from what ...

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Property Type

Kissimmee House

Featured review

"Great Villa"

This is a lovely villa in a beautiful setting overlooking the lake. Great range of shops and restaurants within a short drive. 15 minutes drive to Disney parks. We loved it so much we have booked again ...

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Kissimmee Villa
6 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 5 bathrooms
1 review

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

$286

avg/night

$286
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your elegant vacation retreat in Emerald Island Resort, Orlando, FL! This spacious 6-bedroom, 5-bathroom home has been recently upgraded and is located just 3 miles from Walt Disney World and only minutes from top attractions like Universal Studios, SeaWorld, and Old Town Kissimmee. With plenty ...

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Property Type

Kissimmee Villa

Featured review

"Wonderful stay"

We rented this property for the month of February 2025. As a family of 9 with Grandparents, parents and 2 young grandchildren, we found the villa to be spacious without feeling cavernous. It was well ...

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Kissimmee House
8 BR | 4.5 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 4.5 bathrooms
27 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

$272

avg/night

$272
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

"A Great Family Vacation Destination"

This was our second year staying at a home in Emerald Island Resort. The house was immaculate and set up perfectly when we arrived. We paid to have the pool and hot tub heated which was great because we ...

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

Distance to park: 8 miles to Walt Disney World

$145

avg/night

$145
avg per night
View Details

Key Amenities

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

About this property

**Please email me directly for the most current availability**Private Villa on property at Margaritaville Resort, Kissimmee, Fla. - Complimentary Wi-Fi - In-unit washer/dryer - Unassigned parking in the lot in front of the home (motorcycles allowed) Orlando & Airport - Less than 30 minutes ...

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Property Type

Kissimmee Townhome

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Kissimmee Villa
7 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 5 bathrooms
5 reviews

Distance to park: 7 miles to Disney Magic Kingdom

$251

avg/night

$251
avg per night
View Details

Key Amenities

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

About this property

Special*1/2 price pool heat Feb. * Gated and Guarded Resort 7 -10 minutes to Disney * Stunning Lake Views from Pool Deck * Pool with 24 Hour Spa on Over ride - Handrails * Lots of Baby Equipment - Free to Use * 2 Lounges - Leather sofas * Game Room Disney Themed -Air conditioned - Slate Bed Pool ...

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Property Type

Kissimmee Villa

Featured review

"Fabulous home and perfect location"

The home is absolutely beautiful, very clean and has everything you could possibly need or want in a rental home. The only thing we had to add was our own food and toiletries. The location was perfect, ...

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

Distance to park: 3 miles to Disney Animal Kingdom

$143

avg/night

$143
avg per night
View Details

Key Amenities

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

About this property

Great location - fabulous pool area South West Facing - Fully Fenced Area

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Property Type

Kissimmee Villa

Featured review

"honeypot villa"

This house was perfect for our family vacation. This was my kids first time in Florida - and the house was a much better idea than a hotel. We had 6 people staying with us, and we all fit perfectly. Will ...

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

$152

avg/night

$152
avg per night
View Details

Key Amenities

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

About this property

Beautiful 4 bedroom/3 bathroom house in the luxurious Emerald Island Resort - Only ~ 4 miles from Disney & close to other major attractions! This home is equipped with a heated private pool, spa & game room. There is a large SMART TV in the living room & in each bedroom. There are queen beds ...

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Property Type

Kissimmee House

Featured review

"Beautiful resort"

We stayed for 2 1/2 months at the Villa. It was very clean and had updated living room furniture that was very comfortable. The Manager was very responsive to any of our concerns and checked in with us ...

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

$115

avg/night

$115
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to our beautiful townhome villa located at the luxurious 24-Hour Guard-Gated Emerald Island Resort in Kissimmee, Florida. Just 3 miles from Disney World's main gate.No cramped pool deck! No Shade from nearby houses blocking that fabulous Florida Sun! No shortage of pool chairs, tables ...

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Property Type

Kissimmee Townhome

Featured review

"Outstanding rental!"

We spent three weeks in this rental and had a wonderful stay. Location is terrific. Very close to the pool, yet very quiet. Owner was great to work with and fast with communication. Home is clean and well ...

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

Distance to park: 4 miles to Disney's 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

The Perfect Affordable Family Vacation Home – Just Minutes from Disney!Looking for the ideal family getaway? This spacious vacation home has everything you need for a fun, relaxing, and affordable trip to Disney. Enjoy free WiFi, a fully equipped game room, and TVs in every room to keep everyone ...

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Property Type

Kissimmee Villa

Featured review

"Great and affordable"

Rented this place to go to Halloween horror nights. The place was clean and actually had all the equipment and everything for the game room which I’ve rented more luxurious homes to have pool sticks with ...

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

$159

avg/night

$159
avg per night
View Details

Key Amenities

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

About this property

More info can be found at property website www. dolphinvillas-orlando dot com or directly click the links at end of this page.For over 15 years, Dolphin Villa - Doral Woods has been listed with Holiday Lettings/Trip Advisor, receiving 5-star reviews. If you're interested, we can provide you ...

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Property Type

Kissimmee Villa

Featured review

"Recommend!!"

Great experience during our recent stay at Dolphin House! Clean, spacious and everything you need to have a relaxing time. The welcome gift basket was such a thoughtful and helpful idea. Much appreciated! ...

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

Distance to park: 5 miles to Walt Disney World

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Located in the 5 star gated (guarded) resort of Windsor Palms, this 4 bedroom home is minutes away from Disney World, Universal Studios, and other major attractions. Keyless entry for easy access.You'll find all the comforts of home including a private pool, flat screen HDTVs, XBOX 360 and N64, ...

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Property Type

Kissimmee Villa

Featured review

"Excellent Location to Stay while visiting the Parks"

We visited from Canada and stayed at the condo with another family in January 2025. The villa was spotless upon our arrival and provided more than enough space for four adults and children.The location ...

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Kissimmee House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Distance to park: 2 miles to Disney's Animal Kingdom

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

4 Bedroom /3 Bath / Pool & Spa Vacation HomeCONTACT US AND REQUEST A DETAILED QUOTE !! No Booking Fees - Book Direct with the HomeownerCheck our Reviews on VRBO - Property #284051

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Property Type

Kissimmee House

Featured review

"Awesome"

Thank you Awesome Would do again Very close to everything Great pool sand hot tub Felt safe Thank you again

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Kissimmee Villa
5 BR | 5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 5 bathrooms
2 reviews

$259

avg/night

$259
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Minnie's Mansion! A 5 bd/ 5 bth pool home located in the closest community to Disney World-Windsor Hills Resort!This resort features, $2.1 mil Lagoon Style pool with Zero Depth Entry and Water Slides. Also, with a Water Park for the littles! Clubhouse has Sundry Shop /Deli, Games Room, ...

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Property Type

Kissimmee Villa

Featured review

"Home away from home"

The house was beautiful. Heated pool was so nice. Thank you for providing swim towels. Kids spent a lot of time playing ping pong on the one rainy day. Location was great. Could use new mattresses ...

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Kissimmee House
5 BR | 2 BA | Sleeps 11 | Quick View
Sleeps 11, 5 bedrooms, 2 bathrooms

$149

avg/night

$149
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

The 5 Bedrooms-2 Bathrooms non-smoking house offers free private parking, free Wifi, 5 smart TVs, game room, fence gated private pool, a full equipped kitchen & Washer & Dryer. THIS HOUSE IS SELF-CATERING. Please stop by your nearest supermarket to purchase personal toiletries and desired meals. ...

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Property Type

Kissimmee House

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

Distance to park: 5 miles to Disney World/Animal Kingdom

$304

avg/night

$304
avg per night
View Details

Key Amenities

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

About this property

Our Disney vacation villa is furnished to the highest standard and offers your family the luxury of a Five star hotel combined with the relaxed atmosphere of a family vacation home. Soak up the Florida sun on our extended deck where you can relax in the pool and spa, or simply enjoy the shade of the lanai ...

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Property Type

Kissimmee Villa

Featured review

"Fantastic Stay"

We loved staying at this house it was truly amazing. There were 9 of us altogether, 6 adults and 3 children aged 10,8 & 4. The kids loved the games room and the pool, everything you could wish for in ...

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

Distance to park: 6 miles to Walt Disney World

$169

avg/night

$169
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Name Of Home: Ohana Mouse HouseLocation: Windsor Hills Resort (24/7 guard gated community - Disney World only mins away!)Home Highlights: Recently Renovated Home - Private Pool - Bunk Bedroom with PS4Property Type: Townhouse, Two Stories (1,437 SF)Bedrooms: 3 Total - 1 Master w/ King Bed, ...

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Property Type

Kissimmee Townhome

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

$207

avg/night

$207
avg per night
View Details

Key Amenities

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

About this property

Great Game Room,4/3,Pool,Spa,100mgbps wifi,2 Masters,65' 4KTV, 4 miles to Disney Going on a magical vacation? Why not stay in a magical place! We combine the magic of DisneyWorld with high-end comfort and conveniences to ensure every guest has the best vacation experience. Often referred to as ...

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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
5 reviews

Distance to park: 3 miles to Disney World

$176

avg/night

$176
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Sample the Florida lifestyle in our four-bedroom, three-bathroom spacious air-conditioned villa with 26ft x 13ft privately screened, heated, south-facing swimming pool and spa.Located on the peaceful Indian Creek community, our holiday home is comfortably furnished throughout, only 3 miles away from ...

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Property Type

Kissimmee Villa

Featured review

"Perfect FL Getaway"

My husband and I had a wonderful week at this villa. The house was very clean and had all of the amenities to make our stay very comfortable. The lanai with the pool and spa was where we spent most of our ...

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Kissimmee Villa
8 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 6 bathrooms

$410

avg/night

$410
avg per night
View Details

Key Amenities

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

About this property

Escape to a magical 8-bed 6-bath retreat for up to 16 guests at the Windsor at the Westside resort community. This is an entire home rental. Super Mario game room, Beauty and the Beast dining, Paris-themed kitchen, Guardians of the Galaxy primary bedroom. Upstairs: Hollywood, Pirates, Mickey Mouse, Princesses, ...

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Property Type

Kissimmee Villa

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

Distance to park: 3 miles to Walt Disney World

$184

avg/night

$184
avg per night
View Details

Key Amenities

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

About this property

4 Bedrooms| 2 Baths| Sleeps 8|Private Pool|Games Room|Disney-Themed Kids Rooms| Updated Decor|Seeking the ideal home away from home for your family's magical Disney vacation? Look no further! Our bright and airy residence, in the sought-after 5-star Emerald Island Resort, serves as a perfect ...

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Property Type

Kissimmee House

Featured review

"Fantastic Villa"

We have recently returned from a fantastic stay at Joanna’s villa and couldn’t recommend highly enough. After a long day of travel the immediate comfort we felt opening the door of what would be our ...

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Kissimmee Villa
5 BR | 4 BA | Sleeps 15 | Quick View
Sleeps 15, 5 bedrooms, 4 bathrooms
6 reviews

$349

avg/night

$349
avg per night
View Details

Key Amenities

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

About this property

Villa OverviewNo extra charges!5 bedrooms, 4 full bathroomsSleeps 15 guests~440 square foot Star Wars theme room upstairs with two full over full bunk beds between a 3D TIE Fighter and swirly slideTwin bunk bed with a trundle in the Lego-themed room, complete with multi-color ...

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Property Type

Kissimmee Villa

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Kissimmee Townhome
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms

$108

avg/night

$108
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our stunning townhouse located at 2600 Lodi Crescent in the charming city of Kissimmee, FL. This tastefully furnished property is the perfect choice for your next getaway. Whether you're visiting the magical Walt Disney World or exploring the vibrant attractions of Orlando, our townhouse ...

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Property Type

Kissimmee Townhome

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Kissimmee Villa
6 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 5 bathrooms

Distance to park: 7 miles to Disney's Animal Kingdom Theme Park

$189

avg/night

$189
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Experience Luxury and Comfort at Our 6-Bedroom, 3,200 sq. ft. Villa – Perfect for Families and Groups!Escape to our stunning luxury villa, featuring 6 spacious bedrooms (9 beds) and 3,200 sq. ft. of beautifully appointed living space. With 2 luxurious en-suites, 3 king-sized beds, 2 cozy living ...

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Property Type

Kissimmee Villa

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Kissimmee House
7 BR | 4 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 4 bathrooms

$303

avg/night

$303
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

When it comes to finding Orlando vacation rentals that are conveniently located and fully equipped, Terra Verde 137 is a great option. This 7-bed, 4-bath house is suited for up to 14 guests and is situated in one of the best locations in the incredible Terra Verde Resort community. This home offers all ...

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Kissimmee House

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

$132

avg/night

$132
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

If you're searching for Orlando vacation rentals near Disney, the name of this unit simply says it all: This unique condo with a newly remodel kitchen with all new appliances is set up to accommodate six guests between its three bedrooms and two bathrooms. Not only will you be able to benefit from ...

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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

$328

avg/night

$328
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

If you're bringing a big group with you on your next trip to Florida, you're probably looking for a luxurious vacation rental with plenty of room for everyone. This 6-bedroom Orlando vacation rental fits the bill! Windsor Hills Dream Private Screened Pool Home is an absolute dream come true ...

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Property Type

Kissimmee House

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Kissimmee Villa
5 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 5 bathrooms

$264

avg/night

$264
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Name Of Home: Live Your Adventure Family VillaLocation: Encore Resort (Gated community - Disney World only mins away!)Home Highlights: XBox, Private Pool, Marvel Themed Games RoomProperty Type: Single Family Home, Two Story (2,570 SF)Bedrooms: 5 Total - 2 w/ King Beds, 1 w/ Queen Bed, ...

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Property Type

Kissimmee Villa

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Kissimmee House
6 BR | 3 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 3 bathrooms
1 review

Distance to park: 5 miles to Disney World

$180

avg/night

$180
avg per night
View Details

Key Amenities

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

About this property

Experience a relaxing & unforgettable vacation in this stunning Tiffany Blue-colored villa, nestled in a peaceful & safe residential neighborhood. Enjoy easy access to theme parks, golf, restaurants, and supermarkets, all just a short drive away. Don't miss out - contact me with any questions!...

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Property Type

Kissimmee House

Featured review

"Amazing family-friendly home w/ a stunning pool"

Excellent location very close to Disney World. Beautiful and clean home. Host is very welcoming and helpful. The pool is stunning. The pictures do not do it justice. Wish we would have stayed longer!

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

Distance to park: 2 miles to Fun Spot America Theme Parks

$113

avg/night

$113
avg per night
View Details

Key Amenities

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

About this property

Your family will be close to everything when you stay at this centrally-located place.This property it is fully renovated; first-floor unit with a laminate floor, high ceiling in the living room, open floor plan. The kitchen and bathrooms have been upgraded. The whole community was recently replumbed.Nice ...

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Property Type

Kissimmee Townhome

Featured review

"Great Vacation Home"

We found the townhouse to be nicely decorated with cute little touches, updated, very clean and equipped with all the necessities for a fabulous experience. It's a very safe, quiet, peaceful location, ...

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

$366

avg/night

$366
avg per night
View Details

Key Amenities

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

About this property

5 star Property!Welcome to Sunset Magic Villa!Delightful Windsor at Westside Resort home villa8 bedrooms (2 Downstairs/6 Upstairs) and 6 full bathrooms. Space for up to 16 guests, (stretch out and relax with all the comforts of home) WEST facing private pool ensuring stunning sunset ...

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Property Type

Kissimmee House

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Kissimmee House
9 BR | 7 BA | Sleeps 16 | Quick View
Sleeps 16, 9 bedrooms, 7 bathrooms

$326

avg/night

$326
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Located in the exclusive Encore community. This beautiful and luxurious vacation home is a 2-story home with 9 bedrooms, 7 bathrooms, a laundry room, game room, and a pool with hotube. It is completely fenced. The house has a capacity for 18 guests. This stylish place to stay is perfect for group trips. Charming ...

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Property Type

Kissimmee House

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

$180

avg/night

$180
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Charming brand new 4 br, 3 bath townhouse with pool. Located in the desirable Storey Lake Resort, in the new quiet Preserve Area, It has capacity for 12 guests. Storey Lake has a resort-style clubhouse full of amenities and fun for families, including a business center, basketball court, ping pong table, ...

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Property Type

Kissimmee House

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Kissimmee Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

$79

avg/night

$79
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Beautiful and clean unit with two queen size beds upstairs, it is part of a recently renovated condo-hotel furnished with modern design and great taste, with fenced pool, playground, gym, and indoor and outdoor dining/resting/seating areasTouristic area, super close to the parks, located on the main 192 ...

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Property Type

Kissimmee Condo

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

$175

avg/night

$175
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
4 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4 bathrooms

$222

avg/night

$222
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

If you’re searching for Orlando vacation rentals and want something unique, this home fits the bill! As soon as you pull up, you’ll notice the incredible Mediterranean design, which makes this house stand out from all the others on the block. Inside, you’ll have access to all kinds of ...

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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

$186

avg/night

$186
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

It's hard to find much more luxurious Orlando vacation rentals than this! BellaVida Palms 390 is an excellent option for families of up to 8 people. You’ll not only find all kinds of convenient and luxurious amenities within the house itself, but you'll also have plenty of fun things to ...

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Property Type

Kissimmee House

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Kissimmee Villa
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This newly remodeled pool Villa is the perfect getaway. From the new kitchen and bath to the newly resurfaced pool. Large pool deck with room to spread out. A covered area for dining and tons of pool deck for those who love the sun. The pool is south facing. Sunsets are spectacular.#3 bedrooms. ...

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Property Type

Kissimmee Villa

Featured review

"Awesome !!!"

Super Clean, Everything was excellent. Pool was amazing. Close enoogh tall many immendities for day trips. Had a very relaxing time very fun vacaton.

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Kissimmee Villa
8 BR | 7 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 7 bathrooms

$372

avg/night

$372
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to the perfect vacation place at Encore Resort. beautiful 2 story house, 8 bedroom, 7 bathroom, game room, fenced-in backyard and pool. Perfect place to a family meeting/vacation near Disney. Minutes from Orlando's world-famous excitements. Totally equipped kitchen, towels & linen, Wifi, ...

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Property Type

Kissimmee Villa

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Kissimmee Vacation Rentals

Kissimmee Weather

F° | C°

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 220 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 $173.

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 171 vacation rentals in Kissimmee with a pool on FloridaRentals.com. Search using our filters and book one for your next vacation!