Kissimmee Vacation Rentals

(254 rentals)
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9 BR | 5 BA | Sleeps 20 | Quick View

42

Distance to park: 7 miles to Disneyworld

$550

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

SCAN QR CODE for a VIRTUAL TOUR. Experience luxury and entertainment in this 9-bedroom villa that has 7 different themed rooms, a private pool/hot tub, and unobstructed lake views. Enjoy our Avengers movie room, Star Wars game room, Harry Potter, Frozen, Toy Story, Moana, Mickey bedrooms and 2 exclusive ...

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Property Type

Kissimmee Villa

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4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to park: 2 miles to Disney’s Animal Kingdom Park

$124

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

This huge 1650 sqft condo has 4 bedrooms and 3 full bathrooms. It is located at Sun Lake Resort, just 2 Miles to Disney world Florida.sleeping accommodations for 8.* King-size Master bedroom with bathroom* One queen size sofa bed in family room for extra guests* One 40" HDTV(free ...

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Property Type

Kissimmee Condo

"Nice Vacation Condo Rental"

Located near Disney, shopping, restaurants. Everything on 1st floor was wonderful for a group of oldsters!

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool

About this property

Embark on the ultimate Disney vacation at Jurassic Encanto! With elegantly designed thematic rooms, this spacious home provides ample room for larger groups and multiple families. Compete in the epic game room or take in the lake views while relaxing by the luxurious private pool and spa amidst world-class ...

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Property Type

Kissimmee House

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Key Amenities

  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

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

"Two week stay"

We stayed for two weeks in August/September. Great house and location to the parks. Kids enjoyed the pool table and game systems.Would book again.

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9 BR | 8 BA | Sleeps 18 | Quick View

10

Distance to park: 3 miles to Disney Animal Kingdom

$650

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

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

"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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8 BR | 6 BA | Sleeps 16 | Quick View

8

Distance to park: 8 miles to Disney World

$305

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee,Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, this ...

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Property Type

Kissimmee House

"GREAT"

Great home for large family .. home is located close to shops … it’s a great location to be at! Very nice

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4 BR | 3 BA | Sleeps 8 | Quick View

16

Distance to park: 4 miles to Disney

$162

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

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

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Property Type

Kissimmee House

"Perfect rental for all of our needs!"

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

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9 BR | 6 BA | Sleeps 20 | Quick View

4

Distance to park: 2 miles to Disney’s Animal Kingdom Park

$350

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee,Developed by one of the nation's largest developer. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, This 24 hour guard gated ...

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Property Type

Kissimmee House

"Very comfortable"

I went with my family, very comfortable. Beds 6 out of 10. Pool 7 out of 10. Rest of amenities 10 out of 10.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

NO Party’s but Our mission is to provide excellent service and guest relations for every guest that comes to stay in our home. we wish to provide a fabulous experence of relaxation and comfort thoughout your time with us. But above all, we want to give you the chance to create the great memories ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Welcome to VIPvilla Johanna and Stephen thank you for visiting our website of hand-picked 5 Star quality villas. We manage the bookings for 20 private villa owners at lake Berkley Resort and we can personally assure you that you will be delighted with any of the villas offered to you. We have many ...

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Property Type

Kissimmee Villa

"Fantastic-Excellent."

IWe visited Orlando a lots of time,We are familiar with Lake Berkley.We had always very good impresion of staying in Lake Berkley.This time we stayed in Lake berkley drive 929.We arrived at almost 03;00 ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to our luxurious 6-bedroom, 9-bed, 3,200-square-foot villa. This stunning property features two en-suites, two living rooms, and a private screened-in pool with optional heating.Conveniently located near major attractions such as Disney, Universal, Seaworld, and golf courses, our villa can ...

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Property Type

Kissimmee Villa

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4 BR | 4 BA | Sleeps 8 | Quick View

18

Distance to park: 2 miles to Disney

$297

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Wonderfully Themed villa in the beautiful gated community of Windsor Hills, just two miles from Disney. Enjoy complimentary pool & spa heat, themed rooms, and a fun games room in the garage (air hockey, ping ping, foosball)! This is one of very few 4-bedroom units on the resort. We're nice and ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

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

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4 BR | 3 BA | Sleeps 8 | Quick View

9

Distance to park: 4 miles to Disney World

$159

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

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

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Property Type

Kissimmee House

"Great Villa"

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

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$113

avg/night

View Details

Key Amenities

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

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

"Wonderful stay"

Traveled from the UK. Villa was a little dated but was very clean and the beds comfortable. Pool was a great hit with our teenagers. Parks were easy to get to from the villa. We had a great stay and ...

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3 BR | 3 BA | Sleeps 9 | Quick View

11

Distance to park: 5 miles to Animal Kingdom Lodge

$140

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

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

"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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4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to park: 5 miles to Disney,Seworld

$123

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to our new opening 4 Bedroom/3 bathroom Townhouse in CLUB CORTILE,This gated-community is close to every major Orlando attraction: Disney's Magic Kingdom, Epcot, Animal Kingdom, Universal Studios (Harry Potter), Sea World, and many more. Club Cortile is also conveniently close to WalMart, ...

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Property Type

Kissimmee Townhome

"Well located safe townhouse on a lake with good club facilities"

We are a pensioned couple from the Netherlands and in Florida to play golf in the sunshine. We have rented from the owner on several occasions over the last 15 years. This was our first time in the Club ...

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7 BR | 4.5 BA | Sleeps 16 | Quick View

11

Distance to park: 3 miles to Disney world

$166

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Pool

About this property

Newly furnished luxurious 2-story Villa home opens its door to welcome you! This villa is furnished with two master suite and one large bedroom with upscale King-size beds; two bedrooms with queen-size beds; and two bedrooms with two twin-beds each. All bedding and mattresses are Brand New with top quality ...

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Property Type

Kissimmee Villa

"Wonderful Vacation Home"

Our family of 12 spent 2 weeks at 2662 Emerald Island Blvd. Everyone had a wonderful time and hated to leave when our vacation was over. The house has very comfortable furniture and everyone said their ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

This fantastic 5 bedroom, 4 bath Vacation Villa offers all of the conveniences of home and everything you need for a fun family vacation including a Private Screened-In Pool, Outdoor Spa, Games Room, Fully Equipped Kitchen, Free Wireless High-Speed Internet, Full Size Washer/Dryer, Coffee Maker and Microwave. ...

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Property Type

Kissimmee Villa

"Perfect house for our group"

House was perfect for what we were looking for! It was very clean and comfortable. Pool and hot tub were fantastic! This place was awesome!

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7 BR | 5.5 BA | Sleeps 14 | Quick View

2

Distance to park: 5 miles to Disney World

$244

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

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

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Property Type

Kissimmee House

"Amazing 7 Bed rooms Villa Near Disney"

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

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3 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to park: 1 miles to Disney Animal Kingdom

$97

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

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

"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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5 BR | 4 BA | Sleeps 12 | Quick View

2
last minute deal
LAST MINUTE DEAL 9/25 - 11/6: Discounted September/October rates, message for a quote!

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

$335

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

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

"Family Birthday Vacation"

Everything was great! The house was very spacious. The back area a bit small but still great! We had a blast!

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DEAL

4 BR | 3 BA | Sleeps 9 | Quick View

5
last minute deal
LAST MINUTE DEAL 11/1 - 11/5: Book 4 nights from Nov 1st to 5th - get free pool heat for your stay.

Distance to park: 3 miles to Disney

$182

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

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

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Property Type

Kissimmee House

"5*+ Magic Emerald Island Villa"

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

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DEAL

Key Amenities

  • Air conditioning
  • Kid friendly
  • Pool

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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool

About this property

Experience a magical holiday by renting TWO homes across the street from each other to accommodate large groups, teams and reunions! Queen of Hearts is 8 bedrooms and Moana's Minecraft is 7 bedrooms, both in Windsor at Westside Resort. Enjoy private pools, & game rooms in these fabulously equipped ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

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

"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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Check out this amazing home! The sparkling pool basks in sunlight all day, while the lanai offers refreshing shade. It's the perfect setting for complete relaxation and enjoyment.This spacious family retreat comfortably accommodates up to 16 adults. If there is a mix of children and adults, the ...

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Property Type

Kissimmee House

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7 BR | 6 BA | Sleeps 16 | Quick View

$320

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

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Property Type

Kissimmee House

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5 BR | 4 BA | Sleeps 10 | Quick View

1

Distance to park: 7 miles to Disney Hollywood Studio

$146

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

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

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Property Type

Kissimmee House

"Very good"

The trip was great me and my family really had fun and enjoyed ourselves we will be coming back soon.

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9 BR | 6 BA | Sleeps 24 | Quick View

14

Distance to park: 2 miles to Sunday's Grill

$319

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool

About this property

For last minute rentals or longer extended rentals, please inquiry about our discounted rates.This luxury vacation home is located in the Windsor at Westside upscale resort community - A perfect destination for DISNEY WORLD (10 minutes away), golf, and relaxing and celebrating with family and friends. ...

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Property Type

Kissimmee Villa

"Excellent"

Thank You Ann great service. Me and my family will be renting from you again in the future

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3 BR | 2.5 BA | Sleeps 8 | Quick View

$157

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Gorgeous 3 bedroom townhome in a gated resort community with many activities. The home is located right across the street from one of the pools and playground.

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Property Type

Kissimmee Townhome

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Our luxury 4 bedroom home is located within the top rated community of Indian CreekThe villa is furnished to a very high standard and is fully Air-conditioned throughout keeping the villa cool in the warm Florida weather.Full hi-speed WiFi throughout the villa.The tastefully furnished lounge ...

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Property Type

Kissimmee House

"Brilliant stay at this villa"

\We stayed here a week and all the family loved this villa. Pool is so nice. Highly recommneded, we will stay here again. Tim

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4 BR | 4.5 BA | Sleeps 10 | Quick View

14

$211

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

Stay in our magical residence! This modern 4 bedroom and 4.5 bath villa is filled with high-end finishes & amenities and is just 5 miles from the entrance to Walt Disney World! Every room has its own ensuite bathroom. No need to wait in line. Enjoy the resort style amenities that include a community ...

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Property Type

Kissimmee Townhome

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Beautiful south facing Villa with private pool and hot tub overlooking a peaceful lake.This private gated community is 20 minutes to Disney’s Magic Kingdom and 20 minutes to Universal Studio and 45minutes to the gorgeous Daytona beach where you can actually drive your car onto this huge beach.A ...

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Property Type

Kissimmee House

"This property is very nice I worked out very fine for us and would recommend it"

The area is very fun with lots of things to do We like the area there is plenty of restaurants in the area feels very safe

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool

About this property

Experience the popular "Queen of Hearts" villa in the Windsor at Westside Resort! This home boasts a private heated pool & hot tub, fire pit and outdoor TV. The themed bedrooms are loaded with amazing details. All guests have free access to resort amenities. Your host Vacation Alchemy provides ...

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Property Type

Kissimmee House

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5 BR | 3 BA | Sleeps 10 | Quick View

3

Distance to park: 6 miles to Disney World,Seaworld

$137

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

Welcome to the beautiful Coral Cay Resort. It is one of the most popular resort destinations in the Kissimmee/Orlando area for its proximity to theme parks and other major attractions. Situated 6 miles from Disney,1 mile to Walmart and target, 8 miles to Seaworld and Convention Center.This gorgeous ...

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Property Type

Kissimmee Townhome

"Always a pleasure to stay at Coral Cay, Liu was great!"

Everything was as stated. This is a nice, clean unit, with a ton of space. The hot tub in the screen room is awesome, and great for sore feet and muscles at the end of a Theme Park day. Beds are super ...

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5 BR | 5.5 BA | Sleeps 13 | Quick View

4

Distance to park: 12 miles to Disney's Magic Kingdom Park

$336

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Welcome to Westside Villa! -20 minute drive to all Disney Parks -Private, heated pool; gas grill; EV charger on-site -Modern arcade: racing simulators, virtual reality, vintage games -3 king size suites with smart TVs -2 uniquely themed bunk rooms (Star Wars and Fairy Tale) -All bedrooms have ensuite ...

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Property Type

Kissimmee House

"Amazing"

The house was simply amazing. The family could not believe what I had rented when we arrived, so spacious. So many things games/entertainment in the house. The house was very clean, the beds were really ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool

About this property

Experience a magical holiday at this luxe 7-bedroom home! Nestled in Windsor at Westside Resort, you and your loved ones will be a short drive to many attractions. Stretch out into sprawling living areas where comfort awaits you before heading outside for an exciting time - enjoy a dip in your private ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool

About this property

This gorgeous home was completely redesigned in 2023! Experience unforgettable moments with your family at Solara Resort. The kids will delight in our thoughtfully designed themed bedrooms, while others can unwind on the inviting custom patio or enjoy a refreshing swim in the private heated pool.Is ...

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Property Type

Kissimmee House

"AMAZING customer service"

I was skeptical of booking online with a company I wasn't familiar with, however they ended up being so responsive to any concerns or questions I had, including when me and my kids were in the house. It ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Stunning, designer furnished 7th Heaven Villa! This home has everything that you, your family and friends will ever need and more! Walt Disney World Resort is only 2 traffic signals away. This luxury South facing pool home, completed in June 2004, has 7 bedrooms, 6 bathrooms and will accommodate 15 people ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

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

"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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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Welcome to this stunning lake view vacation home close to Disney. This 5 bed 3 bath home is the perfect place to unwind after a busy day visiting many of the local attractions.The home has 5 bedrooms, 3 bathrooms and sleeps 12.Hi speed WiFi and air con throughout the villa.Our 5 Bed, 3 Bath ...

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Property Type

Kissimmee Villa

"Fantastic Stay"

We have been coming to Florida and resting villas for the last 30 years and this is without a doubt one of my favourites.You are always a bit nervous when you open the door but as soon as entering hearing ...

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4 BR | 3 BA | Sleeps 8 | Quick View

27

$145

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

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

"House rental on Santee Dr"

The house was very clean and well furnished. The location is perfect. I dealt with the homeowner Lisa who was professional and returned my text quickly. The pool and hot tub were also very clean. Quiet ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Luxury Screened-In, Lake Front, Private Pool Home! This amazing 3 bedroom, 2 bathroom, Disney Area Vacation Rental Home is located in the family-friendly residential community of Eagle Pointe. Just a few short miles from Orlando's World-Renowned Theme Parks including the Walt Disney World Resort, ...

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Property Type

Kissimmee Villa

"Great Location for visiting Orlando/Kissimmee area for parks and golf"

Thoroughly enjoyed our 104-night stay (January – April 2024) at this home. Location close to all parks, stores and restaurants. Perfect place for Rest, Relaxation and Peace and Quiet! Outfitted with ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Beautiful south facing lakeside villa with electrically heated pool option. Great location for all the theme parks, Disney 20 mins, Seaworld 15mins, Universal 30 mins and Cocoa Beach/Kennedy Space Centre 45 mins. Local English management contact and fully inspected/licensed by the Florida Hotels Board. ...

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Property Type

Kissimmee Villa

"Had a great stay"

Angie's was clean and cozy with lots of space. Location was very good and the pool was great for families and adults.

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8 BR | 6 BA | Sleeps 16 | Quick View

2
owner special
Owner special: Book 6 nights & Get 1 night FREE. Offer not valid with any other discounts contact for restrictions.

$241

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

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

"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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4 BR | 3 BA | Sleeps 12 | Quick View

Distance to park: 15 miles to Disney World

$200

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Experience this spacious 4 bed/3 bath Home and "Optional Private Heated Pool" with garage transformed into a sensational glow in the dark game room, where both kids and adults can revel in laughter and friendly competition. As if that's not enough, a dazzling LED screened-in pool tailor-made ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

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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7 BR | 4.5 BA | Sleeps 14 | Quick View

13

Distance to park: 3 miles to Disney World Parks

$237

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

This is a spacious vacation rental home located in Orlando, perfect for large families of up to 14 guests. The house has 7 bedrooms and 4.5 bathrooms, including two King Master Suites, one on each floor. The first-floor suite features a walk-in shower and a separate garden tub. Bedroom 3 and 4 have King ...

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Property Type

Kissimmee House

"Brilliant villa and location"

What a lovely place Be Our Guest is, weve just come back and are depressed now..... The villa was well kept, equiped, clean & pleasant. The owner and the management company couldnt do enough for us. The ...

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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 254 Kissimmee vacation rentals available on FloridaRentals.com. From house rentals to villa 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 $27 per night with an average price per night of $174.

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