
Villa holiday rentals in Kissimmee
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Top-rated villa rentals in Kissimmee
Guests agree: these villas are highly rated for location, cleanliness and more.

Villa Sol Peaceful Pool/Hot tub Home
Close to all major attractions, and airport sits this private villa. It has a little something for all ages! Your family can play in the pool or relax in the hot tub. Enjoy fun game nights with a cabinet full of games, or play a game of basketball, pickleball, or tennis right outside our pool. Fun on the playground or enjoy the clubhouse gym. All of your needs for the beach trips or the ball games. All of your baby's needs are covered as well. Ask about Stroller and cart rentals. We have it all

Charming 4 Bdr~ Villa near Disney
We offer a Luxurious Villa with the things you need to enjoy your stay in the most wonderful experience possible. 4 bedrooms, 3 bathrooms,dedicated game room and private pool you will be able to enjoy all day fun while still having space to relax after a long day at Disney World. Brand new Villa extremely comfortable and well-equipped for up to 8 people, free parking,free wifi and more make it a great choice for families or groups of friends. Have fun with the whole family at this stylish place.

150 Inch 4K Movie Theater Pool & Spa sleeps 16
"Just 3 miles from Disney up to 16 guests! Unwind in the pool & jacuzzi. A private cutting-edge Movie Theater, featuring a 150-inch screen, 4K projector, and immersive surround sound. Relive your favorite movie moments like never before! Stream on Roku, game on PS5, and enjoy high-speed Wi-Fi for endless fun. The well-equipped kitchen is perfect for large families and with 6 bedrooms and 4 en-suite baths, privacy is guaranteed. A Star Wars and a Disney-themed rooms so the kids will feel at home.

Disney Villa Retreat - 3mi from Disney & Game Room
Relax and enjoy a peaceful vacation with family and friends at our beautiful home only 3 miles from Disney World. Our newly renovated game room is equipped with 4 Arcade Machines, Pool Table & Air Hockey. Enjoy the private pool and a fully equipped kitchen. Just recently upgraded smart home with smart color LED lights throughout. Our community is the closest to Disney and other theme parks. We are located 6 mins from attractions, dining & shopping. Spa/sauna avail @ clubhouse Just renovated pool

Sleeps 21|Free Pool Heat|15 min to Disney|Hot Tub
Make memories to last a lifetime in our luxurious seven-bedroom home (sleeps 21) at Orlando's premier vacation community. Enjoy your own Batman cave game room, private pool (heated at no extra charge*), and hot tub. Our 100% Five-Star rating from previous guests and our generous cancellation policy means you can book with confidence. Only 15 minutes to Disney and a short walk to a fabulous resort clubhouse with free access to a lavish pool, kids waterpark, restaurant, playground, gym, and more!

OMG! Disney Area, Movie Theater, Game Room & Pool!
"Guest favorite" - This home is in the top 10% of eligible listings based on ratings, reviews, and reliability. Comfort and Space in an Elegant home with a lot of amenities, 4Bed/3Bath. Private Movie Theater, Game Room, Pool and Themed Rooms. A well equipped Kitchen, Laundry, 3 parking spaces, WiFi, Smart TVs. Located at Crystal Cove Resort, a gated community, close to Disney. Few minutes to Walmart, Target, Sams Club, Publix, Outlets, Restaurants, Disney, Sea World, OCCC, EPIC and Universal.

*Private Resort Oasis: Golf-Front, Pool/Spa/Cinema
The perfect balance of STYLISH DESIGN, LUXURIOUS COMFORT, & ENDLESS ENTERTAINMENT, beautifully situated with stunning views in the sprawling 3.5 square mile Reunion Resort. You will have your own private pool, spillover spa, STAR WARS cinema-game room with pinball, classic arcade games, and karaoke, MARVEL kids room with tube slide and double bunks, the latest Xbox Series S, a sprawling 2000 ft2 pool deck, fire pit, and even a HARRY POTTER cupboard hidden under the stairs, minutes to Disney.

Magical 5-Bedroom Villa Near Universal's Wizarding
Ensure an enchanted holiday in Orlando. Inspired by everyone’s favorite castle, this magical home provides an immersive experience with 5 bedrooms, common room with large screen TV with Netflix & Nintendo Switch, dining hall, fully equipped kitchen, swimming pool, patio with grill and laundry room. Located in a quiet residential community, 10 miles to the Wizarding World of Harry Potter, 6 miles to Disney, 5 miles from Celebration, 4 miles from Old Town and 18 miles from downtown Orlando.

8 BR Villa, Private Pool, Theater, Min to Disney!
Big and Beautiful Themed Vacation Villa in premium gated Encore Resort. Spacious main floor for entertaining large groups - bring the family and friends! Enjoy the included resort amenities a minute's walk from the front door. Or, relax around your private pool and custom summer kitchen. Enjoy big-screen movies and sound in the theater in premium loungers, and play classic arcade games! 10-15 min from Disney, one of the closest villa resorts. Tons of shopping and dining nearby!

4mi to Disney | Games | Private Pool
Get ready to make memories of a lifetime just over 3 miles to Disney when you stay at this newly renovated Star Wars and Lego-themed private pool villa. Located in Formosa Gardens Estates, a prestigious gated community, our home is professionally furnished with multigenerational families in mind and can comfortably sleep up to 15 guests. After a trip to the parks, enjoy a refreshing dip in the private pool and rest those tired feet in the spa (pool heat included!).

Gorgeous 3 bed, 2 bath villa w/ pool and jacuzzi
Gorgeous 3 bedroom, 2-bathroom villa set on a 1/4 acre of land, with our own screened, private, heated swimming pool & Jacuzzi, and high speed internet. Situated in a quiet residential community on the sought after Sunridge Woods in Davenport, only 9 miles from Disney. Please note smoking or parties are NOT allowed in house premises. No pool heater available during May through October. **You also MUST be 21 or older to rent this property**

Immaculate 6BR Minutes to Disney & Free Pool Heat
Immaculate and well equipped Stargazer Villas vacation home at Storey Lake Resort! A short drive to Disney & within easy reach of attractions, shopping and dining. This Orlando area vacation home is a guest favorite and has a heated pool (no extra charge) for your family to relax in after a busy day at the parks. Featuring themed Toy Story & Mickey bedrooms, as well as three primary suites, along with Star Wars movie loft & Avatar game room!
Popular amenities for villa rentals in Kissimmee
Private villa rentals

Windsor Hills, Disney/Universal, Pool/SPA, 5BR5BA

Private Villa near Disney & Universal W/Pool & Spa

The Lakeview Oasis - XL Pool & Jacuzzi - Orlando

Amazing home 5 mins to Disney Orlando

Private Pool & Free Heat - Close to Disney!

6BD/ 6 BA Sleeps 13! Storey Lake (4528 TB)

2817 Story Lakes

The Balmoral Manor: Luxurious & Bright 5BR Oasis
Luxury villa rentals

Blue Paradise 15BR 11BA, Sleeps 36, Theater/GameRm

Pickleball PoolsideMovies |WalkToWaterpark| Arcade

NEW Unique 6BR,private pool,Full game room, + MORE

"Disney Serenity": Luxe 8BR Villa/ Privacy/ Pool

Rotating VR Machine, Arcade, Slide | 3mi to Disney

Storey Lake•9BR•Fire Pit•Pool•Hot Tub•Game•EV

Luxury Themed Villa 9 BR | Close to Disney

Walk2Clubhouse|Pool Movies|Arcade|Theater|Themed
Villa rentals with a pool

Casita Kissimmee!Family Vacation Villa! 8minDisney

Epic Escape/9Br/Theater, Game Rm/Theme Rm/Disney

7BR Disney Villa Escape Room+ Pool +Cinema+Game Rm

Vacation 3 bedroom 2 bath Villa+pool

Private Family Villa w/ Pool, Game Room, Resort

Luxury Villa w/ Hot Tub-Grill-Private Heated Pool

Walk to Clubhouse+6BR+Spa&Pool+Theater+ThemedRooms

Epic Luxury Theme Home w/ Private Pool & Game Room
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $290 SGD | $311 SGD | $299 SGD | $294 SGD | $260 SGD | $299 SGD | $320 SGD | $262 SGD | $241 SGD | $254 SGD | $290 SGD | $333 SGD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Quick stats about villa rentals in Kissimmee

Total holiday rentals
Explore 720 holiday rentals in Kissimmee

Nightly prices starting at
Kissimmee holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 20,140 verified reviews to help you choose

Family-friendly holiday rentals
720 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 80 rentals that welcome pets

Holiday rentals with a pool
680 properties feature pools

Rentals with dedicated workspaces
490 properties have a dedicated workspace

Wifi availability
620 of Kissimmee holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Kissimmee rentals

4.6 Average rating
Kissimmee stays receive an average rating of 4.6 out of 5 from guests
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- SeaWorld Orlando
- Disney Springs
- Old Town Kissimmee
- Disney's Animal Kingdom Theme Park
- Magic Kingdom Park
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Walt Disney World Resort Golf
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Aquatica
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- Universal's Islands of Adventure
- Ventura Country Club
- Kissimmee Lakefront Park
- Bok Tower Gardens






