
House holiday rentals in Kissimmee
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Top-rated house rentals in Kissimmee
Guests agree: these houses are highly rated for location, cleanliness and more.

Game Room/HeatedPool/Piano Upscale Waterfront Home
Welcome to one-of-a-kind upscale contemporary waterfront oasis, where luxury meets comfort. This stunning house is nestled in a tranquil neighborhood, just moments away from the airport and all the attractions you desire. Step inside to find a beautifully renovated space: fully equipped open kitchen, game room, gym, pool table, grand piano etc Outside: private screened in heated pool($20/night heating fee)with breathtaking waterviews, patio equipped with grill, dining table, ping pong and more!

Adult Luxury - Magic for Families!
Welcome to our perfect retreat! Subtle Disney accents throughout included! This stunning 2300 sq. ft. modern villa in Davenport, FL, offers luxury and comfort. Enjoy the Nemo-themed black-light games room, a heated pool, and so much more. 25 minutes from Disney, it's close to golf, shopping, and dining. Inside, relax in spacious living areas, a chef's kitchen, and a private, peaceful lot. Located in the gated Aviana Resort, enjoy fitness access and a large oasis pool. Book your stay today!

Villa Resort Club
VILLA LUJOSA - BARRIO SÚPER HERMOSO POOL HEATER HOUSE - Diviértete con toda la familia en este alojamiento con estilo moderno , te encantará el área de picnic frente de la casa , el área de juegos y piscina con calentador , un espacioso lugar de hierba artificial para jugar tus niños y en una zona muy trankila cerca de los parques de Disney y del aereopuerto MCO . TE ENCANTARÁ LA CASA Local utility or county personnel may access exterior areas for maintenance without prior notice.

Gorgeous 5BR @ Encore Next to Disney - 305
Modern 3,000sf luxury home, with 5 bedrooms, at world's renowned Encore Resort at Reunion. Featuring 5 bedrooms, 5 1/2 bathrooms, a game room, a beautiful backyard, a private pool and spa. 6 Minutes away from Super Walmart and Publix supermarket 15 Minutes away from Disney Parks 15 minutes away from Disney Springs 15 Minutes away from Premium Outlets 20 Minutes away from Universal Studios 20 Minutes away from International Drive attractions *PLEASE MAKE SURE TO READ THE HOUSE RULES*

Heated Pool 15 Minutes to Disney PS5 l Switch
Spacious 4BR Home with a Private Heated Pool – 15 Minutes from Disney! Enjoy a large south-facing pool, Propane grill, Smart TVs with Disney+ in every room. Nintendo Switch in Living Room and an 85" screen with a PS5 in a temperature-controlled garage / game room. Fast WiFi, shuffleboard, pool table and plenty of board games. 🌴 Outdoor Fun Patio Seating for 14 + two lounge chairs. Propane Grill: $50 for length of stay Pool heat: $200 per stay (24-hour notice)

Renovated pond view home + pool & outdoor theatre!
Enjoy the elegance of this peaceful and centrally-located place just minutes away from Disney World, Sea World, Universal Studios & all other fun attractions of Florida. The house is tucked away in the tranquil zone next to a beautiful quiet pond that you can enjoy every evening after a busy day playing. Enjoy the pool with the sun all day and a private outdoor home theatre at night. We have a grill for your full enjoyment too. Just an hour away from sandy beaches.

No Airbnb Fee | Newly Renovated 4BR w/ Pool!
**We offer EV Charger for FREE!!! The magic of Orlando starts at home! This incredible house has much more than you need; it has everything you WANT! We offer guests comfort, convenience and an amazing experience!! Transparency and communication is very important to us! We want to make it clear, that we are here at your disposal for any doubts or suggestions. We can't wait to have you here enjoying peace and quiet and having lots of fun!

Pool House in Kissimmee
Quiet and spacious pool house in Kissimmee Florida, 20 minute away from Disney / Universal / Acquatica / SeaWorld theme parks. - 4 bedrooms - 2 bathrooms - Dining Room - Family Room - Kitchen - Double car garage - BBQ - Pool (heater optional) - Security Cameras Outside Only - WiFi 400 MBPS Pool Heater: If you want to use the heater please contact owner This will be your best vacation stay in Kissimmee / Orlando.

Disney Orlando vacation home with private pool
Great location with private saltwater pool. 5 miles from Disney Parks and Disney Springs. 1.5 miles from Margaritaville Resort, which has the H2O water park, and 1.5 miles from Sunset Walk shopping mall, which there are variety of restaurants and entertainment, including the theater( Studio Movie Grill) and live music on the weekend.

Private pool - gatted community
Welcome to this comfortable 4-bedroom home located at Encore Condominium, Southfield Street, Kissimmee, FL. This property offers privacy, spacious common areas, and excellent proximity to Orlando’s top attractions. Please note that guests do not have access to any Encore Resort amenities.

9BR Retreat | Sleep 27 | Theater | Huge Pool & Spa
Welcome to your Storey Lake getaway! This spacious 9-bedroom home with a private pool, spa, and game room is designed for unforgettable family vacations—just minutes from Disney, dining, and top attractions. Relax, recharge, and make memories together.

2026 NEW Brand NEW 07 Bedrooms At Solara Resort
* Accommodates: 18 * Bedrooms: 07 * Bathrooms: 06 * Property type: Single Family * Location: Solara Resort - This is a new property located in the PHASE 3 of the Solara Resort. -The club house is located on PHASE 1 of the same resort.
Popular amenities for house rentals in Kissimmee
House rentals with a pool

The Disney House • Immersive Rooms • Gaming Lounge

Heated pool~Lazy River~Mini Golf~Near DisneyResort

5Bd/ 5 Ba Sleeps 12! Storey Lake (4729 SH)

New! Epic Solara Playhouse | Custom Bunks + Slides

Windsor Hills Home w/Arcade Game Room|Near Disney

Dream Vacation | Sleeps 18 | Themed Arcade & Rooms

Pvt Pool + PS5 + Hot Tub &Themed Rooms | Disney

Luxury 4 Bedroom Home - Resort Access! Disney!
Weekly house rentals

*[NEW]* Your Disney Getaway

7 BR Galactic Favorite Davenport

Experience Luxury Villa at Allevo Homes

6BR 3.5BA Family Vacation Home

Fairy Tale House at Solara Resort

Lakefront 4 BR Retreat w/ pool & Jacuzzi Sleeps 12

Boho Luxe Retreat • Near Disney Parks

Comfy Home with Hot Tub at Kissimmee/Orlando area
Private house rentals

Disney Villa, Heated Pool, Spa and Game Room

Near Disney/Entire home/Parking/Free Club house

Kissimmee, Heated Pool, Game Room. Luxury

Spectacular 8Bd 5.5Bth 4K Movie Theater Pool & Spa

Welcome to the Oasis near Disney!

Theater House / Outdoor Game Area / Pool / Disney!

Home, Private Pool, 10 min to Disney, 3 BR/2 Baths

2.5 Aces Home with King bed & Jacuzzi! 2
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £121 | £124 | £133 | £132 | £115 | £125 | £133 | £115 | £103 | £109 | £121 | £140 |
| 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 house rentals in Kissimmee

Total holiday rentals
Explore 3,600 holiday rentals in Kissimmee

Nightly prices starting at
Kissimmee holiday rentals start at £15 per night before taxes and fees

Verified guest reviews
Over 99,510 verified reviews to help you choose

Family-friendly holiday rentals
3,090 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 630 rentals that welcome pets

Holiday rentals with a pool
3,260 properties feature pools

Rentals with dedicated workspaces
1,880 properties have a dedicated workspace

Wifi availability
3,570 of Kissimmee holiday rentals include wifi access

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

4.7 Average rating
Kissimmee stays receive an average rating of 4.7 out of 5 from guests
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- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Orange County Convention Center
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Give Kids the World Village
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club






