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.

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Guest favourite
An inviting pool area is framed by a screened enclosure, revealing beautiful water views at sunset. Soft lighting enhances the relaxing atmosphere, with lounge seating positioned nearby for comfort. The tranquil setting is ideal for unwinding and enjoying outdoor moments by the pool.
Home in Kissimmee
4.96 out of 5 average rating, 335 reviews

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!

Top guest favourite
A fenced heated pool area is visible, surrounded by lush greenery and palm trees. The villa entrance features a welcoming façade and a spacious driveway. Inside, a games room showcases vibrant Nemo-themed murals, along with seating and game tables for recreational enjoyment.
Home in Davenport
4.95 out of 5 average rating, 37 reviews

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!

Guest favourite
A modern two-story house is showcased, featuring a bright exterior and a spacious driveway. Lush green grass surrounds the property, while palm trees add a tropical touch. Large windows on the upper level allow for ample natural light, highlighting the clean lines of the architecture.
Home in Buenaventura Lakes
4.96 out of 5 average rating, 119 reviews

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.

Top guest favourite
An inviting outdoor area showcases a private pool and spa, surrounded by lounge chairs and colorful beach balls. A dining table and large gas grill offer options for outdoor meals. Lush greenery lines the fence, providing privacy and a vibrant backdrop against a sunny sky.
Home in Citrus Ridge
5 out of 5 average rating, 59 reviews

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*

Top guest favourite
A private heated pool is set within a screened enclosure, surrounded by a patio area. Two blue chairs and a white lounge chair are positioned nearby, with lush greenery visible beyond the pool. The clear water reflects the sky, creating a serene atmosphere.
Home in Kissimmee
4.99 out of 5 average rating, 157 reviews

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)

Superhost
Home in Kissimmee
4.82 out of 5 average rating, 121 reviews

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.

Guest favourite
A game room is presented with a red and neutral color scheme, featuring a billiard table with a set of colorful pool balls arranged on it. A television is mounted on the wall, and a dartboard is visible. The space is accented with vibrant wall art and seating areas.
Home in Citrus Ridge
4.9 out of 5 average rating, 135 reviews

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!

Guest favourite
The exterior of the pool house reveals a welcoming facade with a well-maintained lawn. A screened-in pool area showcases a spacious pool surrounded by tile flooring. The interior features a game room with a billiards table and air hockey, highlighted by modern entertainment options.
Home in Kissimmee
4.84 out of 5 average rating, 135 reviews

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.

Top guest favourite
A spacious pool area is showcased under a protective screen. A large pool is bordered by a textured deck, with several lounge chairs arranged nearby. Lush greenery is visible in the background, and a covered patio area offers shaded seating.
Home in Citrus Ridge
4.94 out of 5 average rating, 288 reviews

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.

Guest favourite
Home in Citrus Ridge
4.83 out of 5 average rating, 12 reviews

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.

Guest favourite
Home in Kissimmee
5 out of 5 average rating, 7 reviews

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.

Guest favourite
Home in Citrus Ridge
5 out of 5 average rating, 5 reviews

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

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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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