House holiday rentals in Kissimmee

A private pool area is showcased, featuring a clear blue pool surrounded by a screened enclosure. Comfortable lounge chairs in turquoise are positioned beside the pool. A serene pond and lush greenery are visible beyond the enclosure, providing a calm backdrop.

4.91 out of 5 average rating, 149 reviews

(Discounted Rates) Vacation Home (4 Miles Disney)

We have the perfect vacation home for You! Fully equipped 3 bedroom home with patio and pool overlooking a pond and conservation area. Just a 10 minute drive from Disney yet in a quiet gated community with playground. Sleeps 6 guests in 3 bedrooms. All beds are new, including king size bed in master bedroom. Folding cots and full size folding crib are available. Master bedroom has a private master bath. Close to local shopping ,dining and attractions. Request heated pool for additional fee.

A spacious living area features a comfortable dark gray sofa and a stylish coffee table, surrounded by neutral decor. A large flat-screen TV is positioned on a modern console against a bright wall, while natural light fills the space through multiple windows.

4.97 out of 5 average rating, 173 reviews

Cozy Disney Oasis Pool Home 10 Mins from Parks!

Our charming, pet-friendly home is located in the prime area of Kissimmee, Florida. Your family will be close to Disney parks, restaurants, Old Town, and Downtown Disney. Just bring your bag—we have everything you need! Settle into our fully equipped home, thoughtfully designed to create lasting memories with family and friends. Enjoy the Florida weather by cooling off in our open-air pool or grilling by the poolside lounges. Relax in our airy bedrooms, including Mickey and Minnie themed rooms!

A private pool area is surrounded by a screened enclosure, featuring a well-shaped pool and a jetted hot tub. Lounge chairs are positioned nearby, with a grassy area beyond. The evening sky displays hues of pink, creating a serene atmosphere, enhanced by string lights that illuminate the space.

4.94 out of 5 average rating, 178 reviews

*Luxe Disney Home* Priv Pool/Spa- 6BR Sleeps 15

JUST ADDED! (Check out our other reviews) New Construction!!! 3000ft2! Welcome to our luxury 6-BR private pool home near Disney World, Universal Studios, and Sea World! With 8 beds, it sleeps 15 people comfortably. Enjoy the private heated pool, hot tub, and game room with ping pong, cornhole, and arcade. Located in Veranda Palms community, you also have access to a large pool, clubhouse, gym, and splash pad. Perfect for large families or groups seeking a memorable Orlando stay. Book now!

4.93 out of 5 average rating, 161 reviews

A private, screened-in pool area features a sparkling blue pool with a built-in hot tub on one side. Sunlight reflects off the water, creating a serene environment, while surrounding greenery provides a sense of privacy.

Home in Clermont

Stylish Villa Private Pool-SPA Near Parks Disney!

Stylish villa 4 bed/3 bath family home with private facing pool & SPA, living room, family room, kitchen, breakfast bar, dining table, a game room, Wi-Fi, smart TVs, wheelchair accessible, close to the parks, shops, and restaurants, Pool & SPA heater at additional cost, located at Glenbrook community. We have it all and much more to enjoy. The pool & SPA heater fee is $25 (USD) per day. The BBQ grill is an additional $45 (USD) charge for the whole stay, including 1 propane gas and cleaning.

The tranquil pool area is framed by a screened enclosure, featuring plush loungers and a small table. Bubbles float in the water, and a vibrant sunset casts a warm glow over the serene setting, highlighting surrounding greenery.

4.93 out of 5 average rating, 147 reviews

"Paradise Found" Sensational 6 Bed Home W/Peloton

Discover 'Paradise Found' at Windsor at Westside, a 6-bed fantasy home near Disney. This 3,300 sq ft gem offers an open-plan living space, gourmet kitchen, and a private pool oasis with a BBQ, dining and lounge. Enjoy a king suite with pool access, a fun-filled garage gym/games area, and a vast upstairs lounge with Xbox. Dream in themed children's rooms or one of the three king bedrooms. Perfect for families seeking a magical retreat! Free resort access, pool heat and BBQ.

A vibrant games room is equipped with various arcade machines, including SpongeBob Racing. A massage chair is positioned nearby, while a theater room features plush seating. An outdoor space highlights a screened-in pool area surrounded by palm trees, visible through large windows.

5 out of 5 average rating, 244 reviews

Windsor Orlando Private Arcades,Theater,Pool-Spa

Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.

A spacious entryway features a stylish staircase with wooden steps and a glass railing. A large Christmas tree decorated in soft colors stands next to a modern living area displaying a cozy sofa and contemporary artwork. A fireplace adds warmth to the ambiance.

4.86 out of 5 average rating, 63 reviews

The Eights House by Disney. Themed Island Dream

Location can't get better! Next to Disney Parks and Restaurant Row! This Guarded and gated place to stay is perfect for family trips. You will fall in love with our year round 12ft tree tastefully decorated by season. Mickey's Camping room, Frozen themed room, the cabin Christmas year round experience & 2 additional modern king rooms perfect for couples! Did I mention the stunning Avengers Home theater/game room and oversized pool?

4.84 out of 5 average rating, 116 reviews

Home in Davenport

Movie Room | Hot Tub | Sunny Pool | Fun House

• 4BR | 3BA | Sleeps 9 – 2 king suites + kids’ bunk room • Private sunny pool & FREE heated hot tub • Movie room with cinema seating, popcorn maker & mini fridge • Games area with pool table for family fun • Two living areas + fully equipped kitchen • Quiet, family-friendly location near Disney & Universal • Close to ChampionsGate golf, shopping & restaurants • 🎁 Complimentary welcome pack on arrival

4.78 out of 5 average rating, 41 reviews

Newly Renovated Luxury Villa| Pool Table &Foosball

Enjoy the perfect getaway at our Luxury Villa! Perfect for families!—just 9 miles from Disney! - Accommodates 12 GUESTS - 5 EN-SUITE - Floor-to-ceiling blackout curtains - New garage GAME ROOM w/ POOL TABLE & FOOSBALL - Large backyard with outdoor shower - Private heatable pool & whirlpool spa - Mickey Mouse-Themed Bedroom -Dedicated Workspace - Smart TVs

A private pool area is showcased, featuring a spacious rectangular pool with a spa attached. Sun loungers are arranged along the patio, surrounded by well-maintained greenery and palm trees. The clear blue sky complements the serene outdoor setting.

4.65 out of 5 average rating, 23 reviews

5 Bd/ 4.5 Ba Sleeps 11! Encore At Reunion (7434MA)

• Resort: Encore At Reunion • THERE IS NO ACCESS TO RESORT AMENITIES • 5 Bedrooms/ 4.5 Bathrooms/ Sleeps 11 • Disney World® (7.5 mi) SeaWorld (17.4 mi) • Convention Center (8.2 mi) ICON Park (16.4 mi) • Universal Studios (18.7 mi) Epic Universe (16.4 mi) • Location: Marker Avenue, Kissimmee FL 34747

A private pool area features a sparkling swimming pool next to a heated spa. The space is enclosed by a screened lanai, allowing sunlight to filter in while providing a view of the surrounding greenery and landscaping.

4.81 out of 5 average rating, 144 reviews

4 Bedroom, 3 bath Kissimmee Vacation Home

Beautiful 4 Bedroom, 3 bathrooms Florida Vacation Home with South Facing Pool with Spa On Quiet Community Off US Hwy 192 in Kissimmee, Close to Disney, Golf and the Attractions

5 out of 5 average rating, 3 reviews

NEW Stuning 09 Bedroom/LED At Pool/ Solara Resort

The Space •⁠ ⁠Accommodates: 22 •⁠ ⁠Bedrooms: 9 •⁠ ⁠Bathrooms: 6 •⁠ ⁠Property type: Luxury Villa •⁠ ⁠Location: Solara Resort

Popular amenities for house rentals in Kissimmee

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 4 reviews

The Disney House • Immersive Rooms • Gaming Lounge

4.85 out of 5 average rating, 47 reviews

Restful 4BR / 3BA with BBQ, Heated Pool & SPA.

The image features a grand castle with tall spires and intricate architectural details. A vibrant flower bed in the foreground displays colorful blooms, enhancing the scene. Clear skies with scattered clouds frame the castle, creating a magical atmosphere.

4.92 out of 5 average rating, 39 reviews

Disney Escape/ 7 Resort Pools/New Built/Pond View

4.94 out of 5 average rating, 48 reviews

Disney Retreat - 6BR 17ppl Pool, Spa - Storey Lake

4.9 out of 5 average rating, 39 reviews

Amazing Solara 7BR/ Pool /Spa /Free Waterpark

4.87 out of 5 average rating, 30 reviews

A dedicated movie theater room is equipped with plush tiered recliners arranged to face a large projector screen. The room is accented with soft blue lighting, and a temperature control unit is visible on the wall, creating a comfortable viewing environment.

Home in Davenport

Epic Villa By Disney Theater/Game Room/Pool & Spa

The private pool area features clear blue water surrounded by a spacious deck. A spa is adjacent to the pool, and patio furniture is visible in the background, providing options for relaxation. A screen enclosure protects the area while allowing natural light to fill the space.

4.75 out of 5 average rating, 20 reviews

Getaway w/ Private Pool & SPA + BBQ | 10min Disney

5 out of 5 average rating, 28 reviews

No cleaning fee, pool, lakeview, parking, cozy

Weekly house rentals

5 out of 5 average rating, 10 reviews

Group Getaway • 14 Beds • Sleeps Up to 20

4.8 out of 5 average rating, 30 reviews

A modern dining area features a spacious table set for six, complemented by soft grey chairs. The open layout connects to a well-equipped kitchen, with white cabinetry and stainless-steel appliances visible in the background. Natural light enhances the inviting ambiance.

Home in Four Corners

Dream Villa at ChampionsGate -15 minutes to Disney

A modern dining area showcases a long wooden table set for meals, complemented by white chairs. A stylish light fixture hangs overhead, and large glass doors provide a view into the outdoor space, allowing natural light to fill the room.

4.96 out of 5 average rating, 48 reviews

Family Fun: Resort Front + Pool | 15 Min Disney

A modern two-story home is showcased, featuring a combination of light-colored stucco and stone accents. A neatly landscaped front yard includes small shrubs and palm trees. A paved walkway leads to the main entrance, while a parking area accommodates multiple spaces in front.

4.86 out of 5 average rating, 29 reviews

4392-SL Great 6 Bd Home, Game Room + Pool & SPA

A modern living space is highlighted by a large sectional sofa and a sleek coffee table. A ceiling fan enhances air circulation, while a smart TV is mounted on the wall. The dining area features a round table and bar-style seating, with a staircase leading to the upper level.

4.91 out of 5 average rating, 44 reviews

The Lake House / Near Disney

4.87 out of 5 average rating, 55 reviews

FL Palm Vibes-4 Bdrm Pool- Perfect for Family

A modern living area features a spacious sectional sofa arranged around a wooden coffee table. Large windows allow natural light to illuminate the room, which is complemented by soft gray tones and stylish light fixtures. A television is mounted on a stone wall, enhancing the contemporary aesthetic.

4.79 out of 5 average rating, 28 reviews

Luxe 3-Bedroom Near Disney Magic - 7527

4.88 out of 5 average rating, 16 reviews

Comfort Home with BBQ, Private Pool & Hot tub

Private house rentals

Home in Loma del Sol

4.8 out of 5 average rating, 5 reviews

Just Renovated - Beautiful 4 BD at Champions Gate

An open living space features two plush sofas in neutral tones, complemented by two accent chairs. A stylish coffee table sits in the center, while large windows with blue valances allow natural light. A dining area with a long table is visible in the background, leading to a kitchen.

Home in Four Corners

4.82 out of 5 average rating, 17 reviews

Epic Villa Near Disney w Arcade, Theater, Spa Pool

4.86 out of 5 average rating, 7 reviews

PP9038 - Spacious 4 Bed 3 Bath pool Home

Home in Davenport

4.83 out of 5 average rating, 6 reviews

Bohanan Villa 5 bed *FREE POOL HEAT with spa*

4.71 out of 5 average rating, 48 reviews

Storey Lake 6BR | Pool | Walk to Clubhouse

5 out of 5 average rating, 3 reviews

Modern 4 bedroom Home with Game Room in Encore

4.92 out of 5 average rating, 12 reviews

Fun & Luxury: Home & Water Park Included