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Vacation rentals with a pool in Kissimmee

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Kissimmee

  • Total vacation rentals

    Explore 6,330 vacation rentals in Kissimmee

  • Nightly prices starting at

    Kissimmee vacation rentals start at ﺩ.ﺇ 73 per night before taxes and fees

  • Verified guest reviews

    Over 252,510 verified reviews to help you choose

  • Family-friendly vacation rentals

    5,450 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 950 rentals that welcome pets

  • Rentals with dedicated workspaces

    3,560 properties have a dedicated workspace

  • Wi-Fi availability

    6,270 of Kissimmee vacation rentals include wi-fi 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

Top-rated rentals with a pool in Kissimmee

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite
A private movie theater features a 150-inch screen displaying a Disney image. Black walls and hardwood flooring create a modern atmosphere. Comfortable reclining seats with cup holders are arranged for a cinematic experience, ensuring a cozy and immersive viewing environment.
Villa in Kissimmee

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.

4.83 out of 5 average rating, 320 reviews
Top guest favorite
A lush outdoor water complex showcases a winding lazy river surrounded by palm trees and landscaped greenery. Lounge chairs are positioned alongside the water, providing ample space for relaxation. In the background, a clubhouse and scenic waterfront can be seen under a bright blue sky.
Townhouse in Kissimmee

Disney 5BR • Private Pool Free Heat • Pet Friendly

Welcome to this gem near all major attractions: Disney (5 miles), SeaWorld (7 miles), Universal (12 miles), Convention Center (9 miles), and Airport (20 miles). Nearby are outlets, restaurants, and supermarkets. This luxurious home features 5 bedrooms, 4 bathrooms, a private heated pool/spa, fully equipped kitchen, laundry, and free stroller, playpen, and highchair. Resort amenities include a water complex, lazy river, bar, fitness center, mini golf, kayaking, and more! Pets friendly & welcome!

4.96 out of 5 average rating, 176 reviews
Guest favorite
Home in Kissimmee

Encanto at Emerald Island-Pool House by Disney

POOL HEATER OPTION!! Make some memories at this unique and family-friendly place. A guarded Resort- neighborhood awaits! As you enter this magical place you will fall in love with the unique landscaping full of palm trees surrounding the neighborhood. This secluded place has everything you need! 5 star location, security, private pool, and also a clubhouse with many activities for the young ones. You will be next to restaurants, shopping and more. Only 3 miles aways from Disney's exit & parks!

4.9 out of 5 average rating, 126 reviews
Top guest favorite
Home in Kissimmee

10 Minutes to Disney | Heated Pool, Arcade, Kings

🏡 Tucked inside a gated community near Kissimmee’s top attractions, this bright, themed home is made for memorable family getaways. Enjoy friendly competition in the game room, unwind in the heated private pool (available upon request), or relax on the covered patio beneath the Florida sun. Just 11 minutes to Fun Spot America, 11 minutes to Old Town, and 12 minutes to Disney World, it’s the perfect home base for your Florida adventure. Book now and start creating unforgettable memories!

4.99 out of 5 average rating, 159 reviews
Guest favorite
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.
Home in Kissimmee

*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!

4.92 out of 5 average rating, 215 reviews
Top guest favorite
The exterior of the house showcases a striking blend of wood and stone finishes, featuring large windows that illuminate the interior. An expansive, clear blue pool reflects the sky, with a bridge extending over the water leading to the main entrance.
Villa in Orlando

The Lakeview Oasis - XL Pool & Jacuzzi - Orlando

Welcome to our stunning lakefront resort, where luxury meets tranquility! Dive into our expansive 100,000-gallon pool, enjoying a refreshing swim surrounded by breathtaking views. Inside, our tastefully designed space features midcentury modern amenities ensuring you have everything for a perfect getaway. Each bedroom offers serene views and plush bedding for a restful night’s sleep. Whether you seek adventure or relaxation, this is your ideal getaway. Book now for unforgettable memories!

4.96 out of 5 average rating, 144 reviews
Top guest favorite
Home in Kissimmee

Near Disney | Heated Pool, King Bed, Arcade

✨ Family-Friendly Retreat Near Disney in a gated, safe & quiet community 🏰 Loved by guests for its cleanliness, comfort, and fast communication. 🏊‍♂️ Unwind after park days in your private HEATED pool 🍔 Enjoy the outdoor BBQ for easy family meals 🎮 Have fun in the upgraded game room with pool table, ping pong, foosball, and a retro arcade ⭐ Hosted by 3 experienced Superhosts known for quick, reliable replies. A perfect balance of fun and relaxation. Book now as dates fill fast!

4.97 out of 5 average rating, 188 reviews
Top guest favorite
The image displays the Summerville Resort sign, highlighting its proximity to Disney. A comfortable bedroom is shown, featuring two spacious beds and colorful wall art. An inviting patio area with outdoor seating is visible, alongside a community pool surrounded by lounge chairs and palm trees.
Home in Kissimmee

Comfy Family Villa|5min->Disney!

Summerville Resort is a new and prestigious collection of town-home villas just 5 miles from the entrance to Walt Disney World! Be among the first to stay in this contemporary vacation rental with pristine finishes & amenities. No need to wait in line to shower here; each of the 4 bedrooms has its own attached bath. After a day exploring the parks, come home to indulgence at the Resort, which features a  community hot tub, heated pool, fitness center, playground, and a sleek Clubhouse. 

4.87 out of 5 average rating, 126 reviews
Guest favorite
The outdoor pool area features a spacious turquoise pool, surrounded by a screened enclosure for comfort. Lounge chairs with bright cushions are positioned nearby, while a basketball hoop stands at one end of the pool, offering fun recreational options.
Home in Kissimmee

Stunning 6BR Lakeview at Storey Lake Disney - 2929

Modern luxury home with lake view, recently built, best location in town, at world-known Storey Lake Resort. Almost 4,000sf of a/c area, featuring 6 bedrooms, 6 full baths, game room, private pool, and spa. 3 Minutes away from Super Target, Publix Supermarket and Walmart 15 Minutes away from Disney Parks 15 Minutes away from Premium Outlets 20 Minutes away from Universal Studios 20 Minutes away from International Dr attractions *PLEASE MAKE SURE TO READ THE HOUSE RULES*

4.91 out of 5 average rating, 278 reviews
Top guest favorite
A private outdoor area features a pool with a spa, surrounded by a spacious deck. A basketball hoop is positioned nearby. A large inflatable swan floats in the water, while a hammock provides a cozy spot for relaxation. Lush greenery frames the scene under a colorful sky.
Home in Kissimmee

Luxury Encore Pool Spa Pets Game Rm Theater Gym

Amazing Brand New Modern Luxurious Home at Encore Resort Reunion. PET-FRIENDLY & Minutes to all Theme Parks. BRAND NEW HOME. Private Pool & Spa / Game Room / Movie Theater / Gym / Massage Chair / Fireplace / PS5 / Board Games & Much More. Embrace the extraordinary and book your stay at our home, where luxury, entertainment come together for an unforgettable vacation experience. ** Please review the rules before booking. Waterpark access is not included. **

4.94 out of 5 average rating, 167 reviews
Top guest favorite
A unique sleeping area features a round bed designed to resemble a giant clam shell. Vibrant murals depicting underwater scenes adorn the walls, complementing the ocean-themed decor. Soft curtains in shades of green flow down from the ceiling, adding color to the tranquil space.
Home in Davenport

Royal Retreat Disney Themed Pool Home, Arcade, Theater

Welcome to The Royal Retreat. Located just 10 miles away from the entrance of WDW, our rental is the perfect place to stay for your Disney vacation. Our 5 star home features 8 themed bedrooms and 5 bathrooms, a fully-equipped kitchen, private heated pool, private arcade, home theater & BBQ! Free Pool heat & the 1st tank of propane for the BBQ are included. Booking with us includes full access to the Champions Gate Clubhouse, Oasis Resort and Retreat Club!

4.96 out of 5 average rating, 119 reviews
Superhost
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

Villa Resort Club

Welcome to Villa Resort Club! Lovely 4BR/2.5BA for 8 with screened private pool and game room. Full kitchen, workspace, washer/dryer, parking, WiFi. Pet-friendly. Minutes from Disney. Quiet, comfy home base! ¡Bienvenidos a Villa Resort Club! Casa 4 hab/2.5 baños para 8, piscina con enclosure y juegos. Cocina completa, trabajo, lavadora/secadora, parking, WiFi. Mascotas OK. Minutos de Disney. ¡Tranquila y cómoda!

4.88 out of 5 average rating, 179 reviews

Popular amenities for Kissimmee rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
Home in Kissimmee

Modern 12 BR 11.5 BA, Sleeps 32, 15 mins to Disney

4.86 out of 5 average rating, 101 reviews
Superhost
A screened-in patio features a private swimming pool and hot tub, surrounded by a tranquil lake view. String lights create a soft illumination against a colorful sunset sky, enhancing the peaceful outdoor setting.
Home in Kissimmee

10 min Disney | Lakeview Hot Tub, BBQ | Game Room

4.8 out of 5 average rating, 228 reviews
Guest favorite
A spacious living area features a large sectional sofa, paired with a round coffee table. Natural light floods in through sliding glass doors that open to the pool area. Decorative accents include coastal-themed artwork and soft lighting fixtures, enhancing the inviting ambiance.
Home in Kissimmee

Park Place! 7 Min from Disney, Pool, Theater

4.84 out of 5 average rating, 150 reviews
Top guest favorite
Aerial view of the resort showcases a large pool with lounge chairs and palm trees surrounding a tranquil pond. Colorful amenities, including slides, are visible, enhancing the outdoor recreational area.
Home in Kissimmee

Fabulous 2BR Home With Hot tub

4.99 out of 5 average rating, 123 reviews
Top guest favorite
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.
Home in Kissimmee

Windsor Orlando Private Arcades,Theater,Pool-Spa

4.99 out of 5 average rating, 256 reviews
Guest favorite
Home in Kissimmee

Private Heated Pool & BBQ Included Near Disney

4.89 out of 5 average rating, 157 reviews
Guest favorite
Home in Kissimmee

Immersive 15 Bd/ 16.5 Ba/ Sonoma Resort (4071Sb)

5.0 out of 5 average rating, 9 reviews
Superhost
Home in Kissimmee

New Themed Luxury 08 Bedrooms At Encore Resort

5.0 out of 5 average rating, 3 reviews

Condo rentals with a pool

Guest favorite
A master bedroom features a spacious bed with a white quilted coverlet, accented by a blue tufted headboard. Two bedside tables with lamps provide soft lighting. A ceiling fan hangs above, while light-colored walls and flooring enhance the room's bright atmosphere.
Condo in Kissimmee

Disney Retreat

4.85 out of 5 average rating, 123 reviews
Top guest favorite
Condo in Kissimmee

Near Disney • 4BR • Perfect for Families

4.97 out of 5 average rating, 266 reviews
Guest favorite
A balcony is depicted with four cushioned chairs arranged around a small table. The railing provides a view of a serene landscape with water and greenery in the background. Light fabric drapes softly from the sliding door frame.
Condo in Kissimmee

Modern Condo with Lake View Near Disney 3151

4.9 out of 5 average rating, 165 reviews
Guest favorite
A cozy bedroom features a spacious bed adorned with light-colored linens, complemented by decorative pillows. The living area offers comfortable seating arranged around a flat-screen TV, while soft natural light filters through sheer curtains. The Mickey-themed room presents vibrant wall art and two plush beds with coordinating bedding.
Condo in Kissimmee

207_ Sparkle Apartment Close to Disney Free Waterp

4.89 out of 5 average rating, 172 reviews
Guest favorite
The image features a spacious bedroom with two separate sleeping areas. One side includes a yellow-accented bed, while the other is themed with a starry wall mural. Light-colored tile flooring enhances the bright atmosphere, complemented by ample natural light from the nearby window.
Condo in Kissimmee

Resort-Style Condo with free Waterpark!

4.82 out of 5 average rating, 228 reviews
Top guest favorite
A clear view of a pool surrounded by lounge chairs and palm trees, reflecting the sunlight. Umbrellas provide shade, and green lawns are visible in the background. The calm water enhances the serene environment, creating a relaxing outdoor space.
Condo in Kissimmee

Disney Dream Condo · Resort Pool · 20 Min to Parks

4.85 out of 5 average rating, 282 reviews
Guest favorite
An open living area features a comfortable seating arrangement with two armchairs and a sectional sofa. A modern coffee table sits atop a soft rug. Large sliding glass doors lead to a balcony, offering a view of the tranquil lake.
Condo in Kissimmee

3171-107 Resort Lake View Disney Universal Orlando

4.87 out of 5 average rating, 198 reviews
Guest favorite
An aerial view captures the expansive resort-style pool area, featuring tropical landscaping and winding water features. Sun loungers and cabanas line the poolside, while a lazy river and splash park invite guests to relax and enjoy. The serene water is bordered by a scenic lake.
Condo in Kissimmee

O-Gated Resort-5 miles to Disney-2 FREE Water Park

4.94 out of 5 average rating, 189 reviews

Other vacation rentals with a pool

Top guest favorite
Apartment in Orlando

Epic stay at Vista Cay!

4.95 out of 5 average rating, 60 reviews
Top guest favorite
Townhouse in Kissimmee

Disney Theme Rooms | Private Pool | Storey Lake

5.0 out of 5 average rating, 47 reviews
Top guest favorite
A vibrant collage of themed spaces showcases the enchanting variety within the home. Featured are a luxurious bedroom with a grand bed, a playful winter-themed room, a themed home theater, and a pool area with a spa set against colorful lighting.
Home in Orlando

12BR Disney Luxury Retreat - Pool, Theater & Fun!

4.98 out of 5 average rating, 58 reviews
Guest favorite
Home in Kissimmee

Amazing Home Near Parks w/ Pool & Spa

5.0 out of 5 average rating, 9 reviews
Superhost
Home in Kissimmee

12 Bd/ 11.5 Ba Sleeps 24! Veranda Palms (2444 RD)

4.76 out of 5 average rating, 41 reviews
Guest favorite
Home in Kissimmee

Disney's Pool House

4.82 out of 5 average rating, 60 reviews
Top guest favorite
Home in Kissimmee

*Modern Condo Resort/Pool/Spa/15 Min to Disney*

4.98 out of 5 average rating, 42 reviews
Top guest favorite
A private heated pool is surrounded by a screened patio, with two lounge chairs positioned nearby. A small dining area with a table and chairs is visible, enhancing the relaxing outdoor space. The backdrop features the home’s elegant design and a cozy seating area beyond.
Home in Kissimmee

Disney/Universal Villa w/ Pool

4.91 out of 5 average rating, 74 reviews

When is the best time to visit Kissimmee?

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Avg. priceﺩ.ﺇ 566ﺩ.ﺇ 591ﺩ.ﺇ 632ﺩ.ﺇ 646ﺩ.ﺇ 547ﺩ.ﺇ 573ﺩ.ﺇ 551ﺩ.ﺇ 485ﺩ.ﺇ 448ﺩ.ﺇ 474ﺩ.ﺇ 533ﺩ.ﺇ 628
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