Vacation rentals with a pool in Osceola County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Osceola County

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

4.84 out of 5 average rating, 317 reviews

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.

LocationFamilyLong stay

Top guest favorite

Villa in Osceola County

4.99 out of 5 average rating, 152 reviews

*Private Golf-Front Oasis with Pool, Spa & Cinema

Escape to one of Reunion Resort's most unforgettable homes, where luxury meets nonstop fun just minutes from Disney. Enjoy your private pool & spillover spa on the sprawling 2,000 sq ft pool deck, then take in golf course views from the separate fire pit terrace & balcony. Inside, discover a Star Wars theater/game room with digital pinball, arcade games & karaoke, a Marvel kids' suite with tube slide, Xbox Series S, and a hidden Harry Potter cupboard. Perfect for unforgettable family vacations.

LocationFamilyGrill

Superhost

Home in Osceola County

4.95 out of 5 average rating, 40 reviews

The Magical Retreat near Disney

Welcome to your Orlando retreat! This spacious 5-bedroom, 4.5-bathroom townhome at the exclusive Azur Resort offers everything you need for an unforgettable vacation. Designed with comfort and style in mind, this home is ideal for families, groups, and anyone looking to explore the magic of Orlando. Located just mins from Orlando's top attractions- Disney World, Universal, and world-class shopping and dining. You’re at the center of it all! Book now and start making memories at the Azur Resort!

LocationValueIndoor spaces

Guest favorite

A well-appointed living area features a light-colored sofa and armchair arranged around a central table. A flat-screen TV is mounted on a wooden cabinet. Natural light filters through the large windows, with sheer curtains partially drawn. A dining area with wooden chairs is seen in the background.

Home in Osceola County

4.86 out of 5 average rating, 216 reviews

Premium location - Near Disney

Beautiful modern home with 3 full suites and 3 bathrooms — a rare find in the area! Located in the gated community THE HUB, featuring new construction, an American-style kitchen integrated with the TV room, and pet-friendly accommodations (rules apply). The community also offers a swimming pool and a small gym for guests. Guests enjoy: 🕒 24h self check-in 🔐 Unique access code valid only during the stay 🛏️ Linens and towels provided 🐾 Pet-friendly (check rules) 🏊 Community pool & small gym

FamilyLocationHospitality

Top guest favorite

Home in Kissimmee

4.97 out of 5 average rating, 183 reviews

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!

LocationFamilyNearby

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

4.88 out of 5 average rating, 171 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.

LocationFamilyAccuracy

Superhost

A modern bedroom features a spacious bed with a light gray patterned comforter. Natural light filters through large windows adorned with soft curtains, illuminating the neutral decor. A nightstand with a lamp adds a touch of warmth.

Townhouse in Kissimmee

4.84 out of 5 average rating, 99 reviews

5 BR 6 BA Villa 5min to 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 5 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.

ValueFamilyComfort

Top guest favorite

Home in Kissimmee

4.84 out of 5 average rating, 154 reviews

Disney 4M+BBQ + Pool/Spa + Arcade+Cinema+ 2master

Mickey’s Movie House – 4 Miles to Disney! 🎉 Complimentary welcome snack basket with sweet & salty treats included with every stay. Amazingly upgraded home with a private pool & spa, arcade, electronic pinball machine and cinema room! power recliners, 85” movie screen, and a video pinball machine! spacious 5BR layout with a luxury master suite and themed kids' rooms. Fast 1GB WiFi, Roku TVs, and a fully equipped kitchen Pet-friendly with a fenced yard! Book your dream getaway today

LocationFamilyComfort

Top guest favorite

The exterior of a large, two-story home is displayed, featuring a light-colored facade and a covered front porch. Lush landscaping surrounds the driveway, which is paved with stone. A garage door is positioned on the right side, complemented by decorative lanterns and palm trees.

Home in Osceola County

4.98 out of 5 average rating, 95 reviews

Large Private Home on Golf course by Disney

Bring the whole family to this great place with lots of room for fun. With fantastic views of the 4th hole on the Tom Watson golf course and your own private pool and hot tub everyone will enjoy this stylish and modern vacation home. Located in premier Reunion Resort and only 10 minutes to Disney you can have it all! This home boats over 4000sq feet, two very large masters suites, 2 additional bedrooms and plenty of space throughout the home. There are 6 tvs! Pets are welcome too!

LocationFamilyIndoor spaces

Top guest favorite

A well-maintained exterior showcases a single-story house with a blue garage door and driveway, framed by a lush lawn and shaded trees. Inside, a bright living area is highlighted by modern decor and a large smart TV. A private screened pool is visible, surrounded by seating.

Home in Kissimmee

4.98 out of 5 average rating, 111 reviews

10 Min to Disney | Kings | Heated Pool | Games

✨ Perfect family getaway just minutes from Disney magic! ✨ This spacious 4-bedroom home sleeps 9 and features 2 king beds, 4 full beds, and 1 twin, plus fun Mickey Mouse & Minion themed rooms kids love. Unwind in your private screened pool, enjoy the game room with arcade games, ping pong, foosball & pool table, or relax with cozy board-game nights. 🏰 Animal Kingdom 10 mins Epcot & Hollywood Studios 15 mins Book now and start making unforgettable family memories!

LocationFamilyHeating

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

4.94 out of 5 average rating, 164 reviews

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. **

LocationFamilyTV

Guest favorite

Home in Kissimmee

4.89 out of 5 average rating, 180 reviews

Luxury Disney Vacation Home on Reunion Golf Resort

This 5 bedroom Luxury family vacation home has one of the most picturesque views in all of Reunion, located on the 14th fairway of the Jack Nicklaus course. 2 MASTER SUITES which over looks your private POOL & SPA. All rooms are professionally decorated with a Disney and a Harry Potter room. Your family will stay busy with the arcade, ping pong table and a large number of board games for all ages. Pool area has a basketball net, New WEBER BBQ and Kamado Joe

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