
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.

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
*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.
4.99 out of 5 average rating, 153 reviews
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
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!
4.95 out of 5 average rating, 40 reviews
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
5390 Vacation Sunset House Private Pool Grill
Relax in this calm, stylish and FULLY RENOVATED residential HOME. Enjoy with the whole family our PRIVATE POOL & BBQ GRILL with LAKE VIEW. Located in Kissimmee Florida, in a quiet residential neighborhood. Master Suite with view to Pool & BBQ outdoor area. 3 bedrooms, 2 bathrooms, fully equipped kitchen, 2 car garage, 3 Smart TV's and strong Wi-Fi all around the house. Have unforgettable moments at our BBQ area next to our private screened pool. Sunsets by the lake are breathtaking.
4.82 out of 5 average rating, 101 reviews
Paradise Suite With Private Pool
Relax with the whole family at this peaceful place to stay. The spacious living area features windows that flood the space with natural light, while the kitchen is equipped with stainless steel appliances and granite countertops. The master bedroom offers a peaceful oasis with a spa-like master bath and walk-in closet. Property is located in a gated Golf community with a 3 mile walking trail that offers beautiful lake views. close to major intersections and shopping mall less than 2 miles
4.93 out of 5 average rating, 116 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!
4.97 out of 5 average rating, 188 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.
4.84 out of 5 average rating, 102 reviews
Cozy House with Pool. Kissimmee/Orlando
Welcome to Your Kissimmee Getaway! 🏠 Enjoy a relaxing stay in beautiful Kissimmee, conveniently located near Orlando’s world-famous theme parks, restaurants, shopping, and entertainment -Pet friendly home🐾( pet fees may apply) Please make sure to include your pet(s) when making your reservation so any applicable fees can be reflected in your booking. -No parties or events of any kind -No smoking inside the property Please respect the home, neighbors, and community during the stay
4.91 out of 5 average rating, 283 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!
4.98 out of 5 average rating, 96 reviews
Amazing townhouse near Orlando theme parks
Welcome! This is your place to gather, relax and enjoy, near everything! Orlando theme parks are only between 6 to 20 miles away, and other attractions for all ages and preferences are also nearby. This spacious 4 beds and 2.5 baths home is fully equipped. It is also family friendly, so you will have the basic items for your children's stay. We are sure that you will experience a cozy ambience and that you will enjoy your stay here!
4.98 out of 5 average rating, 108 reviewsPopular amenities for Osceola County rentals with a pool
House rentals with a pool

4418 Le Reve 4BDRM townhouse close to Disney
4.79 out of 5 average rating, 232 reviews
Luxury Encore Pool Spa Pets Game Rm Theater Gym
4.94 out of 5 average rating, 167 reviews
Park Place! 7 Min from Disney, Pool, Theater
4.84 out of 5 average rating, 150 reviews
9 Bedrooms / 6 Bathrooms / Solara (8901 Cb)
4.85 out of 5 average rating, 61 reviews
House in Kissimmee near Disneyland!
4.95 out of 5 average rating, 38 reviews
Your Dream Vacation—Disney Magic Brought to You!
5.0 out of 5 average rating, 72 reviews
Stylish 12BR 11.5BA, Sleeps 33, 15 mins to Disney
4.93 out of 5 average rating, 72 reviews
Near Disney, free pool heat & resort membership
5.0 out of 5 average rating, 37 reviewsCondo rentals with a pool

Disney Retreat
4.85 out of 5 average rating, 123 reviews
Near Disney • 4BR • Perfect for Families
4.97 out of 5 average rating, 266 reviews
207_ Sparkle Apartment Close to Disney Free Waterp
4.89 out of 5 average rating, 172 reviews
Green View Condo near Disney
4.84 out of 5 average rating, 108 reviews
Stylish Condo 20 mins to Disney/King Bed
4.87 out of 5 average rating, 148 reviews
Modern Condo with Lake View Near Disney 3151
4.9 out of 5 average rating, 165 reviews
Magic Condo at a Resort Near Disney
4.98 out of 5 average rating, 200 reviews
Marvelous apartment near Disney first floor
4.88 out of 5 average rating, 329 reviewsOther vacation rentals with a pool

Resort Champions Gate 2 Bd/2Bh - Golf view
4.78 out of 5 average rating, 83 reviews
6BR Home w/ Priv Pool Near Disney Gated Resort
4.93 out of 5 average rating, 15 reviews
*Modern Condo Resort/Pool/Spa/15 Min to Disney*
4.98 out of 5 average rating, 42 reviews
Luna Del Sol, Close To Disney Attractions & Parks
5.0 out of 5 average rating, 16 reviews
NEW Modern Villa Near Disney w/ Pool & Spa!
4.98 out of 5 average rating, 42 reviews
Peaceful 5BR/5.5BA just minutes to Disney!
4.96 out of 5 average rating, 83 reviews
Disney's Pool House
4.82 out of 5 average rating, 60 reviews
Luxury Home w/ Pool & 6 Beds near Disney
4.98 out of 5 average rating, 87 reviewsDestinations to explore
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- Walt Disney World Resort
- Universal Studios Florida
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Orange County Convention Center
- Orlando / Kissimmee KOA
- Epcot
- Universal's Volcano Bay
- Camping World Stadium
- Kia Center
- University of Central Florida
- Disney's Animal Kingdom Theme Park
- Tinker Field
- Discovery Cove
- Reunion Resort Golf Courses - Palmer & Watson
- LEGOLAND Florida Resort
- Old Town
- ChampionsGate Golf Club
- ICON Park
- Sebastian Inlet
- Disney's Hollywood Studios
- Playalinda Beach
- Aquatica





