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Holiday rentals with a pool in Kissimmee

Find and book unique homes with a pool on Airbnb

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 favourite
A bright pool area is surrounded by a screened enclosure that offers protection from insects. A clear blue pool is visible, accompanied by six chaise lounge chairs positioned nearby. Warm yellow walls frame the space, enhancing the tropical feel of the private outdoor oasis.
Home in Kissimmee
4.93 out of 5 average rating, 341 reviews

*Disney Home* Heated Priv Pool/Spa 7beds, Arcade!

This gorgeous updated pool home is perfect for families and friends for a Florida vacation! Located just 5 mi from Disney! Close to Universal! Approx 2000 sq ft. No stairs! Chill in your own heated private pool and hot tub or enjoy the club house pool of Veranda Palms complete with a water park and splash pad! Work out in the fitness center or walk the gated neighborhood to the new community center, just steps away. Enjoy your private AIR CONDITIONED game room w/ arcade and air hockey table.

Top guest favourite
A private heated pool is surrounded by a screened enclosure, featuring a brightly colored tiled edge. Sun loungers are positioned nearby, offering a relaxing space to unwind. A covered BBQ grill is accessible on the patio, creating an inviting setting for outdoor gatherings.
Home in Kissimmee
4.93 out of 5 average rating, 114 reviews

3BR / 2BR Heated Pool Home 7 Min to Disney |

✨ Experience comfort, style, and a private heated pool 💦 (optional) just 7 minutes from Disney World! This 3BR/2BA Kissimmee home is perfectly located near theme parks, shopping, and dining — and designed for families looking to unwind in a sparkling-clean, beautifully curated space. 📍Prime Kissimmee Location ⭐7 Min– Walt Disney World ⭐5 min–Orlando Premium Outlets ⭐15 min – Universal Studios, SeaWorld, Epic Universe 🎢 ⭐ 25 min – MCO Airport ✈️ ⭐ Walk to Walmart, Publix & Starbucks ☕️

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
Home in Kissimmee
4.98 out of 5 average rating, 156 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!

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
The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.
Flat in Kissimmee
4.99 out of 5 average rating, 142 reviews

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

Top guest favourite
A spacious living room is depicted, featuring a comfortable sofa and a smart TV mounted on the wall. Light wooden flooring complements the inviting decor, which includes artwork and decorative elements. The open layout allows a view into the kitchen and dining area.
Flat in Kissimmee
5 out of 5 average rating, 51 reviews

Warm King Apt w/Pool & Gym Pet Friendly Near Parks

Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

Guest favourite
Townhouse in Kissimmee
4.86 out of 5 average rating, 101 reviews

Disney Area| Private Pool| Resort Waterpark 2956

Minutes from Disney, this spacious 4-bedroom townhome is located in the sought-after Storey Lake Resort. Relax in your private screened pool after a day at the parks and enjoy access to amazing resort amenities including water slides, lazy river, clubhouse, fitness center and kayak rentals. Comfortably sleeps up to 12 guests with a full kitchen, fast WiFi and free parking. Perfect for families visiting Disney and Orlando attractions.

Guest favourite
An outdoor space features a screened-in pool area with a clear blue pool and spa. Comfortable lounge chairs are positioned beside the pool, with a dining table set beside them. Lush greenery is visible beyond the fenced yard, creating a private and relaxing environment.
Home in Kissimmee
4.79 out of 5 average rating, 132 reviews

The Real Florida Whispering Oaks

The Oaktree home is a favorite among returning guests. Once you have stayed in this home you cannot wait to return. The spacious pool /spa and deck area, game room and provides all you could ask for to make your stay one to remember. Recently remodeled kitchen with updated appliances make this home shine! Partially fenced in yard with no rear neighbors offer you a quiet retreat. T.V. on pool deck! Complimentary Hot Tub Heat!

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
4.82 out of 5 average rating, 22 reviews

Harry Potter Villa - 10 Mins to Disney

🧙‍♂️ Live the Magic—Just 10 Min from Disney! Step into a fully themed Harry Potter villa with 6 magical bedrooms, a private saltwater Quidditch pool, and a Platform 9¾ game room. Enjoy a home theater, resort amenities, and wizard-worthy comfort in this unforgettable family retreat!

Top guest favourite
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
4.99 out of 5 average rating, 109 reviews

Fabulous 2BR Home With Hot tub

Enjoy this elegant spacious home with a private hot tub with pond view all for yourself located in the awesome Regal Oaks Resort. Just minutes away from the Disney World parks and many other attractions

Popular amenities for Kissimmee rentals with a pool

When is the best time to visit Kissimmee?

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Avg. price$189 SGD$192 SGD$201 SGD$197 SGD$172 SGD$184 SGD$193 SGD$170 SGD$157 SGD$166 SGD$186 SGD$220 SGD
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Quick stats about holiday rentals with a pool in Kissimmee

  • Total holiday rentals

    Explore 6,620 holiday rentals in Kissimmee

  • Nightly prices starting at

    Kissimmee holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 238,760 verified reviews to help you choose

  • Family-friendly holiday rentals

    5,800 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 1,070 rentals that welcome pets

  • Rentals with dedicated workspaces

    3,700 properties have a dedicated workspace

  • Wifi availability

    6,590 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

Destinations to explore

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  6. Rentals with pools