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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 tranquil outdoor space features a private pool under a protective screen enclosure, framed by reclining lounge chairs. The setting offers a view of the lake, contrasting with the colorful sunset sky, creating a serene atmosphere for relaxation.
Home in Kissimmee
4.96 out of 5 average rating, 114 reviews

Mickey's Lakefront Villa at Sunset Lakes

Updated Pics Dec 2024. We have no gas burning appliances. We abide by the AirBnB enhanced cleaning protocol. We want our guests to be happy, healthy and safe in their home away from home. Please see house rules. Located in beautiful Sunset Lakes – it's hard to find a vacation home closer to Walt Disney World with all that's offered at Mickey’s Lakefront Villa. Be amazed at how quiet and secluded you will feel yet just minutes away from all of the entertainment that you came here to enjoy.

Top guest favourite
The exterior of a modern townhouse complex is displayed, featuring a series of well-defined front entries with minimalist design elements. Lush green grass and a paved walkway enhance the inviting atmosphere. Large windows with vertical blinds allow natural light to brighten the space.
Townhouse in Kissimmee
4.87 out of 5 average rating, 122 reviews

Last minute deal - special prices

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

Guest favourite
A refreshing outdoor pool is surrounded by palm trees and lounge chairs. The water is displayed in a light blue shade, with a shallow entry area visible. A poolside cabana with a roof and seating is located nearby, offering shaded relaxation.
Home in Kissimmee
4.75 out of 5 average rating, 122 reviews

Destination Sunsation!1 Bedroom Villa 1st Floor!

Runaway Beach Club Resort located 2.5 miles from Disney World. You can choose to be part of the Orlando landscape or unwind and relax on the grounds and enjoy a lazy day at the pool. More amenities have been added as you now have access to Calypso Cay, including Mini Golf, additional pools, basketball & volleyball courts & children's playground and splash pad! We are a gated family friendly community. Less than a mile away there is a super walmart for any last minute needs!

Guest favourite
Villa in Kissimmee
4.83 out of 5 average rating, 29 reviews

Luxury Townhouse Near Disney | 3BR

Enjoy a brand new, beautifully designed townhouse located in the exclusive Magic Village community, just minutes away from Disney Parks. What you’ll love: • Private patio with outdoor furniture • Free Wi-Fi • Fresh towels & linens • Fully equipped kitchen • BBQ grill (no additional fee) • Free parking (no extra cost) The pool, tennis court and fitness center should pay $100 extra fee per group per day. ✨ Book now and enjoy a memorable stay near the magic!

Top guest favourite
A private balcony features two black chairs positioned for relaxation. Below, a green landscape borders a calm waterway, with trees lining the banks. Industrial buildings can be seen in the distance under a clear blue sky.
Flat in Kissimmee
4.98 out of 5 average rating, 56 reviews

Modern King Apt w Water view, Pool Gym 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
A sparkling swimming pool is surrounded by lounge chairs and shaded by colorful umbrellas in vibrant shades of pink and green. Lush tropical plants and palm trees add to the inviting outdoor space, creating a relaxing atmosphere for guests.
Flat in Kissimmee
4.85 out of 5 average rating, 129 reviews

3-103 Legacy Dunes, Heated Pool, Free Wifi/Parking

Two Bedrooms 1 Queen Sized Bed 2 Twin Sized Beds 1 Queen Sized Sofa Sleeper bed Sleeps up to 6 Guests Two Full Bathrooms Ground Floor, No Stairs to Climb Fully Equipped Kitchen Close to Shopping and Restaurants Screened Patio with Seating Washer and Dryer Heated Outdoor Swimming Pool Close to Disney Free Wi-Fi and Free Parking Game Room Playground Tennis, Pickleball, Basketball, Volleyball Gated Community

Guest favourite
Villa in Kissimmee
4.88 out of 5 average rating, 164 reviews

Premium 6BR | Theater, Games & Heated Pool

Welcome to your 3,400 sq ft luxury escape just minutes from Disney World! Perfect for families and friends, our villa sleeps 12 with ensuite bathrooms in every bedroom. Enjoy the home theater, game room, and a fully equipped kitchen—plenty of space to gather or relax. Close to shopping, dining, and all the Orlando magic. Book now for unforgettable memories in your private Disney-area villa.

Guest favourite
Townhouse in Kissimmee
4.83 out of 5 average rating, 118 reviews

Luxury 3BR Pool Home at Paradise Palms

Enjoy a relaxing and unforgettable stay at this elegant 3bedroom, 3bathroom home located in the gated Paradise Palms Resort, just 15 minutes from Walt Disney World. Designed for families seeking comfort, fun, and convenience, this home features a private heated pool, open living spaces, and full access to exceptional resort amenities — all within walking distance.

Superhost
A close-up shows Disney-themed plush toys, Mickey and Minnie, placed in a decorative tray on a kitchen counter. The bright colors of the toys contrast with the modern kitchen setting, highlighting a family-friendly atmosphere.
Home in Davenport
4.73 out of 5 average rating, 108 reviews

Perfect Disney Relaxation! Water Park, Lazy River!

Welcome to Perfect Disney Relaxation at the highly-rated Solterra Resort, with one of the best water parks in the area featuring a Water Slide, a Lazy River, Zero entry pools, and spas. This fully equipped and upgraded private pool home offers everything for a perfect vacation, including poolside dining.

Guest favourite
Home in Kissimmee
4.71 out of 5 average rating, 175 reviews

5 BD/3BA Single Level Home! Veranda Palms (4458NP)

• Community: Veranda Palms • 5 Bedrooms/ 3 Bathrooms/ Sleeps 14 • Disney World® (5.8 miles) SeaWorld (9.0 miles) • Convention Center (10.1 miles) Legoland (32.2 miles) • Universal Studios (12.8 miles) Epic Universe (11.8 miles) • Location: Nirvana Parkway, Kissimmee FL 34746

Superhost
Home in Kissimmee
4.81 out of 5 average rating, 21 reviews

6 Bd/5 Ba Sleeps 13! Storey Lake (2664 sq ft)

• Community: Storey Lake • 6 Bedrooms/5 Bathrooms/ Sleeps 13 • Disney (7.0 mi) SeaWorld (9.7 mi) Legoland (37.4 mi) • Convention Center (10.8 mi) Universal Studios (14.0 mi) • Location: Scrapbook Street, Kissimmee FL 34746

Guest favourite
The spacious living area features a comfortable gray couch adorned with vibrant cushions, complemented by two small tables. A large window provides natural light and a view of the outdoor area with a barbecue and pool, while a wall-mounted TV offers entertainment options.
Townhouse in Kissimmee
4.89 out of 5 average rating, 271 reviews

Luxurious Dream 4/3 Bedroom Home w/private Pool

Located a short 15 minute drive to Disney, this luxury design inspired 4 bedroom, 3.5 bath is perfect for a family, multi family or romantic weekend away with your favourite person.

Popular amenities for Kissimmee rentals with a pool

When is the best time to visit Kissimmee?

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Avg. price$188 SGD$190 SGD$199 SGD$195 SGD$171 SGD$183 SGD$191 SGD$168 SGD$156 SGD$165 SGD$185 SGD$218 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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