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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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Top guest favourite
A modern living area features a plush blue sectional sofa complemented by two stylish lounge chairs. A light area rug sits under a chic coffee table, while large sliding glass doors provide a view of the outdoors and allow natural light to enhance the space.
Apartment in Kissimmee
4.93 out of 5 average rating, 211 reviews

3171-206 Resort Lake View Disney Universal Orlando

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 6 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!

Top guest favourite
The image captures a beautiful aerial view of a community near a tranquil body of water at sunset. The surrounding landscape features lush greenery and well-maintained townhouses with a striking view of the water reflecting the colorful sky.
Townhouse in Kissimmee
4.95 out of 5 average rating, 167 reviews

Luxury 5BR free heat private pool Disney Universal

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!

Top guest favourite
A private heated pool is set within a screened enclosure, surrounded by a patio area. Two blue chairs and a white lounge chair are positioned nearby, with lush greenery visible beyond the pool. The clear water reflects the sky, creating a serene atmosphere.
Home in Kissimmee
4.99 out of 5 average rating, 156 reviews

Heated Pool 15 Minutes to Disney PS5 l Switch

Spacious 4BR Home with a Private Heated Pool – 15 Minutes from Disney! Enjoy a large south-facing pool, Propane grill, Smart TVs with Disney+ in every room. Nintendo Switch in Living Room and an 85" screen with a PS5 in a temperature-controlled garage / game room. Fast WiFi, shuffleboard, pool table and plenty of board games. 🌓 Outdoor Fun Patio Seating for 14 + two lounge chairs. Propane Grill: $50 for length of stay Pool heat: $200 per stay (24-hour notice)

Top guest favourite
A private screened-in pool area features a spacious pool and spa, with a view of a serene lake at sunset. Comfortable lounge chairs are positioned around the pool, and a peaceful nature reserve is visible beyond the water.
Home in Kissimmee
4.99 out of 5 average rating, 131 reviews

Spectacular Lake View - Game Room- Close to Disney

Our home has all the features to comfortably provide your family with the amenities while on vacation! A kitchen ready for your cooking needs, a pool and spa(heating fee required), a Game/Media Room, and TVs throughout the house. The resort offers many amenities, including tennis courts, a sand volleyball court, walking trails, bike rentals, a huge pool, a poolside Tiki bar, a fitness center, a mini-golf, and so much more! Just a short walk away.

Top guest favourite
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.
Apartment in Kissimmee
4.92 out of 5 average rating, 142 reviews

Modern Condo with Lake View Near Disney 3151

STOREY LAKE RESORT A premier vacation community just 8 miles from Disney and minutes from Universal & SeaWorld, this community is surrounded by restaurants, shops, and top malls. Only 30 minutes from Orlando Airport, it offers easy access to everything you need. Book your stay for 7 days or more and unlock an exclusive 5% discount ! Stay 30+ nights and save 10% (Discount will apply on selected stays) Reserve now! we would love to be your host!

Guest favourite
The private pool area is surrounded by a screened enclosure, featuring a clear blue pool. A patio with dining furniture and a BBQ grill is visible, alongside lounging chairs. Two homes can be seen in the background, creating a spacious ambiance.
Villa in Kissimmee
4.89 out of 5 average rating, 119 reviews

Retreat w/ Pvt Pool + Club Access | Disney 15min

Experience luxury in this spacious 5-bedroom, 5.5-bathroom home located just 15 minutes from Disney. Relax in elegant living areas with Smart TVs and an Xbox One, or step outside to your private pool with stylish patio furniture and BBQ grill. The open-concept kitchen and dining area are perfect for gathering, while the Windsor at Westside resort offers a lazy river, pools, fitness center, playgrounds, and sports courts, all just steps away.

Top guest favourite
An inviting outdoor space features a private saltwater pool surrounded by lush greenery. Comfortable seating includes a sectional sofa, an umbrella-covered table, and lounge chairs. A TV is mounted on a wooden wall, offering entertainment options, while decorative plants enhance the tranquil atmosphere.
Home in Kissimmee
4.95 out of 5 average rating, 19 reviews

Luxe Saltwater Pool Home | Golf | 1 Exit to Disney

Plentiful Views | Reunion Resort Luxury Home | Private Saltwater Pool + Golf Views | 1 Exit from Disney A private golf-course retreat inside Reunion Resort — just one exit from Walt Disney WorldĀ®. Designed for families and groups who want space, privacy, and elevated comfort, this 5-bedroom home blends resort-level amenities with the ease of a fully private residence. Minutes from Disney. Worlds away from ordinary.

Top guest favourite
Villa in Davenport
4.99 out of 5 average rating, 103 reviews

Amazing Villa near DisneyWorld FREE heated-pool

Have fun with the whole family at this stylish place. Our home has everything you will need for you and your guest to have a great experience. This home is a short drive from Walt Disney World and Orlando Attractions!! Don’t wait book with us now and give you and your family the vacation you all deserve. We can’t wait to welcome you . BBQ ( free to use ) Heated pool (free) Dogs friendly! Extra fee $120 per stay

Guest favourite
Home in Kissimmee
4.89 out of 5 average rating, 9 reviews

Upstay Spacious 5BR Villa Private Pool and Hot Tub

This 5-bedroom, 6-bathroom home is the ultimate family retreat! With over 3,200 sq ft of space, a private pool and hot tub, and fun extras like a foosball table and Roku TVs, it’s built for comfort and entertainment. Located in a secure gated community just minutes from Orlando’s top attractions, it’s perfect for family holidays, group getaways, or a sun-soaked work-from-home escape. Book your stay now!

Top guest favourite
A private courtyard features a hot jacuzzi, dining table, and outdoor seating. The space is surrounded by bright yellow walls, allowing ample natural light. A shaded umbrella offers comfort on sunny days, while the neatly paved area provides easy access to the main house.
Home in Kissimmee
4.89 out of 5 average rating, 210 reviews

3BR-Private Jacuzzi-Resort Amenities-7 mls Disney

Private and Clean 3 bedroom 2.5 bathroom Townhouse in a most prestigious resort near the Disney area - Terra Verde Resort. Private HOT Jacuzzi (professionally cleaned once a week every week), BBQ, WIFI, TVs in all Rooms, and more. Pets are considered (fees/restrictions apply)

Superhost
Townhouse in Kissimmee
5 out of 5 average rating, 6 reviews

4BR Retreat | Pool | Close to Disney

Home at Bella Vida. If you want a heated pool, you must notify us in advance and we charge $30 per day for pool heating and one time fee of $50 for the bbq. Starter amenities are provided for your arrival, intended for short stays or your first night convenience.

Guest favourite
Home in Kissimmee
4.95 out of 5 average rating, 22 reviews

Fairview at Reunion - Games Room

This beautiful 6 bedroom, 6 bathroom villa offers families the enjoyment of a private pool area with plenty of privacy. Located in the prestigious resort of Reunion where our guests receive access to the 7 resort pools.

Popular amenities for Kissimmee rentals with a pool

When is the best time to visit Kissimmee?

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Avg. price$187 SGD$190 SGD$199 SGD$195 SGD$171 SGD$182 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 $26Ā 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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