Some info has been automatically translated. Show original language

Holiday rentals with a pool in Orlando

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Orlando

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Top guest favourite
The expansive lake is showcased during sunset, reflecting vibrant colors in the sky. Surrounding greenery adds a natural touch, while a dock extends into the water, offering a serene view of the landscape. Soft light illuminates the pathway along the lake's edge.
Hotel room in Orlando
4.96 out of 5 average rating, 192 reviews

PentHouse Suite with 2X View

Located at the gates of Walt Disney World, this Awesome PentHouse Suite offers easy access to area theme parks, and entertainment venues in the surrounding area, including Walt Disney World, Universal Studios, Sea-world, Legoland + Amazing Restaurants, Shopping and many more. Best of all wonderful views with 2 Large Balcony's, 1 for Sunrise @ East Side and 1 for Sunset @ West side overlooking Disney World with amazing fireworks every night, Enjoy! **Security camera for safety @ Entry door only!

Top guest favourite
A family-friendly living area is presented with a large, comfortable sectional sofa facing a flat-screen TV. Adjacent, a vibrant children's bedroom features a whimsical Moana theme with a sandy beach mural, complemented by a canopy bed adorned with tropical accents. The ceiling displays playful elements, enhancing the kid-friendly atmosphere.
Apartment in Kissimmee
4.97 out of 5 average rating, 197 reviews

303_To Infinity & the Ocean Breeze Apartment

Welcome to your ultimate family getaway near Disney! This spacious 3-bedroom apartment is perfectly located just minutes from the magic of Disney. Designed with families in mind, it features two beautifully themed kids’ bedrooms—a Toy Story adventure and a Moana-inspired tropical escape—guaranteed to delight the little ones. Enjoy full access to an amazing waterpark, included free of charge, making every day feel like a vacation. Whether you're unwinding after a day at the parks or splashing th

Guest favourite
A spacious pool house is visible behind a lush, green lawn, surrounded by trees. A paved path leads to the inviting pool area, while a gated fence provides added privacy. Sunlight filters through the leaves, creating dappled patterns on the grass.
Bungalow in Maitland
4.88 out of 5 average rating, 589 reviews

Maitland-Orlando Area, FL. Pool House Bungalow

Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.

Top guest favourite
The exterior of the Cozy Cottage is designed with a welcoming green facade, featuring glass doors that open to a charming patio. A stone path leads to a small round table with chairs, complemented by a decorative fountain and lush greenery surrounding the area.
Bungalow in College Park
4.98 out of 5 average rating, 126 reviews

Cozy Cottage in College Park.

Whether you're coming to Orlando for adventure at one of the theme parks, or a little R&R, the Cozy Cottage is the perfect place. It's charming, quiet and nestled in our back garden with a stock tank pool in College Park, in The city of Orlando. Winter Park, Rollins college, lou gardens, Orlando Science Center, Advent Heath, Orlando health, Dr. Phillips center, Ivanhoe, lake eola, camping world stadium and the Kia center, are all in the immediate area. UCF, Full Sail and Florida Central too.

Top guest favourite
A living area features a modern television displaying a virtual fireplace, paired with elegant wall art and a decorative plant. Below, a pool area is illuminated with soft purple lighting against a backdrop of warm string lights, creating a relaxed atmosphere.
Home in Kissimmee
4.98 out of 5 average rating, 120 reviews

Perfect Getaway. Private Pool.Kissimmee/Orlando

This property is accommodated for families looking to vacation with peace of mind, the facilities are perfectly arranged so that you and your family feel at home. It has 3 rooms equipped for adults and children, the patio area is the perfect place to spend time with your family either in the pool or enjoying a barbecue on the grill.( POOL IS NOT HEATED) -No parties allowed in the house. No smoke. Do not park blocking the sidewalk, no park on the grass, nor in front of the neighbors' house.

Top guest favourite
A serene pool area is surrounded by lush tropical greenery, including palm trees and bamboo. A spa is integrated into the pool with a stone wall feature. Chaises with striped cushions are positioned beside the water, and a spacious patio includes various stone pavers.
Guest house in Lake Cherokee
4.97 out of 5 average rating, 117 reviews

1924 Spanish Carriage House Lower

Enjoy a shared but private compound resort in the heart of downtown Orlando! Centrally located and within walking distance to major events at the Kia Center, Dr. Phillips Performing Arts Center, restaurants, and downtown nightlife. Park on site, relax and enjoy all that this historic home has to share! Besides a fresh and clean private lodging, you'll enjoy use of the tropical pool, hot tub, gas grill, covered seating and dining area. A washer and dryer are just steps away for your use.

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, 116 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 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
4.95 out of 5 average rating, 129 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 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. **

Guest favourite
A warm living space features a dark wooden ceiling and an accent wall with textured concrete. Comfortable seating faces a mounted television, while wooden shelves are adorned with books and decorative plants. Natural light enters through large windows, enhancing the inviting atmosphere.
Apartment in Orlando
4.87 out of 5 average rating, 104 reviews

5 mins Universal 10 mins Epic park | Rustic LOFT

Take it easy at this unique oasis and tranquil getaway that is located in the heart of Orlando!! Want to have fun?! Literally walking distance from Universal Studios, Want to go shopping?! 5 mins from Millenia Mall and Premium Outlets. Want to experience Orlandos hottest nightlife or stroll through the city it’s 15 mins from Downtown , Do you want to meet Mickey Mouse or shamu?! 15 mins from Disney and sea-world. Even take a dip in the complex pool or play tennis!!

Top guest favourite
A backyard oasis is highlighted by a heated spa and pool, illuminated in vibrant blue hues. A multi-level deck features outdoor seating and a colorful pride flag. Lush greenery surrounds the area, creating a secluded and inviting atmosphere.
Guest suite in Orlando
5 out of 5 average rating, 466 reviews

LAKEFRONT STUDIO APARTMENT (private entrance)

This studio apartment is located in the lower level of our home and is perfect for one or two people. It has a private entrance, a king bed, overlooks the pool and the lake with views of downtown Orlando. Please note there is no kitchen, but there is a wetbar with microwave and mini fridge. In addition to the indoor shower, there is also a outdoor shower and a dock with canoe. Please also note the inside ceiling height is lower than average at 6'3”.

Top guest favourite
A serene pool area features a vibrant red pool float resting in the clear water, surrounded by lush greenery. Comfortable outdoor seating is arranged near the pool, with large umbrellas providing shade. The backdrop showcases a charming pool house with multiple glass doors, inviting natural light.
Guest house in Lake Eola Heights
5 out of 5 average rating, 265 reviews

Livingston Pool House- In The Heart of Downtown

Welcome to the Pool House! Our newly renovated detached pool house is located in the heart of downtown Orlando, in the Lake Eola Heights Historic District. We are two blocks to beautiful Lake Eola and all the dining and entertainment that Orlando has to offer. The Pool House has everything you need for a relaxing time at home, yet all the entertainment at your finger tips! Downtown living with a tropical escape!

Top guest favourite
A gold keypad lock is mounted on a white door frame, with the blurred outline of a spacious sleeping area behind it. Soft lighting from a nearby table lamp casts a warm glow, while green curtains hang in the background.
Guest suite in Kissimmee
4.97 out of 5 average rating, 167 reviews

It's too much like a elegant mini-hotel (3)

It's too much like a elegant mini hotel with rich artistic atmosphere! All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience.

Popular amenities for Orlando rentals with a pool

When is the best time to visit Orlando?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$177 SGD$184 SGD$182 SGD$169 SGD$162 SGD$184 SGD$173 SGD$155 SGD$149 SGD$158 SGD$169 SGD$185 SGD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Quick stats about holiday rentals with a pool in Orlando

  • Total holiday rentals

    Explore 7,990 holiday rentals in Orlando

  • Verified guest reviews

    Over 190,040 verified reviews to help you choose

  • Family-friendly holiday rentals

    4,700 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 1,800 rentals that welcome pets

  • Rentals with dedicated workspaces

    4,730 properties have a dedicated workspace

  • Wifi availability

    7,860 of Orlando holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Orlando rentals

  • 4.7 Average rating

    Orlando stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Orlando’s top spots include Universal CityWalk, International Drive and Kia Center

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Orange County
  5. Orlando
  6. Rentals with pools