Vacation rentals with a pool in Winter Park

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Winter Park

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

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Top guest favorite

Home in Kissimmee

4.95 out of 5 average rating, 152 reviews

4 bedroom, south facing pool 3 miles to Disney

Create family memories in our stunning pool home with Star Wars, Minnie and Mickie themed twin rooms. Elegant and comfortable king bed master bedroom with your own private bathroom and soaking tub! Delightful queen bedroom that also features its own private bathroom with shower. Enjoy a heated south facing pool (heating extra charge) with no rear neighbors. We are located in a guard gated community that features a large pool, clubhouse with a gym, arcade, movie room, and various sports courts.

Guest favorite

Home in Davenport

4.86 out of 5 average rating, 7 reviews

Acres View 5bed/4bath near Disney. Own Pool & Spa!

Relax with the whole family at this peaceful place to stay. 5 bedrooms and 4 bath private villa with two living rooms . Close to Disney and all theme parks and also only moments to Posner park for the shopping enthusiast. Enjoy nearby events and all the parks yet come back to country views and rejuvenation at your private heated * pool and *spa! 35 to Orlando International Airport! * let us know at booking if you want pool/spa to be heated for $40/day. •BBQ available for cleaning fee of $65.

Superhost

Guesthouse in Orlando

4.93 out of 5 average rating, 255 reviews

Modern Guest Studio (Private) Pool / Spa available

Private Guest Studio (Not Shared ) in a Perfect Orlando location, 5 minutes from I-Drive, Universal Studios, Disney World & Premium Shopping Outlets. Very Quiet lovely neighborhood with Biking distance to "Restaurant Row" where all your favorite restaurants are located. Pool & Spa available (Not Shared) All major highways at your finger tips / ride 15 min to Disney! This space has an industrial modern look with high ceilings, Stay and cook with all the amenities including a Washer and Dryer.

Guest favorite

Home in Davenport

5 out of 5 average rating, 5 reviews

New! Windsor Island Resort with pool by Disney 03

Bring the whole family to this great place with lots of fun! This spectacular home is ideally located within the Windsor Island Resort within a short drive to Disney World, Universal, Disney Springs, and many others! With a private pool/spa, 10 bedrooms and 8 bathrooms, your can enjoy the relaxing and fun atmosphere together! **Walt Disney World --20 min **Grocery & drug store -- less than 5 min **Orlando International Airport -- 40-50min **Universal Studios --35 min **Sea World -- 28 min

Guest favorite

Home in Clermont

4.86 out of 5 average rating, 43 reviews

Lake Vista Getaway

You will enjoy easy access to everything from this place, yet located in a more residential area away from the busiest traffic! Convenient to Disney - 8 miles from property, minutes away from beautiful Lake Louisa, fun spots for outings like Island H2O, shopping galore and dining at the new Margaritaville resort... this spacious home will give you opportunities for togetherness, relaxation, recharging and soaking up the sun! Our home has a community pool and gym for use. NO MAIL ACCEPTED

Top guest favorite

Home in Kissimmee

4.93 out of 5 average rating, 41 reviews

3 BR Private Pool Home 5 miles from Disney

Beautiful 3 bedroom Pool Home. It's located just minutes from Disney World, Sea World, Universal Studios, and other Orlando attractions. This home has one of the largest screened in pool areas in the neighborhood, along with complete privacy! Everyone will love the large game room with air conditioning. New 4K TVs installed in all rooms. This property has been listed on another website and has a 5 star average with 77 reviews. Free Pool and Spa Heat along with Gas Grill are offered.

Top guest favorite

Villa in Davenport

5 out of 5 average rating, 30 reviews

25 Minutes to Disney Parks!

Enjoy a perfect getaway in our modern, detached home located in a quiet gated community, just 25 minutes from Disney parks. Relax in the private pool and hot tub after a day of fun, or enjoy some friendly competition in the fully-equipped game room. With stylish interiors, spacious living areas, and all the comforts you need, this home is an ideal retreat for families and friends seeking both relaxation and adventure. Make lasting memories in a space that feels like your own!

Top guest favorite

Home in Minneola

4.97 out of 5 average rating, 150 reviews

Spacious Getaway ~ Heated LED Pool & Ping Pong

Welcome to your Spacious Getaway! Exterior Features: ★ LED Lights in Pool and on Pool Cage ★ Fenced-in yard & Fire-pit ★ Doorbell & Driveway Camera for safety Interior Features: ★ Ping Pong Table ★Large Shower in Master Bathroom Extras: ★ Heated Pool up to 95 Degrees - $40 per day (Pool Water is normally at 75 degrees without the Pool Heater) ⚠️ Pet-Friendly, but the pet must be added to the reservation ($75 Pet fee)⚠️ {Willing to Negotiate Monthly Prices}

Superhost

Home in Kissimmee

4.92 out of 5 average rating, 36 reviews

Stunning Home with Pool Minutes to Disney!

Relax and unwind in this exceptionally appointed 4 bedroom home with tons of space for your family to enjoy. Fully stocked for your home away from home. Private heated pool (heat included). Large TV in family room, both master bedrooms and 2 family bedrooms. Cozy luxury accommodations. Game room with ping-pong table, basketball and foosball table. Wifi included for your convenience. Have fun with the whole family at this stylish place.

Superhost

Townhouse in Kissimmee

4.84 out of 5 average rating, 174 reviews

Luxury townhome with private pool

Brand new fully furnished townhome with private pool in gated community. Spacious living and dining rooms ideal for large family gatherings. Free parking situated in front of house. Walking distance from lake and short drive from attractions, malls, and golf course. The unit has fast Wi-Fi, and many smart devices can be connected to the Wi-Fi. Extra charges will be added to your reservation for pool heating, BBQ and others.

Superhost

Home in Orlando

4.71 out of 5 average rating, 82 reviews

Rare Heated Pool House close to Downtown Orlando

Spacious ans stylish pool home close to downtown Orlando. Home is accessible to Many major highways including 408, I4, 429, turnpike and only 12 minutes from the Universe Studio. Regardless of long-term or short-term you will have an forgettable experience at this Luxurious pool home with a large patio equip with television outside. You can get the pool heated for an extra charge. Many restaurants and attractions nearby.

Top guest favorite

Townhouse in Kissimmee

4.93 out of 5 average rating, 61 reviews

Pool Townhouse only 5mi from Disney-FREE resort!

No compromises here! This is the personal experience you have come to expect from an AirBnb vacation. We are not a mass-managed unit like most! Gorgeous pool home at Paradise Palms Resort, featuring an elegant Clubhouse with a free vintage movie theater, game room, Convenience and souvenir shop, pool side bar and restaurant, 24 hour security, playground, ball courts, resort pool with Waterfall and the best LOCATION!!!

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What guests are saying

Lake Views! 5BR Home w Pool & Themed Room

4.64 out of 5 average rating, 58 reviews7 months ago

Great stay here. The place was exactly as described and close to Disney. Pros: No crazy list of check out procedures Place was clean and fairly well stocked Open feeling Very comfortable bed 10-20 minutes to Disney with minimal traffic Target and Publix <5 minuets away Cons: Very close to community pool which can be loud Neighbors houses are very close and you will hear them when outside Only parking for 2 cars in the driveway. There is ample steeet parking though Overall I’d highly recommend this place and will book again when we come back. The host was very responsive and the house was great. I’d highly recommend staying here!

Home in Kissimmee

What guests are saying

Luxe Disney Home Heated Priv Pool/Spa, 6Bed/6Ba

4.9 out of 5 average rating, 58 reviews5 days ago

Great stay. Exactly what we were looking for. Quiet peaceful and private. We were a group 9 and we wanted somewhere that had an area for the kids to play, a nice pool and quiet. We were debating between one of the many places that has a water park type area and this place. We chose this place because we heard that the other places had long waits to get in and busy main pool areas. This choice was perfect, the clubhouse area had a nice big pool for the kids to use and a very nice gym. It was more than enough and not crowded at all. We drove by the other places and they were all packed and noisy. You will not be disappointed here.

Home in Kissimmee

What guests are saying

Florida 5 Bedroom,Pool, HotTub,Resort near Disney

4.73 out of 5 average rating, 52 reviews1 month ago

The house is lovely and was super clean. The Florida themed decorations were perfect. While our children are grown and gone, I thought it was such a great idea to have a high chair and some toys available. The owners clearly put thought into their guests’ stay. Would absolutely rent again!

Home in Kissimmee

What guests are saying

Resort Listing! Villa Palma Pool House by Disney

4.83 out of 5 average rating, 41 reviews2 weeks ago

The house was easy to find and in a beautiful neighborhood. The host was very responsive. We only had one issue and when it was brought to their attention they had someone out to fix it same day. We will definitely be looking to book with them again in the future.

Home in Kissimmee

What guests are saying

"Champions Oasis" Spacious Villa & FREE Pool Heat

5 out of 5 average rating, 8 reviews1 month ago

Absolutely Amazing Stay – Perfect for Families & Groups!I recently had the pleasure of staying at an incredible Airbnb in Orlando, Florida, near Disney, and I cannot recommend it enough! From the moment we arrived, we were blown away by how spacious, modern, and impeccably clean this home was. If you’re looking for the perfect place to stay with a large group or family, this is it!This house is absolutely massive! With multiple bedrooms and bathrooms, there was more than enough room for everyone in our group to spread out and relax. The open-concept living area was perfect for gathering, whether we were watching TV, playing games, or just chatting. The beds were super comfortable, and each room was beautifully decorated with a cozy yet elegant touch. It truly felt like a home away from home. It’s clear that the hosts take great care in maintaining the home. The location of this Airbnb was so close to Disney. all expectations. The combination of size, cleanliness, comfort, and location.

Home in Davenport