Vacation rentals with a pool in Winter Garden

Find and book unique homes with a pool on Airbnb

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Popular amenities for Winter Garden rentals with a pool

House rentals with a pool

Guest favorite
A light-filled living area features two inviting sofas arranged around a glass coffee table. A vibrant blue area rug adds color to the floor. The open layout connects to a dining space with a round table and sleek black chairs, creating a relaxed atmosphere.
Home in Clermont
4.93 out of 5 average rating, 211 reviews

Beautiful house in Orlando/heated pool/Disney

KrystalRating, 5 stars2 weeks ago
We absolutely loved staying at Ernesto’s! It was very spacious, beautiful, clean, and not far from everything. The pool is a very nice touch after a long day! Walmart is conveniently no more than 5 mins away and Disney isn’t far at all. We would absolutely stay when coming again!
Top guest favorite
The villa features a modern exterior with a sloped roof and a two-car garage. Palm trees are landscaped around the front yard, which is bordered by well-maintained grass. A clear blue sky provides a bright backdrop to the welcoming entrance.
Home in Kissimmee
4.87 out of 5 average rating, 241 reviews

3 bedroom Villa in Kissimmee

JenniferRating, 5 stars3 weeks ago
I cannot say enough good things about Raymond & our stay. I travel a lot for my son’s lacrosse team & this was our favorite Airbnb so far! Raymond is very responsive & kind! I hope it’s available to book next year when we return.
Guest favorite
A sparkling pool is surrounded by lush greenery and palm trees, with a peaceful lounging area featuring a double canopy bed nearby. Soft blue waters reflect the clear sky, and a patio area with seating offers a comfortable space for relaxation.
Home in Maitland
4.86 out of 5 average rating, 123 reviews

Bonheur Ala Maison

RyanRating, 5 stars2 weeks ago
Leah was a great host and very responsive. The house was great for me and my family while traveling for work. Awesome location in great neighborhood. I felt safe for my family while at work during the day. The pool area was great and the accommodations were suitable for our family. My 3 children had a blast and they had enough room to space out when necessary. Thanks Leah again for our stay and being a great host.
Guest favorite
A screened-in patio features a private swimming pool and hot tub, surrounded by a tranquil lake view. String lights create a soft illumination against a colorful sunset sky, enhancing the peaceful outdoor setting.
Home in Kissimmee
4.92 out of 5 average rating, 116 reviews

10 min Disney | Lakeview Hot Tub, BBQ | Game Room

CarterRating, 5 stars6 days ago
This was definitely a great place to stay, easy to check in and the host was so responsive! I hosted a birthday party and everyone had an amazing time and had everything they needed.
Top guest favorite
The private pool is surrounded by lush greenery and features a gentle waterfall cascading into the water. Colorful plants line the edge, offering a tranquil environment for relaxation. The clear blue water is inviting and complements the serene outdoor setting.
Home in Ocoee
4.96 out of 5 average rating, 110 reviews

BBQ Grill | Wi-Fi | Pool Access | 20 Min Disney

BillRating, 5 stars2 weeks ago
Wonderful hosts, had a great experience. I would definitely revisit if the opportunity comes again.
Top guest favorite
The exterior of the home showcases a modern façade with a manicured lawn and a two-car garage. Inside, a spacious living area is furnished with a comfortable sofa and a large TV displaying a streaming service. A bright bedroom features a queen bed against light-colored walls, with natural light illuminating the space. The outdoor pool area is enclosed by a screened patio, highlighting the inviting water and surrounding lounge chairs.
Home in Kissimmee
4.99 out of 5 average rating, 106 reviews

Traveler's Dream - King Bed, Pool, Games, Disney+

LaverneRating, 5 stars3 days ago
We really enjoyed our stay. It was comfortable, clean, and had everything we needed. Thank you for being such a great host—we’d love to come back in the future!
Guest favorite
A private outdoor space features a sparkling pool with a waterfall and spillover spa. Sun loungers are positioned around the pool deck made of beige pavers. Lush greenery and palm trees create a serene backdrop under a partly cloudy sky.
Home in Four Corners
4.96 out of 5 average rating, 178 reviews

Luxurious Golf Front Oasis: Pool, Spa, View&Cinema

KaylaRating, 5 stars4 weeks ago
We had such a great time staying at Michael’s place! Our five teenagers were never bored with all of the fun amenities! The kids had a great time with the karaoke machine, arcade games and outdoor area! My husband and I love coffee, so we really appreciated the coffee bar and supplies that were provided. The house was beautiful and Michael was extremely responsive. We would stay again!
Top guest favorite
A heated pool surrounded by lush greenery features a stone ledge and a small waterfall. Hammocks are placed for relaxation. The screened patio allows for unobstructed views of the sunset, creating a tranquil setting. Warm lighting highlights the natural textures of the landscape.
Home in Orlando
4.97 out of 5 average rating, 121 reviews

Spacious Home with Pool & Hot Tub near Downtown

HeathRating, 5 stars6 days ago
Me and my daughter really enjoyed our stay, we felt right at home and definitely felt safe!!

Condo rentals with a pool

Guest favorite
A dining area is featured with a wooden table set for four. Soft yellow chairs surround the table, which is topped with a bowl of oranges. Light filters through a large window adorned with blinds, complemented by a colorful artwork on the wall.
Condo in Kissimmee
4.79 out of 5 average rating, 187 reviews

Mickey's Retreat(K2)

JackRating, 5 stars1 month ago
Stayed at Celso’s apartment for 2-weeks. It was a great size for 2 people and an ideal location for those looking to do the Disney and Universal parks. Apartment is just a short drive away from plenty of shops, restaurants and fast food places. It also has a 24h petrol (gas) station just outside of the complex which is really convenient. Overall, really enjoyed our stay the complex is really nice and feels very welcoming. Would highly recommend for two people. Celso was a great host, super responsive to any messages and helpful with any questions we had during our stay. One minor downside, not to the fault of Celso or his apartment, but the complex had a nesting hawk during our stay. This was no issue for 95% of our stay, but did swoop at us once. Would advise being cautious when walking to the car park, especially with young children.
Guest favorite
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.
Condo in Kissimmee
4.9 out of 5 average rating, 120 reviews

Modern Condo with Lake View Near Disney 3151

WilmaryRating, 5 stars4 days ago
Our stay was fantastic! The apartment was spotless and had everything we needed. Dulce was incredibly responsive and provided great local recommendations. Highly recommend
Guest favorite
The open-concept kitchen and dining area features modern appliances, including a stainless-steel refrigerator and microwave. A wooden dining table is surrounded by blue upholstered chairs, set with plates and glassware. Natural light is enhanced by overhead lighting, contributing to a bright atmosphere.
Condo in Orlando
4.92 out of 5 average rating, 149 reviews

VCR1-305 Reserve Deluxe Condo - Convention Center

ShawnaRating, 5 stars2 weeks ago
My family and I truly enjoyed our stay! We were in walking distance to Publix and some great restaurants which was great!!! We ere also around 10 minutes from the Parks, malls, and outlet malls which made calling an Uber for transportation very affordable! The pool was absolutely amazing!!! They had bar at the pool which heighten our enjoyment and relaxation! Definitely would recommend and be back again!
Guest favorite
The open living area features a round dining table with four chairs, a wall-mounted TV, and a comfortable sofa. Natural light enters through sliding glass doors leading to a scenic outdoor view. A rustic wood accent wall adds texture to the space.
Condo in Four Corners
4.87 out of 5 average rating, 142 reviews

"Ocean's Gate" - 2BD/2BA condo near Disney

DiannRating, 5 stars2 weeks ago
Great location, comfortable and clean - perfect spot to visit Orlando and all it has to offer!! This condo was clean, modern, comfy beds & furniture, efficiently equipped kitchen, etc. We liked this being in a quiet, private community and really enjoyed the pool & clubhouse! Nothing negative to share! This is a great choice!
Superhost
A resort-style pool area is shown, featuring a large swimming pool with a gradual entry. Surrounding the pool are multiple lounge chairs and potted plants. A serene pond is visible in the background, complemented by lush greenery and a picturesque building facade.
Condo in Kissimmee
4.79 out of 5 average rating, 240 reviews

Stunning condo close to everything!

RichardRating, 5 stars1 week ago
Would love to be able to come back we didn’t want to leave. One of the best Airbnb stays I’ve had.
Superhost
The aerial view showcases a sparkling pool surrounded by lush tropical landscaping. Palm trees and colorful canopies enhance the inviting outdoor atmosphere. Lounge chairs are arranged around the pool area, providing ample space for relaxation. The surrounding community features well-maintained pathways and gardens.
Condo in Four Corners
4.72 out of 5 average rating, 120 reviews

No BNB fees -Oasis Condo 5 min to Disney

SoniaRating, 5 stars2 weeks ago
Very beautiful location, calm surroundings and very close to all attractions
Guest favorite
A spacious pool area surrounded by vibrant palm trees is showcased. Lounge chairs are arranged neatly along the poolside, while the clubhouse is visible in the background. Umbrellas and colorful seating enhance the inviting atmosphere for relaxation.
Condo in Kissimmee
4.9 out of 5 average rating, 149 reviews

Cheery 2BR Condo w/zero entry pool near Disney

MindyRating, 5 stars2 weeks ago
very cozy private location with lots of stores within 5 mins. beach accessories available for convenience. will book again.
Top guest favorite
The living area is furnished with a blue couch adorned with patterned pillows. Two matching wooden side tables with lamps provide soft lighting, while a wooden coffee table sits in the center. A decorative wall piece featuring palm trees adds a touch of character to the room.
Condo in Orlando
5 out of 5 average rating, 143 reviews

Disney & Epic Free Shuttle, Kitchen

ShelleyRating, 5 stars3 days ago
Ryan's place was awesome! It was convenient to everything nearby as well as suited all of our needs. Ryan was a great host as he was quick to respond to anything we had questions about. I'd definitely stay here again! 10/10 for sure!!!!

Home rentals with a private pool

A themed bedroom featuring a spacious bed with white bedding, set against a vivid space-themed mural. Two modern nightstands are flanked by unique lamps, and a large window allows natural light to illuminate the room while offering a view of the outdoors.
Villa in Four Corners
4.33 out of 5 average rating, 3 reviews

Disney's Championsgate: Private Pool & Arcade Fun!

AurianaRating, 5 stars6 months ago
This property was very nice and matched the photos to a T. The house was spotless & very spacious. The renovated design was modern and the themed rooms were perfectly executed. The only downside was the check-in process at the gate, but after a quick phone call, the issue was resolved. I absolutely loved the space. 10/10.
Superhost
An open-concept kitchen and dining area features a large island with seating for four, illuminated by pendant lights. Light-colored cabinetry and modern appliances complement the clean design. Arched doorways lead to the entrance, where natural light brightens the space from the large front door.
Home in Haines City
4.78 out of 5 average rating, 9 reviews

Minniehaha Castle Retreat

AnetteRating, 5 stars2 months ago
This house was ideal for our weekend. Everything we needed was provided, and the extras pillows, towels, and toiletries were a nice touch. The pool water heater was a great addition, making the water perfect for the time of year ($10 a day was worth it) . We enjoyed our stay and would recommend it to others.
Superhost
Home in Davenport
4.95 out of 5 average rating, 115 reviews

Airy, Stylish Home with Pool Heat Included in Davenport

RachelRating, 5 stars1 month ago
Had a great stay at Phil's place. The home was perfect for mother's day weekend. My daughter loved the pool. The home was clean! 10/10 recommend.
Villa in Kissimmee
4.79 out of 5 average rating, 252 reviews

Visit Disney World from a Sunny Home with a Pool

AngelaRating, 5 stars1 month ago
Home was beautiful! area was quite and close by of of attractions and restaurants. Only thing I advise is bringing extra wash towels, they are not provided. We went to Walmart which is literally right around the corner.
Guest favorite
Villa in Kissimmee
4.92 out of 5 average rating, 50 reviews

Family Retreat Near Disney with Pool & Hot Tub!

JenniferRating, 5 stars1 week ago
This home is just at pictured. Has everything you’ll need. Grill and propane being available on site were a very nice bonus. Hot tub and heated pool were fantastic after walking all day. Host was amazing and communication was very quick. Highly recommend this place and location
Superhost
A vibrant entrance to LEGOLAND Florida is depicted, featuring colorful LEGO sculptures, including a pink cat, a construction worker, and other characters. The iconic sign displays the park's name and is complemented by festive decorations, inviting guests to explore the attractions within.
Home in Haines City
4.67 out of 5 average rating, 15 reviews

Beautiful Lakeview Retreat Drivable to Theme Parks

ChrisRating, 5 stars5 days ago
Great stay! Beautiful property on the lake. Would love to stay again sometime. Kayaks were a bonus! Cool to see the alligator cruising the cove!
Home in Kissimmee
4.82 out of 5 average rating, 17 reviews

Sleeps 20! Near Disney w/ Pool | Twice-as-Nice

KimberlyRating, 5 stars2 months ago
Place was nice. It had a lot of amenities that we enjoyed. The game room and pool table was fantastic. Rooms were nice and comfortable. Would definitely stay again.
A welcoming entrance sign for Solterra Resort is displayed with vibrant mosaic lettering. Surrounding greenery, including tall trees, complements the bright blue sky, creating an inviting first impression of the community.
Villa in Davenport
4.67 out of 5 average rating, 6 reviews

Amazing Dream Solterra Villa -Disney/club/pool/spa

CraigRating, 5 stars48 months ago
They house is exactly like described and had a lot of room. The cleaning could be a bit better, but they apparently had a very short turn-around. Be prepared to have parties going on around you. They do not enforce the noise ordinance at midnight like they should. We were not their to party, so this did have an affect on some of our guests. Overall, it was a pleasant stay. Edward is a super host for a reason. He always returned my emails and texts. When we needed something he was sure to get it to us. He made us feel comfortable about this purchase from the very beginning.

Quick stats about vacation rentals with a pool in Winter Garden

  • Total rentals

    20 properties

  • Total number of reviews

    220 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

  • Local attractions

    Winter Garden Downtown Pavilion and Farmers Market, Best Buy, and Miller's Ale House - Winter Garden

Destinations to explore