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Vacation rentals with a pool in Winter Haven

Find and book unique homes with a pool on Airbnb

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Popular amenities for Winter Haven rentals with a pool

House rentals with a pool

Top guest favorite
An inviting pool area is captured with a winding swimming pool bordered by a concrete deck. Several lounge chairs are positioned around the pool, complemented by a dining table adorned with a small plant. Lush greenery surrounds the space, enhancing the outdoor setting.
Home in Haines City
4.97 out of 5 average rating, 36 reviews

Cozy, Relaxing & Fun Gateway!

ImaniRating, 5 stars2 weeks ago
I want to express my gratitude to Jovanni. The house was lovely and cozy. It was spotless, and we had a great time enjoying the pool. Overall, we had a wonderful experience and truly appreciated our stay.
Guest favorite
A spacious outdoor area features a heated swimming pool with crystal-clear water, framed by a stone border. A screened enclosure captures ample natural light, enhancing views of the surrounding greenery and lake. Comfortable lounge chairs are positioned around the pool for relaxation.
Home in Winter Haven
5 out of 5 average rating, 17 reviews

15% Off Florida Summer Vacation Rentals

ChristopherRating, 5 stars1 month ago
There is so much to be said about this property! Beautiful home! Beautiful view of the lake! Accommodations better than pictured! Full kitchen with every appliance and great quality. The master bedroom bed was as comfortable as our home bed! The bedding was great quality! We will be back to this property!
Top guest favorite
A serene view of a private pool, framed by a screened enclosure, reflects the warm glow of the sunset. The water glistens under the soft light, with lush palm trees providing a tropical backdrop. The expansive lake is visible beyond the pool area.
Home in Winter Haven
5 out of 5 average rating, 13 reviews

Lakefront House w/ Private Pool, Beach & Dock

CaseyRating, 5 stars4 weeks ago
We had a wonderful stay and would love to return! Very clean and comfortable. Lots of amenities and activities, making for a perfect stay! ✨
Guest favorite
A screened-in pool area is visible, showcasing a private pool surrounded by greenery and a golf course view. A dining table with chairs is located nearby, providing an ideal space for outdoor meals, while a ceiling fan adds comfort to the area.
Home in Haines City
4.94 out of 5 average rating, 17 reviews

A beautiful cozy home with heating pool

JohnRating, 5 stars1 month ago
We had a wonderful stay. The host was very accommodating to anything we needed. He is a great host and we will definitely be returning.
Superhost
A private pool is framed by a screened enclosure, providing a serene outdoor space. Nearby, a cozy seating area features a white couch and a wooden table. Lush greenery surrounds the area, and large windows offer views of the tranquil landscape.
Home in Winter Haven
4.92 out of 5 average rating, 36 reviews

Cozy Lakefront Home w/ Pool -7 mins from Legoland

AlejandroRating, 5 stars2 weeks ago
The house in general is fantastic, the beds are very comfortable everything is good but the front yard and the back yard need a little more love to make the house perfect other than that we really enjoyed our stay and recommend the house to anyone who visits Winter Haven
Superhost
The exterior of the luxury home presents a modern two-story design with a neutral color palette. A manicured lawn and colorful landscaping enhance the curb appeal. The driveway leads to a two-car garage, and large windows provide a view of the inviting interior.
Home in Haines City
4.84 out of 5 average rating, 50 reviews

Stunning 4BR home w/Pool

TerryRating, 5 stars1 month ago
I was very well pleased with the stay. The pool was nice and warm. The surrounding was peaceful and quiet. I really would love to come back again. Also, the cleanness of the house was excellent.
Guest favorite
Home in Winter Haven
5 out of 5 average rating, 21 reviews

4/2 New Spacious Pool Home

RickkidaRating, 5 stars3 weeks ago
Everything was great. Home was fully stocked with everything you and your family may need. My babies enjoyed the pool and Lego room. If we’re ever in this area again, I would definitely book with Rachel!
Guest favorite
A private swimming pool is surrounded by a screened lanai, offering views of the home and lounge chairs. Clear blue water reflects the sky, while protective fencing provides safety. The outdoor space is designed for relaxing and enjoying the warm Florida sun.
Home in Haines City
4.92 out of 5 average rating, 66 reviews

Heated Pool | Luxury Design | Disney | Golf Course

KevinRating, 5 stars2 weeks ago
Our family (2 adults and 2 kids under 10 yrs) enjoyed our week long stay. There were a few things that needed attention with this property. I communicated those with Lukasz and he was responsive. I am sure those will be taken care of quickly. Some thing to note is that this property does back up to the golfing fairway. They grounds keepers will be out before dawn mowing and fertilizing before those early tee times. The machines are muffled and you can tell that they try their best to not distribute but you can hear them. It never disturbed our kids but it did wake the adults. If you are a light sleeper or like to sleep in, that may not be great for you. This being said, we LOVED the house, pool, hot tub, outdoor patio and everything that it had with it. The kids enjoyed the themed bedrooms as well. The short drive to Legoland was perfect. We went to a few parks in Haines as well. We would stay here again without question.

Condo rentals with a pool

Guest favorite
A large community pool is framed by tropical palm trees and surrounded by lounge chairs with blue umbrellas. Tiki-style cabanas provide shaded spots nearby. The landscape features lush greenery, with the pool reflecting the overcast sky and a hint of the lake visible in the background.
Condo in Davenport
4.89 out of 5 average rating, 123 reviews

tranquil resort, near Disney, no extra fee.208

ChristoRating, 5 stars5 days ago
I had a great stay at Jennifer’s place. The home was good and the location was perfect for our Disney trip - it was about a 20 - 30 minute drive depending on traffic and which park we were going to. Jennifer was also very responsive to our needs and provided clear instructions that helped us navigate the entire process. I would absolutely stay at this place again as it was worth the price.
Guest favorite
Condo in Four Corners
4.98 out of 5 average rating, 216 reviews

Luxury 3 Bedroom Home at ChampionsGate Golf Resort

JaninaRating, 5 stars2 weeks ago
Excellent service and quality, the host is very concerned about his guests. 100% recommended
Superhost
A large, heated pool features clear, inviting water with marked lanes for lap swimming. Orange cabanas and umbrellas provide shaded seating along the pool's edge, surrounded by lush greenery and palm trees. The space is designed for relaxation and enjoyment under a clear blue sky.
Condo in Davenport
4.82 out of 5 average rating, 119 reviews

15 min from Disney On- site Bar, Restaurant & Gym

EvelynRating, 5 stars2 weeks ago
The accommodation is exactly as described and even better. With easy access to the direct highway to Universal and Disney. The check-in instructions were also very clear, making the check-in process easy. It was sparkling when we entered and had everything you need to cook and feel at home. It is spacious and ideal for 5 people Ellis was very responsive to our questions and always answered immediately. We would definitely choose it again to return! Thank you!!
Top guest favorite
The exterior of the home features a sloped roof and a welcoming red front door. Large windows are positioned symmetrically, allowing natural light to enter. Flanking the entrance, neatly trimmed shrubs and yellow flowering plants enhance the curb appeal.
Condo in Davenport
4.89 out of 5 average rating, 110 reviews

Spacious Apartment Near Disney

La TijeraRating, 5 stars1 day ago
They place was cute and close to get restaurant and entertainment host is responsive
Guest favorite
A large swimming pool is featured, surrounded by a spacious deck lined with lounge chairs. Lush palm trees provide a tropical feel, and a bright blue sky accentuates the inviting water. The clubhouse is visible in the background, enhancing the resort-like atmosphere.
Condo in Davenport
4.83 out of 5 average rating, 166 reviews

3BR/2BA Mediterranean Style Condo Near Disney

BrianRating, 5 stars1 week ago
Our family had a great stay! Close to Disney and suited our family well. Many restaurants and a Publix super close by. Would definitely stay again when in the area.
Superhost
A spacious pool area is surrounded by lush tropical landscaping, featuring tall palm trees and colorful plants. The inviting water reflects the sky, and lounge chairs are placed along the pool's edge, providing a serene atmosphere for relaxation.
Condo in Davenport
4.83 out of 5 average rating, 121 reviews

Orlando Spacious 2-Suites & Resort-Style Pool

AnaRating, 5 stars2 weeks ago
I enjoyed my stay here so much. The apartment was so cute and cozy, super clean and spacious. It is in a gated property so itself safe and overall a great location. If and when I am back in town, I will definitely stay here again.
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
Superhost
Condo in Davenport
4.84 out of 5 average rating, 170 reviews

Full-Service Gated Resort, Disney, Universal, MCO!

AngelRating, 5 stars1 week ago
Thank you AJ and Nicole had a wonderful time this weekend definitely recommend

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, 251 reviews

Visit Disney World from a Sunny Home with a Pool

ClaudiaRating, 5 stars1 month ago
I can’t say enough good things about this Airbnb – it was absolutely incredible from start to finish. The space was spotless, nicely decorated and had every amenity we could have possibly needed (and then some!). It truly felt like a home away from home, with thoughtful touches throughout that made our stay extra special. The host was communicative welcoming and very helpful!
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
4.64 out of 5 average rating, 14 reviews

Beautiful Lakeview Retreat Drivable to Theme Parks

AaronRating, 5 stars3 weeks ago
This place was perfect for our two families (10 people in total) while we visited Legoland. Kitchen and hangout space was great.
A spacious living area features an L-shaped sectional sofa facing a wall-mounted television. Large sliding doors allow light to fill the space, with views of the pool outside. A dining table with stylish chairs complements the modern decor, and warm tones enhance the inviting ambiance.
Home in Davenport
4.83 out of 5 average rating, 48 reviews

Sleeps 16! Pool + Arcade | Orlando Resort Retreat

MindyRating, 5 stars2 weeks ago
Pictures shown is exactly how the place looks. Felt secure in the neighborhood. Plenty of amenities. Pool and hot tub was a plus. Game room was also a plus for the little ones.
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 Haven

  • Total rentals

    150 properties

  • Total number of reviews

    4.5K reviews

  • Family-friendly rentals

    100 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    150 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Polk County
  5. Winter Haven
  6. Rentals with pools