Vacation rentals with a pool in Winter Haven

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Winter Haven

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

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Guest favorite

Home in Haines City

4.88 out of 5 average rating, 136 reviews

3 Bedroom Executive with Private Pool near Disney

Stunning executive home with a south facing screened in-ground pool overlooking the 2nd hole of the Southern Dunes Golf Course. Only 15 minutes from LEGOLAND and 25 minutes from WALT DISNEY WORLD, this is the perfect place to relax after a busy day at the parks. Impeccably maintained, our villa features upgraded furniture, electronics, mattresses and flooring. Southern Dunes is a gated golf community that prides itself on the quality of its golf course and the security and beauty of its homes.

Nov 18 – 25

$112 per night

Superhost

Home in Davenport

4.87 out of 5 average rating, 135 reviews

Insta-worthy getaway near Disney w/ free parking!💎

Welcome to our place! Very quiet neighborhood, with free WIFI, a pool, a gym, and a tennis court. Distance to main places: - Walt Disney World: approx 20 min driving - Disney Springs: approx 30 min driving - Universal Studios: approx 40 min driving IMPORTANT: Clubhouse hours are Mon-Sat, 9:30 am to 5:30 pm. If you arrive after clubhouse hours, you will have to park in the guest parking for the night. Guest parking is a short walk from the property. You can get your parking pass the next day.

Sep 27 – Oct 4

$91 per night

Guest favorite

Home in Winter Haven

4.95 out of 5 average rating, 82 reviews

3/2 House w Heated Pool 5mins to Legoland

Come enjoy our heated pool! Relax with the whole family at this peaceful home in Winter Haven 5mins to Legoland and the new Peppa Pig theme park, perfect for your next family vacation! Right across the street from lake Ned park with lake View from the front porch and office, bring your small water toys as there is a public boat ramp across the street. There are many restaurants as well as a Publix grocery store all within 2 miles from the home! Downtown winter haven is a short 10 minute commute.

Sep 23 – 30

$142 per night

Guest favorite

Guesthouse in Lake Alfred

4.95 out of 5 average rating, 119 reviews

Adorable Agave Suite w/ private pool and entrance

Relax & unwind in The Agave Suite, located in a peaceful lake town. This will be your “shome” away from home. Upon entry of the the property you will find a private back entrance, covered parking, private screened in pool and mature trees. Your guesthouse comes equipped with 1 cozy queen size bed, pull-out sofa bed, walk-in shower, kitchenette, smart tv, wifi and more. Looking to explore? We are centrally located to your nearest parks & Florida attractions. Close to fishing docks & bike trails.

Aug 22 – 29

$78 per night

Guest favorite

Home in Haines City

4.95 out of 5 average rating, 139 reviews

Luxury Home 4/3 near Disney, 2 Masters

Luxury 4 bedroom home located in a quiet, gated community about 15 miles from Disney World. The travel time to Disney will depend on the traffic but is usually between 30 and 40 minutes. Fully furnished with 2 master King bed suites, one queen bedroom and one bedroom with 2 twin beds. 3 full baths. 5 high definition televisions, high speed Wifi, free long distance phone calls to US, Canada and UK. Large pool and spa. Large game room with many games and activities for children of all ages.

Oct 29 – Nov 5

$138 per night

Guest favorite

Home in Haines City

4.82 out of 5 average rating, 106 reviews

Southern Dunes Golf Vacation Villa

This picture perfect executive villa has been awarded Trip Advisor’s Certificate of Excellence is located within the Southern Dunes Golf and Country Club. This open concept villa includes 3 bedrooms that can comfortably accommodate up to 6 guests. This villa is located on the prestigious 4.5 Star Southern Dunes Golf Course and offers guests a beautiful private swimming pool, outdoor dining area with a TV and BBQ within a fully gated community accompanied by 24 hr security at the front gate.

Oct 7 – 14

$115 per night

Guest favorite

Condo in Davenport

4.91 out of 5 average rating, 209 reviews

3/2 King Bed Apartment near Disney Universal

This unit is on the second floor. Elevator in the building. Located in the heart of Disney World, Kissimmee and Orlando best fun spots! You will be close to everything here. Heated Pool, Free Parking, recently renovated and updated! Your much deserved fun vacation starts here! Includes 1 King bed, 1 Queen bed and 2 twin Bed. ***SMART TVs with Disney+ (includes movies from Disney, Marvel, Pixar, Star Wars, National Geographic), HBO Max, Netflix, Amazon Video and more for you to relax in home!

May 5 – 12

$79 per night

Guest favorite

Home in Winter Haven

5.0 out of 5 average rating, 46 reviews

Glass Haven: Serene Getaway 7 min from Legoland!

Come relax with your whole family in this peaceful home! Our 2 bedroom 2.5 bathroom home is very spacious and can accommodate up to 7 people. Enjoy your day only 7 minutes to LEGOLAND. You will have pool access as well as access to many board games and arcade games within the home. Fun for the whole family! Our home is wheelchair accessible with an elevator that goes between floors so your family can accommodate well if needed! We do not allow parties. The home is strictly no-smoking.

Oct 25 – Nov 1

$139 per night

Guest favorite

Home in Winter Haven

4.94 out of 5 average rating, 16 reviews

Kid-friendly Home w/ Pool & BBQ

Enjoy a delightful stay in our Renovated 3BD house for your Winter Haven trip. The unit is equipped with dryer, washer, Wi-Fi, fully equipped kitchen, baby proofed, and BBQ to make your stay comfortable. Enjoy the private pool, free parking, and large patio. Our house is 20 mins away from LEGOLAND and 50 mins away from Disney Parks and attractions. Discover Winter Haven’s chain of lakes with all the water sports and its surroundings in the best way. We look forward to hosting you!

Nov 6 – 13

$133 per night

Superhost

Guesthouse in Winter Haven

4.87 out of 5 average rating, 232 reviews

The Russell Lake House

This is a Cabana. It has 2 sets of bunk beds (4 total beds). Approx 400 sq. Ft. . Includes a bathroom with sink, toilet, and walk-in shower. AC and heat are available. The property has a pool that can be used while onsite. The entire property's back yard is on a lake (lakefront) with a dock. Ample off street parking, quiet neighborhood with a private entrance for guests. **** we are in the process of rebuilding the dock so it will be unavailable until further notice ****

Feb 8 – 15

$76 per night

Guest favorite

Home in Winter Haven

4.9 out of 5 average rating, 154 reviews

Hidden Haven Lakehouse Pool by Legoland

Relax in style in this 96 year old custom built home.Tall ceilings,large rooms and wood floors throughout.With an extra large swimming pool overlooking Little Lake Otis this outdoor area is second to none.Less than 2 miles from Legoland,Chain of Lakes Fieldhouse,and Downtown Winter Haven. It is possible that days may be available and not listed on the calendar. This is to give ample time for cleaning. Feel free to ask for additional availability and shorter stays.

Jun 20 – 27

$154 per night

Guest favorite

Guesthouse in Auburndale

4.97 out of 5 average rating, 193 reviews

Private Poolside Villa

Lovely, private, poolside villa. The apartment is inside a completely enclosed, block walled pool deck. It provides privacy & your own personal oasis! Due to the proximity to the pool, my place is best suited for adults. I will only host young ones 13 & older that are proficient swimmers. I live in a centralized location. I am within walking distance to restaurants, park, arcade, gym & library.

Aug 17 – 24

$56 per night