Vacation rentals with a pool in Winter Haven

5 out of 5 average rating, 118 reviews

The outdoor pool area is surrounded by a wooden privacy fence, featuring two blue sun loungers and a dining table with four chairs. Lush greenery complements the scene, and a large umbrella provides shade over the patio. Clear blue skies create a bright atmosphere.

Home in Auburndale

Stylish 3BR Retreat with Pool Near Attractions - P

Come relax at this clean, modern and cozy home. Hang out in the private pool or play yard games. Family & pet-friendly with fenced backyard. Walking distance to Lake Juliana for great fishing and watersports! At "The EstablishMint" you will experience Central Florida in a professionally designed home close to Disney, Legoland, Golf Courses, Lake Myrtle Sports Complex, Winter Haven Chain of Lakes, Waterskiing, Bike Trails. Between Tampa & Orlando. Minutes from Lakeland. Extended stays welcome!

Apartment in Winter Haven

A balcony view overlooks a serene lake, framed by lush palm trees and vibrant green foliage. Bright blue skies and scattered clouds add to the tranquil setting, while glimpses of the driveway and nearby structures can be seen in the distance.

4.99 out of 5 average rating, 147 reviews

Florida Penthouse in luxurious mansion!

Stay in your own themed Florida apartment . Tropical, palm trees, beaches ,marine life, flamingos throughout this stunning apartment in a multimillion dollar home. After parking on gated driveway walk up to your own private entrance way to paradise. Keyless entrance. One flight up and your viewing gorgeous lake views second to none. Executive kitchen with everything you need to cook a 5 course meal. Outdoor balcony that will leave you amazed. Opulence, security, with Florida Style awaits you!

A screened-in pool area is featured, showcasing a well-maintained swimming pool with a soothing spa. Natural light filters in, highlighting the surrounding greenery and the clean stone deck. A peaceful atmosphere is created by the clear blue water and inviting space.

4.88 out of 5 average rating, 103 reviews

Heated pool/hot tub, near Legoland, Disney,

Relax in the heated pool and hot tub after enjoying theme parks such as Busch Gardens, Disney world, and Universal Studios! LegoLand is 1 mile away! Lego bedroom for kids. Centrally Located in the middle of Florida allows beach trips to both east & west coast. air conditioned garage has been turned into a game room pool table, air hockey and a miss pac-man arcade game! Private boat & RV parking with RV outlet thru gate in backyard. Pool can be heated to 85 degrees for a small fee if $10/ day

The exterior of a spacious home is presented, featuring a blue façade and a welcoming entrance. Lush tropical foliage surrounds the property, which is highlighted by palm trees and manicured lawns. A vibrant sunset casts colorful hues in the sky, enhancing the serene atmosphere.

4.98 out of 5 average rating, 119 reviews

Spectacular Waterfront Home in Winter Haven

Enjoy a wonderful family get away at this premier waterfront home on the famous Chain of (19) Lakes! Separate yourself from the crowd at this beautiful Cypress Gardens home set on an acre with lush tropical foliage and surrounded by 3 sides of water. Featuring a chef's kitchen, 2 private docks, the "New Florida Pool," 2 hot tubs, fire pit and many more amenities. Enjoy relaxed luxury at its finest. We are just a few minutes to Legoland, restaurants and shopping, but miles from ordinary!

Guesthouse in Lake Alfred

A screened-in pool area features a clear, inviting swimming pool with a light blue surface. Two striped lounge chairs are positioned beside the pool, and a small seating arrangement is visible in the background, providing a space for relaxation and outdoor enjoyment.

4.94 out of 5 average rating, 174 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 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.

A spacious living area is presented with a sectional sofa, a wooden coffee table, and a wall-mounted television. Large windows allow natural light and views of the outdoor patio. The room features light-colored walls and art pieces that add a modern touch.

4.96 out of 5 average rating, 120 reviews

Glass House• Family Escape Near 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.

4.94 out of 5 average rating, 111 reviews

Fantastic Water Front Home on the Chain of Lakes

We are sharing our dream home with you! This home offers one of the best open layouts in Winter Haven. Great open kitchen with granite counter tops, stainless steel appliances, and numerous appliances. The large TV room features a Samsung smart 65" TV that connects to the Lanai/Pool area. A must see to believe! Numerous pictures provided to allow your mind to wonder. My interaction with you will be based on you. We have keypad entry for your convenience. I am here for you though!

Guesthouse in Winter Haven

A private pool area is highlighted by a circular pool, surrounded by a stone patio and lush foliage. Lounge chairs are positioned near the edge, offering views of the lake. Palm trees tower in the background against a backdrop of blue skies and scattered clouds.

4.88 out of 5 average rating, 273 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 ****

A spacious outdoor area features a large swimming pool surrounded by concrete and greenery. Comfortable blue lounge chairs are situated nearby, along with a shaded seating area underneath an umbrella. The brick home, seen in the background, is complemented by large windows allowing natural light.

4.91 out of 5 average rating, 176 reviews

Hidden Haven Lakehouse Pool by Legoland

Relax in style in this 100 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.

4.84 out of 5 average rating, 137 reviews

A screened enclosure surrounds a private pool area, featuring two lounge chairs and a small table. A blue umbrella provides shade, and lush greenery can be seen just beyond the pool deck, creating a serene outdoor space.

Villa in Haines City

Sandy's Southern Dunes Villa

This villa is in the Southern Dunes Golf & Country Club, which is an immaculately kept, secure complex, which maintains a 24-hour manned gate, making this a safe place to stay. There are community swimming pools, tennis courts, a gym, library and children's playground for those days when meeting Mickey Mouse is just too much trouble. With a Super-Walmart a minute away plus Dicks and several well-known restaurants just further away, virtually everything is on hand.

4.97 out of 5 average rating, 110 reviews

The Dalt Retreat

The Dalt Retreat in Winter Haven (LEGOLAND) Fl is named after our 9 year old Grandson Dalton. It’s a great spot to relax by the in ground pool and fenced in back yard. Enjoy the outside with your family and cookout. We want you to love The Dalt as much as we do. Located in Winter Haven and Central FL area easy to enjoy the local lakes. Also not too far from other central Fl attractions and beaches from East or West coast.

The exterior of the home features a fresh white brick façade with contrasting dark shutters on the windows. A circular driveway is lined with vibrant landscaping, including flowering plants and greenery. The property is well maintained, with a clear view of the entrance and a sunny blue sky overhead.

4.89 out of 5 average rating, 105 reviews

Villa Blanca

Relax with the whole family at this peaceful pool home located off the quiet roads along the higher elevation of the Florida ridge. Propane tank for home generator. In ground pool covered by enclosed screen. Property fronts the old Sun Air Golf course (not active). An active bar and grill still operates in the old country club at the end of the neighborhood. Right in the center of both Legoland and Disney World

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Popular amenities for Winter Haven rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The exterior of the home features a sleek black façade with large windows allowing natural light in. A neatly landscaped yard includes tropical plants and colorful foliage, enhancing the inviting entrance. The driveway leads to a single-car garage, with ample space to welcome guests.

4.99 out of 5 average rating, 126 reviews

Cheerful 4 Bed, 3 Bath Home with Screened Pool

SarahRating, 5 stars2 weeks ago

We had a great stay at Lauras place. We will be back next time we are in Winter Haven. It’s right next door to my mother in laws place which made it convenient. The kitchen was well stocked.

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.

4.97 out of 5 average rating, 37 reviews

Cozy, Relaxing & Fun Gateway!

KeishaRating, 5 stars1 week ago

I really enjoyed my stay here with my husband and 3 of our children. The home was clean and ready once we arrived and she was feline with our checkout, which we greatly appreciate. We felt really welcomed and appreciated her communication skills and hospitality!

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.

5 out of 5 average rating, 13 reviews

Lakefront House w/ Private Pool, Beach & Dock

CaseyRating, 5 stars1 month 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! ✨

A private pool area is enclosed within a screen for added comfort. The pool features a smooth tile edge and is accompanied by a paved outdoor space with lounge chairs. Adjacent to the pool, a dining area offers seating for outdoor enjoyment.

5 out of 5 average rating, 9 reviews

Spacious 3BR+Den with Pool, Near Disney & More

Linda F.Rating, 5 stars4 weeks ago

Hi the stay at Dan and Emilias lace was wonderful, it was spacious, clean, near stores and restaurants, great place, thy had it well equipped with everything you will want and need ,it was like you were at home for real, I'm a cook and the kitchen had something I needed , they even had a hand mixer, cutting board, all sizes of bowls, and ots and pans, we really enjoyed the stay, THANKS AGAIN..WE WILL COME BACK..

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.

4.84 out of 5 average rating, 51 reviews

Stunning 4BR home w/Pool

TyraRating, 5 stars2 days ago

Me and my family had an amazing time here !! It was spacious , the pool was great , and we felt right at home ! I would recommend this air bnb to anybody I know visiting Orlando Florida. It was a quick drive to EPCOT Walt Disney world. I hope to come back soon !

The two-story home is illuminated under a night sky, featuring clear glass windows that reflect soft light. Landscaped greenery surrounds the property, with a stone driveway leading to a garage. A large patio area is visible on the right side.

4.89 out of 5 average rating, 113 reviews

Breathtaking Home

JasonRating, 5 stars3 weeks ago

I thought the place was great, the kids loved the pool in the backyard. This was drivable to Disney which we opted to do for a few days and Jennifer was always so responsive. There was some live music across at the community pool but I didn't think it was overkill and the kids slept right through it. I will rent again.. hopefully soon!

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!

An indoor pool is visible beneath a blue-tinted enclosure, reflecting soft light from the surrounding room. Lounge chairs are arranged around the pool, and sliding glass doors allow access to the adjoining living area. The atmosphere is calm and welcoming.

5 out of 5 average rating, 5 reviews

Cozy Golf-Pool Home in Davenport

NiobelRating, 5 stars3 weeks ago

We had a great stay host was great very responsive close to everything

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Condo rentals with a pool

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.

4.89 out of 5 average rating, 110 reviews

Spacious Apartment Near Disney

La TijeraRating, 5 stars3 days ago

They place was cute and close to get restaurant and entertainment host is responsive

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.

4.82 out of 5 average rating, 119 reviews

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

EvelynRating, 5 stars2 weeks ago

El alojamiento es tal cual lo descripto y aún mejor. Con facilidad acceso a la autovia directa a universal y Disney. Las instrucciones para ingresar fueron también muy claras haciendo sencillo el proceso de check in. Estaba reluciente cuando ingresamos y contaba con todo lo necesario para poder cocinar y sentirse como en casa. Es amplio e ideal para 5 personas Ellis fue muy responsiva a nuestras preguntas y siempre contestó de inmediato. Sin dudas lo volveríamos a elegir para regresar! Gracias!!

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.

4.83 out of 5 average rating, 166 reviews

3BR/2BA Mediterranean Style Condo Near Disney

BrianRating, 5 stars2 weeks 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.

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.

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.

A scenic outdoor pool area is surrounded by lush greenery and palm trees. Guests are seen enjoying the water, while lounge chairs with blue umbrellas provide shaded seating. The clear blue sky complements the inviting atmosphere of this resort space.

4.93 out of 5 average rating, 107 reviews

Fabulous condo-Bahama Bay Resort, Close to Disney

AndrewRating, 5 stars5 days ago

This was one of my best Airbnb stays in a while. The resort location, amenities, and clubhouse staff were very convenient. The host had very clear instructions and was very communicative. The apartment itself was very spacious. Much larger than I expected. Thanks!

4.72 out of 5 average rating, 120 reviews

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

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

4.77 out of 5 average rating, 126 reviews

Condo in Kissimmee

1-101 Legacy Dunes, Gym, Tennis, Close To Disney!

ValentinaRating, 5 stars1 month ago

I had a great stay! The place was clean, comfortable, and just as described. The host was very friendly and responsive, which made everything super easy. I’d definitely stay here again!

The image features a tranquil pool surrounded by a spacious deck, with lounge chairs available for relaxation. The clear water reflects the sky, while the apartment complex provides a backdrop to the inviting space. Nearby, a covered area offers shade and seating for gatherings.

4.95 out of 5 average rating, 101 reviews

"Stunning Condo Stay Disney Orlando, 2Bed/2Bath"

EmilyRating, 5 stars1 month ago

Stayed here for 4 nights for my first visit to disney world ! Beautiful calm neighborhood only 20 minutes away from the park. Grocery stores and other fast food restaurants were less than 10 minutes away! Host was super nice ! I would definitely book here again whenever i come back !

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Home rentals with a private pool

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.

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.

4.95 out of 5 average rating, 115 reviews

Home in Davenport

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.

4.92 out of 5 average rating, 50 reviews

Villa in Kissimmee

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

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.