House vacation rentals in Winter Haven

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Popular amenities for Winter Haven house rentals

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, 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!
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 private pool, enclosed with a screened lanai, reflects clear blue water under natural light. Lounge chairs are positioned along the edge, and a scenic view of lush greenery and water is visible beyond the enclosure, offering a peaceful outdoor retreat.
Home in Winter Haven
5 out of 5 average rating, 10 reviews

Executive home on private lake.

AnneRating, 5 stars2 weeks ago
I must say that we really enjoyed our stay at the home ..it was like home away from home all the amenities were great, the home is much larger and spacious than what the pictures shows. The area was peaceful, we had no issues. The home was clean and the Host Hospitality was absolutely amazing and stocked with everything a family needed or could ever ask for. We didn't really get to use the pool but it looked very inviting. if ever in the area my family would stay again, over all a great place to stay..
Guest favorite
A private swimming pool is surrounded by a screened patio, offering a clear view of the water. Sunlight reflects off the pool surface, and a spa is visible at one end. Comfortable seating is arranged nearby, creating an inviting outdoor space.
Home in Davenport
4.89 out of 5 average rating, 140 reviews

Awesome Vacation Home w/ Private Heated Pool/Spa

LynseyRating, 5 stars3 weeks ago
We had a wonderful short stay in Orlando. The house was peaceful and relaxing after long days at the Disney parks. The pool was perfect and the outdoor dining and furniture were really nicely designed and comfortable. The house has everything you need to feel right at home. Lovely soft towels and linens. A great laundry room and games room. Wendy our host was so thoughtful and descriptive in the pre arrival communications, so we felt very organised before we arrived and during the stay we had a direct communication with Ron if we needed anything (we didn’t, but it was reassuring to know we had someone to call if needed). I will definitely recommend the home to friends and family looking for a place to stay during a trip to Orlando. Thanks for having us!
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
Guest favorite
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.
Home in Haines City
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!
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!

Family-friendly house rentals

Superhost
An expansive pool area is enclosed by a screen, featuring a swimming pool and a separate spa. Lounge chairs with blue and white stripes line the edge, while a dining table set is positioned under the shaded area, providing a relaxing outdoor space with views of surrounding greenery.
Home in Davenport
4.76 out of 5 average rating, 139 reviews

Luxury near Disney Large extended private pool/spa

Kim & ToryRating, 5 stars5 days ago
It was a very nice home and plenty of room for the 9 of us. The kids really enjoyed the pool and game room, but the video game system did not work. It was very clean and insect free. It was a very nice neighborhood with beautiful views. We meet a very inquisitive racoon that was looking for food, but we didn't provide any and always made sure the garbage was secured. We named him Denny the Disgruntled Racoon. Recommended additions would be a blender. Also, make sure you bring extra toilet paper, paper towels, dish detergent and garbage bags if you plan staying here. Beds were comfortable. Overall it was a great place!
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.
Superhost
The exterior of the home features a welcoming porch with seating, surrounded by lush greenery and colorful plants. A patio area with a black metal table and chairs invites outdoor gatherings, while the pathway is lined with decorative stones, enhancing the rustic charm of the property.
Home in Winter Haven
4.9 out of 5 average rating, 288 reviews

The Old Haven - An Enduring Piece of Nostalgia

ThomasRating, 5 stars2 weeks ago
Great location. Easy access. Hosts were great with communication. Would definitely book again.
Guest favorite
A private screened pool area is visible, featuring a rectangular pool surrounded by a light-colored patio. Sun loungers and a dining set are positioned nearby, with lush greenery creating a natural backdrop and enhancing the sense of seclusion.
Home in Davenport
4.86 out of 5 average rating, 227 reviews

Disney World Area Villa Orlando * Pool * Sleeps 10

YasminRating, 5 stars1 month ago
We stayed here for 3 weeks and had a lovely time. The house itself was well equipped, especially the kitchen, plenty of towels, loads of TV channels to watch and very close to all the parks and amenities. Had a great time thank you.
Superhost
A private screened pool area features a blue pool surrounded by several lounge chairs and a dining set. Lush greenery is visible beyond the enclosure, providing a natural backdrop. The sun shines brightly through the mesh, creating a bright and open space for relaxation.
Home in Kissimmee
4.89 out of 5 average rating, 182 reviews

Luxurious Private Retreat w/Spa & Saltwater Pool

JessicaRating, 5 stars1 month ago
Carrie thank you so much for hosting our family! This was so much better for our family than a hotel! Our kids never said they were bored! The next time we are in the Orlando area we will book again for sure!
Guest favorite
The image captures a serene sunset viewed through a protective mesh enclosure, with silhouetted trees against a vibrant sky. In a second view, a two-story vacation home is presented, showcasing a well-maintained exterior surrounded by lush landscaping and palm trees.
Home in Davenport
4.93 out of 5 average rating, 114 reviews

Beautiful 5 Bed Home With Rear Conservation Views

GaynorRating, 5 stars1 month ago
Fantastic stay in this beautiful home. We have rented before in Florida and this was outstanding. Well equipped, clean and very peaceful around the pool with a nice outlook. Lovely shared pool on Watersong which was very peaceful with well kept gardens. Gary was an excellent host who was very helpful from the day we booked it and I would have no hesitation in recommending. It was an hassle free 2 weeks which is just what we needed.
Guest favorite
A single-story, detached home features a light-colored exterior and a well-maintained lawn. A palm tree is positioned to the left, and a walkway leads to the entrance. The property is framed by greenery and a white fence in the background.
Home in Davenport
4.84 out of 5 average rating, 177 reviews

Amazing 4 bed home, large pool, Disney 12 miles!

AmandaRating, 5 stars2 weeks ago
This place was perfect for our family very spacious and open the safety of the pool and pool alarm was awesome! Quiet private area near everything would absolutely recommend to anyone
Top guest favorite
A private pool is visible, surrounded by a screened-in patio. Lush green grass and trees form a natural backdrop, providing a serene view. Sunlight filters through the foliage, creating a peaceful atmosphere for relaxation.
Home in Davenport
4.93 out of 5 average rating, 206 reviews

Orlando 5BD+Pool, Near Disney & ChampionsGate Golf

AbigailRating, 5 stars4 weeks ago
Just want to say it was a great stay !!! The house is very nice just like the pictures !!! Our host was fast at responding any of our questions I would recommend to anyone to stay here you will not be disappointed!

House rentals with a hot tub

Superhost
A spacious bedroom is furnished with a large bed dressed in a light-colored coverlet. Nightstands with lamps are placed on either side. A dresser and a mirror are positioned against the wall, and subtle decorative elements enhance the relaxing ambiance.
Home in Winter Haven
4.89 out of 5 average rating, 62 reviews

Modern 3br home

TammyRating, 5 stars1 week ago
Listing is very accurate. Comfortable furniture and beds. Exceptionally clean. Close to everything we needed on our trip to Legoland. Highly recommend
Top guest favorite
A spacious lawn is framed by large oak trees draped with Spanish moss. Comfortable lounge chairs are positioned facing the tranquil water, creating a serene outdoor space. The lake is visible in the background, enhancing the natural beauty of the setting.
Home in Auburndale
4.94 out of 5 average rating, 158 reviews

Lake Whistler Beach House with lakefront pool

AndrewRating, 5 stars4 weeks ago
Very rarely do you find an Airbnb that super-exceeds your expectations. This home absolutely did that. Everything was nicely appointed, yet warm and homey feeling. We stayed as 2 adult couples and had a great time. That said, if you're a family of 8, you'll likely have a great time as well. The game room was a lot of fun, the kitchen had everything you'd want to cook inside or out. The pool was perfect sized, clean, and we'll kept. The grounds were beautiful. The lakeside area was awesome. literally zero complaints other than hating to leave.
Superhost
The image displays four separate areas: a Star Wars-themed bedroom with two twin beds, a Frozen-themed bedroom featuring a king bed, a vibrant game room with arcade systems and a foosball table, and a view of the private pool surrounded by a screened enclosure.
Home in Davenport
4.88 out of 5 average rating, 117 reviews

No Airbnb fees!Themed Home Pool/Spa/Gameroom 21811

RicardoRating, 5 stars2 weeks ago
our stay was amazing! host was very responsive and fast. the home was beautiful and my kids and family really enjoyed it. loved they had a crib on site and ready to use. the location is perfect everything super close and easy to find. had all the basics we needed to start our stay. would def tell our friends and family to stay there! 10/10!
Guest favorite
A screened-in patio features a spacious, inviting pool and a private hot tub. Several lounge chairs with colorful cushions are positioned around the pool area. A basketball hoop is visible in the corner, and expansive views of lush greenery extend beyond the pool.
Home in Davenport
4.9 out of 5 average rating, 128 reviews

PRIVATE Pool Villa - Family Holiday Getaway

CheralRating, 5 stars2 weeks ago
The villa is in a great location, 10 minutes drive from shops for groceries and restaurants. We had everything we needed and the kids loved the pool. Richie was quick to respond to any questions we had. Beds, sofas and loungers all really comfortable
Guest favorite
A private pool area featuring a clear blue pool with spa and surrounding palm trees. A giant outdoor chess set is visible nearby, along with a colorful tube slide leading to a vibrant bunk bed room. A game table with billiards is also showcased in the movie theater room.
Home in Four Corners
4.96 out of 5 average rating, 178 reviews

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

KaylaRating, 5 stars3 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!
Guest favorite
A large two-story home is showcased with a well-maintained lawn and framed by palm trees. The exterior features a mix of light and dark colors, with a welcoming front porch and bright exterior lights. A driveway leads to a spacious garage, enhancing the home's curb appeal.
Home in Davenport
4.78 out of 5 average rating, 116 reviews

There is no other place you want to be than here.

SamanthaRating, 5 stars1 week ago
Franks place was perfect, everything in the pictures was accurate plus so much more. We had everything we needed to start and then some, we didn’t feel like we needed to unpack and go right to the store. We spent most of our time out at the pool and with small kids the door alarm, took some getting used to but was such a nice touch. Plenty of restaurants and grocery stores near by and only about 30/40min to universal. We would stay here again in the future, the place had so much space we never felt like we were cramped in the home.
Top guest favorite
A screened-in pool area features a clear, inviting swimming pool surrounded by comfortable lounge chairs. A basketball hoop is positioned at one end of the pool, with a scenic view of the lake and trees visible through the enclosure.
Home in Haines City
4.96 out of 5 average rating, 56 reviews

Southern Dunes Lakeview Poolhome

RuthRating, 5 stars3 days ago
We had to unexpectedly extend our vacation and this place was perfect. Jeffery was kind and responsive. My kids loved the toys and pool. Having Walmart right around the corner was perfect! The community was quiet and lovely. 10/10 recommend!
Top guest favorite
A private, screened-in pool area features a sparkling blue pool with a built-in hot tub on one side. Sunlight reflects off the water, creating a serene environment, while surrounding greenery provides a sense of privacy.
Home in Clermont
4.92 out of 5 average rating, 148 reviews

Stylish Villa Private Pool-SPA Near Parks Disney!

BreannaRating, 5 stars3 weeks ago
We had an amazing stay at this beautiful home! The house was spotless, spacious, and even more stunning in person. The pool and hot tub were absolute highlights and made our trip feel like a true getaway. We felt comfortable and relaxed throughout our entire stay. Highly recommend!

Quick stats about house rentals in Winter Haven

  • Total rentals

    290 properties

  • Total number of reviews

    10K reviews

  • Family-friendly rentals

    210 properties are a good fit for families

  • Pet-friendly rentals

    100 properties allow pets

  • Rentals with a pool

    90 properties have a pool

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

Destinations to explore

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  2. United States
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  4. Polk County
  5. Winter Haven
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