Some info has been automatically translated. Show original language

Vacation rentals in Winter Haven

Book unique homes, vacation rentals, and more on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Winter Haven vacation rentals

Stay near Winter Haven's top sights

LEGOLAND Florida Resort513 locals recommend
LEGOLAND Florida Water Park104 locals recommend
Legoland station88 locals recommend
Winter Haven Hospital4 locals recommend
Harborside25 locals recommend
Harry's Old Place17 locals recommend

Home rentals in Winter Haven

Guest favorite
A vibrant water play area features a colorful pirate ship surrounded by palm trees and outdoor lounge seating. A slide extends from the ship into a shallow splash zone, inviting family fun. Bright umbrellas provide shade in the background, enhancing the lively atmosphere.
Home in Davenport
5 out of 5 average rating, 18 reviews

New Family friendly townhome.

Jean-FrancoisRating, 5 stars1 month ago
Very nice stay, proactive host and always attentive. To keep in mind for a future visit.
Guest favorite
A modern living room features a large, wall-mounted flat screen TV displaying a scenic image. The space is designed in neutral tones with light-colored tile flooring and a cozy area rug. Large sliding doors offer access to an outdoor seating area.
Home in Kissimmee
4.92 out of 5 average rating, 132 reviews

5 Bdrm (sleeps 13), free water park,closeto Disney

EliaRating, 5 stars3 weeks ago
Our family of 5 stayed here- 2 couples and one teenager. Awesome location! Close to all Disney Parks. Plenty of space for all of us! Truly enjoyed the clean house full of amenities. The resort was great! Lots of fun activities all included with our Air BnB. Mohit was very responsive as host and generous! Amazing value! Highly recommend!
Guest favorite
A spacious dining area features a long table set for meals, accompanied by elegant chairs. Soft lighting illuminates the space, enhancing its modern design. A staircase is visible, leading to upper levels, while a well-equipped kitchen can be seen in the background.
Home in Osceola County
4.82 out of 5 average rating, 11 reviews

The Villa Retreat / near Disney

AlejandraRating, 5 stars1 month ago
The house is as shown in the photos, quiet area, great location, you have a super close Publix. Noah was very friendly and quickly answered my concerns! I would definitely consider this house again for a next stay
Guest favorite
A private south-facing pool is surrounded by a screened enclosure, offering a clear view of the lush conservation area beyond. Poolside lounge chairs are arranged neatly, with tropical plants adding a natural touch to the peaceful outdoor space.
Home in Kissimmee
4.88 out of 5 average rating, 188 reviews

4BR,PrvtNOTOverlookedPool,FencedYard,GameRM,WiFi

MustafaRating, 5 stars2 weeks ago
Great house and host was very friendly with clear instructions on check in and check out. Pool was clean and well maintained.
Superhost
The collage showcases the townhouse's interior and amenities: a modern kitchen with dark countertops, a comfortable living area with a sofa and TV, the inviting community pool area with palm trees, and a close-up of the private hot tub, highlighting its bubbling water and easy access.
Home in Kissimmee
4.79 out of 5 average rating, 33 reviews

Renovated 3BR 2.5BA Townhome Free Use of Hot-Tub

MandyRating, 5 stars1 month ago
Great Host with a very nicely stocked home. There are plenty of blankets and pillows, fans in bedrooms, well-stocked towels and plenty of kitchen supplies. This is a greqt place to relax and get away. We enjoyed the community pool with bar service and food poolside as well. Highly recommend!
Superhost
The entrance opens to a bright living area featuring light grey walls and marble-like flooring. Artwork depicting vibrant characters adorns the walls. A ceiling fan is visible above a seating area, and large windows allow natural light to fill the space.
Home in Kissimmee
4.82 out of 5 average rating, 34 reviews

Dream staying in Orlando, FL

MaraRating, 5 starstoday
Everything was great about this place. It looked exactly like the photos. The location was great, close to Walmart, Publix, and lots of restaurants. We didn’t make it to the pool, but it was readily available for our use. Very clean space, will be back for sure!
Guest favorite
A well-maintained home is set against a backdrop of lush greenery. The exterior features a welcoming porch with white railings, surrounded by a neatly landscaped yard and a paved driveway. Clear blue skies with a few clouds are present above.
Home in Kissimmee
4.95 out of 5 average rating, 157 reviews

Magical home! 15 minutes from all parks!

VanessaRating, 5 stars2 weeks ago
Beautiful property and very quiet and peaceful surroundings
Guest favorite
The entrance of a gated community is framed by tall palm trees against a clear blue sky. Decorative stone pillars mark the entryway, with lush greenery and vibrant landscaping visible along the driveway. Cloud formations add texture to the scenic backdrop.
Home in Davenport
4.83 out of 5 average rating, 101 reviews

Family Home Gated 10 Beds Pool Disney 7 miles.

SamanthaRating, 5 stars6 days ago
Great stay! The place was clean, comfortable, and exactly as described. Roy was very responsive and made check-in super easy. Would definitely recommend and stay again!

Other great vacation rentals in Winter Haven

Guest favorite
Home in Davenport
4.84 out of 5 average rating, 32 reviews

Solterra discount slps 18/7 bdm/GR/pool/spa5485

SamanthaRating, 5 stars3 weeks ago
The house is brilliant. We had 11 adults and a 5 month old baby. We all flew in at different times, to different airports but access was easy for everyone. we had been given the details by the host prior to our arrival. Susan is a great host, very communicative but not intrusive. Every detail was taken care of. Passes at the gate, information about the activities and much more. I would highly recommend this AirBnB to anyone. Having a large family, it was great for space but also playing games and spending time together. We had family visit, who live in Florida, which was also easy. Susan was very helpful when my father in law couldnt be located, after visiting us. Thank you Susan, we will be back
Superhost
An outdoor space features a spacious pool surrounded by a sunbathing area. A covered seating area offers shade under a large umbrella, while palm trees add a touch of greenery. The screen enclosure provides protection while allowing for natural light and fresh air.
Home in Kissimmee
5 out of 5 average rating, 3 reviews

Dream vacation, near Disney

ChrisRating, 5 stars3 weeks ago
What an incredible stay we had at Rosario's place! We even extended 2 extra nights. Rosario was responsive, helpful, and so kind - she even left a birthday balloon and some treats for my mom's birthday! The house was impeccable and they were great about everything, from changing dates to heating the pool, and keeping it clean, and the pool was a perfect balmy respite. The next time we're in town (and we will be, this is our old neighborhood!), we will definitely try to book here again. Can't wait to come back!
Superhost
Home in Davenport
4.76 out of 5 average rating, 68 reviews

Vacation home

JaniquaRating, 5 stars3 weeks ago
Me and my Family enjoyed our days there! Miguel was very friendly and nice and welcome us to a little welcome gift I mean who dosen’t love chocolate
Guest favorite
A stylish living room is presented with plush, tufted sofas arranged around a sleek glass coffee table. A large flat-screen TV is mounted on the wall, complemented by minimalist decor. Soft light from a circular ceiling fixture enhances the modern ambiance.
Home in Davenport
5 out of 5 average rating, 5 reviews

New! Windsor Island Resort with pool by Disney 03

IrynaRating, 5 stars15 months ago
Nice house with good layout of rooms. It is very convenient to come with children as there is a lot of entertainment on the territory of the complex. I also liked the themed design of the rooms. Overall, this is a good house for a large and friendly company.
Superhost
A large swimming pool is surrounded by lush palm trees and sun loungers, offering a refreshing escape. The clear blue water reflects the sky, with steps leading into the pool area. A spacious deck provides ample space for relaxation and enjoyment under the sun.
Home in Davenport, Orlando
4.88 out of 5 average rating, 34 reviews

Orlando Retreat: Cozy Escape for Magical Holidays

NicoleRating, 5 stars2 weeks ago
Laura’s place was the perfect spot for our Disney vacation. Close enough to be parks but just far enough that it didn’t feel so busy all the time.
Top guest favorite
A colorful water play area features a wooden pirate ship with multiple water features, including a large water bucket and a slide. Stairs lead up to the main deck, surrounded by a splash area, offering a playful environment for children.
Home in Davenport
4.96 out of 5 average rating, 25 reviews

Pelican Escape

EmiliaRating, 5 stars4 weeks ago
Our stay was very comfortable. Not far from Disney and other attractions. My family had everything they needed, would stay again in the future!
Guest favorite
A docking area extends into the water, featuring a wooden platform with various kayaks neatly arranged. A gazebo provides shaded seating, and a manicured green lawn complements the serene water view under a clear blue sky.
Condo in Kissimmee
4.9 out of 5 average rating, 120 reviews

D-Gated Resort-5 miles to Disney-2 FREE Water Park

LauraRating, 5 stars1 week ago
My husband and I stayed In james apartment with our two children. This was a return trip for us having stayed previously in 2019. We enjoyed our stay just as much this time around. My son and husband are big Star Wars fans so loved the theming of the apartment. Everything was really well maintained and amenities were great. We enjoyed using the clubhouse as well. The location is perfect for visiting all the Disney parks and universal, everything was around a twenty minute drive. James was responsive and helpful to all queries, we hope to return one day soon!
Superhost
Home in Four Corners
4.88 out of 5 average rating, 16 reviews

DisneyVacationHomeLazyRiver9021

SharonRating, 5 stars1 week ago
This beautiful home worked well for our family…4 couples and 3 small children. Pool and hot tub were great and clean! The house was large and we had a ton of fun! The host was super responsive every time we sent a message. We would definitely come back to this house and would highly recommend it!

Quick stats about vacation rentals in Winter Haven

  • Total rentals

    450 properties

  • Total number of reviews

    17K reviews

  • Family-friendly rentals

    260 properties are a good fit for families

  • Pet-friendly rentals

    140 properties allow pets

  • Rentals with a pool

    150 properties have a pool

  • Rentals with dedicated workspaces

    250 properties have a dedicated workspace

Frequently Asked Questions

  • Where should I stay in Winter Haven?

    Make yourself at home in Winter Haven by choosing from our most frequently booked neighborhoods. We have over 310 vacation rentals in Eagle Lake, over 250 vacation rentals in Downtown Winter Haven, and over 250 vacation rentals in Florence Villa.

  • Are there vacation rentals with a dedicated workspace in Winter Haven?

    Yes! Work meets play with ease at over 250 vacation rentals in Winter Haven featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Winter Haven?

    Four-legged friends are welcome in Winter Haven. Choose from more than 140 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in hotel rentals in Winter Haven?

    Experience the best of Winter Haven with our hotel rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Winter Haven vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 150 vacation homes with pools in Winter Haven, available on Airbnb. Make a splash and soak up the sun in style!

  • Do hotel rentals in Winter Haven have wifi?

    Absolutely! We offer over 30 hotel rentals with wifi in Winter Haven. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winter Haven have a bbq area?

    Absolutely! We offer over 50 house rentals with a bbq area in Winter Haven. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winter Haven have a gym?

    Absolutely! We offer over 20 house rentals with a gym in Winter Haven. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winter Haven have self check-in?

    Absolutely! We offer over 80 house rentals with self check-in in Winter Haven. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Winter Haven?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a gym, over 290 homes with wifi, over 80 homes with self check-in, over 50 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Polk County
  5. Winter Haven