
Vacation rentals in Winter Haven
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Top-rated vacation rentals in Winter Haven
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Haven vacation rentals
Home rentals in Winter Haven

New Family friendly townhome.
Very nice stay, proactive host and always attentive. To keep in mind for a future visit.

5 Bdrm (sleeps 13), free water park,closeto Disney
If you plan on staying in the Orlando area- look no further. This place has it all. Large enough for the whole family with a FREE water park and a heated pool in the room. My family had a dream vacation. Stop looking and book Mohit’s place now!!

The Villa Retreat / near Disney
Noah was super nice & always took the time to answer my questions! His home was just as pictured and very pretty, very spacious and easily accommodated our group of 10 without feeling overcrowded! Definitely would come back!!

4BR,PrvtNOTOverlookedPool,FencedYard,GameRM,WiFi
Great house and host was very friendly with clear instructions on check in and check out. Pool was clean and well maintained.

Cozy Home Airport 14 mins Universal 20 mins
There is only one bathroom in the house which make thing hard for large group

Close to Disney 3BR 2.5BA Townhome with Hot Tub
Everything about this property/Stay was immaculate ! , I will most definitely will be booking with you guys again

Dream staying in Orlando, FL
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!

Family Home Gated 10 Beds Pool Disney 7 miles.
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

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

Dream vacation, near Disney
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!

Vacation home
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

New! Windsor Island Resort with pool by Disney 03
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.

Orlando Retreat: Cozy Escape for Magical Holidays
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.

Pelican Escape
Our stay was very comfortable. Not far from Disney and other attractions. My family had everything they needed, would stay again in the future!

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

DisneyVacationHomeLazyRiver9021
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 250 vacation rentals in Florence Villa, over 250 vacation rentals in Downtown Winter Haven, and over 310 vacation rentals in Eagle Lake.
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.
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 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.
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 50 homes with a bbq area, over 290 homes with wifi, over 80 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.
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- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
- Old Town Kissimmee
- Discovery Cove
- Reunion Resort Golf Courses - Palmer & Watson
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