Winter Haven Vacation Rentals

Compare 13 vacation rentals.
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Make Winter Haven your next getaway

Winter Haven, FL vacation rentals

Explore Winter Haven house rentals, apartments, studios, and more

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House rentals

View 9 House rentals
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Apartments

View 2 Apartments
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Studios

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Explore more vacation rental amenities in Winter Haven

Pool | Lake view | Water view | Waterfront | A/C | Washer/dryer | Balcony | Bikes | Golf on-site | Ping-pong table

Winter Haven vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Lanai & Pool: Elegant Villa in Winter Haven!
4 Bed | 4.5 Bath | Sleeps 8

Lanai & Pool: Elegant Villa in Winter Haven! - Winter Haven, FL

$628 avg / night
(excludes fees and taxes)
5.0 (3)
Hot Tub & Fire Pit: Lakefront Home on Lake Eloise
0 Bed | 1 Bath | Sleeps 4

Hot Tub & Fire Pit: Lakefront Home on Lake Eloise - Winter Haven, FL

$275 avg / night
(excludes fees and taxes)
5.0 (19)
Waterfront Winter Haven Home with Dock & Hot Tub!
4 Bed | 3 Bath | Sleeps 12

Waterfront Winter Haven Home with Dock & Hot Tub! - Winter Haven, FL

$548 avg / night
(excludes fees and taxes)
5.0 (13)
6 Mi to Legoland: Retreat w/ Pool & Fenced Yard
3 Bed | 2 Bath | Sleeps 6

6 Mi to Legoland: Retreat w/ Pool & Fenced Yard - Winter Haven, FL

$372 avg / night
(excludes fees and taxes)
3.0 (1)
Walk to Winter Haven Hospital: Convenient Apt
1 Bed | 1 Bath | Sleeps 2

Walk to Winter Haven Hospital: Convenient Apt - Winter Haven, FL

$140 avg / night
(excludes fees and taxes)

View 8 more homes

Recent Winter Haven vacation rental reviews

We enjoyed our stay in Winterhaven, Florida. The house was so spacious and beautifully decorated. We had everything we could need. The pool is amazing. The home owner was very attentive and a pleasure to work with. We will come back.
Julie . | May 2026
Would definitely stay again. It was clean and conveniently located. The owner was very responsive. I was slightly lost coming in because it was after dark and she immediately answer with very helpful information.
Danyelle . | Apr 2026
Very nice house,good location.very clean .I definitely will be back again.I love Florida ,I have good time at this house
Cilese . | Apr 2026
Winter Haven Frequently Asked Questions

Yes. 41 of our Winter Haven vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Winter Haven vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Winter Haven team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Winter Haven, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

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