Winter Haven Vacation Rentals

Compare 13 vacation rentals.
Home > USA > Florida > Winter Haven

Make Winter Haven your next getaway

Winter Haven, FL vacation rentals

Top Winter Haven property types

housing_type_house.jpg

House rentals

View 9 House rentals
housing_type_apartment.jpg

Apartments

View 2 Apartments
housing_type_studio.jpg

Studios

View 1 Studios

Browse 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

Popular amenities for Winter Haven vacation rentals

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

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

$447 avg / night
(excludes fees and taxes)
5.0 (3)
Winter Haven Apt: 1 Mi to Polk State College!
1 Bedroom | 1 Bath | Sleeps 2

Winter Haven Apt: 1 Mi to Polk State College! - Winter Haven, FL

$89 avg / night
(excludes fees and taxes)
5.0 (6)
Hot Tub & Fire Pit: Lakefront Home on Lake Eloise
0 Bedroom | 1 Bath | Sleeps 4

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

$196 avg / night
(excludes fees and taxes)
5.0 (19)
Legoland & Lakes Pool Home | Pet Friendly
4 Bedroom | 3 Bath | Sleeps 10

Legoland & Lakes Pool Home | Pet Friendly - Winter Haven, FL

$322 avg / night
(excludes fees and taxes)
5.0 (2)
Waterfront Winter Haven Home with Dock & Hot Tub!
4 Bedroom | 3 Bath | Sleeps 12

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

$390 avg / night
(excludes fees and taxes)
5.0 (13)

View 8 more homes

Recent Winter Haven guest 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 vacation rental FAQ

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 the 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 problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Winter Haven, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning

Nearby destinations

Central Florida   |   Legoland - Florida   |   Cypress Gardens   |   Eagle Lake   |   Auburndale   |   Dundee   |   Haines City   |   Bartow   |   Lake Wales   |   Davenport   |   Polk City   |   Lakeland   |   Champions Gate   |   Babson Park   |   Poinciana   |   Reunion   |   Four Corners   |   Plant City   |   Frostproof   |   Indian Lake Estates   |   Kissimmee   |   Florida
Show more