Winter Haven vacation rentals
Book unique homes, vacation rentals, and more on Airbnb
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
Winter Haven home rentals
Home in Winter Haven
4.86 out of 5 average rating, 110 reviewsThe Flamingo
Home in Lake Alfred
5.0 out of 5 average rating, 133 reviewsLA Loft, Upstairs private studio
Home in Lakeland
4.9 out of 5 average rating, 391 reviewsCharming guest house
Home in Lakeland
4.99 out of 5 average rating, 103 reviewsSwan Studio Lakeland
Home in Haines City
4.88 out of 5 average rating, 137 reviews3 Bedroom Executive with Private Pool near Disney
Home in Winter Haven
4.9 out of 5 average rating, 154 reviewsHidden Haven Lakehouse Pool by Legoland
Home in Lakeland
4.96 out of 5 average rating, 120 reviewsCute, Historic District Home - GREAT LOCATION
Home in Plant City
4.99 out of 5 average rating, 446 reviewsThe Strawberry Field Stilt House
Other great vacation rentals in Winter Haven
Guesthouse in Lake Hamilton
4.89 out of 5 average rating, 150 reviewsLuxury Cottage Near Legoland & Chain of Lakes
Apartment in Winter Haven
4.99 out of 5 average rating, 141 reviewsSTAR WARS Galaxy WORLD near LEGO land/Disney World
Loft in Auburndale
4.93 out of 5 average rating, 141 reviews2 Bedroom Apartment near Legoland and Disney
Cottage in Winter Haven
4.84 out of 5 average rating, 122 reviews5 Ships Ahoy Bungalow Unit 17
Guesthouse in Winter Haven
4.87 out of 5 average rating, 235 reviewsThe Russell Lake House
Guesthouse in Lakeland
4.94 out of 5 average rating, 375 reviewsQuaint and Charming Pool Cottage....
Cottage in Eagle Lake
4.99 out of 5 average rating, 227 reviewsLake McLeod, Roe Family House - Close to Legoland
Guesthouse in Lakeland
4.98 out of 5 average rating, 215 reviewsModern lakeside retreat by SEU and FSC
Quick stats about vacation rentals in Winter Haven
Total rentals
370 properties
Rentals with dedicated workspaces
210 properties have a dedicated workspace
Rentals with a pool
80 properties have a pool
Pet-friendly rentals
110 properties allow pets
Family-friendly rentals
210 properties are a good fit for families
Total number of reviews
14K reviews
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 250 vacation rentals in Eagle Lake.
Are there vacation rentals with a dedicated workspace in Winter Haven?
Yes! Work meets play with ease at over 210 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 110 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 80 vacation homes with pools in Winter Haven, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in cottage rentals in Winter Haven?
Experience the best of Winter Haven with our cottage rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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 80 homes with self check-in, over 50 homes with a bbq area, over 260 homes with wifi, over 20 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Winter Haven?
Winter Haven has more than 210 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
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 guesthouse rentals in Winter Haven have wifi?
Absolutely! We offer over 20 guesthouse rentals with wifi 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.
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