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
Other great vacation rentals in Winter Haven
Home in Lake Alfred
5.0 out of 5 average rating, 132 reviewsLA Loft, Upstairs private studio
May 25 – Jun 1
Home in Winter Haven
4.9 out of 5 average rating, 153 reviewsHidden Haven Lakehouse Pool by Legoland
Sep 12 – 19
Home in Lakeland
4.96 out of 5 average rating, 115 reviewsCute, Historic District Home - GREAT LOCATION
Aug 27 – Sep 3
Home in Lakeland
4.91 out of 5 average rating, 379 reviewsCharming guest house
Feb 17 – 24
Home in Auburndale
4.95 out of 5 average rating, 136 reviewsthree bedroom family house, near legoland
Jul 6 – 13
Home in Haines City
4.88 out of 5 average rating, 136 reviews3 Bedroom Executive with Private Pool near Disney
Nov 18 – 25
Home in Winter Haven
4.89 out of 5 average rating, 261 reviewsThe Old Haven - An Enduring Piece of Nostalgia
Oct 12 – 19
Home in Haines City
4.95 out of 5 average rating, 139 reviewsLuxury Home 4/3 near Disney, 2 Masters
Oct 31 – Nov 7
Other great vacation rentals in Winter Haven
Loft in Auburndale
4.93 out of 5 average rating, 138 reviews2 Bedroom Apartment near Legoland and Disney
Oct 8 – 15
Guesthouse in Lake Alfred
4.95 out of 5 average rating, 119 reviewsAdorable Agave Suite w/ private pool and entrance
Sep 6 – 13
Guesthouse in Lake Hamilton
4.89 out of 5 average rating, 142 reviewsLuxury Cottage Near Legoland & Chain of Lakes
Sep 22 – 29
Cottage in Davenport
4.92 out of 5 average rating, 129 reviews$79! Cozy Cottage + Outdoor Fun -Close to Disney!
Jun 9 – 16
Guesthouse in Lakeland
4.98 out of 5 average rating, 213 reviewsModern lakeside retreat by SEU and FSC
Jun 17 – 24
Cabin in Davenport
4.92 out of 5 average rating, 169 reviews$89! Cozy Cabin- Disney 20 Miles Away!
Jul 8 – 15
Tiny home in Babson Park
4.92 out of 5 average rating, 290 reviewsLil cedar tiny home, on crooked lake
Condo in Lakeland
4.9 out of 5 average rating, 118 reviewsAdorable 1 bed/1bath with office and free parking
May 22 – 29
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 Downtown Winter Haven, over 250 vacation rentals in Florence Villa, 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 apartment rentals in Winter Haven?
Experience the best of Winter Haven with our apartment rentals, starting at about $20 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 50 homes with a bbq area, over 260 homes with wifi, over 80 homes with self check-in, 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 apartment rentals in Winter Haven have wifi?
Absolutely! We offer over 10 apartment 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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- Monthly Rentals Winter Haven
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