Winter Haven vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

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Popular amenities for Winter Haven vacation rentals

Stay near Winter Haven's top sights

LEGOLAND Florida Water Park104 locals recommend
Winter Haven Hospital4 locals recommend
Harborside25 locals recommend
Manny's Chophouse- Winter Haven9 locals recommend
Andy's Dine-In Restaurant14 locals recommend
Azteca D' Oro8 locals recommend

Winter Haven home rentals

Superhost
Home in Winter Haven
💎LakeFront💎ModernCottageTiny-Home☀🎢4milesLEGOLAND🎢
May 21 – 28
$78 per night
4.86 out of 5 average rating, 188 reviews
Guest favorite
Home in Winter Haven
Hidden Haven Lakehouse Pool by Legoland
Aug 2 – 9
$173 per night
4.91 out of 5 average rating, 149 reviews
Guest favorite
Home in Lake Alfred
LA Loft, Upstairs private studio
Aug 6 – 13
$77 per night
5.0 out of 5 average rating, 133 reviews
Guest favorite
Home in Winter Haven
A Little Slice of "Haven" Home (No Cleaning Fee)
Dec 24 – 31
$130 per night
4.91 out of 5 average rating, 143 reviews
Guest favorite
Home in Haines City
3 Bedroom Executive with Private Pool near Disney
Oct 23 – 30
$114 per night
4.88 out of 5 average rating, 136 reviews
Guest favorite
Home in Auburndale
three bedroom family house, near legoland
May 12 – 19
$113 per night
4.95 out of 5 average rating, 127 reviews
Guest favorite
Home in Winter Haven
Glass Haven: Serene Getaway 7 min from Legoland!
Nov 25 – Dec 2
$141 per night
5.0 out of 5 average rating, 37 reviews
Guest favorite
Home in Winter Haven
Newly remodeled House 3BR/2BA
Oct 23 – 30
$91 per night
4.87 out of 5 average rating, 31 reviews

Other great vacation rentals in Winter Haven

Guest favorite
Guesthouse in Winter Haven
Brutus Way Cottage, a cosy hide away
May 22 – 29
$71 per night
4.87 out of 5 average rating, 140 reviews
Guest favorite
Cottage in Davenport
$79! Cozy Cottage + Outdoor Fun -Close to Disney!
Apr 22 – 29
$82 per night
4.92 out of 5 average rating, 122 reviews
Guest favorite
Guesthouse in Winter Haven
Quiet,Country and Close to Everything!
May 17 – 24
$112 per night
4.98 out of 5 average rating, 122 reviews
Guest favorite
Guesthouse in Auburndale
Private Poolside Villa
May 31 – Jun 7
$67 per night
4.97 out of 5 average rating, 190 reviews
Guest favorite
Guest suite in Dundee
Zetta's Hide-a-Way
May 20 – 27
$59 per night
4.94 out of 5 average rating, 123 reviews
Superhost
Guesthouse in Winter Haven
The Russell Lake House
Dec 26 – Jan 2
$74 per night
4.88 out of 5 average rating, 225 reviews
Guest favorite
Guesthouse in Lake Alfred
Adorable Agave Suite w/ private pool and entrance
Aug 24 – 31
$79 per night
4.96 out of 5 average rating, 113 reviews
Guest favorite
Guesthouse in Winter Haven
Comfy Guest House
May 23 – 30
$77 per night
4.93 out of 5 average rating, 44 reviews

Quick stats about vacation rentals in Winter Haven

Total rentals

360 properties

Rentals with dedicated workspaces

210 properties have a dedicated workspace

Rentals with a pool

80 properties have a pool

Pet-friendly rentals

120 properties allow pets

Family-friendly rentals

200 properties are a good fit for families

Total number of reviews

13K 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 240 vacation rentals in Downtown Winter Haven, over 240 vacation rentals in Florence Villa, and over 240 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 120 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 condo rentals in Winter Haven?

    Experience the best of Winter Haven with our condo rentals, starting at about $60 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 10 homes with a gym, over 250 homes with wifi, 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 200 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 house rentals in Winter Haven have wifi?

    Absolutely! We offer over 250 house 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 10 house rentals with a gym in Winter Haven. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Polk County
  5. Winter Haven