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.
Cottage in Winter Haven
4.8 out of 5 average rating, 113 reviewsJust Beachin' Cabin Unit 10
Experience the tranquility of the Sunshine State from this quaint-yet-modern vacation rental home, complete with 2 bedrooms, 2 bathrooms, a private deck, and modern interior finishes. You’ll enjoy direct access to a boat launch and the Chain of Lakes, a fishing and boating paradise complete with 24 canal-connected lakes! Spend your days out on the water, make incredible memories with your family at LEGOLAND Florida, or opt to visit the theme parks in Orlando - from this home, you can do it all!
Oct 1 – 8
Guesthouse in Winter Haven
4.94 out of 5 average rating, 198 reviewsThe Paradise Hide Away
This is a beautiful and private place newly renovated with private access and parking. It’s a great place to get away and relax with a large and beautiful backyard! Talk to me if you need different check in/out times? Dogs are allowed with permission. There is a $200 fully refundable pet security deposit to cover any damages that may occur since Airbnb doesn’t cover damages caused by pets plus a non refundable pet fee of $50 per pet for every 1-7 day period and must be paid before checking in !
Aug 25 – Sep 1
Apartment in Winter Haven
4.99 out of 5 average rating, 135 reviewsFlorida Penthouse in luxurious mansion!
Stay in your own themed Florida apartment . Tropical, palm trees, beaches ,marine life, flamingos throughout this stunning apartment in a multimillion dollar home. After parking on gated driveway walk up to your own private entrance way to paradise. Keyless entrance. One flight up and your viewing gorgeous lake views second to none. Executive kitchen with everything you need to cook a 5 course meal. Outdoor balcony that will leave you amazed. Opulence, security, with Florida Style awaits you!
Apr 28 – May 5
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
4.79 out of 5 average rating, 269 reviewsFlorida Oasis w/ Pool near LEGOLAND
Jan 26 – Feb 2
Home in Winter Haven
4.86 out of 5 average rating, 189 reviews💎LakeFront💎ModernCottageTiny-Home☀🎢4milesLEGOLAND🎢
Jul 24 – 31
Home in Winter Haven
4.9 out of 5 average rating, 256 reviewsThe Old Haven - An Enduring Piece of Nostalgia
Nov 6 – 13
Home in Haines City
4.88 out of 5 average rating, 136 reviews3 Bedroom Executive with Private Pool near Disney
Oct 23 – 30
Home in Winter Haven
4.91 out of 5 average rating, 150 reviewsHidden Haven Lakehouse Pool by Legoland
Jul 30 – Aug 6
Home in Winter Haven
4.83 out of 5 average rating, 127 reviewsFlorida Getaway near Legoland& Orlando Attractions
Aug 1 – 8
Home in Haines City
4.96 out of 5 average rating, 137 reviewsLuxury Home 4/3 near Disney, 2 Masters
Sep 15 – 22
Home in Winter Haven
4.91 out of 5 average rating, 143 reviewsA Little Slice of "Haven" Home (No Cleaning Fee)
Feb 24 – Mar 3
Home in Lakeland
4.95 out of 5 average rating, 111 reviewsCute, Historic District Home - GREAT LOCATION
Jul 6 – 13
Home in Lakeland
4.91 out of 5 average rating, 376 reviewsCharming guest house
Jul 3 – 10
Home in Winter Haven
4.88 out of 5 average rating, 33 reviewsNewly remodeled House 3BR/2BA
Dec 7 – 14
Home in Winter Haven
4.97 out of 5 average rating, 62 reviewsThe Dalt Retreat
Jul 30 – Aug 6
Other great vacation rentals in Winter Haven
Guesthouse in Auburndale
4.97 out of 5 average rating, 191 reviewsPrivate Poolside Villa
Jul 31 – Aug 7
Villa in Lake Wales
4.99 out of 5 average rating, 179 reviewsLakefront, Dock, 2 Kayaks, near Bok & Legoland
Dec 6 – 13
Apartment in Auburndale
4.96 out of 5 average rating, 211 reviewsAriana Place - Tree House Like Lakefront Views
Dec 2 – 9
Guesthouse in Lake Alfred
4.96 out of 5 average rating, 113 reviewsAdorable Agave Suite w/ private pool and entrance
May 5 – 12
Guesthouse in Winter Haven
4.87 out of 5 average rating, 141 reviewsBrutus Way Cottage, a cosy hide away
Jul 4 – 11
Cottage in Davenport
4.92 out of 5 average rating, 123 reviews$79! Cozy Cottage + Outdoor Fun -Close to Disney!
May 28 – Jun 4
Loft in Auburndale
4.94 out of 5 average rating, 131 reviews2 Bedroom Apartment near Legoland and Disney
Aug 11 – 18
Cabin in Davenport
4.92 out of 5 average rating, 164 reviews$89! Cozy Cabin- Disney 20 Miles Away!
May 6 – 13
Guesthouse in Lake Hamilton
4.9 out of 5 average rating, 134 reviewsLuxury Cottage Near Legoland & Chain of Lakes
Aug 31 – Sep 7
Guesthouse in Winter Haven
4.91 out of 5 average rating, 47 reviewsComfy Guest House
Nov 20 – 27
Guesthouse in Auburndale
4.98 out of 5 average rating, 89 reviewsCozy 2-bedroom guesthouse on the lake
Jan 9 – 16
Guest suite in Winter Haven
4.86 out of 5 average rating, 71 reviewsCute & Cozy Guesthouse in Winter Haven
Jun 8 – 15
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 Eagle Lake, and over 240 vacation rentals in Florence Villa.
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 guesthouse rentals in Winter Haven?
Experience the best of Winter Haven with our guesthouse rentals, starting at about $40 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 10 homes with a gym, over 80 homes with self check-in, 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 apartment rentals in Winter Haven have wifi?
Absolutely! We offer over 20 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 10 house rentals with a gym in Winter Haven. Enjoy a tailored experience with all the comforts you desire.
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