Holiday rentals in Winter Haven
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Winter Haven
Guests agree: these stays are highly rated for location, cleanliness and more.
Guest house 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 !
25 Aug – 1 Sept
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!
1–8 Oct
Flat 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!
28 Apr – 5 May
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Haven holiday rentals
Other great holiday rentals in Winter Haven
Guest house in Auburndale
4.97 out of 5 average rating, 191 reviewsPrivate Poolside Villa
31 Jul – 7 Aug
Home in Winter Haven
4.79 out of 5 average rating, 269 reviewsFlorida Oasis w/ Pool near LEGOLAND
26 Jan – 2 Feb
Guest house in Lake Hamilton
4.9 out of 5 average rating, 134 reviewsLuxury Cottage Near Legoland & Chain of Lakes
9–16 May
Flat in Auburndale
4.96 out of 5 average rating, 211 reviewsAriana Place - Tree House Like Lakefront Views
2–9 Dec
Villa in Lake Wales
4.99 out of 5 average rating, 179 reviewsLakefront, Dock, 2 Kayaks, near Bok & Legoland
6–13 Dec
Guest house in Lake Alfred
4.96 out of 5 average rating, 113 reviewsAdorable Agave Suite w/ private pool and entrance
5–12 May
Guest house in Winter Haven
4.87 out of 5 average rating, 141 reviewsBrutus Way Cottage, a cosy hide away
4–11 Jul
Home in Winter Haven
4.86 out of 5 average rating, 189 reviews💎LakeFront💎ModernCottageTiny-Home☀🎢4milesLEGOLAND🎢
24–31 Jul
Home in Winter Haven
4.88 out of 5 average rating, 33 reviewsNewly remodeled House 3BR/2BA
7–14 Dec
Guest house in Winter Haven
4.91 out of 5 average rating, 47 reviewsComfy Guest House
2–9 Oct
Home in Winter Haven
4.97 out of 5 average rating, 62 reviewsThe Dalt Retreat
30 Jul – 6 Aug
Guest suite in Winter Haven
4.86 out of 5 average rating, 71 reviewsCute & Cozy Guesthouse in Winter Haven
14–21 Nov
Quick stats about holiday 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 |
Destinations to explore
- Kissimmee Holiday rentals
- Orlando Holiday rentals
- Tampa Holiday rentals
- Sarasota Holiday rentals
- Anna Maria Island Holiday rentals
- Naples Holiday rentals
- West Palm Beach Holiday rentals
- Boca Raton Holiday rentals
- Fort Lauderdale Holiday rentals
- Miami Holiday rentals
- Miami Beach Holiday rentals
- Key West Holiday rentals
- Rentals with outdoor seating Winter Haven
- Family-friendly rentals Winter Haven
- Rentals with lake access Winter Haven
- Waterfront rentals Winter Haven
- Rentals with a patio Winter Haven
- Rentals with pools Winter Haven
- Monthly Rentals Winter Haven
- Pet-friendly rentals Winter Haven
- Rentals with a firepit Winter Haven
- Rentals with a hot tub Winter Haven
- House rentals Winter Haven
- Rentals with a washing machine and dryer Winter Haven
- Fitness-friendly rentals Winter Haven
- Rentals with a fireplace Winter Haven
- Family-friendly rentals Winter Haven
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom