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 favourite
Guest house in Winter Haven
The 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 !
22–29 JulIndividual Host,
€ 93 per night
4.94 out of 5 average rating, 195 reviews
Guest favourite
Flat in Winter Haven
Florida 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 MayIndividual Host,
€ 114 per night
4.99 out of 5 average rating, 135 reviews
Guest favourite
Cottage in Eagle Lake
Central FL Lake House, Sleeps 5, Close to Legoland
We can't wait for you to enjoy our fully renovated, family friendly lake house. It's a happy home that provides a wonderful backdrop to any vacation. Centrally located to many Florida destinations- Legoland is only 7 miles away, Disney World is 35 miles away, and you are less than 50 miles from Tampa. The house is located on over an acre of lakefront property. The lake has a public boat launch if your family enjoys water sports or fishing or use the paddle boards we provide on site!
13–20 NovIndividual Host,
€ 182 per night
4.99 out of 5 average rating, 216 reviews

Popular amenities for Winter Haven holiday 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

Other great holiday rentals in Winter Haven

Guest favourite
Guest house in Winter Haven
Brutus Way Cottage, a cosy hide away
22–29 MayIndividual Host,
€ 91 per night
4.87 out of 5 average rating, 140 reviews
Guest favourite
Guest house in Winter Haven
Comfy Guest House
9–16 SepIndividual Host,
€ 90 per night
4.93 out of 5 average rating, 44 reviews
Guest favourite
Guest suite in Winter Haven
Cute & Cozy Guesthouse in Winter Haven
20–27 SepIndividual Host,
€ 90 per night
4.86 out of 5 average rating, 71 reviews
Guest favourite
Home in Winter Haven
Glass Haven: Serene Getaway 7 min from Legoland!
25 Nov – 2 DecIndividual Host,
€ 185 per night
5.0 out of 5 average rating, 37 reviews
Guest favourite
Home in Winter Haven
Newly remodeled House 3BR/2BA
23–30 OctIndividual Host,
€ 127 per night
4.87 out of 5 average rating, 31 reviews
Guest favourite
Home in Winter Haven
The Dalt Retreat
4–11 JunIndividual Host,
€ 149 per night
4.97 out of 5 average rating, 62 reviews
Guest favourite
Home in Winter Haven
Yasin's Rogue One
24 Jun – 1 JulIndividual Host,
€ 166 per night
5.0 out of 5 average rating, 41 reviews
Guest favourite
Home in Winter Haven
The Family Friendly Fun House
6–13 JunIndividual Host,
€ 200 per night
4.97 out of 5 average rating, 36 reviews
Guest favourite
Home in Winter Haven
Beautiful home near downtown - 15 min to Legoland!
13–20 AprIndividual Host,
€ 173 per night
4.98 out of 5 average rating, 47 reviews
Guest favourite
Guest house in Auburndale
Cozy 2-bedroom guesthouse on the lake
16–23 JunIndividual Host,
€ 124 per night
4.98 out of 5 average rating, 87 reviews
Guest favourite
Home in Winter Haven
Cozy Lakefront Home w/ Pool -7 mins from Legoland
8–15 JulIndividual Host,
€ 221 per night
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Winter Haven
Spectacular Waterfront Home in Winter Haven
11–18 AprProfessional Host,
€ 687 per night
4.98 out of 5 average rating, 95 reviews

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

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