Holiday rentals in Winter Haven

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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

4.94 out of 5 average rating, 198 reviews

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 !

25 Aug – 1 Sept

£76 per night
Superhost

Cottage in Winter Haven

4.8 out of 5 average rating, 113 reviews

Just 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

£126 per night
Guest favourite

Flat in Winter Haven

4.99 out of 5 average rating, 135 reviews

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 May

£98 per night

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 Auburndale

4.97 out of 5 average rating, 191 reviews

Private Poolside Villa

31 Jul – 7 Aug

£76 per night
Superhost

Home in Winter Haven

4.79 out of 5 average rating, 269 reviews

Florida Oasis w/ Pool near LEGOLAND

26 Jan – 2 Feb

£140 per night
Guest favourite

Guest house in Lake Hamilton

4.9 out of 5 average rating, 134 reviews

Luxury Cottage Near Legoland & Chain of Lakes

9–16 May

£107 per night
Guest favourite

Flat in Auburndale

4.96 out of 5 average rating, 211 reviews

Ariana Place - Tree House Like Lakefront Views

2–9 Dec

£77 per night
Guest favourite

Villa in Lake Wales

4.99 out of 5 average rating, 179 reviews

Lakefront, Dock, 2 Kayaks, near Bok & Legoland

6–13 Dec

£134 per night
Guest favourite

Guest house in Lake Alfred

4.96 out of 5 average rating, 113 reviews

Adorable Agave Suite w/ private pool and entrance

5–12 May

£82 per night
Guest favourite

Guest house in Winter Haven

4.87 out of 5 average rating, 141 reviews

Brutus Way Cottage, a cosy hide away

4–11 Jul

£78 per night
Superhost

Home in Winter Haven

4.86 out of 5 average rating, 189 reviews

💎LakeFront💎ModernCottageTiny-Home☀🎢4milesLEGOLAND🎢

24–31 Jul

£90 per night
Guest favourite

Home in Winter Haven

4.88 out of 5 average rating, 33 reviews

Newly remodeled House 3BR/2BA

7–14 Dec

£109 per night
Guest favourite

Guest house in Winter Haven

4.91 out of 5 average rating, 47 reviews

Comfy Guest House

2–9 Oct

£78 per night
Guest favourite

Home in Winter Haven

4.97 out of 5 average rating, 62 reviews

The Dalt Retreat

30 Jul – 6 Aug

£131 per night
Guest favourite

Guest suite in Winter Haven

4.86 out of 5 average rating, 71 reviews

Cute & Cozy Guesthouse in Winter Haven

14–21 Nov

£77 per night

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