Vacation rentals in Winter Haven

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Top-rated vacation rentals in Winter Haven

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost
Cottage in Winter Haven
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!
Sep. 24 – Oct. 1
$221 CAD per night
4.79 out of 5 average rating, 110 reviews
Guest favourite
Guesthouse in Lake Alfred
Adorable Agave Suite w/ private pool and entrance
Relax & unwind in The Agave Suite, located in a peaceful lake town. This will be your “shome” away from home. Upon entry of the the property you will find a private back entrance, covered parking, private screened in pool and mature trees. Your guesthouse comes equipped with 1 cozy queen size bed, pull-out sofa bed, walk-in shower, kitchenette, smart tv, wifi and more. Looking to explore? We are centrally located to your nearest parks & Florida attractions. Close to fishing docks & bike trails.
Jun. 22 – 29
$139 CAD per night
4.96 out of 5 average rating, 113 reviews
Guest favourite
Apartment 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!
Apr. 28 – May 5
$167 CAD per night
4.99 out of 5 average rating, 135 reviews

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

Other great vacation rentals in Winter Haven

Guest favourite
Guesthouse in Winter Haven
The Paradise Hide Away
Jul. 22 – 29
$138 CAD per night
4.94 out of 5 average rating, 197 reviews
Guest favourite
Home in Winter Haven
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
Aug. 21 – 28
$243 CAD per night
4.82 out of 5 average rating, 137 reviews
Guest favourite
Guesthouse in Winter Haven
Comfy Guest House
Sep. 9 – 16
$132 CAD per night
4.93 out of 5 average rating, 44 reviews
Guest favourite
Home in Winter Haven
Newly remodeled House 3BR/2BA
Aug. 6 – 13
$185 CAD per night
4.87 out of 5 average rating, 31 reviews
Guest favourite
Guest suite in Winter Haven
Cute & Cozy Guesthouse in Winter Haven
Sep. 20 – 27
$132 CAD per night
4.86 out of 5 average rating, 71 reviews
Guest favourite
Home in Winter Haven
The Dalt Retreat
Jun. 4 – 11
$218 CAD per night
4.97 out of 5 average rating, 62 reviews
Guest favourite
Home in Winter Haven
Glass Haven: Serene Getaway 7 min from Legoland!
Sep. 3 – 10
$270 CAD per night
5.0 out of 5 average rating, 37 reviews
Guest favourite
Guesthouse in Auburndale
Cozy 2-bedroom guesthouse on the lake
Feb. 7 – 14
$183 CAD per night
4.98 out of 5 average rating, 89 reviews
Guest favourite
Home in Winter Haven
Yasin's Rogue One
Jun. 24 – Jul. 1
$243 CAD per night
5.0 out of 5 average rating, 41 reviews
Guest favourite
Home in Winter Haven
Cozy Lakefront Home w/ Pool -7 mins from Legoland
Nov. 19 – 26
$275 CAD per night
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Lake Alfred
2-Bedroom Home, Fully Fenced Yard, Central FL!
Dec. 30 – Jan. 6
$186 CAD per night
4.94 out of 5 average rating, 34 reviews
Guest favourite
Cottage in Lake Wales
Charming, renovated 1917 Cottage
Dec. 17 – 24
$169 CAD per night
4.97 out of 5 average rating, 87 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

Destinations to explore

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