Holiday rentals in Winter Haven

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Top-rated holiday rentals in Winter Haven

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Guest favourite

Guest house in Winter Haven

4.95 out of 5 average rating, 202 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 !

16–23 Dec

$102 SGD per night

Superhost

Cottage in Winter Haven

4.8 out of 5 average rating, 117 reviews

9 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 Jan

$183 SGD per night

Guest favourite

Guest house in Lake Alfred

4.96 out of 5 average rating, 116 reviews

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.

8–15 Sep

$128 SGD per night

Guest favourite

Guest house in Winter Haven

4.87 out of 5 average rating, 142 reviews

Brutus Way Cottage, a cosy hide away

Enjoy a quick get away at Brutus Way Cottage. It is located to the rear of Lili Haven Bed N Breakfast. On your picturesque drive around Lake Howard, with its walking trail, you will take a right onto a quaint curvy lane known as S. Lake Cannon Drive NW . Be my guest at the cottage surrounded by flowers ; the cottage is nestled in the trees to the back past the Iron gates. Use of the Laundry room available upon request. Have a Hallmark Christmas as we decorate with stylish frills and spills

20–27 Jun

$108 SGD per night

Guest favourite

Flat in Auburndale

4.96 out of 5 average rating, 212 reviews

Ariana Place - Tree House Like Lakefront Views

An Upstairs Sumptuous Tree house (like) Apt on Lake Ariana Waterfront. Upper Outside Deck with chairs & table. Quiet and tranquil with Hi-Speed Wifi for Business Travelers, Smart Antenna TV and Incredible Views for Romantic Get-Aways. Located near Disney, Legoland & Busch Gardens in Central Florida. Luxurious Bedding, Full Kitchen with Coffee & Wine Bar. One Complimentary Bottle of Cabernet per Stay. Sorry, No Pets. No Smoking inside Apt but allowed on property. Save 5% monthly

13–20 Jun

$115 SGD per night

Superhost

Guest house in Winter Haven

4.87 out of 5 average rating, 230 reviews

The Russell Lake House

This is a Cabana. It has 2 sets of bunk beds (4 total beds). Approx 400 sq. Ft. . Includes a bathroom with sink, toilet, and walk-in shower. AC and heat are available. The property has a pool that can be used while onsite. The entire property's back yard is on a lake (lakefront) with a dock. Ample off street parking, quiet neighborhood with a private entrance for guests. **** we are in the process of rebuilding the dock so it will be unavailable until further notice ****

9–16 Dec

$115 SGD per night

Guest favourite

Guest house in Winter Haven

4.84 out of 5 average rating, 144 reviews

Adorable 1 bedroom Guesthouse near Lego Land

This is a beautiful and private place offers a queen size bed, newly renovated with private access and parking. It’s a great place to get away and relax with a large and beautiful backyard! We are located less than 8.6 miles from Legoland & under 6.2 miles from the Lake Myrtle Sports complex. Winter Haven is halfway between Orlando and Tampa. Around 29 miles to Disney World, Universal and Sea World. Around 38 miles to Bush Gardens, Dali museum, Aquarium and much more!

23–30 Jun

$117 SGD per night

Guest favourite

Guest house in Winter Haven

4.91 out of 5 average rating, 54 reviews

Comfy Guest House

Welcome to our inviting and family-friendly guest house, designed with your comfort and privacy in mind. Ideal for travellers visiting our wonderful city, our 1-bedroom retreat features a cozy queen bed and a full bathroom, ensuring a relaxing stay for up to 2 guest. The well-equipped kitchen area boasts a sink, refrigarator, microwave, cooking appliances, utensils, and a convenient pantry to store your items. Stay connected with our strong WiFi connection.

27 Aug – 3 Sep

$132 SGD per night

Guest favourite

Home in Winter Haven

4.94 out of 5 average rating, 141 reviews

Cozy Family Home Near Legoland

Relax with the fam after a fun day at LEGOLAND (4.1 miles) or Disney World (36 miles) in our cozy home complete with a well-stocked kitchen, fully-fenced backyard, and comfortable beds. Spend a day on the famous Chain of Lakes (24 canal-connected lakes), catch a free ski show on Lake Silver, wander downtown to shop, or toast a pint at Union Taproom. Winter Haven is centrally located between Tampa and Orlando with plenty of fun nearby for the whole family.

13–20 Aug

$176 SGD per night

Guest favourite

Guest suite in Winter Haven

4.91 out of 5 average rating, 140 reviews

2 Bedroom Winter Haven Guest Suite

Private lock-off unit. Only shared between your party. 1st bedroom -Queen bed and sitting area bathroom attached. 2nd bedroom- two twin sized beds Kitchen and living room included and not shared outside of your party. 3 minutes from Winter Haven hospital. Self check in and out. 20 minutes from Legoland. 45 minutes from Disney and Universal This is an older florida neighborhood with a diverse and working class vibe. Located on Lake Maude

2–9 Dec

$138 SGD per night

Guest favourite

Guest suite in Winter Haven

4.96 out of 5 average rating, 256 reviews

Horse Farm on a Beautiful Lake

Small Thoroughbred Race Horse Farm on a beautiful lake. Fishing available on site. New dock just finished with plenty of benches for fishing, picnicking, or just dreaming. There is a Swimming pool right out your door, horse paddocks and patio overlooking the lake for hanging out or quiet time. Please note price is for studio (sleeps 3 or more with sofa beds)

23–30 Jul

$156 SGD per night

Superhost

Home in Winter Haven

4.87 out of 5 average rating, 109 reviews

The Flamingo

The Flamingo has been completely refreshed with paint, flooring, beds, furniture and many kitchen amenities. It is located 5 miles from Legoland, 30 miles to Disney World, near great restaurants, lakes, downtown Winter Haven and various shopping and attractions.

20–27 Nov

$135 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Winter Haven holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Winter Haven's top sights

LEGOLAND Florida Water Park104 locals recommend

Winter Haven Hospital4 locals recommend

Harborside25 locals recommend

Chain O' Lakes Complex4 locals recommend

Manny's Chophouse- Winter Haven9 locals recommend

Andy's Dine-In Restaurant14 locals recommend

Other great holiday rentals in Winter Haven

Guest favourite

Home in Winter Haven

4.89 out of 5 average rating, 36 reviews

Newly remodeled House 3BR/2BA

19–26 Feb

$144 SGD per night

Guest favourite

Home in Winter Haven

4.99 out of 5 average rating, 93 reviews

Beautiful Lake House Boating Fishing near Legoland

17–24 Jun

$162 SGD per night

Guest favourite

Tiny home in Winter Haven

4.95 out of 5 average rating, 19 reviews

Tiny home in Winter Haven hosted by Bob & Susana

24 Jun – 1 Jul

$126 SGD per night

Guest favourite

Guest suite in Winter Haven

4.86 out of 5 average rating, 73 reviews

Cute & Cozy Guesthouse in Winter Haven

23–30 Mar

$110 SGD per night

Guest favourite

Home in Winter Haven

4.97 out of 5 average rating, 62 reviews

The Dalt Retreat

24–31 Jul

$174 SGD per night

Guest favourite

Home in Winter Haven

5.0 out of 5 average rating, 44 reviews

Glass Haven: Serene Getaway 7 min from Legoland!

28 Feb – 7 Mar

$220 SGD per night

Guest favourite

Guest house in Auburndale

4.98 out of 5 average rating, 94 reviews

Cozy 2-bedroom guesthouse on the lake

10–17 Dec

$157 SGD per night

Guest favourite

Home in Winter Haven

4.93 out of 5 average rating, 14 reviews

Kid-friendly Home w/ Pool & BBQ

5–12 Aug

$211 SGD per night

Show all

Quick stats about holiday rentals in Winter Haven

Total rentals	370 properties
Rentals with dedicated workspaces	210 properties have a dedicated workspace
Rentals with a pool	80 properties have a pool
Pet-friendly rentals	110 properties allow pets
Family-friendly rentals	210 properties are a good fit for families
Total number of reviews	14K reviews

Holiday rentals in Winter Haven

Top-rated holiday rentals in Winter Haven

Guest house in Winter Haven

Cottage in Winter Haven

Guest house in Lake Alfred

Guest house in Winter Haven

Flat in Auburndale

Guest house in Winter Haven

Guest house in Winter Haven

Guest house in Winter Haven

Home in Winter Haven

Guest suite in Winter Haven

Guest suite in Winter Haven

Home in Winter Haven

Holiday rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Winter Haven holiday rentals

Stay near Winter Haven's top sights

Other great holiday rentals in Winter Haven

Home in Winter Haven

Home in Winter Haven

Tiny home in Winter Haven

Guest suite in Winter Haven

Home in Winter Haven

Home in Winter Haven

Guest house in Auburndale

Home in Winter Haven

Quick stats about holiday rentals in Winter Haven

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Destinations to explore