A castle entrance with flags and banners, including a LEGO Kingdoms banner.

Search Winter Haven Cottage Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Winter Haven cottages

A small, single-story house with a gray roof and white siding, featuring two white plastic chairs outside.

1. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (198 reviews)
"Clean room and private area loved it"
United States
Heather
The price is S$86
includes taxes & fees
29 Oct - 30 Oct
Lake Ida Beach Resort
A covered porch with two wooden chairs and a bench, overlooking a road and a body of water.

2. Lakefront Retreat on Lake Ariana w/ EV Charger

Lakefront Retreat on Lake Ariana w/ EV Charger
3.0 star property
Auburndale
8.0 out of 10, Very good, (1 review)
"This house has beautiful views of Lake Ariana and you can walk to old town and access the lake easily. The house is an old classic central Florida house with some quirks, but had room for family and entertaining. Auburndale beautiful and was a great place to visit and had quick access to highways. "
United States
Katrina
The price is S$449
includes taxes & fees
27 Oct - 28 Oct
Lakefront Retreat on Lake Ariana w/ EV Charger
A residential street with houses, a parking lot, and a car.

3. Ei8555 - 3BR House Near Disney

Ei8555 - 3BR House Near Disney
3.0 star property
Kissimmee
The price is S$410
includes taxes & fees
31 Oct - 1 Nov
Ei8555 - 3BR House Near Disney
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

4. Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is S$455
includes taxes & fees
5 Nov - 6 Nov
Family Resort Home w Pool, BBQ & Game Room
A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

5. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is S$508
includes taxes & fees
27 Oct - 28 Oct
Serenity - Family & Pet Friendly, Amazing Location
A residential neighborhood with two houses, a driveway, and a lawn.

6. Walkable Dixieland District Gem With Yard

Walkable Dixieland District Gem With Yard
2.0 star property
Dixieland
The price is S$355
includes taxes & fees
27 Oct - 28 Oct
Walkable Dixieland District Gem With Yard
A two-story house with a balcony, two garages, and a brick driveway.

7. Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas

Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
3.5 star property
Reunion
The price is S$943
includes taxes & fees
23 Nov - 24 Nov
Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Haven Hotel Reviews

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"Very clean, nice staff. Rob was very helpful"
cathy 2-night trip
Posted 1 hour ago
Kompose Boutique Resort at Theme Parks

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
1
Accommodation
1936 Cottages
Lowest Price
S$86
Highest Price
S$943

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between S$86 and S$943 per night. These properties offer a chance to get in tune with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Winter Haven?
Pack your suitcases and pick from 1936 cottages in Winter Haven. Thinking about a place where you can get in touch with nature? Expedia can help you find your ideal stay in only a click or two.
Are there any family-friendly cottages in Winter Haven?
If you're looking to get back to nature in Winter Haven, you can't beat Lake Ida Beach Resort. With a 3-star rating and amenities like housekeeping services and WiFi, you'll find it easy to relax at this family-friendly cottage. After checking in and chilling out in your comfy new digs, it's time to head out and start exploring. LEGOLAND® Florida and Indigo's Family Fun Centre are among the best family-friendly attractions in Winter Haven.
Why book your cottage in Winter Haven with Expedia?
Booking a cottage in Winter Haven is as simple as working out your travel dates and picking your ideal place for a getaway in nature. From chic retreats to low-cost stays and cottages that have amenities like laundry facilities, Expedia has something for all tastes and styles. As for the best offers around? We've got them too!
How can I find cheap cottages in Winter Haven?
A great way to track down cheap cottages in Winter Haven is with Expedia's useful filter tool. Tailor your search results by star rating, amenities and budget to discover unbeatable bargains in a few clicks.
What is there to do in Winter Haven near my cottage?
You'll find plenty of fabulous things that'll fill up your itinerary in Winter Haven. Head for top attractions like Indigo's Family Fun Centre, Lake Henry Golf Club and Cypresswood Golf and Country Club. LEGOLAND® Florida, Chain of Lakes Park and Theatre Winter Haven are other must-see's.

Explore a world of travel with Expedia