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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

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 HK$620
HK$694 total
includes taxes & fees
15 Nov - 16 Nov
Lake Ida Beach Resort
A swimming pool with lounge chairs, surrounded by palm trees and a dock extending into a body of water, during sunset.

2. The Russell Lake House

The Russell Lake House
Winter Haven
9.8 out of 10, Exceptional, (25 reviews)
"Nice place!"
United States
Jake D.
The price is HK$530
HK$1,574 total
includes taxes & fees
13 Nov - 14 Nov
The Russell Lake House
A wooden deck with outdoor seating, a shed, and a view of the surrounding landscape.

3. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

Lakefront Tiny Cottage 4 Miles to LEGOLAND.
winter have
9.0 out of 10, Wonderful, (42 reviews)
"Awesome location, very nice"
United States
Kyle P.
The price is HK$549
HK$1,105 total
includes taxes & fees
22 Nov - 23 Nov
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
A single-story house with a front porch, a garage, and a small backyard.

4. Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
9.2 out of 10, Wonderful, (7 reviews)
"Wonderful little cottage filled with fun for the whole family. Cozy backyard to enjoy some sunshine and read a book. Close to downtown shops and restaurants. Owners were quick to respond to questions. Would happily stay here again."
United States
Rachel B.
The price is HK$902
HK$2,108 total
includes taxes & fees
18 Nov - 19 Nov
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
A covered porch with two wooden chairs and a bench, overlooking a road and a body of water.

5. 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 HK$1,020
HK$2,754 total
includes taxes & fees
26 Nov - 27 Nov
Lakefront Retreat on Lake Ariana w/ EV Charger
A two-story building with a blue exterior, a front porch, and a visible garage door.

6. Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland

Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland
Lake Hamilton
The price is HK$1,222
HK$2,300 total
includes taxes & fees
13 Nov - 14 Nov
Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland
A single-story house with a stone retaining wall, a front porch, and a small garden.

7. Charming Historic Cottage with Cozy Porch and Garden Retreat

Charming Historic Cottage with Cozy Porch and Garden Retreat
Polk City
10.0 out of 10, Exceptional, (7 reviews)
"Clean comfort all ok"
United States
Donald P.
The price is HK$675
HK$1,612 total
includes taxes & fees
22 Nov - 23 Nov
Charming Historic Cottage with Cozy Porch and Garden Retreat
A small cabin with a porch and a garage, surrounded by trees and a clear sky.

8. Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Davenport
6.8 out of 10, (3 reviews)
"Needs some upgrades. The bed was a full size, very small for a couple, should really think of upgrading to a king. Pans were old and could use replacing. Bugs and ants constant. Shower was small. Very small tv. Stovetop had missing nob and was difficult to operate. Definitely needs upgrading, left a day early, didn’t feel comfortable there. "
United States
Rebecca F.
The price is HK$558
HK$1,158 total
includes taxes & fees
18 Nov - 19 Nov
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

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

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is HK$816
HK$2,574 total
includes taxes & fees
29 Nov - 30 Nov
Family Resort Home w Pool, BBQ & Game Room
A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

10. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is HK$672
HK$3,052 total
includes taxes & fees
15 Nov - 16 Nov
Serenity - Family & Pet Friendly, Amazing Location
A poolside area with lounge chairs and palm trees, a clear blue sky, and a building with a modern design.

11. Mvy7664 - 3BR House Near Disney With Hot Tub

Mvy7664 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
Mvy7664 - 3BR House Near Disney With Hot Tub
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

12. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
9.0 out of 10, Wonderful, (2 reviews)
"Clean. A little confusing on the location. Gate guard was a little tough. Price a little high for a double wide."
United States
Michael R.
The price is HK$657
HK$1,471 total
includes taxes & fees
18 Nov - 19 Nov
Perfect Place for a Perfect Vacation
A modern living room with a sofa, a large wall clock, and a mirror.

13. Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"Perfect location to enjoy Universal Epic and Islands of Adventure with only a 15 minute ride. The beds were very comfortable and the place is clean. We were welcomed with a cute sign, bottled water and cookies. Will definitely stay here again!"
United States
Joyce R.
The price is HK$800
HK$1,641 total
includes taxes & fees
18 Nov - 19 Nov
Family-Friendly Cottage Near Orlando’s Top Attractions
A single-story house with a gabled roof, a front porch, and a small front yard with a large agave plant.

14. Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
The price is HK$775
HK$2,371 total
includes taxes & fees
18 Nov - 19 Nov
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
A two-story residential building with a garage, a small tree, and a well-maintained lawn.

15. Golf, Dine & Unwind Poolside! Haines City Getaway

Golf, Dine & Unwind Poolside! Haines City Getaway
3.0 star property
Haines City
The price is HK$1,326
HK$3,366 total
includes taxes & fees
1 Dec - 2 Dec
Golf, Dine & Unwind Poolside! Haines City Getaway
A compact kitchen with a built-in TV, a dining area with a bench, and a wall decorated with motivational posters.

16. Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Kissimmee
The price is HK$727
HK$1,593 total
includes taxes & fees
16 Nov - 17 Nov
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
A two-story house with a balcony, two garages, and a brick driveway.

17. 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 HK$1,949
HK$5,931 total
includes taxes & fees
23 Nov - 24 Nov
Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
A residential neighborhood with two houses, a driveway, and a lawn.

18. Walkable Dixieland District Gem With Yard

Walkable Dixieland District Gem With Yard
2.0 star property
Dixieland
The price is HK$989
HK$2,182 total
includes taxes & fees
15 Nov - 16 Nov
Walkable Dixieland District Gem With Yard
A modern hotel with a curved driveway, large windows, and palm trees.

19. Mvv7561 - 4BR House Near Disney World

Mvv7561 - 4BR House Near Disney World
3.0 star property
Kissimmee
The price is HK$1,785
HK$4,020 total
includes taxes & fees
8 Dec - 9 Dec
Mvv7561 - 4BR House Near Disney World
A single-story house with a white exterior, a front door, and a garage.

20. 9 Mi to Walt Disney World: Family Home w/ Pool!

9 Mi to Walt Disney World: Family Home w/ Pool!
3.0 star property
Clear Creek
9 Mi to Walt Disney World: Family Home w/ Pool!
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.
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Learn more about Winter Haven

Glide through LEGOLAND's colourful rides before cooling off at their water park on hot Florida afternoons. Chain of Lakes offers peaceful kayaking spots where you can paddle between waterways and spot wildlife at your own pace.

See all hotels in Winter Haven
A LEGO-themed welcome sign with 'LEGO FLORIDA' and 'WELCOME' in large letters, surrounded by greenery.

Frequently Asked Questions

How much do cottages in Winter Haven cost?

Cottages in Winter Haven range between HK$529 and HK$1,948 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 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.