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

Search Cottages in Winter Haven

  • 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 €63
includes taxes & fees
29 Oct - 30 Oct
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 €194
includes taxes & fees
30 Oct - 31 Oct
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 €137
includes taxes & fees
27 Oct - 28 Oct
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
A residential area with a large house, a smaller attached garage, and a view of the water.

4. Charming Lakeside Cottage

Charming Lakeside Cottage
Winter Haven
10.0 out of 10, Exceptional, (2 reviews)
"Truly great people. We had a wonderful time! Peaceful and relaxing!!"
United States
Jeremy Kyle W.
The price is €162
includes taxes & fees
27 Oct - 28 Oct
Charming Lakeside Cottage
A single-story house with a front porch, a garage, and a small backyard.

5. 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 €256
includes taxes & fees
27 Oct - 28 Oct
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.

6. 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 €313
includes taxes & fees
27 Oct - 28 Oct
Lakefront Retreat on Lake Ariana w/ EV Charger
A two-story building with a blue exterior, a front porch, and a visible garage door.

7. 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
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.

8. 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, (6 reviews)
"Clean comfort all ok"
United States
Donald P.
Charming Historic Cottage with Cozy Porch and Garden Retreat
A small, single-story house with a porch, surrounded by a well-maintained lawn and a gravel path leading to the entrance.

9. Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland

Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland
Lakeland
The price is €210
includes taxes & fees
27 Oct - 28 Oct
Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland
A small cabin with a porch and a garage, surrounded by trees and a clear sky.

10. 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 €143
includes taxes & fees
27 Oct - 28 Oct
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
A residential street with houses, a parking lot, and a car.

11. Ei8555 - 3BR House Near Disney

Ei8555 - 3BR House Near Disney
3.0 star property
Kissimmee
The price is €291
includes taxes & fees
6 Nov - 7 Nov
Ei8555 - 3BR House Near Disney
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

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

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is €318
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.

13. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is €353
includes taxes & fees
27 Oct - 28 Oct
Serenity - Family & Pet Friendly, Amazing Location
A modern living room with a sofa, a large wall clock, and a mirror.

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

Family-Friendly Cottage Near Orlando’s Top Attractions
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"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 €189
includes taxes & fees
2 Nov - 3 Nov
Family-Friendly Cottage Near Orlando’s Top Attractions
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

15. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is €177
includes taxes & fees
1 Nov - 2 Nov
Perfect Place for a Perfect Vacation
A residential neighborhood with two houses, a driveway, and a lawn.

16. Walkable Dixieland District Gem With Yard

Walkable Dixieland District Gem With Yard
2.0 star property
Dixieland
The price is €248
includes taxes & fees
27 Oct - 28 Oct
Walkable Dixieland District Gem With Yard
A single-story house with a gabled roof, a front porch, and a small front yard with a large agave plant.

17. 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 €285
includes taxes & fees
1 Nov - 2 Nov
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
A compact kitchen with a built-in TV, a dining area with a bench, and a wall decorated with motivational posters.

18. 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 €198
includes taxes & fees
27 Oct - 28 Oct
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
A restaurant with outdoor seating and a thatched roof.

19. "Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.4 out of 10, Exceptional, (14 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is €264
includes taxes & fees
27 Oct - 28 Oct
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
A two-story house with a balcony, two garages, and a brick driveway.

20. 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 €682
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

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"Siempre vengo y recibo el mismo trato, lo recomiendo 100%"
Carlos Rafael Gabriel 2-night trip
Posted 1 hour ago
Hilton Vacation Club Mystic Dunes Orlando

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
100
Accommodation
2409 Cottages
Lowest Price
€63
Highest Price
€682

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between €63 and €682 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 2409 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.