Book a Winter Haven Cottage

  • 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

Find holiday rentals that suit your style

Apartment image
Apartments
Apartments
apart-hotel image
Aparthotels
Aparthotels

Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Winter Haven cottages

A swimming pool with lounge chairs, surrounded by palm trees and a dock extending into a body of water, during sunset.

1. 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 NZ$348
includes taxes & fees
17 Nov - 18 Nov
The Russell Lake House
A small, single-story house with a gray roof and white siding, featuring two white plastic chairs outside.

2. 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 NZ$131
includes taxes & fees
20 Nov - 21 Nov
Lake Ida Beach Resort
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 NZ$252
includes taxes & fees
2 Dec - 3 Dec
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.
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 NZ$475
includes taxes & fees
8 Nov - 9 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.

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 NZ$628
includes taxes & fees
9 Nov - 10 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.

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
The price is NZ$497
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.

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.
The price is NZ$362
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.

9. 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 NZ$264
includes taxes & fees
8 Nov - 9 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.

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

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is NZ$587
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.

11. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is NZ$728
includes taxes & fees
9 Nov - 10 Nov
Serenity - Family & Pet Friendly, Amazing Location
A modern hotel with a curved driveway, large windows, and palm trees.

12. Mvv7482 - 3BR House Near Disney at Magic Village

Mvv7482 - 3BR House Near Disney at Magic Village
3.0 star property
Kissimmee
The price is NZ$859
includes taxes & fees
16 Nov - 17 Nov
Mvv7482 - 3BR House Near Disney at Magic Village
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

13. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
Perfect Place for a Perfect Vacation
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 NZ$353
includes taxes & fees
7 Dec - 8 Dec
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.

15. 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.
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.

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

Golf, Dine & Unwind Poolside! Haines City Getaway
3.0 star property
Haines City
The price is NZ$767
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.

17. 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
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.

18. 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 NZ$1,331
includes taxes & fees
23 Nov - 24 Nov
Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
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 NZ$548
includes taxes & fees
20 Nov - 21 Nov
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
A residential neighborhood with two houses, a driveway, and a lawn.

20. Walkable Dixieland District Gem With Yard

Walkable Dixieland District Gem With Yard
2.0 star property
Dixieland
The price is NZ$497
includes taxes & fees
9 Nov - 10 Nov
Walkable Dixieland District Gem With Yard
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

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 NZ$131 and NZ$1,331 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.

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