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

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Check prices for these dates

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

Our top choices for Winter Haven cottages

A swimming pool with a fence, lounge chairs, and a palm tree.

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 CA $93
CA $104 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $94
CA $296 total
includes taxes & fees
Nov 5 - Nov 6
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 CA $98
CA $208 total
includes taxes & fees
Nov 5 - Nov 6
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 CA $161
CA $394 total
includes taxes & fees
Nov 5 - Nov 6
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
A residential area with a large house, a smaller attached garage, and a view of the water.

5. 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 CA $126
CA $247 total
includes taxes & fees
Nov 10 - Nov 11
Charming Lakeside Cottage
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 CA $159
CA $358 total
includes taxes & fees
Oct 31 - Nov 1
Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland
A covered porch with two wooden chairs and a bench, overlooking a road and a body of water.

7. 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 CA $182
CA $491 total
includes taxes & fees
Nov 10 - Nov 11
Lakefront Retreat on Lake Ariana w/ EV Charger
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 CA $119
CA $300 total
includes taxes & fees
Nov 22 - Nov 23
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 CA $99
CA $218 total
includes taxes & fees
Oct 31 - Nov 1
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
A small, single-story house with a porch, surrounded by a well-maintained lawn and a gravel path leading to the entrance.

10. 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 CA $170
CA $320 total
includes taxes & fees
Nov 2 - Nov 3
Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

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

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is CA $157
CA $471 total
includes taxes & fees
Nov 5 - Nov 6
Family Resort Home w Pool, BBQ & Game Room
A residential street with houses, a parking lot, and a car.

12. Ei8555 - 3BR House Near Disney

Ei8555 - 3BR House Near Disney
3.0 star property
Kissimmee
The price is CA $203
CA $455 total
includes taxes & fees
Nov 6 - Nov 7
Ei8555 - 3BR House Near Disney
A row of yellow buildings with numbered doors, a sidewalk, and greenery.

13. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is CA $128
CA $553 total
includes taxes & fees
Oct 31 - Nov 1
Serenity - Family & Pet Friendly, Amazing Location
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

14. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is CA $113
CA $269 total
includes taxes & fees
Nov 1 - Nov 2
Perfect Place for a Perfect Vacation
A modern living room with a sofa, a large wall clock, and a mirror.

15. 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 CA $137
CA $300 total
includes taxes & fees
Nov 3 - Nov 4
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.

16. 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 CA $131
CA $435 total
includes taxes & fees
Nov 3 - Nov 4
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
A residential neighborhood with two houses, a driveway, and a lawn.

17. Walkable Dixieland District Gem With Yard

Walkable Dixieland District Gem With Yard
2.0 star property
Dixieland
The price is CA $176
CA $389 total
includes taxes & fees
Nov 5 - Nov 6
Walkable Dixieland District Gem With Yard
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 CA $130
CA $308 total
includes taxes & fees
Nov 1 - Nov 2
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.

19. 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 CA $444
CA $1,112 total
includes taxes & fees
Nov 23 - Nov 24
Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
A two-story house with a green front door, a balcony, and a small garden with palm trees.

20. "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 CA $208
CA $481 total
includes taxes & fees
Nov 29 - Nov 30
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
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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Top Winter Haven Hotel Reviews

Delta Hotels by Marriott Orlando Celebration

Delta Hotels by Marriott Orlando Celebration

10/10 Excellent
"Every thing was great"
Ronaldo 6-night trip
Posted 6 hours ago
Delta Hotels by Marriott Orlando Celebration

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
100
Accommodation
2411 Cottages
Lowest Price
CA $104
Highest Price
CA $1,112

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between CA $104 and CA $1,112 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 2411 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 Center, 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.

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