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

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 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, (194 reviews)
"The cabins were great loved it there"
United States
Jennifer
The price is €68
includes taxes & fees
20 Sept - 21 Sept
Lake Ida Beach Resort
A wooden deck with outdoor seating, a shed, and a view of the surrounding landscape.

2. 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 €132
includes taxes & fees
14 Sept - 15 Sept
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
A single-story house with a front porch, a garage, and a small backyard.

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

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
9.0 out of 10, Wonderful, (6 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 €239
includes taxes & fees
9 Oct - 10 Oct
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.

4. Charming Lakeside Cottage

Charming Lakeside Cottage
Winter Haven
The price is €152
includes taxes & fees
12 Sept - 13 Sept
Charming Lakeside Cottage
A two-story house with a front porch, a garage, and a well-maintained lawn.

5. Hook, Line & Leisure: Lakefront Gem w/ Porch!

Hook, Line & Leisure: Lakefront Gem w/ Porch!
3.0 star property
Florence Villa
10.0 out of 10, Exceptional, (3 reviews)
"We stayed here because our soccer team had a tournament in the area. We had a couple families stay and the price was much cheaper than hotels around the area. The house is beautiful and spacious inside. Has alot of upgrades. At first we thought the neighborhood looked a little off, but we had no issues at all with our stay. We have some other tournaments in this area later in the year and we will definitely be booking to stay here again."
United States
John
The price is €348
includes taxes & fees
13 Sept - 14 Sept
Hook, Line & Leisure: Lakefront Gem w/ Porch!
A single-story house with a garage, a front door, and a small front yard.

6. Legoland & Lakes Pool Home w/ Private Suite

Legoland & Lakes Pool Home w/ Private Suite
3.0 star property
Winter Haven
The price is €435
includes taxes & fees
25 Sept - 26 Sept
Legoland & Lakes Pool Home w/ Private Suite
A covered porch with rustic wooden chairs and a view of a road and water body.

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 €287
includes taxes & fees
22 Sept - 23 Sept
Lakefront Retreat on Lake Ariana w/ EV Charger
A two-story building with a blue exterior, a front porch, and a visible garage door.

8. 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.

9. 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, (5 reviews)
"Clean comfort all ok"
United States
Donald P.
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.

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 €138
includes taxes & fees
13 Sept - 14 Sept
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.

11. 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 €201
includes taxes & fees
10 Oct - 11 Oct
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.

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 €290
includes taxes & fees
30 Sept - 1 Oct
Family Resort Home w Pool, BBQ & Game Room
A residential building with a covered patio area, outdoor seating, and a well-maintained lawn.

13. Family 4BR Home w/ Resort Pool Near Disney

Family 4BR Home w/ Resort Pool Near Disney
3.0 star property
Regal Palms
The price is €280
includes taxes & fees
5 Oct - 6 Oct
Family 4BR Home w/ Resort Pool Near Disney
A covered outdoor area with a concrete floor, surrounded by grass and trees.

14. Enchanted Cottage with Pool and Mini-Golf Near Disney

Enchanted Cottage with Pool and Mini-Golf Near Disney
Kissimmee
9.4 out of 10, Exceptional, (42 reviews)
"This place was the perfect little hideaway during our trip to the parks. Would most definitely stay again."
United States
Shane B.
The price is €163
includes taxes & fees
17 Sept - 18 Sept
Enchanted Cottage with Pool and Mini-Golf Near Disney
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 €170
includes taxes & fees
11 Sept - 12 Sept
Perfect Place for a Perfect Vacation
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 €268
includes taxes & fees
13 Sept - 14 Sept
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.

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

Golf, Dine & Unwind Poolside! Haines City Getaway
3.0 star property
Haines City
The price is €369
includes taxes & fees
1 Oct - 2 Oct
Golf, Dine & Unwind Poolside! Haines City Getaway
A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a black microwave.

18. Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very good, (9 reviews)
"Proximity to theme parks, restaurants, and shopping"
United States
NOLI
The price is €151
includes taxes & fees
14 Sept - 15 Sept
Tiny house close to Disney KISSIMMEE
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, (13 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is €235
includes taxes & fees
13 Sept - 14 Sept
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
A modern living room with a sofa, a large wall clock, and a mirror.

20. 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 €181
includes taxes & fees
21 Sept - 22 Sept
Family-Friendly Cottage Near Orlando’s Top Attractions
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

Embassy Suites By Hilton Orlando Sunset Walk

Embassy Suites By Hilton Orlando Sunset Walk

10/10 Excellent
"Todo estaba bien limpio, la atención del personal excelente y para los niños súper recomendado , el desayuno muy bueno también en general todo espectacular volveremos pronto."
Dayana 2-night trip
Posted 1 hour ago
Embassy Suites By Hilton Orlando Sunset Walk

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
318
Accommodation
2254 Cottages
Lowest Price
€68
Highest Price
€435

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between €68 and €435 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 2254 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.