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Our top choices for Winter Haven cottages

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
10.0 out of 10, Exceptional, (2 reviews)
"Just what we needed for a weekend trip with our grandsons for the weekend "
United States
Christine B.
The price is ¥17,906
¥43,869 total
includes taxes & fees
Jan 26 - Jan 27
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
Winter Haven
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 ¥26,625
¥68,237 total
includes taxes & fees
Feb 3 - Feb 4
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (188 reviews)
"We have stayed here several times. "
United States
Martha
The price is ¥12,300
¥13,776 total
includes taxes & fees
Jan 25 - Jan 26
Lake Ida Beach Resort

4716-4-ww-blend of Relaxation and Convenience

4716-4-ww-blend of Relaxation and Convenience
2.0 star property
Windward Cay
The price is ¥364,596
¥466,530 total
includes taxes & fees
Jan 26 - Jan 27
4716-4-ww-blend of Relaxation and Convenience

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.6 out of 10, Excellent, (4 reviews)
"Just needed a place to stay close to Disney for the night and the place was clean and easy to check in and out. "
United States
Jena B.
The price is ¥12,682
¥29,260 total
includes taxes & fees
Feb 13 - Feb 14
Tiny house close to Disney KISSIMMEE

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 ¥14,013
¥31,701 total
includes taxes & fees
Feb 2 - Feb 3
Family-Friendly Cottage Near Orlando’s Top Attractions

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 ¥15,693
¥44,740 total
includes taxes & fees
Feb 10 - Feb 11
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Luxury Cottage Near Legoland & Chain of Lakes

Luxury Cottage Near Legoland & Chain of Lakes
Lake Hamilton
10.0 out of 10, Exceptional, (6 reviews)
"This place is tiny but everything you need for a comfortable stay! Would definitely stay here again."
United States
Dallas C.
The price is ¥15,570
¥31,887 total
includes taxes & fees
Feb 22 - Feb 23
Luxury Cottage Near Legoland & Chain of Lakes

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 ¥14,433
¥33,632 total
includes taxes & fees
Feb 3 - Feb 4
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
Indian Ridge
The price is ¥18,061
¥73,423 total
includes taxes & fees
Feb 3 - Feb 4
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Davenport
5.0 out of 10, (2 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 ¥11,911
¥25,175 total
includes taxes & fees
Feb 5 - Feb 6
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

Encore Swanky

Encore Swanky
3.0 star property
Kissimmee
The price is ¥32,844
¥101,234 total
includes taxes & fees
Feb 1 - Feb 2
Encore Swanky

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.6 out of 10, Exceptional, (8 reviews)
"Wonderful place to stay overnight. Nice furnishings. Good room layout for family. Convenience of washer and dryer. Host was quick and responsive. Thank you for a terrific stay."
United States
George L.
The price is ¥16,675
¥44,494 total
includes taxes & fees
Feb 2 - Feb 3
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

1061 Lake Berkley 4 Bed With Pool

1061 Lake Berkley 4 Bed With Pool
2.5 star property
Lake Berkley
The price is ¥339,074
¥436,504 total
includes taxes & fees
Jan 26 - Jan 27
1061 Lake Berkley 4 Bed With Pool

Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.

Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.
Kissimmee
Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.

Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Cheerful Villa near Disney with Margaritaville Resort and Island H20 Waterpark.

Cheerful Villa near Disney with Margaritaville Resort and Island H20 Waterpark.
Kissimmee
The price is ¥50,914
¥109,062 total
includes taxes & fees
Feb 24 - Feb 25
Cheerful Villa near Disney with Margaritaville Resort and Island H20 Waterpark.

Sun Baked Cottage with Hot Tub near Disney with Margaritaville Resort & Island.

Sun Baked Cottage with Hot Tub near Disney with Margaritaville Resort & Island.
Kissimmee
Sun Baked Cottage with Hot Tub near Disney with Margaritaville Resort & Island.

Bright Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Bright Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
Bright Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Orlando Theme Park Basecamp: Family Home w/ Patio

Orlando Theme Park Basecamp: Family Home w/ Patio
3.0 star property
Davenport
The price is ¥21,954
¥56,605 total
includes taxes & fees
Feb 5 - Feb 6
Orlando Theme Park Basecamp: Family Home w/ Patio
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

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
199
Accommodation
1732 Cottages
Lowest Price
¥13,776
Highest Price
¥109,062

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between ¥13,776 and ¥109,062 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 1732 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 Center 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.