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Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

Our top choices for Winter Haven cottages

Exterior

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
2.0 star property
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 AED 422
AED 1,020 total
includes taxes & fees
18 Jan - 19 Jan
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
House (3 Bedrooms) | Interior

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 AED 628
AED 1,610 total
includes taxes & fees
18 Jan - 19 Jan
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Porch

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 AED 275
AED 309 total
includes taxes & fees
18 Jan - 19 Jan
Lake Ida Beach Resort
Microwave, stovetop

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
2.0 star property
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 AED 257
AED 636 total
includes taxes & fees
18 Jan - 19 Jan
Tiny house close to Disney KISSIMMEE
Smart TV, books

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

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 AED 364
AED 1,026 total
includes taxes & fees
10 Feb - 11 Feb
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Dining

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 AED 324
AED 782 total
includes taxes & fees
18 Jan - 19 Jan
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Exterior

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 AED 367
AED 752 total
includes taxes & fees
18 Jan - 19 Jan
Luxury Cottage Near Legoland & Chain of Lakes
House (4 Bedrooms) | Interior

~ 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 AED 426
AED 1,732 total
includes taxes & fees
17 Jan - 18 Jan
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Interior

Encore Swanky

Encore Swanky
3.0 star property
Kissimmee
The price is AED 806
AED 2,398 total
includes taxes & fees
1 Feb - 2 Feb
Encore Swanky
Exterior

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 AED 281
AED 594 total
includes taxes & fees
19 Jan - 20 Jan
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Exterior

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.8 out of 10, Exceptional, (7 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 AED 393
AED 1,061 total
includes taxes & fees
26 Jan - 27 Jan
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Exterior

Wellerden at Reunion Resort!by Shine Villas

Wellerden at Reunion Resort!by Shine Villas
3.5 star property
Reunion
The price is AED 732
AED 2,430 total
includes taxes & fees
21 Jan - 22 Jan
Wellerden at Reunion Resort!by Shine Villas
Exterior

Pineapple Dream Cottage with Private Hot Tub near Disney with Margaritaville.

Pineapple Dream Cottage with Private Hot Tub near Disney with Margaritaville.
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"We loved our experience, from the time we walked into our cottage, we knew we would have a great time. The Cottage was spaces enough for our party of five. This vacation was a graduation gift for my grandson. I loved the proximity to the theme parks. I also loved the amenities that were offered by the property’s management team, Awesome! "
United States
Patricia B.
Pineapple Dream Cottage with Private Hot Tub near Disney with Margaritaville.
Exterior

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

Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.
2.0 star property
Kissimmee
Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.
Exterior

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 -.
Exterior

Lush Garden Oasis Cottage near Disney with Margaritaville Resort and Island H2O.

Lush Garden Oasis Cottage near Disney with Margaritaville Resort and Island H2O.
2.0 star property
Kissmmmee
Lush Garden Oasis Cottage near Disney with Margaritaville Resort and Island H2O.
Exterior

Inviting Cottage with Private Hot Tub near Disney with Margaritaville Resort &.

Inviting Cottage with Private Hot Tub near Disney with Margaritaville Resort &.
Kissimmee
Inviting Cottage with Private Hot Tub near Disney with Margaritaville Resort &.
Exterior

Dreamy Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.

Dreamy Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Kissimmee
Dreamy Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Exterior

Vivid Cottage Near Disney with Margaritaville Resort & Island H2O Access -.

Vivid Cottage Near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
Vivid Cottage Near Disney with Margaritaville Resort & Island H2O Access -.
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

Margaritaville Resort Orlando

Margaritaville Resort Orlando

10/10 Excellent
"The room was very spacious & the resort is beautiful! "
Teresa 4-night trip
Posted 2 days ago
Margaritaville Resort Orlando

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between AED 309 and AED 2,430 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.
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.

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