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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

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
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 1,024 total
includes taxes & fees
8 Feb - 9 Feb
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
8 Feb - 9 Feb
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
10 Feb - 11 Feb
Lake Ida Beach Resort
Microwave, stovetop

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 AED 294
AED 682 total
includes taxes & fees
13 Feb - 14 Feb
Tiny house close to Disney KISSIMMEE
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 756 total
includes taxes & fees
9 Feb - 10 Feb
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
8 Feb - 9 Feb
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
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 327
AED 991 total
includes taxes & fees
26 Feb - 27 Feb
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
House (Multiple Bedrooms) | Interior

7613-8-bl-only 10 Minutes From Disney

7613-8-bl-only 10 Minutes From Disney
2.5 star property
Kissimmee
The price is AED 8,448
AED 12,084 total
includes taxes & fees
9 Feb - 10 Feb
7613-8-bl-only 10 Minutes From Disney
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 228
AED 535 total
includes taxes & fees
8 Feb - 9 Feb
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
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 340
AED 812 total
includes taxes & fees
9 Feb - 10 Feb
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Interior

Encore Swanky

Encore Swanky
3.0 star property
Kissimmee
The price is AED 690
AED 1,846 total
includes taxes & fees
13 Feb - 14 Feb
Encore Swanky
Exterior

"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 AED 360
AED 1,012 total
includes taxes & fees
9 Feb - 10 Feb
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Interior

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, (1 review)
"The communication with the property owner was excellent. The cottage is attached to the owners home but is quite private and comfortable. I’ve already recommended it to family members who wish to visit that area."
United States
Tina O.
The price is AED 420
AED 908 total
includes taxes & fees
14 Feb - 15 Feb
Charming Historic Cottage with Cozy Porch and Garden Retreat
Exterior

Playa Verde Cottage with Private Hot Tub near Disney with Margaritaville Resort.

Playa Verde Cottage with Private Hot Tub near Disney with Margaritaville Resort.
Kissimmee
The price is AED 760
AED 1,789 total
includes taxes & fees
2 Mar - 3 Mar
Playa Verde Cottage with Private Hot Tub near Disney with Margaritaville Resort.
Exterior

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
The price is AED 760
AED 1,789 total
includes taxes & fees
2 Mar - 3 Mar
Sun Baked Cottage with Hot Tub near Disney with Margaritaville Resort & Island.
Interior

Orlando Theme Park Basecamp: Family Home w/ Patio

Orlando Theme Park Basecamp: Family Home w/ Patio
3.0 star property
Davenport
The price is AED 518
AED 1,335 total
includes taxes & fees
20 Feb - 21 Feb
Orlando Theme Park Basecamp: Family Home w/ Patio
Exterior

Lovely Cottage 3 miles from Disney w/ Hot Tub and Margaritaville Resort &.

Lovely Cottage 3 miles from Disney w/ Hot Tub and Margaritaville Resort &.
Kissimmee
The price is AED 760
AED 1,789 total
includes taxes & fees
2 Mar - 3 Mar
Lovely Cottage 3 miles from Disney w/ Hot Tub and Margaritaville Resort &.
Interior

201-4-hb-beautiful Home at Terraverde

201-4-hb-beautiful Home at Terraverde
2.5 star property
Kissimmee
The price is AED 7,857
AED 10,353 total
includes taxes & fees
11 Feb - 12 Feb
201-4-hb-beautiful Home at Terraverde
Exterior

Caraway Cove Cottage near Disney with Margaritaville Resort & Island H2O Access.

Caraway Cove Cottage near Disney with Margaritaville Resort & Island H2O Access.
Kissimmee
The price is AED 760
AED 1,789 total
includes taxes & fees
2 Mar - 3 Mar
Caraway Cove Cottage near Disney with Margaritaville Resort & Island H2O Access.
Exterior

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

Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
The price is AED 760
AED 1,785 total
includes taxes & fees
2 Mar - 3 Mar
Comfy 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

Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

10/10 Excellent
"Staff friendly, hotel not only smells great but also spotless. Excellent amenities "
leanora 1-night trip
Posted 16 hours ago
Holiday Inn Resort Kissimmee by the Parks by IHG

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between AED 309 and AED 1,846 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.