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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Cottages in Winter Haven

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)
"Just what we needed for a weekend trip with our grandsons for the weekend "
United States
Christine B.
The price is AED 422
AED 1,031 total
includes taxes & fees
2 Dec - 3 Dec
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Porch
Lake Ida Beach Resort

Lake Ida Beach Resort

3.0 star property
Winter Haven
7.4 out of 10, Good, (185)
"We have stayed here several times. "
United States
Martha
The price is AED 275
AED 309 total
includes taxes & fees
3 Dec - 4 Dec
Lake Ida Beach Resort
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)
"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
10 Dec - 11 Dec
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Property grounds
Hidden Lake View Cottage 5 miles from Disney!

Hidden Lake View Cottage 5 miles from Disney!

Kissimmee
9.0 out of 10, Wonderful, (2)
"Awesome"
United States
Bulmaro S.
The price is AED 294
AED 803 total
includes taxes & fees
13 Dec - 14 Dec
Hidden Lake View Cottage 5 miles from Disney!
Exterior
Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation

3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1)
The price is AED 298
AED 707 total
includes taxes & fees
5 Dec - 6 Dec
Perfect Place for a Perfect Vacation
Exterior
Disney, Universal and Legoland Getaway

Disney, Universal and Legoland Getaway

Kissimmee
9.2 out of 10, Wonderful, (9)
"I love the place ! It was beautiful! Enough room for everyone "
United States
Anthony M.
The price is AED 364
AED 901 total
includes taxes & fees
2 Dec - 3 Dec
Disney, Universal and Legoland Getaway
Microwave, stovetop
Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE

2.0 star property
Kissimmee
9.0 out of 10, Wonderful, (2)
"The location was great. We really just needed somewhere to sleep because we spent the day at the Disney Parks. The place had enough beds and was a great price."
United States
Christine M.
The price is AED 257
AED 636 total
includes taxes & fees
7 Dec - 8 Dec
Tiny house close to Disney KISSIMMEE
Interior
Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions

Kissimmee
10.0 out of 10, Exceptional, (1)
"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 AED 331
AED 744 total
includes taxes & fees
2 Dec - 3 Dec
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)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
The price is AED 386
AED 1,058 total
includes taxes & fees
31 Dec - 1 January 2026
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Terrace/patio
Cozy Tropical Cottage - 4 mi to Disney

Cozy Tropical Cottage - 4 mi to Disney

Kissimmee
The price is AED 489
AED 1,047 total
includes taxes & fees
2 Dec - 3 Dec
Cozy Tropical Cottage - 4 mi to Disney
Property grounds
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
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)
"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 767 total
includes taxes & fees
15 Dec - 16 Dec
Luxury Cottage Near Legoland & Chain of Lakes
Private kitchen
Cozy Lake Cottage - 4 miles to Disney

Cozy Lake Cottage - 4 miles to Disney

Kissimmee
The price is AED 489
AED 1,029 total
includes taxes & fees
31 Dec - 1 January 2026
Cozy Lake Cottage - 4 miles to Disney
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
2 Dec - 3 Dec
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
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)
"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 235
AED 542 total
includes taxes & fees
6 Dec - 7 Dec
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Property grounds
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)
"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.
The price is AED 819
AED 1,959 total
includes taxes & fees
14 Dec - 15 Dec
Pineapple Dream Cottage with Private Hot Tub near Disney with Margaritaville.
Exterior
Parrot Bay Cottage with Private Hot Tub near Disney with Margaritaville Resort.

Parrot Bay Cottage with Private Hot Tub near Disney with Margaritaville Resort.

Kissimmee
10.0 out of 10, Exceptional, (1)
"Booked for my friends visiting. Perfect location"
United States
Eric Allan G.
The price is AED 819
AED 1,977 total
includes taxes & fees
14 Dec - 15 Dec
Parrot Bay Cottage with Private Hot Tub near Disney with Margaritaville Resort.
Exterior
Sunrise Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.

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

Kissimmee
10.0 out of 10, Exceptional, (1)
"Comfy, cozy and room for everyone to have their own space . Easy to get around. Places to eat and shop right outside the property, so convenient."
United States
Marilou J.
Sunrise Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
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
"Good staff"
Noah 3-night trip
Posted 19 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 1,977 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 1744 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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