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Our top choices for Winter Haven cottages

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (190 reviews)
"We have stayed here several times. "
United States
Martha
The price is AED 290
AED 325 total
includes taxes & fees
29 Mar - 30 Mar
Lake Ida Beach Resort

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
8.6 out of 10, Excellent, (4 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 1,002 total
includes taxes & fees
25 Mar - 26 Mar
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 AED 628
AED 1,610 total
includes taxes & fees
28 Mar - 29 Mar
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Lakefront Babson Park Escape: Pet Friendly!

Lakefront Babson Park Escape: Pet Friendly!
3.0 star property
Babson Park
The price is AED 720
AED 1,738 total
includes taxes & fees
1 Apr - 2 Apr
Lakefront Babson Park Escape: Pet Friendly!

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very Good, (6 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 290
AED 674 total
includes taxes & fees
13 Apr - 14 Apr
Tiny house close to Disney KISSIMMEE

Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is AED 331
AED 741 total
includes taxes & fees
13 Apr - 14 Apr
Perfect Place for a Perfect Vacation

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 341
AED 797 total
includes taxes & fees
29 Mar - 30 Mar
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

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 AED 356
AED 770 total
includes taxes & fees
21 Apr - 22 Apr
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 AED 364
AED 1,026 total
includes taxes & fees
13 Apr - 14 Apr
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

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 364
AED 686 total
includes taxes & fees
25 Mar - 26 Mar
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

Luxury Cottage Near Legoland & Chain of Lakes

Luxury Cottage Near Legoland & Chain of Lakes
Lake Hamilton
10.0 out of 10, Exceptional, (8 reviews)
"This place is tiny but everything you need for a comfortable stay! Would definitely stay here again."
United States
Dallas C.
Luxury Cottage Near Legoland & Chain of Lakes

Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.

Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
Kissimmee
The price is AED 907
AED 2,092 total
includes taxes & fees
14 Apr - 15 Apr
Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.

"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)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is AED 426
AED 1,080 total
includes taxes & fees
6 Apr - 7 Apr
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

~ 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
11 Apr - 12 Apr
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is AED 422
AED 1,566 total
includes taxes & fees
25 Mar - 26 Mar
Serenity - Family & Pet Friendly, Amazing Location

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

Sunny Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Kissimmee
The price is AED 907
AED 2,092 total
includes taxes & fees
13 Apr - 14 Apr
Sunny Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.

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 731
AED 1,759 total
includes taxes & fees
13 Apr - 14 Apr
Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.

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

Sunny Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
The price is AED 731
AED 1,763 total
includes taxes & fees
13 Apr - 14 Apr
Sunny Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Livin' for the Weekend Cottage near Disney with Margaritaville Resort & Island.

Livin' for the Weekend Cottage near Disney with Margaritaville Resort & Island.
Kissimmee
The price is AED 760
AED 1,797 total
includes taxes & fees
19 Apr - 20 Apr
Livin' for the Weekend Cottage near Disney with Margaritaville Resort & Island.

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

Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
The price is AED 731
AED 1,749 total
includes taxes & fees
20 Apr - 21 Apr
Crystal 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

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between AED 325 and AED 2,092 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.