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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 June - 28 June

Our top choices for Winter Haven cottages

Porch

Cottage in Winter Haven

Lake Ida Beach Resort
3.0 star property
7.2 out of 10, Good, (190 reviews)
"We have stayed here several times. "
United States
Martha
The price is AU$126
includes taxes & fees
14 Mar - 15 Mar
Lake Ida Beach Resort
Exterior

Cottage in Winter Haven

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
8.8 out of 10, Excellent, (3 reviews)
"Just what we needed for a weekend trip with our grandsons for the weekend "
United States
Christine B.
The price is AU$394
includes taxes & fees
16 Mar - 17 Mar
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
House (3 Bedrooms) | Interior

Cottage in Winter Haven

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
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 AU$625
includes taxes & fees
28 Mar - 29 Mar
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Exterior

Cottage in Cumbrian Lakes

NEW King Bed Glow In The Dark Kid Cave
3.0 star property
The price is AU$835
includes taxes & fees
18 Mar - 19 Mar
NEW King Bed Glow In The Dark Kid Cave
Microwave, stovetop

Cottage in Kissimmee

Tiny house close to Disney KISSIMMEE
8.4 out of 10, Very good, (6 reviews)
"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 AU$278
includes taxes & fees
16 Mar - 17 Mar
Tiny house close to Disney KISSIMMEE
House (3 Bedrooms) | Interior

Cottage in Babson Park

Lakefront Babson Park Escape: Pet Friendly!
3.0 star property
The price is AU$673
includes taxes & fees
1 Apr - 2 Apr
Lakefront Babson Park Escape: Pet Friendly!
Exterior

Cottage in Kissimmee

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, 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 AU$393
includes taxes & fees
21 Mar - 22 Mar
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Dining

Cottage in Kissimmee

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
The price is AU$316
includes taxes & fees
15 Mar - 16 Mar
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Exterior

Cottage in Davenport

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
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 AU$234
includes taxes & fees
8 Mar - 9 Mar
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Interior

Cottage in Crestwynd Bay

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
The price is AU$646
includes taxes & fees
8 Mar - 9 Mar
Serenity - Family & Pet Friendly, Amazing Location
Exterior

Cottage in Lake Hamilton

Luxury Cottage Near Legoland & Chain of Lakes
10.0 out of 10, Exceptional, (7 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 AU$299
includes taxes & fees
22 Mar - 23 Mar
Luxury Cottage Near Legoland & Chain of Lakes
Exterior

Cottage in Kissimmee

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
9.6 out of 10, Exceptional, (8 reviews)
"Everything was great… Super location, easy parking, quiet."
United States
Cory & Denise
The price is AU$514
includes taxes & fees
21 Mar - 22 Mar
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Property grounds

Cottage in Kissimmee

Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
The price is AU$863
includes taxes & fees
26 Mar - 27 Mar
Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
Exterior

Cottage in Kissimmee

Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.
The price is AU$742
includes taxes & fees
8 Mar - 9 Mar
Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Exterior

Cottage in Kissimmee

Sunny Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Sunny Cottage near Disney with Margaritaville Resort & Island H2O Access -.
House (4 Bedrooms) | Interior

Cottage in Indian Ridge

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
The price is AU$673
includes taxes & fees
16 Mar - 17 Mar
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Exterior

Cottage in Kissimmee

Dreamy Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
The price is AU$891
includes taxes & fees
24 Mar - 25 Mar
Dreamy Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Exterior

Cottage in Kissimmee

Sunny Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
The price is AU$1,035
includes taxes & fees
13 Mar - 14 Mar
Sunny Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Exterior

Cottage in Kissimmee

Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
The price is AU$735
includes taxes & fees
26 Mar - 27 Mar
Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Exterior

Cottage in Kissimmee

Relaxing Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
The price is AU$902
includes taxes & fees
24 Mar - 25 Mar
Relaxing 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.
View all properties

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Top Winter Haven Hotel Reviews

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

8/10 Good
"Very clean. I would stay here again. The reason for 4 stars is there is a very strong perfume smell in the building and no laundry facility’s. Very comfortable beds. "
Dylan 1-night trip
Posted 2 hours ago
Kompose Boutique Resort at Theme Parks

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
210
Accommodation
1732 Cottages
Lowest Price
AU$126
Highest Price
AU$1,035

Frequently asked questions

How much do cottages in Winter Haven cost?
Rates for cottages in Winter Haven range between AU$126 and AU$1,035 per night. Whatever your budget, you'll find the ideal place to get in tune with nature. This price was 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?
There are 1732 cottages in Winter Haven. Whether you're travelling with the kids or planning a weekend retreat with your besties, Expedia can help you find the ideal property to immerse yourself in nature.
What is there to do in Winter Haven near my cottage?
Whatever your tastes or interests, Winter Haven has loads to capture your imagination. LEGOLAND® Florida, Theatre Winter Haven and Indigos Billiards, Bowling & Games are on many visitors' lists. Don't forget about Chain of Lakes Park, The Circle B Bar Reserve and Auburndale City Park either. With Expedia's hotel deals in Winter Haven, you'll be able to discover even more terrific attractions like these with the cash you save.