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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Winter Haven cottages

Exterior

Cottage in Winter Haven

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
2.0 star property
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 €244
includes taxes & fees
18 Jan - 19 Jan
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 €376
includes taxes & fees
18 Jan - 19 Jan
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Porch

Cottage in Winter Haven

Lake Ida Beach Resort
3.0 star property
7.2 out of 10, Good, (188 reviews)
"We have stayed here several times. "
United States
Martha
The price is €72
includes taxes & fees
18 Jan - 19 Jan
Lake Ida Beach Resort
Microwave, stovetop

Cottage in Kissimmee

Tiny house close to Disney KISSIMMEE
2.0 star property
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 €163
includes taxes & fees
13 Feb - 14 Feb
Tiny house close to Disney KISSIMMEE
Smart TV, books

Cottage in Kissimmee

Family-Friendly Cottage Near Orlando’s Top Attractions
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 €180
includes taxes & fees
19 Jan - 20 Jan
Family-Friendly Cottage Near Orlando’s Top Attractions
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 €250
includes taxes & fees
10 Feb - 11 Feb
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 €186
includes taxes & fees
29 Jan - 30 Jan
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Exterior

Cottage in Lake Hamilton

Luxury Cottage Near Legoland & Chain of Lakes
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 €180
includes taxes & fees
18 Jan - 19 Jan
Luxury Cottage Near Legoland & Chain of Lakes
House (4 Bedrooms) | Interior

Cottage in Indian Ridge

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
The price is €405
includes taxes & fees
24 Jan - 25 Jan
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Interior

Cottage in Kissimmee

Encore Swanky
3.0 star property
The price is €565
includes taxes & fees
1 Feb - 2 Feb
Encore Swanky
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 €143
includes taxes & fees
19 Jan - 20 Jan
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Exterior

Cottage in Kissimmee

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
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 €254
includes taxes & fees
26 Jan - 27 Jan
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Exterior

Cottage in Reunion

Wellerden at Reunion Resort!by Shine Villas
3.5 star property
The price is €570
includes taxes & fees
21 Jan - 22 Jan
Wellerden at Reunion Resort!by Shine Villas
Exterior

Cottage in Kissimmee

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

Cottage in Kissimmee

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

Cottage in Kissimmee

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

Cottage in Kissmmmee

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

Cottage in Kissimmee

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

Cottage in Kissimmee

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

Cottage in Kissimmee

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

Parkway International Resort

Parkway International Resort

10/10 Excellent
"Everything about Parkway is excellent. The rooms are very spacious and the facilities are perfect"
Peter 21-night trip
Posted 12 hours ago
Parkway International Resort

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
200
Accommodation
1732 Cottages
Lowest Price
€72
Highest Price
€570

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between €72 and €570 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.
Are there any family-friendly cottages in Winter Haven?
If you're looking to get back to nature in Winter Haven, you can't beat Lake Ida Beach Resort. With a 3-star rating and amenities like housekeeping services and WiFi, you'll find it easy to relax at this family-friendly cottage. After checking in and chilling out in your comfy new digs, it's time to head out and start exploring. LEGOLAND® Florida and Indigo's Family Fun Centre are among the best family-friendly attractions in Winter Haven.
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.
What is there to do in Winter Haven near my cottage?
You'll find plenty of fabulous things that'll fill up your itinerary in Winter Haven. Head for top attractions like Indigo's Family Fun Centre, Lake Henry Golf Club and Cypresswood Golf and Country Club. LEGOLAND® Florida, Chain of Lakes Park and Theatre Winter Haven are other must-see's.