Search Cottages in Winter Haven

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Winter Haven cottages

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 HK$616
HK$690 total
includes taxes & fees
31 Jan - 1 Feb
Lake Ida Beach Resort
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 HK$897
HK$2,197 total
includes taxes & fees
27 Jan - 28 Jan
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
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 HK$1,333
HK$3,417 total
includes taxes & fees
3 Feb - 4 Feb
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Smart TV, books

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 HK$702
HK$1,587 total
includes taxes & fees
2 Feb - 3 Feb
Family-Friendly Cottage Near Orlando’s Top Attractions
Interior

Terra Verde Swanky

Terra Verde Swanky
3.0 star property
Kissimmee
The price is HK$912
HK$2,612 total
includes taxes & fees
1 Feb - 2 Feb
Terra Verde Swanky
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 HK$624
HK$1,439 total
includes taxes & fees
13 Feb - 14 Feb
Tiny house close to Disney KISSIMMEE
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 HK$772
HK$2,201 total
includes taxes & fees
10 Feb - 11 Feb
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Interior

161-4-cb-cozy Villa at Terra Verde

161-4-cb-cozy Villa at Terra Verde
2.5 star property
Kissimmee
The price is HK$16,141
HK$20,860 total
includes taxes & fees
25 Feb - 26 Feb
161-4-cb-cozy Villa at Terra Verde
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 HK$780
HK$1,597 total
includes taxes & fees
9 Feb - 10 Feb
Luxury Cottage Near Legoland & Chain of Lakes
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 HK$663
HK$1,335 total
includes taxes & fees
22 Feb - 23 Feb
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
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 HK$904
HK$3,677 total
includes taxes & fees
27 Jan - 28 Jan
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
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 HK$723
HK$1,700 total
includes taxes & fees
27 Jan - 28 Jan
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
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 HK$835
HK$2,228 total
includes taxes & fees
4 Feb - 5 Feb
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Exterior

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

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

Encore Swanky

Encore Swanky
3.0 star property
Kissimmee
The price is HK$1,615
HK$4,979 total
includes taxes & fees
1 Feb - 2 Feb
Encore Swanky
Interior

1061 Lake Berkley 4 Bed With Pool

1061 Lake Berkley 4 Bed With Pool
2.5 star property
Lake Berkley
The price is HK$16,679
HK$21,471 total
includes taxes & fees
4 Feb - 5 Feb
1061 Lake Berkley 4 Bed With Pool
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 HK$1,045
HK$2,139 total
includes taxes & fees
14 Feb - 15 Feb
Charming Historic Cottage with Cozy Porch and Garden Retreat
Exterior

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 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

Cheerful Villa near Disney with Margaritaville Resort and Island H20 Waterpark.

Cheerful Villa near Disney with Margaritaville Resort and Island H20 Waterpark.
Kissimmee
The price is HK$2,550
HK$5,461 total
includes taxes & fees
23 Feb - 24 Feb
Cheerful Villa near Disney with Margaritaville Resort and Island H20 Waterpark.
Exterior

Love, Luck and Magic Cottage with Private Hot Tub near Disney and.

Love, Luck and Magic Cottage with Private Hot Tub near Disney and.
Kissimmee
The price is HK$2,737
HK$5,705 total
includes taxes & fees
23 Feb - 24 Feb
Love, Luck and Magic Cottage with Private Hot Tub near Disney and.
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Haven Hotel Reviews

Margaritaville Resort Orlando

Margaritaville Resort Orlando

10/10 Excellent
"Entrance looks amazing the environment is warm pleasant "
Isabella 1-night trip
Posted 2 days ago
Margaritaville Resort Orlando

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
200
Accommodation
1732 Cottages
Lowest Price
HK$690
Highest Price
HK$5,705

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between HK$690 and HK$5,705 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.

Explore a world of travel with Expedia