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
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

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 HK$619
HK$693 total
includes taxes & fees
2 Apr - 3 Apr
Lake Ida Beach Resort
Outdoor dining

Cottage in Winter Haven

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
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 HK$901
HK$2,113 total
includes taxes & fees
20 Apr - 21 Apr
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
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 HK$1,339
HK$3,433 total
includes taxes & fees
20 Apr - 21 Apr
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 HK$1,751
HK$4,465 total
includes taxes & fees
25 Mar - 26 Mar
NEW King Bed Glow In The Dark Kid Cave
Interior

Cottage in Babson Park

Lakefront Babson Park Escape: Pet Friendly!
3.0 star property
The price is HK$1,535
HK$3,706 total
includes taxes & fees
1 Apr - 2 Apr
Lakefront Babson Park Escape: Pet Friendly!
Microwave, stovetop

Cottage in Kissimmee

Tiny house close to Disney 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 HK$627
HK$1,446 total
includes taxes & fees
13 Apr - 14 Apr
Tiny house close to Disney KISSIMMEE
Dining

Cottage in Kissimmee

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
The price is HK$726
HK$1,692 total
includes taxes & fees
22 Mar - 23 Mar
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
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 HK$781
HK$2,202 total
includes taxes & fees
25 Mar - 26 Mar
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Exterior

Cottage in Kissimmee

Perfect Place for a Perfect Vacation
10.0 out of 10, Exceptional, (1 review)
The price is HK$705
HK$1,579 total
includes taxes & fees
20 Apr - 21 Apr
Perfect Place for a Perfect Vacation
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 HK$783
HK$1,668 total
includes taxes & fees
21 Apr - 22 Apr
Family-Friendly Cottage Near Orlando’s Top Attractions
Exterior

Cottage in Lake Hamilton

Luxury Cottage Near Legoland & Chain of Lakes
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.
The price is HK$783
HK$1,620 total
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 HK$1,010
HK$2,402 total
includes taxes & fees
20 Apr - 21 Apr
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
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 HK$775
HK$1,464 total
includes taxes & fees
24 Mar - 25 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 HK$901
HK$3,340 total
includes taxes & fees
22 Mar - 23 Mar
Serenity - Family & Pet Friendly, Amazing Location
Interior

Cottage in Indian Ridge

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
The price is HK$909
HK$3,694 total
includes taxes & fees
20 Apr - 21 Apr
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Property grounds

Cottage in Kissimmee

Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
The price is HK$1,935
HK$4,406 total
includes taxes & fees
14 Apr - 15 Apr
Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
Exterior

Cottage in Kissimmee

Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
The price is HK$1,559
HK$3,736 total
includes taxes & fees
20 Apr - 21 Apr
Comfy 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 HK$1,559
HK$3,729 total
includes taxes & fees
21 Apr - 22 Apr
Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Exterior

Cottage in Kissimmee

Sunny Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
The price is HK$1,935
HK$4,430 total
includes taxes & fees
21 Apr - 22 Apr
Sunny Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Exterior

Cottage in Kissimmee

Dreamy Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
The price is HK$4,888
HK$8,009 total
includes taxes & fees
4 Apr - 5 Apr
Dreamy 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
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

Westgate Town Center Resort

Westgate Town Center Resort

4/10 Poor
"Pictures are extremely misleading. We thought "
Sharnjit 5-night trip
Posted 1 hour ago
Westgate Town Center Resort

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
224
Accommodation
1732 Cottages
Lowest Price
HK$693
Highest Price
HK$8,009

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between HK$693 and HK$8,009 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