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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

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, (192 reviews)
"We have stayed here several times. "
United States
Martha
The price is €71
includes taxes & fees
20 Apr - 21 Apr
Lake Ida Beach Resort
House (3 Bedrooms) | 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 €373
includes taxes & fees
20 Apr - 21 Apr
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
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
8.8 out of 10, Excellent, (5 reviews)
"Just what we needed for a weekend trip with our grandsons for the weekend "
United States
Christine B.
The price is €241
includes taxes & fees
20 Apr - 21 Apr
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
House (4 Bedrooms) | Interior

9 Mi to Disney: Home w/ Pool Table & Water Views!

9 Mi to Disney: Home w/ Pool Table & Water Views!
3.0 star property
Lake Berkley
The price is €348
includes taxes & fees
22 Apr - 23 Apr
9 Mi to Disney: Home w/ Pool Table & Water Views!
Microwave, stovetop

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 €152
includes taxes & fees
11 May - 12 May
Tiny house close to Disney KISSIMMEE
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 €190
includes taxes & fees
26 Apr - 27 Apr
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Exterior

Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is €167
includes taxes & fees
20 Apr - 21 Apr
Perfect Place for a Perfect Vacation
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 €249
includes taxes & fees
21 Apr - 22 Apr
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
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 €177
includes taxes & fees
4 May - 5 May
Family-Friendly Cottage Near Orlando’s Top Attractions
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 €136
includes taxes & fees
20 Apr - 21 Apr
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
House (3 Bedrooms) | Interior

Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is €330
includes taxes & fees
20 Apr - 21 Apr
Serenity - Family & Pet Friendly, Amazing Location
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)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is €238
includes taxes & fees
22 Apr - 23 Apr
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Property grounds

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 €473
includes taxes & fees
4 May - 5 May
Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
House (4 Bedrooms) | 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 €401
includes taxes & fees
20 Apr - 21 Apr
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Exterior

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

Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
The price is €402
includes taxes & fees
21 Apr - 22 Apr
Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Exterior

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

Sunny Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Kissimmee
The price is €473
includes taxes & fees
4 May - 5 May
Sunny Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Exterior

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

Luxurious Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
The price is €584
includes taxes & fees
4 May - 5 May
Luxurious Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Exterior

Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.

Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.
Kissimmee
The price is €473
includes taxes & fees
5 May - 6 May
Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.
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 €561
includes taxes & fees
21 Apr - 22 Apr
Cheerful Villa near Disney with Margaritaville Resort and Island H20 Waterpark.
Property grounds

Pastel Paradise Villa near Disney With Margaritaville Resort and Island H20.

Pastel Paradise Villa near Disney With Margaritaville Resort and Island H20.
Kissimmee
The price is €373
includes taxes & fees
5 May - 6 May
Pastel Paradise Villa near Disney With Margaritaville Resort and Island H20.
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

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

8/10 Good
"Really enjoyed this property ! "
Matthew 4-night trip
Posted 1 hour ago
Margaritaville Resort Orlando with H2O Waterpark

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
219
Accommodation
2122 Cottages
Lowest Price
€71
Highest Price
€584

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between €71 and €584 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 2122 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.