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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 Jun - 28 Jun

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, (189 reviews)
"We have stayed here several times. "
United States
Martha
The price is €75
includes taxes & fees
4 Mar - 5 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 €237
includes taxes & fees
31 Mar - 1 Apr
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 €375
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 €526
includes taxes & fees
18 Mar - 19 Mar
NEW King Bed Glow In The Dark Kid Cave
House (3 Bedrooms) | Interior

Cottage in Babson Park

Lakefront Babson Park Escape: Pet Friendly!
3.0 star property
The price is €401
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)
"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 €169
includes taxes & fees
16 Mar - 17 Mar
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 €187
includes taxes & fees
16 Mar - 17 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.
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
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 €179
includes taxes & fees
22 Mar - 23 Mar
Luxury Cottage Near Legoland & Chain of Lakes
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 €142
includes taxes & fees
4 Mar - 5 Mar
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
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 €274
includes taxes & fees
2 Apr - 3 Apr
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Interior

Cottage in Crestwynd Bay

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Serenity - Family & Pet Friendly, Amazing Location
Property grounds

Cottage in Kissimmee

Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
The price is €604
includes taxes & fees
16 Mar - 17 Mar
Seas the Day 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 €488
includes taxes & fees
4 Mar - 5 Mar
Sunny Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
House (4 Bedrooms) | Interior

Cottage in Indian Ridge

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
The price is €399
includes taxes & fees
15 Mar - 16 Mar
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Exterior

Cottage in Kissimmee

Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
The price is €441
includes taxes & fees
26 Mar - 27 Mar
Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Interior

Cottage in Kissimmee

Encore Swanky
3.0 star property
3.4 out of 10, (3 reviews)
"Ck in was at 4pm. Place wasn't ready till 5:15. Place was clean. Pool was dirty n cold. Had to pay to have it heated. 1st day it was still cold. So only got 1 day of heated pool.place was kinda run down as well. Fire alarms kept beeping. Communication could have been better as well. It wasn't terrible, but wouldn't stay here again. "
United States
Christine
The price is €516
includes taxes & fees
4 Mar - 5 Mar
Encore Swanky
Exterior

Cottage in Kissimmee

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

Cottage in Kissimmee

Livin' for the Weekend Cottage near Disney with Margaritaville Resort & Island.
Livin' for the Weekend Cottage near Disney with Margaritaville Resort & Island.
Exterior

Cottage in Kissimmee

Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.
The price is €435
includes taxes & fees
8 Mar - 9 Mar
Crystal 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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Was a wonderful stay "
Sharlene 5-night trip
Posted 15 hours ago
The Grove Resort & Water Park Orlando

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
211
Accommodation
1732 Cottages
Lowest Price
€75
Highest Price
€604

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between €75 and €604 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.