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Check prices for these dates

Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan
In one month
23 Jan - 25 Jan
In two months
20 Feb - 22 Feb

Our top choices for Winter Haven cottages

Exterior
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

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)
"Just what we needed for a weekend trip with our grandsons for the weekend "
United States
Christine B.
The price is NZ$480
includes taxes & fees
30 Dec - 31 Dec
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Porch
Lake Ida Beach Resort

Cottage in Winter Haven

Lake Ida Beach Resort
3.0 star property
7.2 out of 10, Good, (187)
"We have stayed here several times. "
United States
Martha
The price is NZ$163
includes taxes & fees
15 Jan - 16 Jan 2026
Lake Ida Beach Resort
House (3 Bedrooms) | Interior
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Cottage in Winter Haven

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
10.0 out of 10, Exceptional, (3)
"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 NZ$750
includes taxes & fees
28 Dec - 29 Dec
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Microwave, stovetop
Tiny house close to Disney KISSIMMEE

Cottage in Kissimmee

Tiny house close to Disney KISSIMMEE
2.0 star property
9.0 out of 10, Wonderful, (2)
"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 NZ$302
includes taxes & fees
6 Jan - 7 Jan 2026
Tiny house close to Disney KISSIMMEE
Interior
Family-Friendly Cottage Near Orlando’s Top Attractions

Cottage in Kissimmee

Family-Friendly Cottage Near Orlando’s Top Attractions
10.0 out of 10, Exceptional, (1)
"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 NZ$345
includes taxes & fees
7 Jan - 8 Jan 2026
Family-Friendly Cottage Near Orlando’s Top Attractions
House (6 Bedrooms) | Interior
Bella Vida House With Pool and Games - Near Disney!

Cottage in Bellavida

Bella Vida House With Pool and Games - Near Disney!
3.0 star property
Bella Vida House With Pool and Games - Near Disney!
Property grounds
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Cottage in Kissimmee

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
The price is NZ$385
includes taxes & fees
23 Jan - 24 Jan 2026
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Private kitchen
Cozy Lake Cottage - 4 miles to Disney

Cottage in Kissimmee

Cozy Lake Cottage - 4 miles to Disney
Cozy Lake Cottage - 4 miles to Disney
Terrace/patio
Cozy Tropical Cottage - 4 mi to Disney

Cottage in Kissimmee

Cozy Tropical Cottage - 4 mi to Disney
The price is NZ$492
includes taxes & fees
28 Dec - 29 Dec
Cozy Tropical Cottage - 4 mi to Disney
Exterior
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

Cottage in Davenport

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
5.0 out of 10, (2)
"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 NZ$301
includes taxes & fees
24 Jan - 25 Jan 2026
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Interior
Watersong Swanky

Cottage in Davenport

Watersong Swanky
3.0 star property
The price is NZ$1,721
includes taxes & fees
8 Jan - 9 Jan 2026
Watersong Swanky
Exterior
Luxury Cottage Near Legoland & Chain of Lakes

Cottage in Lake Hamilton

Luxury Cottage Near Legoland & Chain of Lakes
10.0 out of 10, Exceptional, (6)
"This place is tiny but everything you need for a comfortable stay! Would definitely stay here again."
United States
Dallas C.
The price is NZ$352
includes taxes & fees
29 Dec - 30 Dec
Luxury Cottage Near Legoland & Chain of Lakes
House (4 Bedrooms) | Interior
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

Cottage in Indian Ridge

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
The price is NZ$814
includes taxes & fees
24 Jan - 25 Jan 2026
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Exterior
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

Cottage in Kissimmee

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
9.8 out of 10, Exceptional, (6)
"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 NZ$489
includes taxes & fees
7 Jan - 8 Jan 2026
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Exterior
Sunrise Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.

Cottage in Kissimmee

Sunrise Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
10.0 out of 10, Exceptional, (1)
"Comfy, cozy and room for everyone to have their own space . Easy to get around. Places to eat and shop right outside the property, so convenient."
United States
Marilou J.
Sunrise Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Exterior
Inviting Cottage with Private Hot Tub near Disney with Margaritaville Resort &.

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

Cottage in Kissimmee

Celestial Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Celestial Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Exterior
Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.

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 &.
Property grounds
Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.

Cottage in Kissimmee

Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
Exterior
Sandy Cottage! 3 Miles from Disney with Margaritaville Resort & Island H2O.

Cottage in Kissimmee

Sandy Cottage! 3 Miles from Disney with Margaritaville Resort & Island H2O.
8.0 out of 10, Very good, (2)
"Wonderful"
United States
Anonymous traveller
Sandy Cottage! 3 Miles from Disney with Margaritaville Resort & Island H2O.
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
"Room was spacious clean and great overall. "
Gabriel 3-night trip
Posted 8 hours ago
The Grove Resort & Water Park Orlando

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
198
Accommodation
1732 Cottages
Lowest Price
NZ$163
Highest Price
NZ$1,721

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between NZ$163 and NZ$1,721 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.
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.

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