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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

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, (190 reviews)
"We have stayed here several times. "
United States
Martha
The price is NZ$152
includes taxes & fees
29 Mar - 30 Mar
Lake Ida Beach Resort
Outdoor dining

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
8.6 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 NZ$476
includes taxes & fees
26 Mar - 27 Mar
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
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 NZ$751
includes taxes & fees
14 Apr - 15 Apr
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
House (3 Bedrooms) | Interior

Lakefront Babson Park Escape: Pet Friendly!

Lakefront Babson Park Escape: Pet Friendly!
3.0 star property
Babson Park
The price is NZ$810
includes taxes & fees
1 Apr - 2 Apr
Lakefront Babson Park Escape: Pet Friendly!
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 NZ$318
includes taxes & fees
15 Apr - 16 Apr
Tiny house close to Disney KISSIMMEE
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 NZ$330
includes taxes & fees
8 Apr - 9 Apr
Perfect Place for a Perfect Vacation
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 NZ$373
includes taxes & fees
29 Mar - 30 Mar
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
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.
Family-Friendly Cottage Near Orlando’s Top Attractions
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 NZ$487
includes taxes & fees
21 Apr - 22 Apr
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
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 NZ$320
includes taxes & fees
26 Mar - 27 Mar
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Exterior

Luxury Cottage Near Legoland & Chain of Lakes

Luxury Cottage Near Legoland & Chain of Lakes
Lake Hamilton
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.
Luxury Cottage Near Legoland & Chain of Lakes
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 NZ$1,104
includes taxes & fees
17 Apr - 18 Apr
Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
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 NZ$510
includes taxes & fees
6 Apr - 7 Apr
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
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 NZ$808
includes taxes & fees
11 Apr - 12 Apr
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Interior

Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is NZ$776
includes taxes & fees
26 Mar - 27 Mar
Serenity - Family & Pet Friendly, Amazing Location
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 NZ$968
includes taxes & fees
13 Apr - 14 Apr
Sunny Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
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 NZ$816
includes taxes & fees
13 Apr - 14 Apr
Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Exterior

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

Sunny Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
The price is NZ$818
includes taxes & fees
14 Apr - 15 Apr
Sunny Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Exterior

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

Livin' for the Weekend Cottage near Disney with Margaritaville Resort & Island.
Kissimmee
The price is NZ$826
includes taxes & fees
19 Apr - 20 Apr
Livin' for the Weekend Cottage near Disney with Margaritaville Resort & Island.
Exterior

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

Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
The price is NZ$808
includes taxes & fees
21 Apr - 22 Apr
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

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"Free EV charging, nice! And they have like 6 spots for EV charging. The property is very nice with lots of amenities, excellent location and good breakfast. The rooms could be better - No real nightstands, tables or desks to put things on, not enough lighting, and shower is somewhat difficult to figure out water temp. Overall, good stay. I would stay here again if the price is right."
Nelson 1-night trip
Posted 1 hour ago
Kompose Boutique Resort at Theme Parks

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
224
Accommodation
1732 Cottages
Lowest Price
NZ$152
Highest Price
NZ$1,104

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between NZ$152 and NZ$1,104 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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