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Check prices for these dates

Next weekend
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec

Featured Cottages in Winter Haven

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
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 AU$578
includes taxes & fees
21 Oct - 22 Oct
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
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 AU$433
includes taxes & fees
22 Oct - 23 Oct
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Porch
Lake Ida Beach Resort
Lake Ida Beach Resort
3.0 star property
7.4 out of 10, Good, (181)
"This room served my needs well. I enjoyed the full kitchen and bathtub."
United States
Rafael
The price is AU$129
includes taxes & fees
22 Oct - 23 Oct
Lake Ida Beach Resort
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
10.0 out of 10, Exceptional, (2)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
The price is AU$374
includes taxes & fees
26 Oct - 27 Oct
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Exterior
Perfect Place for a Perfect Vacation
Perfect Place for a Perfect Vacation
3.0 star property
10.0 out of 10, Exceptional, (1)
The price is AU$319
includes taxes & fees
18 Nov - 19 Nov
Perfect Place for a Perfect Vacation
Exterior
Jedi cottage 4 miles from Disney! Mins from universal!
Jedi cottage 4 miles from Disney! Mins from universal!
9.4 out of 10, Exceptional, (23)
"We loved staying here! "
United States
Emma Kate y.
The price is AU$338
includes taxes & fees
21 Oct - 22 Oct
Jedi cottage 4 miles from Disney! Mins from universal!
Property grounds
Hidden Lake View Cottage 5 miles from Disney!
Hidden Lake View Cottage 5 miles from Disney!
9.0 out of 10, Wonderful, (2)
"Awesome"
United States
Bulmaro S.
The price is AU$346
includes taxes & fees
22 Oct - 23 Oct
Hidden Lake View Cottage 5 miles from Disney!
Exterior
Luxury Cottage Near Legoland & Chain of Lakes
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 AU$320
includes taxes & fees
21 Oct - 22 Oct
Luxury Cottage Near Legoland & Chain of Lakes
Exterior
Disney, Universal and Legoland Getaway
Disney, Universal and Legoland Getaway
9.2 out of 10, Wonderful, (9)
"I love the place ! It was beautiful! Enough room for everyone "
United States
Anthony M.
The price is AU$338
includes taxes & fees
26 Oct - 27 Oct
Disney, Universal and Legoland Getaway
Interior
5180 Spectacular 5bd4ba- Private Pool&spa
5180 Spectacular 5bd4ba- Private Pool&spa
3.0 star property
The price is AU$590
includes taxes & fees
22 Oct - 23 Oct
5180 Spectacular 5bd4ba- Private Pool&spa
2 bedrooms, iron/ironing board, WiFi, bed sheets
Tiny house close to Disney KISSIMMEE
Tiny house close to Disney KISSIMMEE
2.0 star property
The price is AU$245
includes taxes & fees
21 Oct - 22 Oct
Tiny house close to Disney KISSIMMEE
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
The price is AU$651
includes taxes & fees
22 Oct - 23 Oct
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
House (6 Bedrooms) | Interior
411 Wanderlust Heaven 5bed/pool
411 Wanderlust Heaven 5bed/pool
3.0 star property
The price is AU$839
includes taxes & fees
21 Oct - 22 Oct
411 Wanderlust Heaven 5bed/pool
House (4 Bedrooms) | Interior
Southern Dunes Family Retreat: Hot Tub & Game Room
Southern Dunes Family Retreat: Hot Tub & Game Room
3.0 star property
The price is AU$560
includes taxes & fees
29 Oct - 30 Oct
Southern Dunes Family Retreat: Hot Tub & Game Room
Exterior
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
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 AU$236
includes taxes & fees
21 Oct - 22 Oct
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Microwave, oven, stovetop
Charming Historic Cottage with Cozy Porch and Garden Retreat
Charming Historic Cottage with Cozy Porch and Garden Retreat
The price is AU$413
includes taxes & fees
26 Oct - 27 Oct
Charming Historic Cottage with Cozy Porch and Garden Retreat
Interior
Family-Friendly Cottage Near Orlando’s Top Attractions
Family-Friendly Cottage Near Orlando’s Top Attractions
The price is AU$313
includes taxes & fees
4 Nov - 5 Nov
Family-Friendly Cottage Near Orlando’s Top Attractions
Property grounds
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
The price is AU$318
includes taxes & fees
3 Nov - 4 Nov
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Exterior
Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!
Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!
The price is AU$338
includes taxes & fees
2 Nov - 3 Nov
Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!
House, 6 Bedrooms | Exterior
Wellerden at Reunion Resort!by Shine Villas
Wellerden at Reunion Resort!by Shine Villas
3.5 star property
The price is AU$995
includes taxes & fees
2 Nov - 3 Nov
Wellerden at Reunion Resort!by Shine Villas
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

Parkway International Resort

Parkway International Resort

10/10 Excellent
"Good"
César 4-night trip
Posted 13 hours ago
Parkway International Resort

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
219
Accommodation
1744 Cottages
Lowest Price
AU$129
Highest Price
AU$995

Frequently asked questions

How much do cottages in Winter Haven cost?
Rates for cottages in Winter Haven range between AU$129 and AU$995 per night. Whatever your budget, you'll find the ideal place to get in tune with nature. This price was 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?
There are 1744 cottages in Winter Haven. Whether you're travelling with the kids or planning a weekend retreat with your besties, Expedia can help you find the ideal property to immerse yourself in nature.
What is there to do in Winter Haven near my cottage?
Whatever your tastes or interests, Winter Haven has loads to capture your imagination. LEGOLAND® Florida, Theatre Winter Haven and Indigos Billiards, Bowling & Games are on many visitors' lists. Don't forget about Chain of Lakes Park, The Circle B Bar Reserve and Auburndale City Park either. With Expedia's hotel deals in Winter Haven, you'll be able to discover even more terrific attractions like these with the cash you save.