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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

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, (194 reviews)
"The cabins were great loved it there"
United States
Jennifer
The price is €66
includes taxes & fees
30 Jul - 31 Jul
Lake Ida Beach Resort
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)
"Wonderful little cottage filled with fun for the whole family. Cozy backyard to enjoy some sunshine and read a book. Close to downtown shops and restaurants. Owners were quick to respond to questions. Would happily stay here again."
United States
Rachel B.
The price is €246
includes taxes & fees
31 Jul - 1 Aug
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Front of property

Mvy7664 - 3BR House Near Disney With Hot Tub

Mvy7664 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
The price is €403
includes taxes & fees
20 Aug - 21 Aug
Mvy7664 - 3BR House Near Disney With Hot Tub
1 bedroom, iron/ironing board, WiFi, bed sheets

Private Cozy Studio, Free Parking, Near Legoland

Private Cozy Studio, Free Parking, Near Legoland
Lake Horney
The price is €165
includes taxes & fees
25 Jul - 26 Jul
Private Cozy Studio, Free Parking, Near Legoland
Exterior

Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland

Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland
Lake Hamilton
The price is €250
includes taxes & fees
14 Aug - 15 Aug
Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland
Exterior

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
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 €149
includes taxes & fees
30 Jul - 31 Jul
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
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 €174
includes taxes & fees
4 Aug - 5 Aug
Perfect Place for a Perfect Vacation
Microwave, stovetop

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very good, (8 reviews)
"Nice, Cute little place"
United States
Brenda N.
The price is €156
includes taxes & fees
8 Aug - 9 Aug
Tiny house close to 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 €190
includes taxes & fees
24 Aug - 25 Aug
Family-Friendly Cottage Near Orlando’s Top Attractions
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 €194
includes taxes & fees
27 Jul - 28 Jul
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
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 €278
includes taxes & fees
4 Aug - 5 Aug
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
House (3 Bedrooms) | Interior

Oasis Near Disney w Golf View, Family&pet Friendly

Oasis Near Disney w Golf View, Family&pet Friendly
3.0 star property
Reunion
The price is €319
includes taxes & fees
28 Jul - 29 Jul
Oasis Near Disney w Golf View, Family&pet Friendly
Front of property

Mvv7561 - 4BR House Near Disney World

Mvv7561 - 4BR House Near Disney World
3.0 star property
Kissimmee
The price is €463
includes taxes & fees
27 Jul - 28 Jul
Mvv7561 - 4BR House Near Disney World
House (3 Bedrooms) | Interior

Davenport Basecamp! 3BR Family Home w/ Patio

Davenport Basecamp! 3BR Family Home w/ Patio
3.0 star property
Davenport
The price is €322
includes taxes & fees
31 Jul - 1 Aug
Davenport Basecamp! 3BR Family Home w/ Patio
House (4 Bedrooms) | Interior

Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is €314
includes taxes & fees
17 Aug - 18 Aug
Family Resort Home w Pool, BBQ & Game Room
Exterior

Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas

Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
3.5 star property
Reunion
The price is €658
includes taxes & fees
6 Aug - 7 Aug
Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
Exterior

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.4 out of 10, Exceptional, (11 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is €270
includes taxes & fees
9 Aug - 10 Aug
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Exterior

Vivid Cottage Near Disney with Margaritaville Resort & Island H2O Access -.

Vivid Cottage Near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
The price is €478
includes taxes & fees
23 Aug - 24 Aug
Vivid 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 €478
includes taxes & fees
24 Aug - 25 Aug
Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.
Exterior

Another Day In Paradise Cottage with Private Hot Tub near Disney with.

Another Day In Paradise Cottage with Private Hot Tub near Disney with.
Kissimmee
The price is €478
includes taxes & fees
23 Aug - 24 Aug
Another Day In Paradise Cottage with Private Hot Tub near Disney with.
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

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"Clean place to stay et very clean"
Marthe 10-night trip
Posted 1 hour ago
Hilton Vacation Club Mystic Dunes Orlando

Find out more about Winter Haven

Winter Haven Cottages information

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Frequently asked questions

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