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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

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, (193 reviews)
"Was probably once a great time place. Owner was nice. Night time neighborhood is a bit noisy guess it's just how people act now no respect for property."
United States
wade
The price is CA $101
CA $113 total
includes taxes & fees
Jul 15 - Jul 16
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 CA $161
CA $394 total
includes taxes & fees
Jun 15 - Jun 16
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
House (3 Bedrooms) | Interior

Hook, Line & Leisure: Lakefront Gem w/ Porch!

Hook, Line & Leisure: Lakefront Gem w/ Porch!
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 CA $190
CA $558 total
includes taxes & fees
Jul 13 - Jul 14
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Exterior

The Cozy Cottage 1 bedroom plus studio bed and 2 bathrooms in charming Lakeland

The Cozy Cottage 1 bedroom plus studio bed and 2 bathrooms in charming Lakeland
East Lake Morton
10.0 out of 10, Exceptional, (1 review)
"There is not words for how comfortable the space and the host were. Beautiful experience. You are lucky if you get to stay here."
United States
Catherine S.
The price is CA $134
CA $178 total
includes taxes & fees
Jun 25 - Jun 26
The Cozy Cottage 1 bedroom plus studio bed and 2 bathrooms in charming Lakeland
Exterior

Charming Historic Cottage with Cozy Porch and Garden Retreat

Charming Historic Cottage with Cozy Porch and Garden Retreat
Polk City
10.0 out of 10, Exceptional, (3 reviews)
"Clean comfort all ok"
United States
Donald P.
The price is CA $107
CA $284 total
includes taxes & fees
Jun 15 - Jun 16
Charming Historic Cottage with Cozy Porch and Garden Retreat
House (3 Bedrooms) | Interior

Golf, Dine & Unwind Poolside! Haines City Getaway

Golf, Dine & Unwind Poolside! Haines City Getaway
3.0 star property
Haines City
The price is CA $197
CA $547 total
includes taxes & fees
Jun 15 - Jun 16
Golf, Dine & Unwind Poolside! Haines City Getaway
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 CA $125
CA $512 total
includes taxes & fees
Jun 15 - Jun 16
Oasis Near Disney w Golf View, Family&pet Friendly
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 CA $113
CA $271 total
includes taxes & fees
Jun 15 - Jun 16
Perfect Place for a Perfect Vacation
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 CA $136
CA $296 total
includes taxes & fees
Jun 16 - Jun 17
Family-Friendly Cottage Near Orlando’s Top Attractions
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 CA $313
CA $647 total
includes taxes & fees
Jun 26 - Jun 27
Family Resort Home w Pool, BBQ & Game Room
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 CA $130
CA $306 total
includes taxes & fees
Jun 27 - Jun 28
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 CA $118
CA $418 total
includes taxes & fees
Jun 15 - Jun 16
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
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 CA $99
CA $218 total
includes taxes & fees
Jun 15 - Jun 16
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Microwave, stovetop

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very good, (7 reviews)
"Nice, Cute little place"
United States
Brenda N.
The price is CA $95
CA $239 total
includes taxes & fees
Jun 23 - Jun 24
Tiny house close to Disney KISSIMMEE
Exterior

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.6 out of 10, Exceptional, (10 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is CA $137
CA $388 total
includes taxes & fees
Jun 17 - Jun 18
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
House (2 Bedrooms) | Interior

Dog-friendly Yard! Walkable Dixieland District Gem

Dog-friendly Yard! Walkable Dixieland District Gem
2.0 star property
Dixieland
The price is CA $137
CA $384 total
includes taxes & fees
Jun 21 - Jun 22
Dog-friendly Yard! Walkable Dixieland District Gem
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 CA $482
CA $1,156 total
includes taxes & fees
Jul 6 - Jul 7
Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
House (6 Bedrooms) | Interior

Family Home With Pool, BBQ & Cinema Near Disney

Family Home With Pool, BBQ & Cinema Near Disney
3.0 star property
Kissimmee
Family Home With Pool, BBQ & Cinema Near Disney
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 CA $197
CA $509 total
includes taxes & fees
Jun 15 - Jun 16
Davenport Basecamp! 3BR Family Home w/ Patio
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 CA $162
CA $660 total
includes taxes & fees
Jun 15 - Jun 16
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
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 Adventure Hotel by the parks

The Adventure Hotel by the parks

8/10 Good
"Ubicación genial cerca de todo el hotel en muy buenas condiciones"
Eduardo 4-night trip
Posted less than an hour ago
The Adventure Hotel by the parks

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
227
Accommodation
2153 Cottages
Lowest Price
CA $113
Highest Price
CA $1,156

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between CA $113 and CA $1,156 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 2153 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 Center, 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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