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Our top choices for Winter Haven cottages

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 AED 280
AED 314 total
includes taxes & fees
5 Jun - 6 Jun
Lake Ida Beach Resort

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)
"Just what we needed for a weekend trip with our grandsons for the weekend "
United States
Christine B.
The price is AED 422
AED 1,020 total
includes taxes & fees
8 Jun - 9 Jun
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

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 AED 628
AED 1,610 total
includes taxes & fees
9 May - 10 May
Hook, Line & Leisure: Lakefront Gem w/ Porch!

Explore & Relax: Chic & Cozy Retreat in Lakeland!

Explore & Relax: Chic & Cozy Retreat in Lakeland!
3.0 star property
Lakeland
10.0 out of 10, Exceptional, (1 review)
"We had a great time. The house was beautiful. Decor was beautiful and bedding comforting. I sleep so good. The house was family friendly and plenty of rooms. "
United States
Debra
The price is AED 900
AED 1,990 total
includes taxes & fees
11 May - 12 May
Explore & Relax: Chic & Cozy Retreat in Lakeland!

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, (1 review)
"The communication with the property owner was excellent. The cottage is attached to the owners home but is quite private and comfortable. I’ve already recommended it to family members who wish to visit that area."
United States
Tina O.
The price is AED 281
AED 742 total
includes taxes & fees
11 May - 12 May
Charming Historic Cottage with Cozy Porch and Garden Retreat

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 AED 257
AED 636 total
includes taxes & fees
11 May - 12 May
Tiny house close to Disney KISSIMMEE

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 AED 331
AED 752 total
includes taxes & fees
11 May - 12 May
Family-Friendly Cottage Near Orlando’s Top Attractions

Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is AED 298
AED 703 total
includes taxes & fees
10 May - 11 May
Perfect Place for a Perfect Vacation

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 AED 297
AED 1,079 total
includes taxes & fees
11 May - 12 May
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.6 out of 10, Exceptional, (9 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is AED 474
AED 1,156 total
includes taxes & fees
8 Jun - 9 Jun
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

Upstay: Pet-friendly Family Home w Pool & Sundeck

Upstay: Pet-friendly Family Home w Pool & Sundeck
3.0 star property
Kissimmee
The price is AED 375
AED 1,213 total
includes taxes & fees
12 May - 13 May
Upstay: Pet-friendly Family Home w Pool & Sundeck

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 AED 341
AED 793 total
includes taxes & fees
12 May - 13 May
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is AED 322
AED 1,438 total
includes taxes & fees
9 May - 10 May
Serenity - Family & Pet Friendly, Amazing Location

Dog-friendly Yard! Walkable Dixieland District Gem

Dog-friendly Yard! Walkable Dixieland District Gem
2.0 star property
Dixieland
The price is AED 360
AED 1,007 total
includes taxes & fees
14 May - 15 May
Dog-friendly Yard! Walkable Dixieland District Gem

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 AED 261
AED 572 total
includes taxes & fees
9 May - 10 May
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

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

Orlando Theme Park Basecamp: Family Home w/ Patio

Orlando Theme Park Basecamp: Family Home w/ Patio
3.0 star property
Davenport
The price is AED 518
AED 1,335 total
includes taxes & fees
13 May - 14 May
Orlando Theme Park Basecamp: Family Home w/ Patio

~ 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 AED 426
AED 1,732 total
includes taxes & fees
8 Jun - 9 Jun
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

Bella Vida House With Pool and Games - Near Disney!

Bella Vida House With Pool and Games - Near Disney!
3.0 star property
Bellavida
The price is AED 874
AED 2,155 total
includes taxes & fees
10 May - 11 May
Bella Vida House With Pool and Games - Near Disney!
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

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between AED 314 and AED 2,155 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 2122 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.
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.