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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Winter Haven cottages

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 ฿5,416
฿13,881 total
includes taxes & fees
28 Mar - 29 Mar
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
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 ฿2,497
฿2,796 total
includes taxes & fees
18 Mar - 19 Mar
Lake Ida Beach Resort
Interior

Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
Serenity - Family & Pet Friendly, Amazing Location
House (2 Bedrooms) | Interior

Home w/ Private Yard < 2 Mi to Hollis Garden!

Home w/ Private Yard < 2 Mi to Hollis Garden!
3.0 star property
Lakeland
The price is ฿3,611
฿9,255 total
includes taxes & fees
15 Mar - 16 Mar
Home w/ Private Yard < 2 Mi to Hollis Garden!
Exterior

NEW King Bed Glow In The Dark Kid Cave

NEW King Bed Glow In The Dark Kid Cave
3.0 star property
Cumbrian Lakes
The price is ฿8,028
฿19,105 total
includes taxes & fees
25 Mar - 26 Mar
NEW King Bed Glow In The Dark Kid Cave
House (3 Bedrooms) | Front of property

Orlando Theme Park Basecamp: Family Home w/ Patio

Orlando Theme Park Basecamp: Family Home w/ Patio
3.0 star property
Davenport
The price is ฿4,456
฿11,490 total
includes taxes & fees
19 Mar - 20 Mar
Orlando Theme Park Basecamp: Family Home w/ Patio
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 ฿6,195
฿14,953 total
includes taxes & fees
1 Apr - 2 Apr
Lakefront Babson Park Escape: Pet Friendly!
House (3 Bedrooms) | Interior

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 ฿4,973
฿12,951 total
includes taxes & fees
1 Apr - 2 Apr
Explore & Relax: Chic & Cozy Retreat in Lakeland!
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
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
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 ฿3,097
฿8,669 total
includes taxes & fees
25 Mar - 26 Mar
Dog-friendly Yard! Walkable Dixieland District Gem
House (3 Bedrooms) | Interior

Modern Lakeland Golf Retreat w/ Putting Green

Modern Lakeland Golf Retreat w/ Putting Green
3.0 star property
Lake Hollingsworth
10.0 out of 10, Exceptional, (1 review)
The price is ฿7,348
฿16,002 total
includes taxes & fees
13 Mar - 14 Mar
Modern Lakeland Golf Retreat w/ Putting Green
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
"This was a nice place to stay with my family during an Orlando vacation. Plenty of breakfast options. We enjoyed a full-sized fridge in our room, and everything was clean."
Carol 4-night trip
Posted 3 hours ago
Kompose Boutique Resort at Theme Parks

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
194
Accommodation
1427 Cottages
Lowest Price
฿2,796
Highest Price
฿19,105

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between ฿2,796 and ฿19,105 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 1427 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.