Search Cottages in Lakeland - Winter Haven

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Lakeland - 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

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
Winter Haven
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 ₩252,651
₩647,525 total
includes taxes & fees
Dec 27 - Dec 28
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
House (3 Bedrooms) | Interior
Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is ₩132,974
₩400,792 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Upstay: Bright Family-friendly Retreat With Patio
Porch
Lake Ida Beach Resort

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (187)
"We have stayed here several times. "
United States
Martha
The price is ₩125,587
₩140,658 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Lake Ida Beach Resort
House (2 Bedrooms) | Interior
2BR Dog-friendly w/ Yard, Screened Porch, & Grill

2BR Dog-friendly w/ Yard, Screened Porch, & Grill

2BR Dog-friendly w/ Yard, Screened Porch, & Grill
2.0 star property
Dixieland
The price is ₩144,794
₩405,261 total
includes taxes & fees
Dec 27 - Dec 28
2BR Dog-friendly w/ Yard, Screened Porch, & Grill
House (6 Bedrooms) | Interior
Encore Swanky

Encore Swanky

Encore Swanky
3.0 star property
Kissimmee
The price is ₩590,996
₩1,275,443 total
includes taxes & fees
Dec 29 - Dec 30
Encore Swanky
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 Lakeland - Winter Haven Hotel Reviews

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"Festive"
Constance 3-night trip
Posted 9 hours ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Cottages information

Number of reviews
190
Accommodation
59 Cottages
Lowest Price
₩140,658
Highest Price
₩1,275,443

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Cottages in Lakeland - Winter Haven range between ₩140,658 and ₩1,275,443 per night. These properties offer a chance to get in touch 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 Lakeland - Winter Haven?
Choose from 59 cottages in Lakeland - Winter Haven. Whether you're traveling with the whole family, as a twosome or with a group of besties, Expedia can help you secure your perfect fit.
Why book your cottage in Lakeland - Winter Haven with Expedia?
Reserving a cottage in Lakeland - Winter Haven is as simple as entering your travel dates and choosing an ideal place for outdoor relaxation and recreation. From chic retreats to inexpensive properties and cottages that offer conveniences like a kitchen, Expedia has something for all traveler styles. As for irresistible deals? We've got you covered!
How can I find cheap cottages in Lakeland - Winter Haven?
Expedia can help you locate cheap cottages in Lakeland - Winter Haven. To reserve your perfect stay in just a few clicks, use our convenient filter tool to refine your search results by amenities, budget and star rating.
What is there to do in Lakeland - Winter Haven near my cottage?
One of the best travel accessories for your Lakeland - Winter Haven adventure is an awesome itinerary! Polk Museum of Art, RP Funding Center and Publix Field at Joker Marchant Stadium are among the leading sights if you're off to Lakeland. Winter Haven also lures travelers with its wonderful attractions, such as Indigo's Family Fun Center. Eager to add to your to-do list? Drop by Chain of Lakes Park and Theatre Winter Haven too.