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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

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
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 €369
includes taxes & fees
24 Feb - 25 Feb
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Interior

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.6 out of 10, Excellent, (4 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.
Tiny house close to Disney KISSIMMEE
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
10.0 out of 10, Exceptional, (2 reviews)
"Just what we needed for a weekend trip with our grandsons for the weekend "
United States
Christine B.
The price is €234
includes taxes & fees
1 Mar - 2 Mar
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
House (Multiple Bedrooms) | Interior

541-7-ld-dream Home - Private Pool&spa

541-7-ld-dream Home - Private Pool&spa
2.5 star property
Kissimmee
The price is €2,666
includes taxes & fees
16 Feb - 17 Feb
541-7-ld-dream Home - Private Pool&spa
House (6 Bedrooms) | Interior

Encore Swanky

Encore Swanky
3.0 star property
Kissimmee
The price is €420
includes taxes & fees
13 Feb - 14 Feb
Encore Swanky
Smart TV

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 €227
includes taxes & fees
15 Mar - 16 Mar
Charming Historic Cottage with Cozy Porch and Garden Retreat
Exterior

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.6 out of 10, Exceptional, (8 reviews)
"Wonderful place to stay overnight. Nice furnishings. Good room layout for family. Convenience of washer and dryer. Host was quick and responsive. Thank you for a terrific stay."
United States
George L.
The price is €259
includes taxes & fees
10 Mar - 11 Mar
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Exterior

Luxury Cottage Near Legoland & Chain of Lakes

Luxury Cottage Near Legoland & Chain of Lakes
Lake Hamilton
10.0 out of 10, Exceptional, (6 reviews)
"This place is tiny but everything you need for a comfortable stay! Would definitely stay here again."
United States
Dallas C.
The price is €177
includes taxes & fees
26 Feb - 27 Feb
Luxury Cottage Near Legoland & Chain of Lakes
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.
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Pool

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 €187
includes taxes & fees
21 Feb - 22 Feb
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Interior

Orlando Theme Park Basecamp: Family Home w/ Patio

Orlando Theme Park Basecamp: Family Home w/ Patio
3.0 star property
Davenport
The price is €306
includes taxes & fees
25 Feb - 26 Feb
Orlando Theme Park Basecamp: Family Home w/ Patio
Porch

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (188 reviews)
"We have stayed here several times. "
United States
Martha
The price is €71
includes taxes & fees
15 Feb - 16 Feb
Lake Ida Beach Resort
Exterior

Cozy Cottage with Hot Tub Near Disney with Margaritaville Resort & Island H2O.

Cozy Cottage with Hot Tub Near Disney with Margaritaville Resort & Island H2O.
Kissimmee
The price is €403
includes taxes & fees
3 Mar - 4 Mar
Cozy Cottage with Hot Tub Near Disney with Margaritaville Resort & Island H2O.
House (Multiple Bedrooms) | Interior

7613-8-bl-only 10 Minutes From Disney

7613-8-bl-only 10 Minutes From Disney
2.5 star property
Kissimmee
The price is €2,768
includes taxes & fees
23 Feb - 24 Feb
7613-8-bl-only 10 Minutes From Disney
Exterior

Lovely Cottage 3 miles from Disney w/ Hot Tub and Margaritaville Resort &.

Lovely Cottage 3 miles from Disney w/ Hot Tub and Margaritaville Resort &.
Kissimmee
The price is €403
includes taxes & fees
2 Mar - 3 Mar
Lovely Cottage 3 miles from Disney w/ Hot Tub and Margaritaville Resort &.
Exterior

Sun Baked Cottage with Hot Tub near Disney with Margaritaville Resort & Island.

Sun Baked Cottage with Hot Tub near Disney with Margaritaville Resort & Island.
Kissimmee
The price is €403
includes taxes & fees
2 Mar - 3 Mar
Sun Baked Cottage with Hot Tub near Disney with Margaritaville Resort & Island.
Exterior

Playa Verde Cottage with Private Hot Tub near Disney with Margaritaville Resort.

Playa Verde Cottage with Private Hot Tub near Disney with Margaritaville Resort.
Kissimmee
The price is €403
includes taxes & fees
2 Mar - 3 Mar
Playa Verde Cottage with Private Hot Tub near Disney with Margaritaville Resort.
Exterior

Cozy Peach Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Cozy Peach Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
The price is €403
includes taxes & fees
3 Mar - 4 Mar
Cozy Peach Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Exterior

Casa Blanca Cottage with Hot Tub near Disney with Margaritaville Resort &.

Casa Blanca Cottage with Hot Tub near Disney with Margaritaville Resort &.
Kissimmee
The price is €412
includes taxes & fees
4 Mar - 5 Mar
Casa Blanca Cottage with Hot Tub near Disney with Margaritaville Resort &.
Exterior

Caraway Cove Cottage near Disney with Margaritaville Resort & Island H2O Access.

Caraway Cove Cottage near Disney with Margaritaville Resort & Island H2O Access.
Kissimmee
The price is €403
includes taxes & fees
2 Mar - 3 Mar
Caraway Cove Cottage near Disney with Margaritaville Resort & Island H2O Access.
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

Westgate Towers Resort

Westgate Towers Resort

10/10 Excellent
"Clean rooms. Friendly staff. Great location "
Mike 2-night trip
Posted 12 hours ago
Westgate Towers Resort

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Cottages information

Number of reviews
199
Accommodation
78 Cottages
Lowest Price
€71
Highest Price
€420

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Cottages in Lakeland - Winter Haven range between €71 and €420 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 78 cottages in Lakeland - Winter Haven. Whether you're travelling 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 traveller 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 Centre and Publix Field at Joker Marchant Stadium are among the leading sights if you're off to Lakeland. Winter Haven also lures travellers with its wonderful attractions, such as Indigo's Family Fun Centre. Eager to add to your to-do list? Drop by Chain of Lakes Park and Theatre Winter Haven too.

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