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1 Aug - 3 Aug
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22 Aug - 24 Aug
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19 Sept - 21 Sept

Featured Cottages in Lakeland - Winter Haven

Lafitte's Landing Lakeview Cottage - Lakefront!
Relax with a glass of wine in this serene outdoor space overlooking the water.

Lafitte's Landing Lakeview Cottage - Lakefront!

3.0 star property
10.0 out of 10, Exceptional, (7)
"Beautiful Cottage and enjoyed the back deck overlooking the lake. Great family vacation spot."
Lafitte's Landing Lakeview Cottage - Lakefront!
Family 4BR Home w/ Resort Pool Near Disney
Enjoy a shaded retreat in our outdoor space with a bench.

Family 4BR Home w/ Resort Pool Near Disney

3.0 star property
Family 4BR Home w/ Resort Pool Near Disney
Lake Ida Beach Resort
Situated in a lush environment, this charming house offers a serene setting with a well-maintained lawn and trees.

Lake Ida Beach Resort

3.0 star property
7.4 out of 10, Good, (175)
"Good sized cabins. A bit best up but very comfortable. "
The price is S$129
includes taxes & fees
23 Jul - 24 Jul
Lake Ida Beach Resort
Winter Haven Home w/ Pool Near Legoland!
Stroll through the charming grounds of this single-story home, surrounded by a well-manicured lawn and mature trees.

Winter Haven Home w/ Pool Near Legoland!

3.0 star property
6.0 out of 10, (2)
"Very spacious, clean and recently remodeled property. Very close to LEGO Land, great alternative to staying at Legoland "
Winter Haven Home w/ Pool Near Legoland!
Sleek Home Near Downtown Lakeland w/ Yard!
Enjoy a peaceful retreat in this charming home surrounded by lush greenery and a picturesque white picket fence.

Sleek Home Near Downtown Lakeland w/ Yard!

3.0 star property
10.0 out of 10, Exceptional, (2)
Sleek Home Near Downtown Lakeland w/ Yard!
Mid-century Modern Escape in Central Lakeland!
Contemporary home with a flat roof, large windows, and a garden area.

Mid-century Modern Escape in Central Lakeland!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Communication with the host was simple and she was accessible. The basic amenities were readily available and we did not have to rush to go to the supermarket when we arrived. The place is spacious, clean and neighbourhood very quiet."
Mid-century Modern Escape in Central Lakeland!
Lakeland Cottage w/ Pool Access + Screened Porch!
Interior

Lakeland Cottage w/ Pool Access + Screened Porch!

3.0 star property
Lakeland Cottage w/ Pool Access + Screened Porch!
Lakefront Frostproof Vacation Rental w/ Beach!
Surrounded by lush greenery, this single-story home offers a serene atmosphere.

Lakefront Frostproof Vacation Rental w/ Beach!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We thoroughly enjoyed our stay! The home was very clean. The floors were so clean when wiping up some water drips, there was not one spec of dirt on the paper towel! That is my measure for being clean! Home owners were excellent to work with. Texting answers to my many questions. We stayed while we were in town for the 12 Hours of Sebring race. Easy 30 minute drive to the track. Beautiful view of the lake with lounge chairs on a private beach behind the house. I can't say enough about...
Lakefront Frostproof Vacation Rental w/ Beach!
8 Mi to Legoland: Winter Haven Home w/ Lanai!
Stylish home with a welcoming front door, beautifully manicured lawn, and a small porch area.

8 Mi to Legoland: Winter Haven Home w/ Lanai!

3.0 star property
8 Mi to Legoland: Winter Haven Home w/ Lanai!
Up to Scale With Margaritas
Experience the grand entrance and scenic views of the surrounding landscape from our outdoor seating area.

Up to Scale With Margaritas

3.0 star property
9.0 out of 10, Wonderful, (7)
"Everything was perfect "
Up to Scale With Margaritas
8081 Knee Deep Rd
Enjoy a view of the surrounding residential area from this balcony.

8081 Knee Deep Rd

3.0 star property
10.0 out of 10, Exceptional, (2)
"greqt host"
8081 Knee Deep Rd
3 Mi to Disney: Home w/ Hot Tub in Margaritaville!
Interior

3 Mi to Disney: Home w/ Hot Tub in Margaritaville!

3.0 star property
9.4 out of 10, Exceptional, (3)
"This place is great on all concerts, clean, right location, at lots of things to do around the property very practical for family get together ❤️ "
3 Mi to Disney: Home w/ Hot Tub in Margaritaville!
Winter Haven Vacation Rental w/ Patio & Gas Grill!
Property grounds

Winter Haven Vacation Rental w/ Patio & Gas Grill!

3.0 star property
Winter Haven Vacation Rental w/ Patio & Gas Grill!
Stylish Waterfront Lake Wales Home Rental w/ Dock!
Enjoy a serene stay in this two-story house surrounded by a well-maintained lawn and trees.

Stylish Waterfront Lake Wales Home Rental w/ Dock!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great coffee bar! Clean and delightful place to stay. Would definitely come again!"
Stylish Waterfront Lake Wales Home Rental w/ Dock!
Lakefront Home w/ Screened Porches in Frostproof!
Relax in a scenic outdoor space with a grill and hammock, surrounded by trees and a body of water.

Lakefront Home w/ Screened Porches in Frostproof!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Excellent relaxing location on a beautiful lake. Perfect for the little ones to play in the shallow water at the edge of the lake in the backyard, or to take the boat out for fishing, tubing, or wakeboarding. The dock was very convenient, and the boat ramp was not far away. The host is very friendly, accommodating, and helpful. The kitchen was surprisingly well-stocked with cookware and dishes for a large family. The outdoor covered grill area and games provided were also a nice plus."
Lakefront Home w/ Screened Porches in Frostproof!
4 Mi to Legoland: Newly Built Home in Winter Haven
Interior

4 Mi to Legoland: Newly Built Home in Winter Haven

3.0 star property
10.0 out of 10, Exceptional, (1)
"Robert the property manager was awesome. I enjoyed the stay would definitely recommend to anyone wanting to stay somewhere safe and I didn’t need anything came with everything."
4 Mi to Legoland: Newly Built Home in Winter Haven
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Interior

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

3.0 star property
10.0 out of 10, Exceptional, (2)
"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."
The price is S$479
includes taxes & fees
23 Jul - 24 Jul
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Lake Wales Vacation Rental w/ Direct Canal Access!
Step into this charming cabin, featuring a spacious porch and a covered outdoor seating area, perfect for taking in the surroundings.

Lake Wales Vacation Rental w/ Direct Canal Access!

3.0 star property
Lake Wales Vacation Rental w/ Direct Canal Access!
Lake Wales Vacation Rental Near Lake Kissimmee!
Relax in the covered patio area, complete with a grill station and comfortable seating for a leisurely meal.

Lake Wales Vacation Rental Near Lake Kissimmee!

3.0 star property
Lake Wales Vacation Rental Near Lake Kissimmee!
Family-friendly Winter Haven Home w/ Pool!
Relax in a serene outdoor space with a seating area featuring large windows and a grassy view.

Family-friendly Winter Haven Home w/ Pool!

3.0 star property
8.0 out of 10, Very good, (1)
"Property was clean and very functional. Had the opportunity to speak with the host after a miscommunication with his property manager and he was first class. Great property and would stay again for sure. Host was exceptional!!"
Family-friendly Winter Haven 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 Lakeland - Winter Haven Hotel Reviews

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

10/10 Excellent
"Great hotel. Very nice and great pool area."
Angelo 4-night trip
Posted 1 day ago
Margaritaville Resort Orlando with H2O Waterpark

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Cottages in Lakeland - Winter Haven range between S$129 and S$479 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 46 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!