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8 Aug - 10 Aug
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29 Aug - 31 Aug
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26 Sept - 28 Sept

Featured Cottages in Lakeland - Winter Haven

Lafitte's Landing Lakeview Cottage - Lakefront!
House, Multiple Beds, Patio, Garden View (Lafitte's Landing Lakeview Cottage) | Property grounds

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!
8000 Lost Shaker Lane
Welcome to Margaritaville, a charming two-story residence with a front porch and lush garden.

8000 Lost Shaker Lane

3.0 star property
9.6 out of 10, Exceptional, (7)
"The house is absolutely beautiful. Very clean and has everything you need. Unfortunately you can’t use the pool which I didn’t understand so that was the only downside. The property is gorgeous. "
8000 Lost Shaker Lane
Family 4BR Home w/ Resort Pool Near Disney
House (4 Bedrooms) | Floor plan

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, (176)
"Good sized cabins. A bit best up but very comfortable. "
The price is AU$140
includes taxes & fees
4 Aug - 5 Aug
Lake Ida Beach Resort
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Stroll up to the charming front porch and enter through the covered entryway.

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

2.0 star property
10.0 out of 10, Exceptional, (1)
"We absolutely loved our stay here! The house was well stocked with lots of games, movies, toys. All combined with the piano, foosball table, screened in porch and private backyard gave us plenty to do as a family with all ages. Everything was of very high quality and comfortable. We also really appreciated how responsive, friendly, and accommodating our hosts and their staff were. We will definitely stay here again!"
The price is AU$435
includes taxes & fees
4 Aug - 5 Aug
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
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!
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!
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!
Lakefront Frostproof Vacation Rental w/ Beach!
House (2 Bedrooms) | Interior

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!
Lakeland Cottage w/ Pool Access + Screened Porch!
Cottage (2 Bedrooms) | Interior

Lakeland Cottage w/ Pool Access + Screened Porch!

3.0 star property
Lakeland Cottage w/ Pool Access + Screened Porch!
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!
Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready!
Surrounded by lush greenery and a well-maintained lawn, this serene lakeside property offers an and peaceful atmosphere.

Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready!

10.0 out of 10, Exceptional, (7)
"This place is great. Can hold 4 boats with 4 people. Great place!!!"
Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready!
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
8918 Sydney Avenue
Stunning two-story building with a central entrance, surrounded by lush greenery and a beautifully manicured lawn.

8918 Sydney Avenue

3.0 star property
10.0 out of 10, Exceptional, (1)
8918 Sydney Avenue
Up to Scale With Margaritas
Exterior

Up to Scale With Margaritas

3.0 star property
9.0 out of 10, Wonderful, (8)
"The property the check-in everything is excellent. I enjoy staying other place."
Up to Scale With Margaritas
*Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*
Relax on the deck, steps from a charming single-story retreat with a grassy field and trees.

*Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*

9.2 out of 10, Wonderful, (34)
"Perfect size, price with all amenities along with location. We were very pleased with our experience. Will definitely stay again if available next visit!"
*Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*
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!
Lake Home - 2 bd rm w/dock & pier on Lake Rosalie, Lake Wales
Enjoy waterfront views from the covered pier, featuring a seating area and boat launch.

Lake Home - 2 bd rm w/dock & pier on Lake Rosalie, Lake Wales

10.0 out of 10, Exceptional, (4)
"Beautiful view. Enjoyed our short getaway and will certainly look into staying here again. "
Lake Home - 2 bd rm w/dock & pier on Lake Rosalie, Lake Wales
Cottage w/ Private Pool - Walk to Lake Wales!
Traditional home with a covered arbor, well-manicured yard, and classic American architecture.

Cottage w/ Private Pool - Walk to Lake Wales!

9.8 out of 10, Exceptional, (67)
"Perfect cottage for a weekend getaway! Fully stocked with everything you need. Great communication with host and easy check in process. Would definitely stay here again. "
Cottage w/ Private Pool - Walk to Lake Wales!
Charming Mid-century House - Just Steps to Lake!
House (3 Bedrooms) | Interior

Charming Mid-century House - Just Steps to Lake!

3.0 star property
Charming Mid-century House - Just Steps to Lake!
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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Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Prices for cottages in Lakeland - Winter Haven range between AU$140 and AU$435 per night. Whatever your budget, you'll find the perfect place to relax and reconnect with nature. This price was 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?
Lakeland - Winter Haven has 66 cottages on offer. Select your travel dates, enter your destination and plan your perfect stay today.
What is there to do in Lakeland - Winter Haven near my cottage?
The most important travel accessory for your Lakeland - Winter Haven trip is a well-thought-out itinerary! Polk Museum of Art, Polk Theatre and Explorations V Children s Museum are some of the biggest sights if you're making your way to Lakeland. Winter Haven is also home to big-name attractions, such as Theatre Winter Haven. Eager to add to your to-do list? Pencil in a visit to Indigos Billiards, Bowling & Games and Chain of Lakes Park too.