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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Cottages in Lakeland - Winter Haven and around

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

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
House (4 Bedrooms) | Front of property

Family 4BR Home w/ Resort Pool Near Disney

3.0 star property
Family 4BR Home w/ Resort Pool Near Disney
Lake Ida Beach Resort
Relax by the pool surrounded by a secure fence and lush surroundings.

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 €77
includes taxes & fees
29 Jul - 30 Jul
Lake Ida Beach Resort
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Relax in this inviting living space with a comfortable sofa and glass coffee table, perfect for socializing and unwinding.

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 €243
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!
Enjoy cooking in this well-lit kitchen with a range hood, microwave, and double sink.

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 cooking in this well-equipped kitchen with a dishwasher, oven, and refrigerator, plus a window with blinds.

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!
Enjoy cooking in this well-equipped kitchen with a large island, sink, microwave, and coffee maker.

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!
Cottage (2 Bedrooms) | 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!
Enjoy a serene view of the water and lush surroundings from this sunroom, featuring a ceiling fan, large windows, and comfortable seating areas.

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!
Enjoy a stylish kitchen and dining area with granite countertops, stainless steel appliances, and a glass-top table.

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!
Up to Scale With Margaritas
Outdoor dining

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
8081 Knee Deep Rd
Experience the elegant lobby with a striking abstract sculpture, comfortable seating, and a tropical ambiance.

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!
House (3 Bedrooms) | 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!
*Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*
Compact kitchen with a stainless steel refrigerator, microwave, and white cabinetry, featuring a dining area with a table and chairs.

*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!
Microwave, oven, stovetop, blender

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
Lakeland Cottage w/ Pool Access + Screened Porch!
Cozy living space with a well-equipped kitchen and comfortable seating area.

Lakeland Cottage w/ Pool Access + Screened Porch!

9.8 out of 10, Exceptional, (6)
"Our stay was very enjoyable and the location was good for us. Would certainly do it again."
Lakeland Cottage w/ Pool Access + Screened Porch!
Cottage w/ Private Pool - Walk to Lake Wales!
Cozy retreat with a dining table set for two, a comfortable chair, and a beautiful rug.

Cottage w/ Private Pool - Walk to Lake Wales!

9.8 out of 10, Exceptional, (66)
"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!
Lake Wales Vacation Rental w/ Screened-In Porch!
Relax in a stylish living room with a sofa, armchairs, and dining table.

Lake Wales Vacation Rental w/ Screened-In Porch!

10.0 out of 10, Exceptional, (19)
"Perfect place for a family wedding we were attending. Close to downtown Lake Wales which was really cute and not too far from Disney world which we went to for 1 day."
Lake Wales Vacation Rental w/ Screened-In Porch!
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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Great"
Olivia 3-night trip
Posted 13 hours ago
The Grove Resort & Water Park Orlando

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Cottages in Lakeland - Winter Haven range between €77 and €77 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 74 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!