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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

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) | 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!
Lake Ida Beach Resort
Porch

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 €78
includes taxes & fees
11 Aug - 12 Aug
Lake Ida Beach Resort
8000 Lost Shaker Lane
Miscellaneous

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
Mid-century Modern Escape in Central Lakeland!
Interior

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!
Interior

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!
Interior

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!
Property grounds

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!
8918 Sydney Avenue
Miscellaneous

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*
Terrace/patio

*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
Terrace/patio

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!
Exterior

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!
Lake Wales Vacation Rental w/ Screened-In Porch!
Exterior

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!
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Exterior

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!"
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Lakeland Cottage w/ Pool Access + Screened Porch!
Exterior

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!
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

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"Amazing accommodations "
Nathaniel 2-night trip
Posted 12 hours ago
Hilton Vacation Club Mystic Dunes Orlando

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Cottages in Lakeland - Winter Haven range between €78 and €78 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 66 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!