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Check prices for these dates

In two weeks
26 Sept - 28 Sept
In one month
10 Oct - 12 Oct
In two months
7 Nov - 9 Nov
In three months
5 Dec - 7 Dec

Featured Cottages in Lakeland - Winter Haven

Our top choices for Lakeland - Winter Haven cottages

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
9.8 out of 10, Exceptional, (8)
"Beautiful Cottage and enjoyed the back deck overlooking the lake. Great family vacation spot."
Lafitte's Landing Lakeview Cottage - Lakefront!
8000 Lost Shaker Lane
Miscellaneous

8000 Lost Shaker Lane

3.0 star property
9.6 out of 10, Exceptional, (7)
"Lots of room , beautifully decorated. Close to everything we needed for the weekend . "
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
Townhome Splash Pool BBQ Free Water Park!
Miscellaneous

Townhome Splash Pool BBQ Free Water Park!

3.5 star property
9.6 out of 10, Exceptional, (10)
"10/10 stay "
Townhome Splash Pool BBQ Free Water Park!
3000 Latitude Lane
Outdoor spa tub

3000 Latitude Lane

3.0 star property
9.6 out of 10, Exceptional, (4)
"Great stay!"
3000 Latitude Lane
Villa w/ Private Pool & Free Resort Access!
Miscellaneous

Villa w/ Private Pool & Free Resort Access!

4.5 star property
9.0 out of 10, Wonderful, (6)
"Good stay "
Villa w/ Private Pool & Free Resort Access!
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)
"The place was even better than I suspected and so convient."
Lake Home - 2 bd rm w/dock & pier on Lake Rosalie, Lake Wales
Mid-century Modern Escape in Central Lakeland!
House (3 Bedrooms) | 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!
Game Room + Fenced Yard: Home Near Disney World!
Interior

Game Room + Fenced Yard: Home Near Disney World!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We will definitely be staying at this property again "
Game Room + Fenced Yard: Home Near Disney World!
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!
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)
"We had a wonderful stay. Great communication with the hosts, very clean, and a wonderful location for what we needed. Would definitely stay again."
Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready!
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!
Lake Ida Beach Resort
Porch

Lake Ida Beach Resort

3.0 star property
7.4 out of 10, Good, (177)
"We have stayed here several times. "
The price is AU$115
includes taxes & fees
12 Sept - 13 Sept
Lake Ida Beach Resort
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)
"Great place had a awesome time."
3 Mi to Disney: Home w/ Hot Tub in Margaritaville!
Spacious Kissimmee Family Home w/ Game Room & Pool
House (Multiple Bedrooms) | Interior

Spacious Kissimmee Family Home w/ Game Room & Pool

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great host Stay was such a pleasure. He even gave us a checkout time extension at a short notice "
Spacious Kissimmee Family Home w/ Game Room & Pool
Large Villa W/private Pool & Game Room! Waterpark
Miscellaneous

Large Villa W/private Pool & Game Room! Waterpark

3.5 star property
9.6 out of 10, Exceptional, (11)
"Great property! Was perfect for our family and made down time from the parks really nice."
Large Villa W/private Pool & Game Room! Waterpark
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
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, (2)
"Just what we needed for a weekend trip with our grandsons for the weekend "
The price is AU$427
includes taxes & fees
10 Sept - 11 Sept
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
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

Find out more about Lakeland - Winter Haven

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Cottages information

Number of reviews
Accommodation
66 Cottages
Lowest Price
AU$115
Highest Price
AU$427

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Explore a world of travel with Expedia

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Prices for cottages in Lakeland - Winter Haven range between AU$115 and AU$427 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.