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Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Featured Cottages in Lakeland - Winter Haven

Lake Ida Beach Resort
Outdoor pool, pool umbrellas, pool loungers

Lake Ida Beach Resort

3.0 star property
7.4 out of 10, Good, (168)
"Very nice stay...2 days. Very comfortable. Recommend. "
The price is S$108
includes taxes & fees
1 Mar - 2 Mar
Lake Ida Beach Resort
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, (10)
"Great property! Was perfect for our family and made down time from the parks really nice."
Large Villa W/private Pool & Game Room! Waterpark
Sleek Home Near Downtown Lakeland w/ Yard!
Interior

Sleek Home Near Downtown Lakeland w/ Yard!

3.0 star property
Sleek Home Near Downtown Lakeland w/ Yard!
Family-friendly Winter Haven Home w/ Pool!
Books

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!
Lakeland House < Half Mi to Tigers Spring Training
Private kitchen

Lakeland House < Half Mi to Tigers Spring Training

3.0 star property
Lakeland House < Half Mi to Tigers Spring Training
Charming Tiny Home w/ Private Hot Tub!
Private kitchen

Charming Tiny Home w/ Private Hot Tub!

3.0 star property
8.0 out of 10, Very good, (3)
"It was a great little place but is a bit run down. There’s broken furniture and the hot tub seemed a bit cloudy"
Charming Tiny Home w/ Private Hot Tub!
Family-friendly Lakeland Home w/ Private Hot Tub!
Private kitchen

Family-friendly Lakeland Home w/ Private Hot Tub!

3.0 star property
9.0 out of 10, Wonderful, (2)
"This home is laid out nicely and met our needs for a quick weekend stay in Lakeland. The host, Letty, was a pleasure and provided very clear and easy to follow instructions. The home needs some updating, but was clean, comfortable and in a great location. "
Family-friendly Lakeland Home w/ Private Hot Tub!
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!
Lakefront Frostproof Vacation Rental w/ Beach!
Beach

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!
Private Pool/spa, Free Waterpark, Lazy River!
Miscellaneous

Private Pool/spa, Free Waterpark, Lazy River!

4.0 star property
10.0 out of 10, Exceptional, (5)
"Nice house good upkeep and good communication."
Private Pool/spa, Free Waterpark, Lazy River!
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 Wales Vacation Rental w/ Direct Canal Access!
Terrace/patio

Lake Wales Vacation Rental w/ Direct Canal Access!

3.0 star property
Lake Wales Vacation Rental w/ Direct Canal Access!
Auburndale Vacation Rental w/ Yard & Lake Views
Microwave, oven, stovetop, dishwasher

Auburndale Vacation Rental w/ Yard & Lake Views

3.0 star property
Auburndale Vacation Rental w/ Yard & Lake Views
Winter Haven Retreat w/ Private Pool!
Interior

Winter Haven Retreat w/ Private Pool!

3.0 star property
Winter Haven Retreat w/ Private Pool!
Winter Haven Home w/ Pool Near Legoland!
Private kitchen

Winter Haven Home w/ Pool Near Legoland!

3.0 star property
10.0 out of 10, Exceptional, (1)
"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!
Pet-friendly Auburndale House w/ Lake Views!
Miscellaneous

Pet-friendly Auburndale House w/ Lake Views!

3.0 star property
8.0 out of 10, Very good, (1)
"This house has beautiful views of Lake Ariana and you can walk to old town and access the lake easily. The house is an old classic central Florida house with some quirks, but had room for family and entertaining. Auburndale beautiful and was a great place to visit and had quick access to highways. "
Pet-friendly Auburndale House w/ Lake Views!
Bright Cypress Gardens Home Near Legoland!
Private kitchen

Bright Cypress Gardens Home Near Legoland!

3.0 star property
9.0 out of 10, Wonderful, (2)
"Pros: communication was great; key lime pie was very good; extremely convenient location to Legoland; pictures were accurate; place was obviously swept and linens were clean; appliances and bathroom fixtures were in good condition. Cons: Noticeable cigarette smell (we used a Glade plugin which helped); HVAC returns also showed signs of smoking; found a dead roach in kitchen on second night of stay; not much seating (we are a family of 5 and seating was meant for 4); more dinnerware would have...
Bright Cypress Gardens Home Near Legoland!
Lakefront Home w/ Screened Porch & Grill
Interior

Lakefront Home w/ Screened Porch & Grill

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."
Lakefront Home w/ Screened Porch & Grill
Lakeland Retreat w/ Private Pool & Yard Games!
Outdoor pool

Lakeland Retreat w/ Private Pool & Yard Games!

3.0 star property
Lakeland Retreat w/ Private Pool & Yard Games!
Lakefront Home w/ Screened Porches in Frostproof!
Outdoor dining

Lakefront Home w/ Screened Porches in Frostproof!

3.0 star property
Lakefront Home w/ Screened Porches in Frostproof!
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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Other property types in Lakeland - Winter Haven

Margaritaville Resort Orlando Cottages by Rentyl
Interior

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1195)
"Cottage could’ve been a bit cleaner in regards to the floors/stairs, and some stains on the furniture in living room. The transportation was great with the free pick up and drop off around the property with the shuttle. Beds were comfortable. I had issues with my card from out of the country and Margaritaville worked with me on that. Overall a great time"
Margaritaville Resort Orlando Cottages by Rentyl
Summer Bay Orlando by Exploria Resorts
5 outdoor pools

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very good, (5133)
"It was a great experience. Will come back again "
The price is S$227
includes taxes & fees
26 Feb - 27 Feb
Summer Bay Orlando by Exploria Resorts
The Berkley, Orlando
Lobby sitting area

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1671)
"The best staff at any resort we have ever stayed at. It was clean, very well taken care of. The pool and hot tub area was always in pristine cleanliness. My only complaint is the furniture, it’s not a comfortable couch and the living room chairs weren’t any better. "
The price is S$337
includes taxes & fees
26 Feb - 27 Feb
The Berkley, Orlando
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.

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Rates for cottages in Lakeland - Winter Haven range between S$108 and S$108 per night. No matter your budget, you’re sure to find the ideal place to get reacquainted with nature. 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?
You can choose from 37 cottages in Lakeland - Winter Haven. Whether you’re travelling with the kids, as a table-for-two or with a group of close friends, Expedia makes it simple to find your ideal digs.
Why book your cottage in Lakeland - Winter Haven with Expedia?
Expedia has some wonderful cottages in Lakeland - Winter Haven, so start packing your bags for an unforgettable holiday on nature’s doorstep. If you have a budget, choose how much you want to spend and the star rating of your property. Or, try out our filters to search for cottages with a kitchen or a pool. We’ll help you find a suitable place whatever your plans or style of travel.
How can I find cheap cottages in Lakeland - Winter Haven?
A wonderful way to spot cheap cottages in Lakeland - Winter Haven is with Expedia’s useful filter tool. Refine your search by budget, star rating and amenities to snag excellent rates with only a few clicks.
What is there to do in Lakeland - Winter Haven near my cottage?
Whatever you’re into, there are so many things to do in Lakeland - Winter Haven. If you’re visiting Lakeland, don’t miss Polk Museum of Art, Polk Theatre and Explorations V Children s Museum. Planning a getaway in Lake Wales? KICCO Wildlife Management Area, Bok Tower Gardens and Mountain Lake are among the top sights in this city.