Search Cottages in Lakeland - Winter Haven

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Compare 46 Cottages in Lakeland - Winter Haven with updated reviews, rates, and availability.

Lake Ida Beach Resort

3.0 star property
7.4 out of 10, Good, (171)
"Good sized cabins. A bit best up but very comfortable. "
The price is ₩109,848
₩123,030 total
includes taxes & fees
Mar 30 - Mar 31
Lake Ida Beach Resort

Townhome W/private Pool & Themed Rooms, Near Wdw!

4.0 star property
9.6 out of 10, Exceptional, (5)
"Great home and great resort! Loved having a private pool at the house and then all amenities included with the resort. Family had a great time. "
Townhome W/private Pool & Themed Rooms, Near Wdw!

8000 Lost Shaker Lane

3.0 star property
9.8 out of 10, Exceptional, (6)
"Beautiful and clean! Easy to find, great location, easy check in and out and very roomy space! Everything you need is provided! Comfortable beds! Only thing I’d change is find an easier way to contact host with questions, such as direct texting. Otherwise, it’s call them, leave a message and wait for a call back. Or send a message through their chat and days to get a response. That said everything I needed - check in/check out proceedings was sent on time through email . Overall, a great...
8000 Lost Shaker Lane

Margarita Porch Paradise

5.0 star property
10.0 out of 10, Exceptional, (2)
"The house was beautiful and comfortable for our family, we would have stayed longer! The resort is fun, plenty of stores and good restaurants. We will definitely come back. "
Margarita Porch Paradise

8081 Knee Deep Rd

3.0 star property
10.0 out of 10, Exceptional, (2)
"greqt host"
8081 Knee Deep Rd

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!

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!

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!

Winter Haven Vacation Rental w/ Patio & Gas Grill!

3.0 star property
Winter Haven Vacation Rental w/ Patio & Gas Grill!

8 Mi to Legoland: Winter Haven Home w/ Lanai!

3.0 star property
8 Mi to Legoland: Winter Haven Home w/ Lanai!

Sleek Home Near Downtown Lakeland w/ Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This was a REALLY NICE place. The host provided everything you could possibly need. The residence was spotless. The beds were firm but comfortable. The neighborhood was quiet. We will stay here again next time we’re in the area (if it’s available!). "
Sleek Home Near Downtown Lakeland w/ Yard!

Lake Wales Vacation Rental w/ Direct Canal Access!

3.0 star property
Lake Wales Vacation Rental w/ Direct Canal Access!

4 Mi to Golf: Quiet Lake Wales Retreat

3.0 star property
10.0 out of 10, Exceptional, (1)
"Excellent experience! Would stay here again."
4 Mi to Golf: Quiet Lake Wales Retreat

Auburndale Vacation Rental w/ Yard & Lake Views

3.0 star property
Auburndale Vacation Rental w/ Yard & Lake Views

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!

4 Mi to Legoland: Newly Built Home in Winter Haven

3.0 star property
4 Mi to Legoland: Newly Built Home in Winter Haven

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!

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!

Winter Haven Retreat w/ Private Pool!

3.0 star property
Winter Haven Retreat w/ Private Pool!

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
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

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very Good, (5282)
"The Employees were courteous and the property is beautiful. We had a junior condo and it worked perfectly! The only negatives were the washer didn't work properly and the mattress wasn't super comfortable. We wouldn't hesitate to book with Summer Bay again, the next time we visit FL."
The price is ₩183,080
₩251,993 total
includes taxes & fees
Mar 30 - Mar 31
Summer Bay Orlando by Exploria Resorts

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1293)
"We stayed in a villa and it was very clean, comfy and felt just like home. The only disadvantage is that it is about a mile away from the main pool and amenities so we did need to use our car to get around. Overall, Beautiful place and great for a family getaway! We really enjoyed sunset walk as they had lots of kids activities and plenty for the adults as well. We will stay again! "
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1717)
"Best hotel stay ever"
The price is ₩264,551
₩314,244 total
includes taxes & fees
Apr 24 - Apr 25
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?
Cottages in Lakeland - Winter Haven range between ₩109,848 and ₩109,848 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 46 cottages in Lakeland - Winter Haven. Whether you’re traveling 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 traveler styles. As for irresistible deals? We’ve got you covered!
How can I find cheap cottages in Lakeland - Winter Haven?
Expedia can help you locate cheap cottages in Lakeland - Winter Haven. To reserve your perfect stay in just a few clicks, use our convenient filter tool to refine your search results by amenities, budget and star rating.
What is there to do in Lakeland - Winter Haven near my cottage?
One of the best travel accessories for your Lakeland - Winter Haven adventure is an awesome itinerary! Polk Museum of Art, RP Funding Center and Publix Field at Joker Marchant Stadium are among the leading sights if you’re off to Lakeland. Winter Haven also lures travelers with its wonderful attractions, such as Indigo’s Family Fun Center. Eager to add to your to-do list? Drop by Chain of Lakes Park and Theatre Winter Haven too.