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Search Cottages in Lakeland - Winter Haven

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Lakeland - Winter Haven cottages

Porch

1. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (194 reviews)
"The cabins were great loved it there"
United States
Jennifer
The price is AED 251
AED 281 total
includes taxes & fees
28 Sep - 29 Sep
Lake Ida Beach Resort
Interior

2. This old Florida feeling getaway is 420 friendly and a great place to just relax

This old Florida feeling getaway is 420 friendly and a great place to just relax
Avon Park
8.0 out of 10, Very Good, (4 reviews)
"We were very fascinated by the farm animals and the dogs "
United States
Debi D.
The price is AED 281
AED 534 total
includes taxes & fees
31 Aug - 1 Sep
This old Florida feeling getaway is 420 friendly and a great place to just relax
Terrace/patio

3. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

Lakefront Tiny Cottage 4 Miles to LEGOLAND.
winter have
9.0 out of 10, Wonderful, (42 reviews)
"Awesome location, very nice"
United States
Kyle P.
The price is AED 257
AED 547 total
includes taxes & fees
30 Aug - 31 Aug
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
House (3 Bedrooms) | Interior

4. Lakefront Home w/ EV Charger in Auburndale

Lakefront Home w/ EV Charger in Auburndale
3.0 star property
Auburndale
8.0 out of 10, Very Good, (1 review)
"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. "
United States
Katrina
The price is AED 444
AED 1,253 total
includes taxes & fees
30 Aug - 31 Aug
Lakefront Home w/ EV Charger in Auburndale
Property grounds

5. Charming Lakeside Cottage

Charming Lakeside Cottage
Winter Haven
The price is AED 314
AED 631 total
includes taxes & fees
31 Aug - 1 Sep
Charming Lakeside Cottage
Exterior

6. Charming Historic Cottage with Cozy Porch and Garden Retreat

Charming Historic Cottage with Cozy Porch and Garden Retreat
Polk City
10.0 out of 10, Exceptional, (4 reviews)
"Clean comfort all ok"
United States
Donald P.
The price is AED 281
AED 749 total
includes taxes & fees
30 Aug - 31 Aug
Charming Historic Cottage with Cozy Porch and Garden Retreat
Exterior

7. Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
9.0 out of 10, Wonderful, (6 reviews)
"Wonderful little cottage filled with fun for the whole family. Cozy backyard to enjoy some sunshine and read a book. Close to downtown shops and restaurants. Owners were quick to respond to questions. Would happily stay here again."
United States
Rachel B.
The price is AED 422
AED 1,035 total
includes taxes & fees
29 Aug - 30 Aug
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Interior

8. Private Cozy Studio, Free Parking, Near Legoland

Private Cozy Studio, Free Parking, Near Legoland
Lake Horney
The price is AED 261
AED 678 total
includes taxes & fees
29 Aug - 30 Aug
Private Cozy Studio, Free Parking, Near Legoland
Exterior

9. Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Davenport
6.8 out of 10, (3 reviews)
"Needs some upgrades. The bed was a full size, very small for a couple, should really think of upgrading to a king. Pans were old and could use replacing. Bugs and ants constant. Shower was small. Very small tv. Stovetop had missing nob and was difficult to operate. Definitely needs upgrading, left a day early, didn’t feel comfortable there. "
United States
Rebecca F.
The price is AED 261
AED 572 total
includes taxes & fees
29 Aug - 30 Aug
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
House (4 Bedrooms) | Interior

10. Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is AED 364
AED 1,185 total
includes taxes & fees
1 Sep - 2 Sep
Family Resort Home w Pool, BBQ & Game Room
Exterior

11. Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland

Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland
Lake Hamilton
The price is AED 498
AED 1,042 total
includes taxes & fees
11 Sep - 12 Sep
Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland
Exterior

12. Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland

Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland
Lakeland
The price is AED 446
AED 844 total
includes taxes & fees
29 Aug - 30 Aug
Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland
House (3 Bedrooms) | Interior

13. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
Serenity - Family & Pet Friendly, Amazing Location
House (3 Bedrooms) | Interior

14. Hook, Line & Leisure: Lakefront Gem w/ Porch!

Hook, Line & Leisure: Lakefront Gem w/ Porch!
3.0 star property
Florence Villa
10.0 out of 10, Exceptional, (3 reviews)
"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."
United States
John
The price is AED 606
AED 1,484 total
includes taxes & fees
31 Aug - 1 Sep
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Exterior

15. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is AED 298
AED 703 total
includes taxes & fees
30 Aug - 31 Aug
Perfect Place for a Perfect Vacation
Microwave, stovetop

16. Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very Good, (9 reviews)
"Proximity to theme parks, restaurants, and shopping"
United States
NOLI
The price is AED 231
AED 607 total
includes taxes & fees
1 Sep - 2 Sep
Tiny house close to Disney KISSIMMEE
Smart TV, books

17. Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Perfect location to enjoy Universal Epic and Islands of Adventure with only a 15 minute ride. The beds were very comfortable and the place is clean. We were welcomed with a cute sign, bottled water and cookies. Will definitely stay here again!"
United States
Joyce R.
The price is AED 331
AED 752 total
includes taxes & fees
1 Sep - 2 Sep
Family-Friendly Cottage Near Orlando’s Top Attractions
Exterior

18. Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
The price is AED 345
AED 1,142 total
includes taxes & fees
1 Sep - 2 Sep
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Exterior

19. "Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.4 out of 10, Exceptional, (12 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is AED 400
AED 1,069 total
includes taxes & fees
13 Sep - 14 Sep
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
House (3 Bedrooms) | Interior

20. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is AED 303
AED 965 total
includes taxes & fees
21 Sep - 22 Sep
Upstay: Bright Family-friendly Retreat With Patio
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

Westgate Town Center Resort

Westgate Town Center Resort

10/10 Excellent
"This is a very nice hotel/resort. Our room was very nice and clean. I recommend if you do stay to walk around the whole resort and see what it has to offer. Multiple pools around the area that is free if you don’t want to pay for the water park. If you’re a guest you pay to get in the water park ($25/person, kids are free to a certain age) but honored guests are free. We stay in a one bedroom suite/villa. Lots of space for my toddler to run around he also loved the jacuzzi inside the master bedroom, he pretty much had a bath in the jacuzzi tub every night while we were there. I loved the dual shower as well. Fridge, stove, microwave, washer/dryer, pots and pans, 4 guest dinnerware and utensils (fork, spoons, knives) , cooking utensils (your basics, can opener, wine opener, scissors). There’s a Walmart right across the resort which I found very convenient for those staying in the resort, if you want to buy food and cook inside yiur villa. Our first night we made baked zitti. The Walmart was pretty packed lots of people all day all night, disney items (clothing, accessories etc.. cheaper than if you buy at the theme park.) what else?? This is our second time staying in this resort and we prefer it since we have our 2 little puppies and some resorts don’t allow pets. The staff was also very nice and friendly and very accommodating and wanting to make sure our stay was a great experience and comfortable. I would come back here every time."
ODESA 3-night trip
Posted 8 hours ago
Westgate Town Center Resort

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Cottages in Lakeland - Winter Haven range between AED 281 and AED 1,484 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 30 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?
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