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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

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, (196 reviews)
"Clean room and private area loved it"
United States
Heather
The price is AED 253
AED 284 total
includes taxes & fees
18 Oct - 19 Oct
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
19 Sep - 20 Sep
This old Florida feeling getaway is 420 friendly and a great place to just relax
Exterior

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

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
9.2 out of 10, Wonderful, (7 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 1,024 total
includes taxes & fees
18 Sep - 19 Sep
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
House (4 Bedrooms) | Interior

4. Legoland & Lakes Pool Home w/ Private Suite

Legoland & Lakes Pool Home w/ Private Suite
3.0 star property
Winter Haven
The price is AED 536
AED 1,859 total
includes taxes & fees
25 Sep - 26 Sep
Legoland & Lakes Pool Home w/ Private Suite
Terrace/patio

5. 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
20 Sep - 21 Sep
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
Exterior

6. Charming Lakeside Cottage

Charming Lakeside Cottage
Winter Haven
The price is AED 314
AED 631 total
includes taxes & fees
19 Sep - 20 Sep
Charming Lakeside Cottage
House (4 Bedrooms) | Interior

7. 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 382
AED 1,205 total
includes taxes & fees
21 Sep - 22 Sep
Family Resort Home w Pool, BBQ & Game Room
Exterior

8. 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 539 total
includes taxes & fees
18 Sep - 19 Sep
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Exterior

9. 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 468
AED 1,004 total
includes taxes & fees
3 Oct - 4 Oct
Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland
Exterior

10. 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 841 total
includes taxes & fees
22 Sep - 23 Sep
Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland
Microwave, stovetop

11. 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
18 Sep - 19 Sep
Tiny house close to Disney KISSIMMEE
Exterior

12. Enchanted Cottage with Pool and Mini-Golf Near Disney

Enchanted Cottage with Pool and Mini-Golf Near Disney
Kissimmee
9.4 out of 10, Exceptional, (43 reviews)
"This place was the perfect little hideaway during our trip to the parks. Would most definitely stay again."
United States
Shane B.
The price is AED 215
AED 567 total
includes taxes & fees
18 Sep - 19 Sep
Enchanted Cottage with Pool and Mini-Golf Near Disney
House (4 Bedrooms) | Floor plan

13. Family 4BR Home w/ Resort Pool Near Disney

Family 4BR Home w/ Resort Pool Near Disney
3.0 star property
Regal Palms
The price is AED 331
AED 1,197 total
includes taxes & fees
5 Oct - 6 Oct
Family 4BR Home w/ Resort Pool Near Disney
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
20 Sep - 21 Sep
Hook, Line & Leisure: Lakefront Gem w/ Porch!
House (3 Bedrooms) | Interior

15. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is AED 306
AED 1,419 total
includes taxes & fees
20 Sep - 21 Sep
Serenity - Family & Pet Friendly, Amazing Location
Exterior

16. 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
19 Sep - 20 Sep
Perfect Place for a Perfect Vacation
House (5 Bedrooms) | Interior

17. Stylish Home With Pool Hot Tub and Parking

Stylish Home With Pool Hot Tub and Parking
3.0 star property
Reunion
The price is AED 547
AED 1,659 total
includes taxes & fees
20 Sep - 21 Sep
Stylish Home With Pool Hot Tub and Parking
Exterior

18. Mvy7632 - 4BR House Near Disney

Mvy7632 - 4BR House Near Disney
3.0 star property
Kissimmee
Mvy7632 - 4BR House Near Disney
Exterior

19. 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)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
The price is AED 345
AED 1,123 total
includes taxes & fees
20 Sep - 21 Sep
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Smart TV, books

20. 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 744 total
includes taxes & fees
21 Sep - 22 Sep
Family-Friendly Cottage Near Orlando’s Top Attractions
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

8/10 Good
"Just Beautiful highly recommend"
Shanee 3-night trip
Posted 3 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 AED 284 and AED 1,859 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?
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.

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