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Search Cottages in Lakeland - Winter Haven

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

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
4 Aug - 5 Aug
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
4 Aug - 5 Aug
This old Florida feeling getaway is 420 friendly and a great place to just relax
Exterior

3. 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 738 total
includes taxes & fees
4 Aug - 5 Aug
Charming Historic Cottage with Cozy Porch and Garden Retreat
House (4 Bedrooms) | Interior

4. 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
4 Aug - 5 Aug
Family Resort Home w Pool, BBQ & Game Room
Exterior

5. 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 1,024 total
includes taxes & fees
4 Aug - 5 Aug
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
House (3 Bedrooms) | Interior

6. 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 639
AED 1,521 total
includes taxes & fees
31 Aug - 1 Sep
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Front of property

7. Mvv7485 - 3BR House Near Disney With Hot Tub

Mvv7485 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
The price is AED 776
AED 1,729 total
includes taxes & fees
19 Aug - 20 Aug
Mvv7485 - 3BR House Near Disney With Hot Tub
1 bedroom, iron/ironing board, WiFi, bed sheets

8. Private Cozy Studio, Free Parking, Near Legoland

Private Cozy Studio, Free Parking, Near Legoland
Lake Horney
The price is AED 261
AED 675 total
includes taxes & fees
4 Aug - 5 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
5.0 out of 10, (2 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
4 Aug - 5 Aug
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
House (3 Bedrooms) | Interior

10. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is AED 370
AED 1,492 total
includes taxes & fees
5 Aug - 6 Aug
Serenity - Family & Pet Friendly, Amazing Location
House (3 Bedrooms) | Interior

11. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is AED 310
AED 973 total
includes taxes & fees
25 Aug - 26 Aug
Upstay: Bright Family-friendly Retreat With Patio
Exterior

12. 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 710 total
includes taxes & fees
12 Aug - 13 Aug
Perfect Place for a Perfect Vacation
Exterior

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

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.4 out of 10, Exceptional, (11 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is AED 393
AED 1,053 total
includes taxes & fees
9 Aug - 10 Aug
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Microwave, stovetop

14. 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 327
AED 715 total
includes taxes & fees
31 Aug - 1 Sep
Tiny house close to Disney KISSIMMEE
Exterior

15. 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 364
AED 1,162 total
includes taxes & fees
1 Sep - 2 Sep
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
House (4 Bedrooms) | Front of property

16. Pond Access & Grill! Group Escape, 19 Mi to WDW

Pond Access & Grill! Group Escape, 19 Mi to WDW
3.0 star property
Kissimmee
The price is AED 540
AED 1,174 total
includes taxes & fees
4 Aug - 5 Aug
Pond Access & Grill! Group Escape, 19 Mi to WDW
Front of property

17. Mvy7632 - 4BR House Near Disney

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

18. Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Kissimmee
The price is AED 340
AED 812 total
includes taxes & fees
11 Aug - 12 Aug
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Smart TV, books

19. 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 364
AED 793 total
includes taxes & fees
12 Aug - 13 Aug
Family-Friendly Cottage Near Orlando’s Top Attractions
House (5 Bedrooms) | Interior

20. Upstay - Resort Home w Cinema, Pool & Lake View

Upstay - Resort Home w Cinema, Pool & Lake View
3.0 star property
Kissimmee
The price is AED 720
AED 1,772 total
includes taxes & fees
10 Aug - 11 Aug
Upstay - Resort Home w Cinema, Pool & Lake View
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

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"We stayed in a Villa. It was perfect for our needs. Although it rained one day we were able to review all the amenities. Got to do the Lazy River. The unit was clean and easy to move around. Liked the Dove products. Hoping we can visit again soon."
Patricia 3-night trip
Posted less than an hour ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Cottages in Lakeland - Winter Haven range between AED 281 and AED 1,772 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 34 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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