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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

Front of property

1. Mvy7632 - 4BR House Near Disney

Mvy7632 - 4BR House Near Disney
3.0 star property
Kissimmee
The price is AED 721
AED 1,748 total
includes taxes & fees
6 Aug - 7 Aug
Mvy7632 - 4BR House Near Disney
Porch

2. 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
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
9.0 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 (2 Bedrooms) | Interior

4. Walkable Dixieland District Gem With Yard

Walkable Dixieland District Gem With Yard
2.0 star property
Dixieland
The price is AED 463
AED 1,022 total
includes taxes & fees
4 Aug - 5 Aug
Walkable Dixieland District Gem With Yard
Exterior

5. 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 742 total
includes taxes & fees
4 Aug - 5 Aug
Charming Historic Cottage with Cozy Porch and Garden Retreat
House (4 Bedrooms) | Interior

6. 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

7. Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas

Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
3.5 star property
Reunion
The price is AED 959
AED 2,687 total
includes taxes & fees
6 Aug - 7 Aug
Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
Dining

8. 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 793 total
includes taxes & fees
4 Aug - 5 Aug
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Interior

9. 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
Smart TV, books

10. 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 356
AED 770 total
includes taxes & fees
24 Aug - 25 Aug
Family-Friendly Cottage Near Orlando’s Top Attractions
Front of property

11. Mvy7664 - 3BR House Near Disney With Hot Tub

Mvy7664 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
The price is AED 684
AED 1,622 total
includes taxes & fees
9 Aug - 10 Aug
Mvy7664 - 3BR House Near Disney With Hot Tub
1 bedroom, iron/ironing board, WiFi, bed sheets

12. 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

13. 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 1,127 total
includes taxes & fees
4 Aug - 5 Aug
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
House (4 Bedrooms) | Interior

14. ~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
Indian Ridge
The price is AED 529
AED 1,748 total
includes taxes & fees
21 Aug - 22 Aug
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
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
4 Aug - 5 Aug
Perfect Place for a Perfect Vacation
House (6 Bedrooms) | Interior

16. Upstay Championsgate Home w Pool & Hot Tub

Upstay Championsgate Home w Pool & Hot Tub
3.0 star property
Davenport
Upstay Championsgate Home w Pool & Hot Tub
Microwave, stovetop

17. 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 331
AED 723 total
includes taxes & fees
31 Aug - 1 Sep
Tiny house close to Disney KISSIMMEE
Exterior

18. 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
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, (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
House (5 Bedrooms) | Interior

20. Upstay Spacious 5BR Villa Private Pool and Hot Tub

Upstay Spacious 5BR Villa Private Pool and Hot Tub
3.0 star property
Kissimmee
Upstay Spacious 5BR Villa Private Pool and Hot Tub
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 Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"Todo excelente , apartamento y habitaciones llenas de espacio y confort muy limpio y todo muy completo el área de la piscina me encanta ya no busco más opciones en mi estadía en Orlando siempre opto por este lugar no tengo mas nada que buscar para mi estadía lo recomiendo al 100%"
Marggi 2-night trip
Posted 4 hours ago
Hilton Vacation Club Aqua Sol Orlando West

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Cottages in Lakeland - Winter Haven range between AED 281 and AED 2,687 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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