A baseball player in a white uniform with the number 20, a catcher in an orange uniform, and an umpire standing behind the catcher.

Search Cottages in Lakeland - Winter Haven

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 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 HK$1,539
HK$3,733 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 HK$558
HK$624 total
includes taxes & fees
6 Aug - 7 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 HK$902
HK$2,186 total
includes taxes & fees
8 Aug - 9 Aug
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Interior

4. Walkable Dixieland District Gem With Yard

Walkable Dixieland District Gem With Yard
2.0 star property
Dixieland
The price is HK$988
HK$2,181 total
includes taxes & fees
12 Aug - 13 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, (3 reviews)
"Clean comfort all ok"
United States
Donald P.
The price is HK$607
HK$1,607 total
includes taxes & fees
3 Aug - 4 Aug
Charming Historic Cottage with Cozy Porch and Garden Retreat
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 HK$816
HK$2,574 total
includes taxes & fees
3 Aug - 4 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 HK$2,056
HK$5,748 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 HK$727
HK$1,702 total
includes taxes & fees
1 Aug - 2 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 HK$600
HK$1,141 total
includes taxes & fees
8 Aug - 9 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 HK$769
HK$1,652 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 HK$1,461
HK$3,464 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 HK$558
HK$1,440 total
includes taxes & fees
1 Aug - 2 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 HK$738
HK$2,430 total
includes taxes & fees
3 Aug - 4 Aug
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
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 HK$1,129
HK$3,732 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 HK$635
HK$1,509 total
includes taxes & fees
3 Aug - 4 Aug
Perfect Place for a Perfect Vacation
Interior

16. Upstay Championsgate Home w Pool & Hot Tub

Upstay Championsgate Home w Pool & Hot Tub
3.0 star property
Davenport
The price is HK$2,008
HK$4,763 total
includes taxes & fees
2 Aug - 3 Aug
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 HK$549
HK$1,359 total
includes taxes & fees
8 Aug - 9 Aug
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 HK$558
HK$1,221 total
includes taxes & fees
1 Aug - 2 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 HK$840
HK$2,249 total
includes taxes & fees
9 Aug - 10 Aug
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
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
The price is HK$2,580
HK$4,967 total
includes taxes & fees
2 Aug - 3 Aug
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Lakeland - Winter Haven Hotel Reviews

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

10/10 Excellent
"Love love loved it here!!"
ariel 1-night trip
Posted less than an hour ago
Margaritaville Resort Orlando with H2O Waterpark

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Cottages information

Number of reviews
232
Accommodation
27 Cottages
Lowest Price
HK$624
Highest Price
HK$5,748

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Cottages in Lakeland - Winter Haven range between HK$624 and HK$5,748 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 27 cottages in Lakeland - Winter Haven. Whether you're travelling 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 traveller 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 Centre and Publix Field at Joker Marchant Stadium are among the leading sights if you're off to Lakeland. Winter Haven also lures travellers with its wonderful attractions, such as Indigo's Family Fun Centre. Eager to add to your to-do list? Drop by Chain of Lakes Park and Theatre Winter Haven too.

Explore a world of travel with Expedia