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 Lakeland - Winter Haven Cottages

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

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 £57
includes taxes & fees
6 Sept - 7 Sept
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 £111
includes taxes & fees
8 Aug - 9 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 £154
includes taxes & fees
5 Sept - 6 Sept
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 £257
includes taxes & fees
12 Aug - 13 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 £210
includes taxes & fees
9 Aug - 10 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 £307
includes taxes & fees
31 Aug - 1 Sept
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Exterior

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 £350
includes taxes & fees
19 Aug - 20 Aug
Mvv7485 - 3BR House Near Disney With Hot Tub
Interior

8. Private Cozy Studio, Free Parking, Near Legoland

Private Cozy Studio, Free Parking, Near Legoland
Lake Horney
The price is £139
includes taxes & fees
8 Aug - 9 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 £119
includes taxes & fees
8 Aug - 9 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 £300
includes taxes & fees
11 Aug - 12 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 £204
includes taxes & fees
17 Aug - 18 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 £154
includes taxes & fees
31 Aug - 1 Sept
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 £216
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 £148
includes taxes & fees
31 Aug - 1 Sept
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 £237
includes taxes & fees
1 Sept - 2 Sept
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
House (4 Bedrooms) | Interior

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 £237
includes taxes & fees
11 Aug - 12 Aug
Pond Access & Grill! Group Escape, 19 Mi to WDW
Exterior

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 £167
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 £167
includes taxes & fees
30 Aug - 31 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 £361
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.
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

Embassy Suites By Hilton Orlando Sunset Walk

Embassy Suites By Hilton Orlando Sunset Walk

10/10 Excellent
"Loved the location, the attention staff was very kind and helpful. Facility os very clean and breakfast was very good."
Katherine 10-night trip
Posted 2 hours ago
Embassy Suites By Hilton Orlando Sunset Walk

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Cottages information

Number of reviews
Accommodation
 Cottages
Lowest Price
Highest Price

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Cottages in Lakeland - Winter Haven range between and 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 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