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
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Lakeland - Winter Haven cottages

Porch

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$529
HK$593 total
includes taxes & fees
30 Jul - 31 Jul
Lake Ida Beach Resort
Exterior

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
8.8 out of 10, Excellent, (5 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$2,178 total
includes taxes & fees
21 Aug - 22 Aug
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Interior

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$1,140 total
includes taxes & fees
31 Jul - 1 Aug
This old Florida feeling getaway is 420 friendly and a great place to just relax
Interior

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 HK$1,286
HK$3,159 total
includes taxes & fees
24 Jul - 25 Jul
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Exterior

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$600
HK$1,583 total
includes taxes & fees
27 Jul - 28 Jul
Charming Historic Cottage with Cozy Porch and Garden Retreat
Interior

Oasis Near Disney w Golf View, Family&pet Friendly

Oasis Near Disney w Golf View, Family&pet Friendly
3.0 star property
Reunion
The price is HK$690
HK$2,857 total
includes taxes & fees
28 Jul - 29 Jul
Oasis Near Disney w Golf View, Family&pet Friendly
Exterior

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 HK$1,055
HK$2,214 total
includes taxes & fees
8 Aug - 9 Aug
Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland
Exterior

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$628
HK$1,299 total
includes taxes & fees
24 Jul - 25 Jul
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Interior

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$1,019
HK$2,802 total
includes taxes & fees
17 Aug - 18 Aug
Family Resort Home w Pool, BBQ & Game Room
Exterior

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$1,501 total
includes taxes & fees
30 Jul - 31 Jul
Perfect Place for a Perfect Vacation
Microwave, stovetop

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very good, (8 reviews)
"Nice, Cute little place"
United States
Brenda N.
The price is HK$596
HK$1,412 total
includes taxes & fees
27 Jul - 28 Jul
Tiny house close to Disney KISSIMMEE
Smart TV, books

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$792
HK$1,718 total
includes taxes & fees
3 Aug - 4 Aug
Family-Friendly Cottage Near Orlando’s Top Attractions
Exterior

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$752
HK$2,447 total
includes taxes & fees
4 Aug - 5 Aug
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Interior

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
2 Aug - 3 Aug
Walkable Dixieland District Gem With Yard
Exterior

"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$933
HK$2,370 total
includes taxes & fees
20 Aug - 21 Aug
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Dining

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$1,725 total
includes taxes & fees
27 Jul - 28 Jul
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Outdoor dining

Comfy Cottage with Hot Tub near Disney with Margaritaville Resort & Island H2O.

Comfy Cottage with Hot Tub near Disney with Margaritaville Resort & Island H2O.
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,780
HK$4,240 total
includes taxes & fees
23 Aug - 24 Aug
Comfy Cottage with Hot Tub near Disney with Margaritaville Resort & Island H2O.
Exterior

Pineapple Dream Cottage with Private Hot Tub near Disney with Margaritaville.

Pineapple Dream Cottage with Private Hot Tub near Disney with Margaritaville.
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"We loved our experience, from the time we walked into our cottage, we knew we would have a great time. The Cottage was spaces enough for our party of five. This vacation was a graduation gift for my grandson. I loved the proximity to the theme parks. I also loved the amenities that were offered by the property’s management team, Awesome! "
United States
Patricia B.
The price is HK$1,780
HK$4,240 total
includes taxes & fees
23 Aug - 24 Aug
Pineapple Dream Cottage with Private Hot Tub near Disney with Margaritaville.
Interior

Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is HK$565
HK$1,967 total
includes taxes & fees
18 Aug - 19 Aug
Upstay: Bright Family-friendly Retreat With Patio
Exterior

Sunrise Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.

Sunrise Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Comfy, cozy and room for everyone to have their own space . Easy to get around. Places to eat and shop right outside the property, so convenient."
United States
Marilou J.
The price is HK$1,937
HK$3,258 total
includes taxes & fees
21 Aug - 22 Aug
Sunrise Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
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
"I did not want to leave. The resort was beautiful. This resort is great for families, couples or even solo travelers. Self parking was only 20 or $25. My room was spotless spacious and decorated beautifully. Book your room and go."
Michaela 2-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
235
Accommodation
27 Cottages
Lowest Price
HK$593
Highest Price
HK$4,240

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Cottages in Lakeland - Winter Haven range between HK$593 and HK$4,240 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