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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Featured Cottages in Lakeland - Winter Haven

House (3 Bedrooms) | Interior
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

3.0 star property
Winter Haven
10.0 out of 10, Exceptional, (3)
"This house is absolutely beautiful! Prior to arrival, all needed info- check-in, wifi code, door access, everything was communicated. The master bedroom, with it's own hallway and bathroom, has a lounge style sitting room attached. The patio is larger than it appears in the photos. The lake out back is so peaceful. The kitchen is fully equipped with all you'll need. The owner/ manager texted just to see how things were going. Very thoughtful! It was a great vacation rental and i will definitely...
United States
ANGELA G
The price is NZ$663
includes taxes & fees
12 Dec - 13 Dec
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Children’s area
Charming 2-bedroom cottage in Kissimmee

Charming 2-bedroom cottage in Kissimmee

2.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1)
"Kudos to the hosts. A seamless experience. My first ever vacation rental and I was very impressed. The cottage was super clean and was equipped with everything and then some. "
United States
Gail E.
The price is NZ$361
includes taxes & fees
26 Nov - 27 Nov
Charming 2-bedroom cottage in Kissimmee
Interior
Solterra Swanky

Solterra Swanky

3.0 star property
Solterra Resort
The price is NZ$722
includes taxes & fees
1 Dec - 2 Dec
Solterra Swanky
Property grounds
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
10.0 out of 10, Exceptional, (1)
"We loved our stay at Kellie’s farm, the property is big and has a big pond or little lake at the back, the scenery looks like you’re somewhere in the wild side of Montana and feels like a grizzly bear can come out of the trees at any moment! Haha but it’s very safe, nothing to worry about. The farm has chickens, pigs, a calf, dogs, etc. if you love animals you will love this place for sure! We would definitely come back and we 100% recommend this place."
United States
Steve M.
The price is NZ$257
includes taxes & fees
25 Nov - 26 Nov
This old Florida feeling getaway is 420 friendly and a great place to just relax
Property grounds
Hidden Lake View Cottage 5 miles from Disney!

Hidden Lake View Cottage 5 miles from Disney!

Kissimmee
9.0 out of 10, Wonderful, (2)
"Awesome"
United States
Bulmaro S.
The price is NZ$396
includes taxes & fees
26 Nov - 27 Nov
Hidden Lake View Cottage 5 miles from Disney!
Exterior
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

2.0 star property
Winter Haven
10.0 out of 10, Exceptional, (2)
"Just what we needed for a weekend trip with our grandsons for the weekend "
United States
Christine B.
The price is NZ$492
includes taxes & fees
14 Dec - 15 Dec
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Exterior
Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation

3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1)
The price is NZ$338
includes taxes & fees
26 Nov - 27 Nov
Perfect Place for a Perfect Vacation
Porch
Lake Ida Beach Resort

Lake Ida Beach Resort

3.0 star property
Winter Haven
7.4 out of 10, Good, (184)
"Lakeside view was great."
United States
Kenneth
The price is NZ$148
includes taxes & fees
16 Nov - 17 Nov
Lake Ida Beach Resort
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)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
The price is NZ$434
includes taxes & fees
26 Nov - 27 Nov
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Microwave, stovetop
Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE

2.0 star property
Kissimmee
8.0 out of 10, Very good, (1)
"The location was great. We really just needed somewhere to sleep because we spent the day at the Disney Parks. The place had enough beds and was a great price."
United States
Christine M.
The price is NZ$278
includes taxes & fees
7 Dec - 8 Dec
Tiny house close to Disney KISSIMMEE
House (4 Bedrooms) | Interior
~ 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 NZ$747
includes taxes & fees
14 Nov - 15 Nov
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Exterior
Luxury Cottage Near Legoland & Chain of Lakes

Luxury Cottage Near Legoland & Chain of Lakes

Lake Hamilton
10.0 out of 10, Exceptional, (6)
"We enjoyed our stay in this cosy cottage. It has everything you need for a stay. Clean and very responsive to any issues. We would definitely recommend."
Germany
Stephanie B.
The price is NZ$364
includes taxes & fees
25 Nov - 26 Nov
Luxury Cottage Near Legoland & Chain of Lakes
Exterior
Disney, Universal and Legoland Getaway

Disney, Universal and Legoland Getaway

Kissimmee
9.2 out of 10, Wonderful, (9)
"I love the place ! It was beautiful! Enough room for everyone "
United States
Anthony M.
The price is NZ$424
includes taxes & fees
26 Nov - 27 Nov
Disney, Universal and Legoland Getaway
Microwave, oven, stovetop
Charming Historic Cottage with Cozy Porch and Garden Retreat

Charming Historic Cottage with Cozy Porch and Garden Retreat

Polk City
The price is NZ$466
includes taxes & fees
14 Dec - 15 Dec
Charming Historic Cottage with Cozy Porch and Garden Retreat
Interior
Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions

Kissimmee
The price is NZ$356
includes taxes & fees
16 Nov - 17 Nov
Family-Friendly Cottage Near Orlando’s Top Attractions
Property grounds
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 NZ$372
includes taxes & fees
26 Nov - 27 Nov
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Terrace/patio
Cozy Tropical Cottage - 4 mi to Disney

Cozy Tropical Cottage - 4 mi to Disney

Kissimmee
The price is NZ$495
includes taxes & fees
26 Nov - 27 Nov
Cozy Tropical Cottage - 4 mi to Disney
House, Multiple Beds, Patio, Garden View (Lafitte's Landing Lakeview Cottage) | Property grounds
Lafitte's Landing Lakeview Cottage - Lakefront!

Lafitte's Landing Lakeview Cottage - Lakefront!

3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (12)
"We really enjoyed our stay, the home was so clean and comfortable.. "
United States
Geraldine
Lafitte's Landing Lakeview Cottage - Lakefront!
Exterior
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

Davenport
5.0 out of 10, (2)
"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.
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Exterior
Charming 1-bedroom cottage in Kissimmee

Charming 1-bedroom cottage in Kissimmee

Kissimmee
Charming 1-bedroom cottage in Kissimmee
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
"La tercera vez que me quedo aqui . Todo limpio, las facilidades muy buenas, el personal muy amable y siempre pendientes a mis necesidades. Excelente. "
Jonathan 4-night trip
Posted 2 days ago
Hilton Vacation Club Aqua Sol Orlando West

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Cottages information

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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.
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.

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