Search Lakeland - Winter Haven Cottage Accommodations

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Check prices for these dates

Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan
In one month
6 Feb - 8 Feb
In two months
6 Mar - 8 Mar

Our top choices for Lakeland - Winter Haven cottages

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

Cottage in Winter Haven

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
10.0 out of 10, Exceptional, (3)
"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 AU$651
includes taxes & fees
8 Jan - 9 Jan
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Property grounds
This old Florida feeling getaway is 420 friendly and a great place to just relax

Cottage in Avon Park

This old Florida feeling getaway is 420 friendly and a great place to just relax
10.0 out of 10, Exceptional, (2)
"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 AU$219
includes taxes & fees
14 Jan - 15 Jan
This old Florida feeling getaway is 420 friendly and a great place to just relax
Porch
Lake Ida Beach Resort

Cottage in Winter Haven

Lake Ida Beach Resort
3.0 star property
7.2 out of 10, Good, (188)
"We have stayed here several times. "
United States
Martha
The price is AU$150
includes taxes & fees
2 Feb - 3 Feb
Lake Ida Beach Resort
Exterior
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

Cottage in Winter Haven

Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
2.0 star property
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 AU$416
includes taxes & fees
8 Jan - 9 Jan
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Microwave, stovetop
Tiny house close to Disney KISSIMMEE

Cottage in Kissimmee

Tiny house close to Disney KISSIMMEE
2.0 star property
8.6 out of 10, Excellent, (4)
"Just needed a place to stay close to Disney for the night and the place was clean and easy to check in and out. "
United States
Jena B.
The price is AU$277
includes taxes & fees
13 Jan - 14 Jan
Tiny house close to Disney KISSIMMEE
Microwave, oven, stovetop
Charming Historic Cottage with Cozy Porch and Garden Retreat

Cottage in Polk City

Charming Historic Cottage with Cozy Porch and Garden Retreat
10.0 out of 10, Exceptional, (1)
"The communication with the property owner was excellent. The cottage is attached to the owners home but is quite private and comfortable. I’ve already recommended it to family members who wish to visit that area."
United States
Tina O.
The price is AU$325
includes taxes & fees
25 Jan - 26 Jan
Charming Historic Cottage with Cozy Porch and Garden Retreat
Exterior
Luxury Cottage Near Legoland & Chain of Lakes

Cottage in Lake Hamilton

Luxury Cottage Near Legoland & Chain of Lakes
10.0 out of 10, Exceptional, (6)
"This place is tiny but everything you need for a comfortable stay! Would definitely stay here again."
United States
Dallas C.
The price is AU$310
includes taxes & fees
11 Jan - 12 Jan
Luxury Cottage Near Legoland & Chain of Lakes
Property grounds
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Cottage in Kissimmee

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
The price is AU$321
includes taxes & fees
13 Jan - 14 Jan
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Exterior
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

Cottage in Kissimmee

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
9.8 out of 10, Exceptional, (7)
"Wonderful place to stay overnight. Nice furnishings. Good room layout for family. Convenience of washer and dryer. Host was quick and responsive. Thank you for a terrific stay."
United States
George L.
The price is AU$410
includes taxes & fees
12 Jan - 13 Jan
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
House (6 Bedrooms) | Interior
Encore Swanky

Cottage in Kissimmee

Encore Swanky
3.0 star property
The price is AU$979
includes taxes & fees
1 Feb - 2 Feb
Encore Swanky
House (2 Bedrooms) | Interior
2BR Dog-friendly w/ Yard, Screened Porch, & Grill

Cottage in Dixieland

2BR Dog-friendly w/ Yard, Screened Porch, & Grill
2.0 star property
The price is AU$407
includes taxes & fees
8 Jan - 9 Jan
2BR Dog-friendly w/ Yard, Screened Porch, & Grill
Interior
Family-Friendly Cottage Near Orlando’s Top Attractions

Cottage in Kissimmee

Family-Friendly Cottage Near Orlando’s Top Attractions
10.0 out of 10, Exceptional, (1)
"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 AU$307
includes taxes & fees
19 Jan - 20 Jan
Family-Friendly Cottage Near Orlando’s Top Attractions
Exterior
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Cottage in Kissimmee

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, 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 AU$475
includes taxes & fees
1 Feb - 2 Feb
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Exterior
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

Cottage in Davenport

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
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.
The price is AU$249
includes taxes & fees
8 Jan - 9 Jan
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Property grounds
Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.

Cottage in Kissimmee

Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
Exterior
Charming Cottage with Private Hot Tub near Disney with Margaritaville Resort &.

Cottage in Kissimmee

Charming Cottage with Private Hot Tub near Disney with Margaritaville Resort &.
Charming Cottage with Private Hot Tub near Disney with Margaritaville Resort &.
Exterior
Dreamy Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.

Cottage in Kissimmee

Dreamy Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Dreamy Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Exterior
Coral Reef Cottage! near Disney with Margaritaville Resort & Island H2O Access.

Cottage in Kissimmee

Coral Reef Cottage! near Disney with Margaritaville Resort & Island H2O Access.
Coral Reef Cottage! near Disney with Margaritaville Resort & Island H2O Access.
Property grounds
Lively Cottage with Hot Tub near Disney with Margaritaville Resort & Island H2O.

Cottage in Kissimmee

Lively Cottage with Hot Tub near Disney with Margaritaville Resort & Island H2O.
Lively Cottage with Hot Tub near Disney with Margaritaville Resort & Island H2O.
Interior
Watersong Swanky

Cottage in Davenport

Watersong Swanky
3.0 star property
The price is AU$1,492
includes taxes & fees
8 Jan - 9 Jan
Watersong Swanky
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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Our overall experience was phenomenal. Our children aren’t interested in theme parks and we aren’t interested in dining out 3 times a day so The Grove checks all the boxes. I would recommend to management to invest in common area upkeep. "
Christopher Michael 5-night trip
Posted 22 hours ago
The Grove Resort & Water Park Orlando

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Cottages information

Number of reviews
200
Accommodation
78 Cottages
Lowest Price
AU$150
Highest Price
AU$1,492

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Prices for cottages in Lakeland - Winter Haven range between AU$150 and AU$1,492 per night. Whatever your budget, you'll find the perfect place to relax and reconnect with nature. This price was 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?
Lakeland - Winter Haven has 78 cottages on offer. Select your travel dates, enter your destination and plan your perfect stay today.
What is there to do in Lakeland - Winter Haven near my cottage?
The most important travel accessory for your Lakeland - Winter Haven trip is a well-thought-out itinerary! Polk Museum of Art, Polk Theatre and Explorations V Children s Museum are some of the biggest sights if you're making your way to Lakeland. Winter Haven is also home to big-name attractions, such as Theatre Winter Haven. Eager to add to your to-do list? Pencil in a visit to Indigos Billiards, Bowling & Games and Chain of Lakes Park too.

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