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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

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, (196 reviews)
"Clean room and private area loved it"
United States
Heather
The price is AU$107
includes taxes & fees
18 Oct - 19 Oct
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 AU$207
includes taxes & fees
22 Sept - 23 Sept
This old Florida feeling getaway is 420 friendly and a great place to just relax
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
9.2 out of 10, Wonderful, (7 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 AU$394
includes taxes & fees
18 Sept - 19 Sept
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
House (4 Bedrooms) | Interior

4. Legoland & Lakes Pool Home w/ Private Suite

Legoland & Lakes Pool Home w/ Private Suite
3.0 star property
Winter Haven
The price is AU$714
includes taxes & fees
25 Sept - 26 Sept
Legoland & Lakes Pool Home w/ Private Suite
Terrace/patio

5. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

Lakefront Tiny Cottage 4 Miles to LEGOLAND.
winter have
9.0 out of 10, Wonderful, (42 reviews)
"Awesome location, very nice"
United States
Kyle P.
The price is AU$213
includes taxes & fees
20 Sept - 21 Sept
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
Exterior

6. Charming Lakeside Cottage

Charming Lakeside Cottage
Winter Haven
The price is AU$245
includes taxes & fees
19 Sept - 20 Sept
Charming Lakeside Cottage
House (4 Bedrooms) | Interior

7. Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is AU$463
includes taxes & fees
20 Sept - 21 Sept
Family Resort Home w Pool, BBQ & Game Room
Exterior

8. Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Davenport
6.8 out of 10, (3 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 AU$208
includes taxes & fees
18 Sept - 19 Sept
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Exterior

9. 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 AU$387
includes taxes & fees
3 Oct - 4 Oct
Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland
Exterior

10. Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland

Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland
Lakeland
The price is AU$326
includes taxes & fees
22 Sept - 23 Sept
Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland
Microwave, stovetop

11. 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 AU$236
includes taxes & fees
18 Sept - 19 Sept
Tiny house close to Disney KISSIMMEE
Exterior

12. Enchanted Cottage with Pool and Mini-Golf Near Disney

Enchanted Cottage with Pool and Mini-Golf Near Disney
Kissimmee
9.4 out of 10, Exceptional, (44 reviews)
"This place was the perfect little hideaway during our trip to the parks. Would most definitely stay again."
United States
Shane B.
The price is AU$221
includes taxes & fees
18 Sept - 19 Sept
Enchanted Cottage with Pool and Mini-Golf Near Disney
House (4 Bedrooms) | Floor plan

13. Family 4BR Home w/ Resort Pool Near Disney

Family 4BR Home w/ Resort Pool Near Disney
3.0 star property
Regal Palms
The price is AU$460
includes taxes & fees
5 Oct - 6 Oct
Family 4BR Home w/ Resort Pool Near Disney
House (3 Bedrooms) | Interior

14. 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 AU$567
includes taxes & fees
30 Sept - 1 Oct
Hook, Line & Leisure: Lakefront Gem w/ Porch!
House (3 Bedrooms) | Interior

15. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is AU$545
includes taxes & fees
20 Sept - 21 Sept
Serenity - Family & Pet Friendly, Amazing Location
Exterior

16. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is AU$276
includes taxes & fees
21 Sept - 22 Sept
Perfect Place for a Perfect Vacation
House (5 Bedrooms) | Interior

17. Stylish Home With Pool Hot Tub and Parking

Stylish Home With Pool Hot Tub and Parking
3.0 star property
Reunion
The price is AU$643
includes taxes & fees
20 Sept - 21 Sept
Stylish Home With Pool Hot Tub and Parking
Exterior

18. Mvy7632 - 4BR House Near Disney

Mvy7632 - 4BR House Near Disney
3.0 star property
Kissimmee
Mvy7632 - 4BR House Near Disney
Exterior

19. 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 AU$434
includes taxes & fees
20 Sept - 21 Sept
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Smart TV, books

20. 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 AU$289
includes taxes & fees
20 Sept - 21 Sept
Family-Friendly Cottage Near Orlando’s Top Attractions
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

Howard Johnson by Wyndham Lakeland

Howard Johnson by Wyndham Lakeland

10/10 Excellent
"Staf nice and revering good"
Jarlene 6-night trip
Posted 1 hour ago
Howard Johnson by Wyndham Lakeland

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Cottages information

Number of reviews
308
Accommodation
38 Cottages
Lowest Price
AU$107
Highest Price
AU$714

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Prices for cottages in Lakeland - Winter Haven range between AU$107 and AU$714 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 38 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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