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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

Exterior

1. 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 AED 446
AED 866 total
includes taxes & fees
7 Sep - 8 Sep
Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland
House (4 Bedrooms) | Interior

2. 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 AED 540
AED 1,174 total
includes taxes & fees
11 Aug - 12 Aug
Pond Access & Grill! Group Escape, 19 Mi to WDW
Exterior

3. Mvv7485 - 3BR House Near Disney With Hot Tub

Mvv7485 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
Mvv7485 - 3BR House Near Disney With Hot Tub
Porch

4. 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 AED 253
AED 284 total
includes taxes & fees
9 Sep - 10 Sep
Lake Ida Beach Resort
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.
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
House (3 Bedrooms) | Interior

6. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is AED 364
AED 1,486 total
includes taxes & fees
10 Aug - 11 Aug
Serenity - Family & Pet Friendly, Amazing Location
House (6 Bedrooms) | Interior

7. Upstay Spacious Home w Private Pool & Hot Tub

Upstay Spacious Home w Private Pool & Hot Tub
3.0 star property
Solana
The price is AED 502
AED 1,710 total
includes taxes & fees
10 Aug - 11 Aug
Upstay Spacious Home w Private Pool & Hot Tub
Exterior

8. 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 AED 312
AED 787 total
includes taxes & fees
27 Aug - 28 Aug
Charming Historic Cottage with Cozy Porch and Garden Retreat
Interior

9. 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 AED 281
AED 534 total
includes taxes & fees
10 Aug - 11 Aug
This old Florida feeling getaway is 420 friendly and a great place to just relax
Property grounds

10. Perfect Vacay, Themed Rooms, Game Room & Theater

Perfect Vacay, Themed Rooms, Game Room & Theater
3.0 star property
Champions Gate
The price is AED 1,208
AED 2,554 total
includes taxes & fees
23 Aug - 24 Aug
Perfect Vacay, Themed Rooms, Game Room & Theater
Interior

11. Private Cozy Studio, Free Parking, Near Legoland

Private Cozy Studio, Free Parking, Near Legoland
Lake Horney
The price is AED 261
AED 675 total
includes taxes & fees
12 Aug - 13 Aug
Private Cozy Studio, Free Parking, Near Legoland
House (3 Bedrooms) | Interior

12. 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 AED 639
AED 1,521 total
includes taxes & fees
31 Aug - 1 Sep
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Exterior

13. Mvy7664 - 3BR House Near Disney With Hot Tub

Mvy7664 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
The price is AED 707
AED 1,649 total
includes taxes & fees
20 Aug - 21 Aug
Mvy7664 - 3BR House Near Disney With Hot Tub
Dining

14. 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 AED 340
AED 804 total
includes taxes & fees
11 Aug - 12 Aug
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Smart TV, books

15. 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 AED 331
AED 748 total
includes taxes & fees
7 Sep - 8 Sep
Family-Friendly Cottage Near Orlando’s Top Attractions
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 AED 331
AED 748 total
includes taxes & fees
7 Sep - 8 Sep
Perfect Place for a Perfect Vacation
House (5 Bedrooms) | Interior

17. Upstay - Resort Home w Cinema, Pool & Lake View

Upstay - Resort Home w Cinema, Pool & Lake View
3.0 star property
Kissimmee
Upstay - Resort Home w Cinema, Pool & Lake View
Outdoor dining

18. Comfortable Cottage near Disney with Margaritaville Resort & Island H20.

Comfortable Cottage near Disney with Margaritaville Resort & Island H20.
Kissimmee
The price is AED 687
AED 1,706 total
includes taxes & fees
26 Aug - 27 Aug
Comfortable Cottage near Disney with Margaritaville Resort & Island H20.
Exterior

19. Tequila Sunrise Cottage with Private Hot Tub near Disney with Margaritaville.

Tequila Sunrise Cottage with Private Hot Tub near Disney with Margaritaville.
Kissimmee
The price is AED 687
AED 1,706 total
includes taxes & fees
17 Aug - 18 Aug
Tequila Sunrise Cottage with Private Hot Tub near Disney with Margaritaville.
Microwave, stovetop

20. 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 AED 231
AED 607 total
includes taxes & fees
1 Sep - 2 Sep
Tiny house close to Disney 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

Embassy Suites By Hilton Orlando Sunset Walk

Embassy Suites By Hilton Orlando Sunset Walk

10/10 Excellent
"The breakfast was awesome and house keeping does a fantastic job being very attentive to rooms and guest request. The rooms are excellent."
Michele 4-night trip
Posted less than an hour ago
Embassy Suites By Hilton Orlando Sunset Walk

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Cottages in Lakeland - Winter Haven range between AED 284 and AED 2,554 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 34 cottages in Lakeland - Winter Haven. Whether you're traveling 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 traveler 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.

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