A baseball player in a white uniform with the number 20, a catcher in an orange uniform, and an umpire standing behind the catcher.

Book a Lakeland - Winter Haven Cottage

  • 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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

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, (194 reviews)
"The cabins were great loved it there"
United States
Jennifer
The price is NZ$132
includes taxes & fees
17 Aug - 18 Aug
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 NZ$247
includes taxes & fees
17 Aug - 18 Aug
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
9.0 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.
The price is NZ$466
includes taxes & fees
10 Sept - 11 Sept
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
Exterior

4. 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 NZ$388
includes taxes & fees
17 Aug - 18 Aug
Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland
House (4 Bedrooms) | Interior

5. 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 NZ$460
includes taxes & fees
30 Aug - 31 Aug
Pond Access & Grill! Group Escape, 19 Mi to WDW
Exterior

6. 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 NZ$341
includes taxes & fees
15 Sept - 16 Sept
Charming Historic Cottage with Cozy Porch and Garden Retreat
Exterior

7. 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
House (4 Bedrooms) | Interior

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

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is NZ$557
includes taxes & fees
17 Aug - 18 Aug
Family Resort Home w Pool, BBQ & Game Room
Interior

9. Private Cozy Studio, Free Parking, Near Legoland

Private Cozy Studio, Free Parking, Near Legoland
Lake Horney
The price is NZ$312
includes taxes & fees
18 Aug - 19 Aug
Private Cozy Studio, Free Parking, Near Legoland
Exterior

10. 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 NZ$264
includes taxes & fees
17 Aug - 18 Aug
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Exterior

11. 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 NZ$483
includes taxes & fees
12 Sept - 13 Sept
Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland
House (3 Bedrooms) | Interior

12. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is NZ$656
includes taxes & fees
17 Aug - 18 Aug
Serenity - Family & Pet Friendly, Amazing Location
Exterior

13. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is NZ$328
includes taxes & fees
30 Aug - 31 Aug
Perfect Place for a Perfect Vacation
Microwave, stovetop

14. 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 NZ$280
includes taxes & fees
1 Sept - 2 Sept
Tiny house close to Disney KISSIMMEE
House (3 Bedrooms) | Interior

15. Lake Views & Private Porch: Auburndale Family Home

Lake Views & Private Porch: Auburndale Family Home
3.0 star property
Auburndale
8.0 out of 10, Very good, (1 review)
"This house has beautiful views of Lake Ariana and you can walk to old town and access the lake easily. The house is an old classic central Florida house with some quirks, but had room for family and entertaining. Auburndale beautiful and was a great place to visit and had quick access to highways. "
United States
Katrina
The price is NZ$607
includes taxes & fees
17 Aug - 18 Aug
Lake Views & Private Porch: Auburndale Family Home
Dining

16. 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$368
includes taxes & fees
17 Aug - 18 Aug
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Exterior

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

Mvy7664 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
Mvy7664 - 3BR House Near Disney With Hot Tub
House (3 Bedrooms) | Interior

18. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is NZ$417
includes taxes & fees
17 Aug - 18 Aug
Upstay: Bright Family-friendly Retreat With Patio
Smart TV, books

19. 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 NZ$342
includes taxes & fees
7 Sept - 8 Sept
Family-Friendly Cottage Near Orlando’s Top Attractions
Exterior

20. 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 NZ$512
includes taxes & fees
15 Sept - 16 Sept
Beautiful Cottage! Your Home Away From Home. 4 miles from 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.
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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

8/10 Good
"There were ants in the bed and bugs that bit my daughter and made her scratch. When we told the property they did nothing about the situation. The pool was nice the onsite restaurant wasn't the best."
Leslie Pierre 8-night trip
Posted less than an hour ago
The Grove Resort & Water Park Orlando

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Cottages information

Number of reviews
198
Accommodation
30 Cottages
Lowest Price
NZ$132
Highest Price
NZ$852

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Cottages in Lakeland - Winter Haven range between NZ$132 and NZ$852 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 30 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.

Explore a world of travel with Expedia