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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Lakeland - Winter Haven cottages

A swimming pool with lounge chairs, surrounded by palm trees and a dock extending into a body of water, during sunset.

1. The Russell Lake House

The Russell Lake House
Winter Haven
9.8 out of 10, Exceptional, (25 reviews)
"Nice place!"
United States
Jake D.
The price is ￥10,631
￥31,594 total
includes taxes & fees
Nov 8 - Nov 9
The Russell Lake House
A swimming pool with a fence, lounge chairs, and a palm tree.

2. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (198 reviews)
"Clean room and private area loved it"
United States
Heather
The price is ￥11,073
￥12,402 total
includes taxes & fees
Nov 8 - Nov 9
Lake Ida Beach Resort
A compact kitchenette with a microwave, coffee maker, and storage cabinets.

3. 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 ￥12,615
￥24,942 total
includes taxes & fees
Nov 7 - Nov 8
This old Florida feeling getaway is 420 friendly and a great place to just relax
A wooden deck with outdoor seating, a shed, and a view of the surrounding landscape.

4. 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 ￥11,024
￥22,174 total
includes taxes & fees
Nov 8 - Nov 9
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

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

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is ￥16,379
￥51,683 total
includes taxes & fees
Nov 29 - Nov 30
Family Resort Home w Pool, BBQ & Game Room
A residential area with a large house, a smaller attached garage, and a view of the water.

6. Charming Lakeside Cottage

Charming Lakeside Cottage
Winter Haven
10.0 out of 10, Exceptional, (2 reviews)
"Truly great people. We had a wonderful time! Peaceful and relaxing!!"
United States
Jeremy Kyle W.
The price is ￥14,174
￥26,584 total
includes taxes & fees
Nov 8 - Nov 9
Charming Lakeside Cottage
A single-story house with a front porch, a garage, and a small backyard.

7. 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 ￥18,111
￥42,010 total
includes taxes & fees
Nov 7 - Nov 8
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
A two-story residential building with a garage, a small tree, and a well-maintained lawn.

8. Golf, Dine & Unwind Poolside! Haines City Getaway

Golf, Dine & Unwind Poolside! Haines City Getaway
3.0 star property
Haines City
The price is ￥26,616
￥67,570 total
includes taxes & fees
Dec 1 - Dec 2
Golf, Dine & Unwind Poolside! Haines City Getaway
A row of yellow buildings with numbered doors, a sidewalk, and greenery.

9. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is ￥16,253
￥64,411 total
includes taxes & fees
Nov 9 - Nov 10
Serenity - Family & Pet Friendly, Amazing Location
A single-story house with a stone retaining wall, a front porch, and a small garden.

10. 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, (6 reviews)
"Clean comfort all ok"
United States
Donald P.
The price is ￥13,387
￥32,034 total
includes taxes & fees
Nov 22 - Nov 23
Charming Historic Cottage with Cozy Porch and Garden Retreat
A poolside area with lounge chairs and palm trees, a clear blue sky, and a building with a modern design.

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

Mvy7664 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
The price is ￥30,317
￥70,699 total
includes taxes & fees
Nov 11 - Nov 12
Mvy7664 - 3BR House Near Disney With Hot Tub
A two-story building with a blue exterior, a front porch, and a visible garage door.

12. 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 ￥22,666
￥43,921 total
includes taxes & fees
Nov 13 - Nov 14
Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland
A small cabin with a porch and a garage, surrounded by trees and a clear sky.

13. 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 ￥11,198
￥22,780 total
includes taxes & fees
Nov 7 - Nov 8
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
A single-story house with a gabled roof, a front porch, and a small front yard with a large agave plant.

14. 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 ￥15,261
￥47,104 total
includes taxes & fees
Nov 16 - Nov 17
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
A residential area with houses featuring sloped roofs and solar panels.

15. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is ￥11,157
￥39,298 total
includes taxes & fees
Dec 2 - Dec 3
Upstay: Bright Family-friendly Retreat With Patio
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

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 ￥12,757
￥29,040 total
includes taxes & fees
Nov 9 - Nov 10
Perfect Place for a Perfect Vacation
A compact kitchen with a built-in TV, a dining area with a bench, and a wall decorated with motivational posters.

17. 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 ￥14,599
￥33,074 total
includes taxes & fees
Nov 7 - Nov 8
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
A covered porch with two wooden chairs and a bench, overlooking a road and a body of water.

18. Lakefront Retreat on Lake Ariana w/ EV Charger

Lakefront Retreat on Lake Ariana w/ EV Charger
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 ￥20,474
￥55,297 total
includes taxes & fees
Nov 9 - Nov 10
Lakefront Retreat on Lake Ariana w/ EV Charger
A modern living room with a sofa, a large wall clock, and a mirror.

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 ￥15,277
￥30,798 total
includes taxes & fees
Dec 7 - Dec 8
Family-Friendly Cottage Near Orlando’s Top Attractions
A two-story house with a balcony, two garages, and a brick driveway.

20. Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas

Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
3.5 star property
Reunion
The price is ￥42,924
￥117,275 total
includes taxes & fees
Nov 23 - Nov 24
Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
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

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

10/10 Excellent
"The sheets had stains on them"
Kenya 4-night trip
Posted less than an hour ago
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Cottages information

Number of reviews
90
Accommodation
46 Cottages
Lowest Price
￥12,402
Highest Price
￥117,275

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Cottages in Lakeland - Winter Haven range between ￥12,402 and ￥117,275 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 46 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.
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 Center and Publix Field at Joker Marchant Stadium are among the leading sights if you're off to Lakeland. Winter Haven also lures travelers with its wonderful attractions, such as Indigo's Family Fun Center. Eager to add to your to-do list? Drop by Chain of Lakes Park and Theatre Winter Haven too.

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