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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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, (24 reviews)
"Host was attentive and excellent!!!"
United States
jason s.
The price is €193
includes taxes & fees
14 Oct - 15 Oct
The Russell Lake House
A small, single-story house with a gray roof and white siding, featuring two white plastic chairs outside.

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 €71
includes taxes & fees
14 Oct - 15 Oct
Lake Ida Beach Resort
A wooden deck with outdoor seating, a shed, and a view of the surrounding landscape.

3. 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 €137
includes taxes & fees
26 Oct - 27 Oct
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
A residential property with a brick pathway, a white house with a red chimney, and various trees and shrubs.

4. 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 €163
includes taxes & fees
26 Oct - 27 Oct
Charming Lakeside Cottage
A kitchen shelf with jars of spices, a bottle of cooking spray, and a white candle.

5. 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 €134
includes taxes & fees
14 Oct - 15 Oct
This old Florida feeling getaway is 420 friendly and a great place to just relax
A covered porch with two wooden chairs and a bench, overlooking a road and a body of water.

6. 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 €300
includes taxes & fees
14 Oct - 15 Oct
Lakefront Retreat on Lake Ariana w/ EV Charger
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

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 €293
includes taxes & fees
18 Oct - 19 Oct
Family Resort Home w Pool, BBQ & Game Room
A single-story house with a front porch, a garage, and a small backyard.

8. 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 €254
includes taxes & fees
26 Oct - 27 Oct
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

9. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is €356
includes taxes & fees
14 Oct - 15 Oct
Serenity - Family & Pet Friendly, Amazing Location
A two-story building with a blue exterior, a front porch, and a visible garage door.

10. 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
Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland
A modern hotel with a curved driveway, large windows, and palm trees.

11. Mvv7482 - 3BR House Near Disney at Magic Village

Mvv7482 - 3BR House Near Disney at Magic Village
3.0 star property
Kissimmee
The price is €438
includes taxes & fees
27 Oct - 28 Oct
Mvv7482 - 3BR House Near Disney at Magic Village
A small, single-story house with a porch, surrounded by a well-maintained lawn and a gravel path leading to the entrance.

12. 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 €209
includes taxes & fees
14 Oct - 15 Oct
Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland
A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a black microwave.

13. 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
Tiny house close to Disney KISSIMMEE
A small cabin with a porch and a garage, surrounded by trees and a clear sky.

14. 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 €143
includes taxes & fees
14 Oct - 15 Oct
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

15. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is €176
includes taxes & fees
14 Oct - 15 Oct
Perfect Place for a Perfect Vacation
A two-story house with a front porch, a garage, and a well-maintained lawn.

16. Lakefront Vibes w/ Lanai! Bird-watching Paradise

Lakefront Vibes w/ Lanai! Bird-watching Paradise
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 €361
includes taxes & fees
20 Oct - 21 Oct
Lakefront Vibes w/ Lanai! Bird-watching Paradise
A residential area with houses featuring sloped roofs and solar panels.

17. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is €224
includes taxes & fees
19 Oct - 20 Oct
Upstay: Bright Family-friendly Retreat With Patio
A compact kitchen with a built-in TV, a dining area with a bench, and a wall decorated with motivational posters.

18. 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
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
A single-story house with a gabled roof, a front porch, and a small front yard with a large agave plant.

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.
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
A modern living room with a sofa, a large wall clock, and a mirror.

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.
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

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"We loved this hotel/resort!"
Kevin 4-night trip
Posted 4 hours ago
Hilton Vacation Club Aqua Sol Orlando West

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Cottages information

Number of reviews
95
Accommodation
35 Cottages
Lowest Price
€71
Highest Price
€438

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Cottages in Lakeland - Winter Haven range between €71 and €438 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 35 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.
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 traveller 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 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.

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