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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Lakeland - Winter Haven cottages

A small, single-story house with a gray roof and white siding, featuring two white plastic chairs outside.

1. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (197 reviews)
"Clean room and private area loved it"
United States
Heather
The price is NZ$141
includes taxes & fees
13 Oct - 14 Oct
Lake Ida Beach Resort
A kitchen shelf with jars of spices, a bottle of cooking spray, and a white candle.

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$258
includes taxes & fees
2 Oct - 3 Oct
This old Florida feeling getaway is 420 friendly and a great place to just relax
A two-story house with a front porch, a garage, and a well-maintained lawn.

3. 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 NZ$717
includes taxes & fees
4 Oct - 5 Oct
Hook, Line & Leisure: Lakefront Gem w/ Porch!
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 NZ$264
includes taxes & fees
4 Oct - 5 Oct
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
A single-story house with a front porch, a garage, and a small backyard.

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
9.2 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 NZ$496
includes taxes & fees
2 Oct - 3 Oct
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
A residential property with a brick pathway, a white house with a red chimney, and various trees and shrubs.

6. Charming Lakeside Cottage

Charming Lakeside Cottage
Winter Haven
10.0 out of 10, Exceptional, (1 review)
"Very nice property. The cottage was very clean and well laid out. Recommend 10/10"
United States
Ron O.
The price is NZ$305
includes taxes & fees
30 Oct - 31 Oct
Charming Lakeside Cottage
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 NZ$582
includes taxes & fees
4 Oct - 5 Oct
Family Resort Home w Pool, BBQ & Game Room
A two-story building with a blue exterior, a front porch, and a visible garage door.

8. 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$451
includes taxes & fees
2 Oct - 3 Oct
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.

9. 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$294
includes taxes & fees
2 Oct - 3 Oct
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
A small, single-story house with a porch, surrounded by a well-maintained lawn and a gravel path leading to the entrance.

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 NZ$406
includes taxes & fees
13 Oct - 14 Oct
Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland
A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

11. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is NZ$705
includes taxes & fees
2 Oct - 3 Oct
Serenity - Family & Pet Friendly, Amazing Location
A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a black microwave.

12. 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$293
includes taxes & fees
13 Oct - 14 Oct
Tiny house close to Disney KISSIMMEE
A covered porch with two wooden chairs and a bench, overlooking a road and a body of water.

13. 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 NZ$593
includes taxes & fees
11 Oct - 12 Oct
Lakefront Retreat on Lake Ariana w/ EV Charger
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

14. 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$340
includes taxes & fees
14 Oct - 15 Oct
Perfect Place for a Perfect Vacation
A resort with a central swimming pool, sun loungers, and palm trees.

15. Mvy7632 - 4BR House Near Disney

Mvy7632 - 4BR House Near Disney
3.0 star property
Kissimmee
The price is NZ$845
includes taxes & fees
6 Oct - 7 Oct
Mvy7632 - 4BR House Near Disney
A single-story house with a gabled roof, a front porch, and a small front yard with a large agave plant.

16. 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$550
includes taxes & fees
6 Oct - 7 Oct
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
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 NZ$485
includes taxes & fees
21 Oct - 22 Oct
Upstay: Bright Family-friendly Retreat With Patio
A modern living room with a sofa, a large wall clock, and a mirror.

18. 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$358
includes taxes & fees
14 Oct - 15 Oct
Family-Friendly Cottage Near Orlando’s Top Attractions
A compact kitchen with a built-in TV, a dining area with a bench, and a wall decorated with motivational posters.

19. 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$383
includes taxes & fees
14 Oct - 15 Oct
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
A restaurant with outdoor seating and a thatched roof.

20. "Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.4 out of 10, Exceptional, (14 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is NZ$528
includes taxes & fees
27 Oct - 28 Oct
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
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
"Everything was great."
Jeffrey 14-night trip
Posted 8 hours ago
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Cottages information

Number of reviews
84
Accommodation
30 Cottages
Lowest Price
NZ$141
Highest Price
NZ$845

Frequently asked questions

How much do cottages in Lakeland - Winter Haven cost?
Cottages in Lakeland - Winter Haven range between NZ$141 and NZ$845 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.

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