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Our top choices for Winter Haven cottages

1. 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 AU$114
includes taxes & fees
16 Nov - 17 Nov
Lake Ida Beach Resort

2. 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 AU$293
includes taxes & fees
13 Nov - 14 Nov
The Russell Lake House

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 AU$205
includes taxes & fees
23 Nov - 24 Nov
Lakefront Tiny Cottage 4 Miles to LEGOLAND.

4. 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 AU$386
includes taxes & fees
16 Nov - 17 Nov
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn

5. 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 AU$507
includes taxes & fees
24 Nov - 25 Nov
Lakefront Retreat on Lake Ariana w/ EV Charger

6. 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 AU$446
includes taxes & fees
14 Nov - 15 Nov
Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland

7. 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, (7 reviews)
"Clean comfort all ok"
United States
Donald P.
The price is AU$301
includes taxes & fees
24 Nov - 25 Nov
Charming Historic Cottage with Cozy Porch and Garden Retreat

8. 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 AU$217
includes taxes & fees
14 Nov - 15 Nov
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

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

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is AU$474
includes taxes & fees
29 Nov - 30 Nov
Family Resort Home w Pool, BBQ & Game Room

10. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is AU$562
includes taxes & fees
15 Nov - 16 Nov
Serenity - Family & Pet Friendly, Amazing Location

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 AU$673
includes taxes & fees
15 Nov - 16 Nov
Mvy7664 - 3BR House Near Disney With Hot Tub

12. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
9.0 out of 10, Wonderful, (2 reviews)
"Clean. A little confusing on the location. Gate guard was a little tough. Price a little high for a double wide."
United States
Michael R.
The price is AU$267
includes taxes & fees
12 Nov - 13 Nov
Perfect Place for a Perfect Vacation

13. Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"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 AU$283
includes taxes & fees
17 Nov - 18 Nov
Family-Friendly Cottage Near Orlando’s Top Attractions

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 AU$421
includes taxes & fees
17 Nov - 18 Nov
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

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

Golf, Dine & Unwind Poolside! Haines City Getaway
3.0 star property
Haines City
The price is AU$620
includes taxes & fees
6 Dec - 7 Dec
Golf, Dine & Unwind Poolside! Haines City Getaway

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 AU$305
includes taxes & fees
12 Nov - 13 Nov
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

17. 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 AU$1,070
includes taxes & fees
23 Nov - 24 Nov
Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas

18. Walkable Dixieland District Gem With Yard

Walkable Dixieland District Gem With Yard
2.0 star property
Dixieland
The price is AU$402
includes taxes & fees
16 Nov - 17 Nov
Walkable Dixieland District Gem With Yard

19. Mvv7561 - 4BR House Near Disney World

Mvv7561 - 4BR House Near Disney World
3.0 star property
Kissimmee
The price is AU$737
includes taxes & fees
8 Dec - 9 Dec
Mvv7561 - 4BR House Near Disney World

20. 9 Mi to Walt Disney World: Family Home w/ Pool!

9 Mi to Walt Disney World: Family Home w/ Pool!
3.0 star property
Clear Creek
The price is AU$534
includes taxes & fees
22 Nov - 23 Nov
9 Mi to Walt Disney World: Family Home w/ Pool!
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 Winter Haven Hotel Reviews

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
88
Accommodation
2246 Cottages
Lowest Price
AU$114
Highest Price
AU$1,070

Frequently asked questions

How much do cottages in Winter Haven cost?
Rates for cottages in Winter Haven range between AU$114 and AU$1,070 per night. Whatever your budget, you'll find the ideal place to get in tune with nature. This price was 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 Winter Haven?
There are 2246 cottages in Winter Haven. Whether you're travelling with the kids or planning a weekend retreat with your besties, Expedia can help you find the ideal property to immerse yourself in nature.
What is there to do in Winter Haven near my cottage?
Whatever your tastes or interests, Winter Haven has loads to capture your imagination. LEGOLAND® Florida, Theatre Winter Haven and Indigos Billiards, Bowling & Games are on many visitors' lists. Don't forget about Chain of Lakes Park, The Circle B Bar Reserve and Auburndale City Park either. With Expedia's hotel deals in Winter Haven, you'll be able to discover even more terrific attractions like these with the cash you save.