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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Winter Haven cottages

Porch

1. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, 196, (196 reviews)
"Clean room and private area loved it"
United States
Heather
The price is CA $95
CA $106 total
includes taxes & fees
Sep 15 - Sep 16
Lake Ida Beach Resort
Terrace/patio

2. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

Lakefront Tiny Cottage 4 Miles to LEGOLAND.
winter have
9.0 out of 10, 42, (42 reviews)
"Awesome location, very nice"
United States
Kyle P.
The price is CA $97
CA $206 total
includes taxes & fees
Sep 15 - Sep 16
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
House (3 Bedrooms) | Interior

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, 3, (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 CA $229
CA $560 total
includes taxes & fees
Sep 15 - Sep 16
Hook, Line & Leisure: Lakefront Gem w/ Porch!
Exterior

4. Charming Lakeside Cottage

Charming Lakeside Cottage
Winter Haven
The price is CA $119
CA $238 total
includes taxes & fees
Sep 16 - Sep 17
Charming Lakeside Cottage
Exterior

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
9.0 out of 10, 6, (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 CA $160
CA $391 total
includes taxes & fees
Sep 15 - Sep 16
Sweet Cottage 5 mi to Legoland & 0.5 mi to dwntwn
House (4 Bedrooms) | Interior

6. Legoland & Lakes Pool Home w/ Private Suite

Legoland & Lakes Pool Home w/ Private Suite
3.0 star property
Winter Haven
The price is CA $203
CA $702 total
includes taxes & fees
Sep 25 - Sep 26
Legoland & Lakes Pool Home w/ Private Suite
House (3 Bedrooms) | Interior

7. 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, 1, (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 CA $160
CA $464 total
includes taxes & fees
Sep 15 - Sep 16
Lakefront Retreat on Lake Ariana w/ EV Charger
Exterior

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 CA $182
CA $387 total
includes taxes & fees
Oct 3 - Oct 4
Lakeside Escape, 2BR 1 BA, Cozy Lux Cottage near Disney, Universal and Legoland
Exterior

9. 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, 5, (5 reviews)
"Clean comfort all ok"
United States
Donald P.
The price is CA $106
CA $279 total
includes taxes & fees
Sep 15 - Sep 16
Charming Historic Cottage with Cozy Porch and Garden Retreat
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, (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 CA $99
CA $216 total
includes taxes & fees
Sep 15 - Sep 16
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Exterior

11. 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 CA $169
CA $317 total
includes taxes & fees
Sep 23 - Sep 24
Peaceful 2-bedroom Tiny House with private parking lot in charming Lakeland
House (4 Bedrooms) | Interior

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

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is CA $155
CA $468 total
includes taxes & fees
Sep 30 - Oct 1
Family Resort Home w Pool, BBQ & Game Room
House (4 Bedrooms) | Floor plan

13. Family 4BR Home w/ Resort Pool Near Disney

Family 4BR Home w/ Resort Pool Near Disney
3.0 star property
Regal Palms
The price is CA $125
CA $452 total
includes taxes & fees
Oct 5 - Oct 6
Family 4BR Home w/ Resort Pool Near Disney
Exterior

14. Pastel Paradise Villa near Disney With Margaritaville Resort and Island H20.

Pastel Paradise Villa near Disney With Margaritaville Resort and Island H20.
Kissimmee
The price is CA $232
CA $713 total
includes taxes & fees
Sep 15 - Sep 16
Pastel Paradise Villa near Disney With Margaritaville Resort and Island H20.
Exterior

15. Comfy Cottage near Disney | Margaritaville Resort & Waterpark Access - 8087KD

Comfy Cottage near Disney | Margaritaville Resort & Waterpark Access - 8087KD
Kissimmee
The price is CA $265
CA $753 total
includes taxes & fees
Sep 15 - Sep 16
Comfy Cottage near Disney | Margaritaville Resort & Waterpark Access - 8087KD
Exterior

16. Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
The price is CA $265
CA $755 total
includes taxes & fees
Sep 15 - Sep 16
Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.
House (3 Bedrooms) | Interior

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

Golf, Dine & Unwind Poolside! Haines City Getaway
3.0 star property
Haines City
The price is CA $234
CA $595 total
includes taxes & fees
Oct 1 - Oct 2
Golf, Dine & Unwind Poolside! Haines City Getaway
House (3 Bedrooms) | Interior

18. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
Serenity - Family & Pet Friendly, Amazing Location
Exterior

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

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.4 out of 10, 13, (13 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is CA $124
CA $368 total
includes taxes & fees
Sep 16 - Sep 17
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Exterior

20. Breezy Green Cottage with Private Hot Tub near Disney with Margaritaville.

Breezy Green Cottage with Private Hot Tub near Disney with Margaritaville.
Kissimmee
8.0 out of 10, 1, (1 review)
"We’ve stayed at Margaritaville at least 4-5 times in different houses and we always have a great time. This house had a great location, as it was close to the gym and pool area. Negatives: on the listing it says there is a king bed, definitely no king bed. The first night was cold and none of the beds had anything other than sheets and when we called and requested additional blankets, we were told it was going to be $10 each blanket! The room did not come with sheets for the pull out couch so...
United States
Chad A.
The price is CA $265
CA $755 total
includes taxes & fees
Sep 15 - Sep 16
Breezy Green Cottage with Private Hot Tub near Disney with Margaritaville.
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

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG

10/10 Excellent
"It was an awesome stay."
Jacqueline 2-night trip
Posted less than an hour ago
Staybridge Suites Winter Haven Auburndale by IHG

Find out more about Winter Haven

Winter Haven Cottages information

Number of reviews
200
Accommodation
2248 Cottages
Lowest Price
CA $106
Highest Price
CA $702

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between CA $106 and CA $702 per night. These properties offer a chance to get in tune 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 Winter Haven?
Pack your suitcases and pick from 2248 cottages in Winter Haven. Thinking about a place where you can get in touch with nature? Expedia can help you find your ideal stay in only a click or two.
Are there any family-friendly cottages in Winter Haven?
If you're looking to get back to nature in Winter Haven, you can't beat Lake Ida Beach Resort. With a 3-star rating and amenities like housekeeping services and WiFi, you'll find it easy to relax at this family-friendly cottage. After checking in and chilling out in your comfy new digs, it's time to head out and start exploring. LEGOLAND® Florida and Indigo's Family Fun Centre are among the best family-friendly attractions in Winter Haven.
Why book your cottage in Winter Haven with Expedia?
Booking a cottage in Winter Haven is as simple as working out your travel dates and picking your ideal place for a getaway in nature. From chic retreats to low-cost stays and cottages that have amenities like laundry facilities, Expedia has something for all tastes and styles. As for the best offers around? We've got them too!
How can I find cheap cottages in Winter Haven?
A great way to track down cheap cottages in Winter Haven is with Expedia's useful filter tool. Tailor your search results by star rating, amenities and budget to discover unbeatable bargains in a few clicks.
What is there to do in Winter Haven near my cottage?
You'll find plenty of fabulous things that'll fill up your itinerary in Winter Haven. Head for top attractions like Indigo's Family Fun Center, Lake Henry Golf Club and Cypresswood Golf and Country Club. LEGOLAND® Florida, Chain of Lakes Park and Theatre Winter Haven are other must-see's.

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