Search Cottages in Winter Haven

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Compare 1437 Cottages in Winter Haven with updated reviews, rates, and availability.

Lake Ida Beach Resort

3.0 star property
7.4 out of 10, Good, (163)
"What would I say? I love this place. Very clean and very quiet. They have a kitchenette inside you can definitely cook and make your own meal no need to eat out.The Bed is very comfortable. Its been a year since I started coming here and here I am still loving this place. The price is better than anyone else. Owners are helpful and friendly. Highly recommend for those who want a cheap but comfortable stay. "
The price is SAR 314
SAR 352 total
includes taxes & fees
15 Jan - 16 Jan
Lake Ida Beach Resort

Cottage w/ Private Pool - Walk to Lake Wales!

10.0 out of 10, Exceptional, (56)
"Very pleasant home with responsive owner."
Cottage w/ Private Pool - Walk to Lake Wales!

Lake Wales Vacation Rental w/ Screened-In Porch!

10.0 out of 10, Exceptional, (7)
"We were visiting Lake Wales for an event. This was the perfect location; walkable to downtown restaurants as well as lake. The house was clean and as depicted in pictures. The communication with property manager was excellent."
Lake Wales Vacation Rental w/ Screened-In Porch!

~ 10 Mi to Animal Kingdom: Davenport Family Home

3.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect two day stay for us … close to everything we n ended it to be. "
~ 10 Mi to Animal Kingdom: Davenport Family Home

Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly

10.0 out of 10, Exceptional, (4)
"SO nice that each couple had a queen or king sized bed and each bedroom had its own bathroom. Hot tub was a huge bonus after long days on your feet at the theme parks. Very nice house in a beautiful area convenient to the Disney parks."
Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly

Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

3.0 star property
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621

3.0 star property
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621

Parkside Serenity by Avantstay Private Pool!

3.0 star property
Parkside Serenity by Avantstay Private Pool!

Lakeland Cottage w/ Pool Access + Screened Porch!

10.0 out of 10, Exceptional, (1)
Lakeland Cottage w/ Pool Access + Screened Porch!

1-bedroom cottage just a 13-minute walk to Old Town

9.2 out of 10, Wonderful, (124)
"Hostess very quick to answer our inqiiries before and during our stay. Quiant cottage perfect for two. Close to many attractions including Old Town Kissimmee , downtown Celebration and of course, Disney parks. Located in Tropical Palms resort, easy in and out from there."
1-bedroom cottage just a 13-minute walk to Old Town

4 miles from Disney 5 Star RV Resort! Location Location !The Hidden Gem Cottage!

10.0 out of 10, Exceptional, (23)
"Everything was super clean and great service "
4 miles from Disney 5 Star RV Resort! Location Location !The Hidden Gem Cottage!

Spacious Vacation Rental w/ Yard in Kissimmee!

3.0 star property
8.0 out of 10, Very Good, (1)
"Communication on the property was excellent. Comfortable"
Spacious Vacation Rental w/ Yard in Kissimmee!

Enchanted Cottage with Pool and Mini-Golf Near Disney

9.6 out of 10, Exceptional, (14)
"This location was perfect for me and my two dogs. "
Enchanted Cottage with Pool and Mini-Golf Near Disney

6 Br / 4,5 Bath + Pool/Spa + Game Room / Less than 4 miles from Disney

9.6 out of 10, Exceptional, (7)
"Excellent property for a Florida holiday base. Will be staying again in the future"
6 Br / 4,5 Bath + Pool/Spa + Game Room / Less than 4 miles from Disney

Lakeview Cottage Escape. Close to BOK Tower Gardens, Legoland and Disney

10.0 out of 10, Exceptional, (34)
"The cottage is immaculate and was just the right space for my family. We wanted something near my parents for a short visit, and this was simply perfect. So much nicer than staying in a hotel also. "
Lakeview Cottage Escape. Close to BOK Tower Gardens, Legoland and Disney

Townhome Splash Pool BBQ Free Water Park!

3.5 star property
9.6 out of 10, Exceptional, (9)
"Nice and relaxing quiet neighborhood "
Townhome Splash Pool BBQ Free Water Park!

Family-friendly Winter Haven Home w/ Pool!

3.0 star property
8.0 out of 10, Very Good, (1)
"Property was clean and very functional. Had the opportunity to speak with the host after a miscommunication with his property manager and he was first class. Great property and would stay again for sure. Host was exceptional!!"
Family-friendly Winter Haven Home w/ Pool!

Spacious Resort Home w/ Pool - 11 Mi to Disney!

3.0 star property
8.6 out of 10, Excellent, (4)
"The house was perfect for my family of 14. It was beautiful, large and very spacious. The property manager was not resposnive but the owner wss excellent.There were a couple of minor issues, but absolutely nothing that affected our stay. I'd definitely stay there again and would recommend to everyone. "
Spacious Resort Home w/ Pool - 11 Mi to Disney!

Family-friendly Lakeland Home w/ Private Hot Tub!

3.0 star property
9.0 out of 10, Wonderful, (2)
"This home is laid out nicely and met our needs for a quick weekend stay in Lakeland. The host, Letty, was a pleasure and provided very clear and easy to follow instructions. The home needs some updating, but was clean, comfortable and in a great location. "
Family-friendly Lakeland Home w/ Private Hot Tub!

Charming Tiny Home w/ Private Hot Tub!

3.0 star property
8.0 out of 10, Very Good, (3)
"It was a great little place but is a bit run down. There’s broken furniture and the hot tub seemed a bit cloudy"
Charming Tiny Home w/ Private Hot Tub!
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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Other property types in Winter Haven

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very Good, (5087)
"Great Resort for families and close to Disney World!"
The price is SAR 456
SAR 631 total
includes taxes & fees
26 Jan - 27 Jan
Summer Bay Orlando by Exploria Resorts

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1153)
"The unit was a townhouse style and was beautiful. It also appeared to be very new. The only complaint I had would be in the lower level shower. The water was hot and there was no way of making it cold. It was bearable for me and we were so busy at the resorts, that I never alerted the main office of this, so someone may want to look into that. Otherwise, it couldn't have been much better. Beautiful townhouse and I would absolutely stay here again."
Margaritaville Resort Orlando Cottages by Rentyl

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very Good, (1412)
"Great price and value for a family vacation! "
The price is SAR 412
SAR 523 total
includes taxes & fees
14 Jan - 15 Jan
Vacation Village at Parkway
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.

Frequently asked questions

How much do cottages in Winter Haven cost?
Cottages in Winter Haven range between SAR 314 and SAR 314 per night. These retreats offer a chance to touch base 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 choose from 1437 cottages in Winter Haven. Dreaming of a place where you can immerse yourself in nature? Expedia can help you find the ideal getaway in a few easy clicks.
Why book your cottage in Winter Haven with Expedia?
We think that traveling should be easy, so if you’re seeking cottages in Winter Haven at a competitive price, Expedia has you covered. Keep costs down and choose an inexpensive option far away from the hustle and bustle, or book an upmarket cottage to pamper your loved ones.
How can I find cheap cottages in Winter Haven?
With Expedia’s helpful filter tool, sourcing cheap cottages in Winter Haven is a snap. To view accommodations that’ll make your wallet happy, tailor your search results by amenities, budget and star rating.