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
7.6 out of 10, Good, (159)
"The room could use an upgrade but it had everything I needed and I was comfortable staying there. The pool was really clean "
The price is SAR 297
SAR 328 total
includes taxes & fees
4 Dec - 5 Dec
Lake Ida Beach Resort

Margarita Porch Paradise

5.0 star property
10.0 out of 10, Exceptional, (1)
"The house was beautiful and comfortable for our family, we would have stayed longer! The resort is fun, plenty of stores and good restaurants. We will definitely come back. "
Margarita Porch Paradise

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

9.2 out of 10, Wonderful, (120)
"This is a super cute little cottage. It is easily accessible on the property. I saw deer and other wildlife on the property. It was very peaceful and perfect lovation for our trip. "
1-bedroom cottage just a 13-minute walk to Old Town

Davenport Family Home ~ 10 Mi to Animal Kingdom

3.0 star property
Davenport Family Home ~ 10 Mi to Animal Kingdom

Contemporary Home w/ Hot Tub: 4 Mi to Disney Magic

9.6 out of 10, Exceptional, (27)
"Great place to stay. "
Contemporary Home w/ Hot Tub: 4 Mi to Disney Magic

Private Pool/spa, Free Waterpark, Lazy River!

4.0 star property
10.0 out of 10, Exceptional, (4)
"Very comfortable "
Private Pool/spa, Free Waterpark, Lazy River!

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

Jedi cottage 4 miles from Disney! Mins from universal!

10.0 out of 10, Exceptional, (17)
"Extended our stay at Disney and decided to stay off property the one day! Kathryn was a great host!"
The price is SAR 319
SAR 850 total
includes taxes & fees
24 Nov - 25 Nov
Jedi cottage 4 miles from Disney! Mins from universal!

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

Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready!

10.0 out of 10, Exceptional, (5)
"G"
Cozy Lakeside Cottage near Legoland, Winter Haven! Florida vacation ready!

Cottage w/ Private Pool - Walk to Lake Wales!

10.0 out of 10, Exceptional, (53)
"The location was great for our stay. The cottage was as advertised & was stocked with many amenities. Our Host was excellent & very easy to communicate with. Look forward to staying there again on our next trip. "
Cottage w/ Private Pool - Walk to Lake Wales!

Lake Wales Vacation Rental w/ Screened-In Porch!

10.0 out of 10, Exceptional, (6)
"The stay was wonderful but ended up being cut short due to a hurricane in the area. The host was very helpful and understanding."
Lake Wales Vacation Rental w/ Screened-In Porch!

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!

Lakefront Frostproof Vacation Rental w/ Beach!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We thoroughly enjoyed our stay! The home was very clean. The floors were so clean when wiping up some water drips, there was not one spec of dirt on the paper towel! That is my measure for being clean! Home owners were excellent to work with. Texting answers to my many questions. We stayed while we were in town for the 12 Hours of Sebring race. Easy 30 minute drive to the track. Beautiful view of the lake with lounge chairs on a private beach behind the house. I can't say enough about...
Lakefront Frostproof Vacation Rental w/ Beach!

Sunlit Davenport Family Home w/ Lanai & Gas Grill!

3.0 star property
8.0 out of 10, Very Good, (1)
"House nicely kept, lots of room and beds for large gatherings. Clean, convenient washer and dryer in unit, great location, close to shops and restaurants. Overall, really nice place to stay. "
Sunlit Davenport Family Home w/ Lanai & Gas Grill!

3000 Latitude Lane

3.0 star property
10.0 out of 10, Exceptional, (2)
"Great stay!"
3000 Latitude Lane

Davenport Home w/ Game Room, Home Theater, Pool

3.0 star property
10.0 out of 10, Exceptional, (1)
"What an amazing home! Clean and everything you need for a staycation or trip to Disney! The pictures online do not do this Gargage justice. It’s an arcade in the home. So much fun! I would recommend this home for all. "
Davenport Home w/ Game Room, Home Theater, Pool

Kissimmee Vacation Home: Heated Pool, Near Disney!

3.0 star property
Kissimmee Vacation Home: Heated Pool, Near Disney!

Magical Themed Villa in Windsor Isalnd

3.0 star property
Magical Themed Villa in Windsor Isalnd
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

Seralago Hotel & Suites Main Gate East

3.0 star property
5.2 out of 10, (5565)
"I had to wait 20 minutes for the front counter lady to come in from smoking. The security guard was sitting in the lobby playing on his phone and he just kept saying she will be back soon.. Then she told me I had booked a double bed room and I said no I booked a family suite.. So I had to show her my email and she said well I don't know why they put you in another room, let me make sure I have a clean one.. After standing in the lobby for a total of 40 minutes (including her smoke break time), I...
The price is SAR 147
SAR 244 total
includes taxes & fees
24 Nov - 25 Nov
Seralago Hotel & Suites Main Gate East

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very Good, (5025)
"Our unit was clean but in definite need of an update. The carpet was threadbare and torn in some areas. We still had a great stay and appreciated the prompt attention from security when we needed access to our unit."
The price is SAR 490
SAR 669 total
includes taxes & fees
8 Dec - 9 Dec
Summer Bay Orlando by Exploria Resorts

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1084)
"This is our third time staying at Margaritaville (cottage the first time, villas the second and third time); I must say this villa was the least taken care of. It wasn’t super clean and the slider had some damage regarding opening/closing the blinds and locking/unlocking the sliding glass door. The front door didn’t have a safety lock at all (it looked to have been removed) so that made us a little uneasy. Our bed (queen) was very bouncy and it seemed to cave a little in the middle. Overall, it...
Margaritaville Resort Orlando Cottages by Rentyl
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 297 and SAR 319 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?
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