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Our top choices for Winter Haven Station vacation homes

Historic, private, updated, 5 Bedroom Plantation Home, lake, fishing, leasure

Historic, private, updated, 5 Bedroom Plantation Home, lake, fishing, leasure
Winter Haven
9.8 out of 10, Exceptional, (23)
"Awesome look forward to future stay "
United States
cheryl d.
$382 nightly
The price is $423
Dec 22 - Dec 23
Total with taxes and fees
Historic, private, updated, 5 Bedroom Plantation Home, lake, fishing, leasure

Large Family Home, Legoland, Pet Friendly, 7 Beds

Large Family Home, Legoland, Pet Friendly, 7 Beds
Winter Haven
10.0 out of 10, Exceptional, (21)
"The property was immaculate, and the stay was great. It's in a great neighborhood, and the yard is big enough for children to enjoy themselves."
United States
Tavares J.
$336 nightly
The price is $371
Dec 14 - Dec 15
Total with taxes and fees
Large Family Home, Legoland, Pet Friendly, 7 Beds

Lakefront Retreat at 6BR Escape w/ Heated Pool | Private Dock | Game Room | Deck | Perfect

Lakefront Retreat at 6BR Escape w/ Heated Pool | Private Dock | Game Room | Deck | Perfect
2.0 star property
Winter Haven
10.0 out of 10, Exceptional, (11)
"House was absolutely beautiful! Family left completely rested and relaxed! Will stay there again!"
United States
Julie D.
Lakefront Retreat at 6BR Escape w/ Heated Pool | Private Dock | Game Room | Deck | Perfect

Cheerful 4 Bed, 3 Bath Home with Screened Pool

Cheerful 4 Bed, 3 Bath Home with Screened Pool
Winter Haven
9.8 out of 10, Exceptional, (20)
"Great place, lots of space and very clean. Communication was top notch. "
United States
Darr
Cheerful 4 Bed, 3 Bath Home with Screened Pool

Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi

Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi
Winter Haven
10.0 out of 10, Exceptional, (1)
"Wonderful home "
United States
Joshlynn
$155 nightly
The price is $171
Dec 15 - Dec 16
Total with taxes and fees
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi

The Old Haven - An Enduring Piece of Nostalgia

The Old Haven - An Enduring Piece of Nostalgia
2.0 star property
Winter Haven
9.6 out of 10, Exceptional, (9)
"Had a great time. Great location. Looking forward to my next visit. Great hosts as well. "
United States
James K.
$271 nightly
The price is $297
Dec 14 - Dec 15
Total with taxes and fees
The Old Haven - An Enduring Piece of Nostalgia

Awesome Lake House With Private Dock, Canoe, Kayaks, Game-Room, & Lots To Do!!!

Awesome Lake House With Private Dock, Canoe, Kayaks, Game-Room, & Lots To Do!!!
Winter Haven
9.0 out of 10, Wonderful, (32)
"We loved the lake house. The kids had an awesome time with the tree swings. Thank you for having us!"
United States
Christina
Awesome Lake House With Private Dock, Canoe, Kayaks, Game-Room, & Lots To Do!!!

Charming 3-bedroom house in tranquil Winter Haven w/Lake Access

Charming 3-bedroom house in tranquil Winter Haven w/Lake Access
Winter Haven
10.0 out of 10, Exceptional, (2)
"The house is super clean and beautiful. "
United States
Lai
Charming 3-bedroom house in tranquil Winter Haven w/Lake Access

Lake Front: Charming 3-bedroom house with WiFi and AC in wonderful Winter Haven

Lake Front: Charming 3-bedroom house with WiFi and AC in wonderful Winter Haven
Winter Haven
9.6 out of 10, Exceptional, (4)
"Nice, peaceful place right on the lake. Would rent it again. "
United States
Erikka H.
Lake Front: Charming 3-bedroom house with WiFi and AC in wonderful Winter Haven

Luxury StayComfy at WinterHeaven

Luxury StayComfy at WinterHeaven
Winter Haven
8.4 out of 10, Very Good, (19)
"It was amazing. The beds felt and slept so good. It was just perfect. "
United States
Linda P.
Luxury StayComfy at WinterHeaven

Charming 2-bedroom country house with AC, WiFi in Winter Haven

Charming 2-bedroom country house with AC, WiFi in Winter Haven
2.0 star property
Winter Haven
6.6 out of 10, (7)
"This is a small, cute cottage. It feels like home away from home. Decor is pretty, beds are comfortable, and location is quiet. Only criticism would be: there is no heat and one morning was a little chilly to a native FL gal. "
United States
Kristian B.
Charming 2-bedroom country house with AC, WiFi in Winter Haven

Modern Comfort, Pet Friendly, 2 King Beds

Modern Comfort, Pet Friendly, 2 King Beds
2.0 star property
Winter Haven
10.0 out of 10, Exceptional, (3)
"Great welcoming and answered every question I had. Highly recommend this lovely cottage. "
United States
Kristofer G.
$212 nightly
The price is $234
Dec 15 - Dec 16
Total with taxes and fees
Modern Comfort, Pet Friendly, 2 King Beds

Large 3/1 Near DownTown and Dining

Large 3/1 Near DownTown and Dining
Winter Haven
7.4 out of 10, Good, (10)
"Clean, quiet and comfortable beds. "
United States
Jason
$233 nightly
The price is $257
Dec 14 - Dec 15
Total with taxes and fees
Large 3/1 Near DownTown and Dining

6 Mi to Legoland: Retreat w/ Pool & Fenced Yard

6 Mi to Legoland: Retreat w/ Pool & Fenced Yard
Winter Haven
9.8 out of 10, Exceptional, (13)
"This house is perfect! We loved staying here!"
United States
Debbie D.
6 Mi to Legoland: Retreat w/ Pool & Fenced Yard

Peaceful Lakeside Retreat

Peaceful Lakeside Retreat
Winter Haven
9.0 out of 10, Wonderful, (10)
"This property was very nice! It was very relaxing and provided me with a very nice host location for family that I was visiting in the area. The property manager was extremely professional and accommodating."
United States
Shelby R.
$375 nightly
The price is $419
Dec 16 - Dec 17
Total with taxes and fees
Peaceful Lakeside Retreat

Lakeside Adventure Retreat w/ Heated Pool, Fishing Dock, Game Room & Optional 1 hr Boat Cruise*

Lakeside Adventure Retreat w/ Heated Pool, Fishing Dock, Game Room & Optional 1 hr Boat Cruise*
Winter Haven
10.0 out of 10, Exceptional, (8)
"We loved our stay! The house was very clean and exactly as described. The hosts were VERY responsive and helpful for all questions we had! Check out was a breeze and we would love to come back here!"
United States
Shelby
Lakeside Adventure Retreat w/ Heated Pool, Fishing Dock, Game Room & Optional 1 hr Boat Cruise*

Lake Silver Retreat – Waterfront Pet Friendly Home w/ Dock, Kayaks & Legoland-Themed Room!

Lake Silver Retreat – Waterfront Pet Friendly Home w/ Dock, Kayaks & Legoland-Themed Room!
Winter Haven
9.8 out of 10, Exceptional, (20)
"The location was convenient for our needs and the property was clean and well stocked."
United States
Mark W.
Lake Silver Retreat – Waterfront Pet Friendly Home w/ Dock, Kayaks & Legoland-Themed Room!

2 bedroom private vacation home in winter haven

2 bedroom private vacation home in winter haven
Winter Haven
9.6 out of 10, Exceptional, (14)
"We really enjoyed staying here. Everything was as described and so clean. The extra little touches were so nice. I definitely recommend staying here if you are in the area. "
United States
Mandi G.
2 bedroom private vacation home in winter haven

Private lakefront retreat

Private lakefront retreat
Winter Haven
10.0 out of 10, Exceptional, (5)
"Brian we thoroughly enjoyed our stay and highly recommend your property. The house was in excellent condition and very clean. We had a great week of fishing and relaxation. See you again in the future!"
United States
STEPHEN K.
Private lakefront retreat

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
2.0 star property
Winter Haven
9.8 out of 10, Exceptional, (7)
"Great location, clean and great communication with hosts "
United States
Angie Y.
$282 nightly
The price is $310
Dec 14 - Dec 15
Total with taxes and fees
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
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 Station Hotel Reviews

Find out more about Winter Haven Station

What types of Vacation Homes can I find in Winter Haven Station?

At Expedia, you’ll find great Winter Haven Station Vacation Homes for your family vacation, business trip, romantic weekend break, and more. If you’re planning a vacation with kids, try using the traveler experience filter to select “Family-friendly” Winter Haven Station Vacation Homes. Or, if you’re traveling for work, you can check the “Business-friendly” box to find business-oriented places to stay in Winter Haven Station. While you’re making your decision, you can use our map facility to view your shortlisted properties and their distance from Winter Haven Station, or nearby places of interest. There are great places to stay for every budget, so if you need cheap Vacation Homes in Winter Haven Station, use our simple search function to help you secure a great deal.

How much do Vacation Homes cost in Winter Haven Station?

The price per night for Winter Haven Station Vacation Homes in 2026 can start from as low as *. The cost of Vacation Homes varies depending on a number of factors: the dates of your stay, the exact location of the accommodation, and whether there are any special events taking place near Winter Haven Station, to name just three. When there’s a high demand for rooms in Winter Haven Station, this can cause prices to increase, whereas traveling during a quieter time of the year can mean lower prices. Booking through Expedia can help you find some of the best deals for cheap Vacation Homes in Winter Haven Station, so you can sleep easy without going over your budget.

How to find the best deals on Winter Haven Station Vacation Homes?

Expedia’s search function can help you find some of the best deals on Winter Haven Station Vacation Homes. You can select a minimum and maximum price per night according to your budget, and filter by guest ratings and star ratings to ensure you find the right Vacation Homes for your needs. Changing the sort order according to price can also help you to view cheap Vacation Homes in Winter Haven Station at a glance, and you can combine this with our own picks to highlight some of the best available offers. Don’t forget, if you’re an Expedia Rewards member, you can use the “Member Prices” filter to make extra savings on your booking.

Why should I choose Expedia to book Winter Haven Station Vacation Homes?

Booking with Expedia allows you to browse a wide selection of places to stay in Winter Haven Station, complete with search filters that make it easy to locate Vacation Homes that best meet your specific requirements. Our clear and easy-to-use search function makes it effortless to compare amenities, prices, property types, neighborhoods, and much more. At Expedia, you can also find flights, car rental, and activities, and you can combine your bookings for greater savings. Plus, Expedia Rewards members accrue points on all eligible purchases. Build your points total to gain discounts on subsequent bookings in the future. Membership is free, so go ahead and join.

What is the cancellation policy on booking Winter Haven Station Vacation Homes?

At Expedia, we understand that plans change, and the good news is you can cancel many bookings for Winter Haven Station Vacation Homes with a full refund, depending on the rules and restrictions. For example, some Vacation Homes may not give refunds if you cancel your booking within 24 or 48 hours of your arrival date, and some bookings are non-refundable. Be sure to view the policies provided by the Winter Haven Station Vacation Homes, and confirm the exact cancellation window on your selected location’s details page. If free cancellation is important to you, you can filter for the “Fully refundable” payment type when you search for your Vacation Homes.

*Prices and availability are subject to change. Additional terms may apply 

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