Search Vacation Homes in Winter Park Station

Start date: Check-in selected.
To Date
End date: Check-out
  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Winter Park Station vacation homes

CHARMING - Cozy Retreat Near Lake Killarney in Winter Park

CHARMING - Cozy Retreat Near Lake Killarney in Winter Park
Fairview Shores
9.4 out of 10, Exceptional, (27)
"Great stay. Charming property. Master room was a little hot but it was also brutally hot in Orlando. Hope to return soon. "
United States
cristina a.
CHARMING - Cozy Retreat Near Lake Killarney in Winter Park

Winter Park Gem, 2BR Near Parks, 3MI to Downtown

Winter Park Gem, 2BR Near Parks, 3MI to Downtown
College Park
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay — the house was spotless, comfortable, and offered plenty of space. The peaceful neighborhood and convenient location made it easy to explore the area."
United States
Danielle H.
$304 nightly
The price is $337
Dec 20 - Dec 21
Total with taxes and fees
Winter Park Gem, 2BR Near Parks, 3MI to Downtown

Lakefront Paradise Near Attractions

Lakefront Paradise Near Attractions
2.5 star property
Winter Park
10.0 out of 10, Exceptional, (6)
"great house and location, perfect for our family."
United States
Lillian K.
Lakefront Paradise Near Attractions

Winter Park Oasis

Winter Park Oasis
Winter Park
9.6 out of 10, Exceptional, (27)
"We had a wonderful stay! Such a cute little house. Walking distance from the bars and restaurants. Rubi was a great host!"
United States
Emily M.
Winter Park Oasis

5/4 King bed LUX Arcade near WP/CP & DT Orlando ‼️

5/4 King bed LUX Arcade near WP/CP & DT Orlando ‼️
College Park
10.0 out of 10, Exceptional, (1)
"had a great time. beautiful house"
United States
katie L.
5/4 King bed LUX Arcade near WP/CP & DT Orlando ‼️

Cheerful 4-bedroom with large and lush backyard

Cheerful 4-bedroom with large and lush backyard
Orwin Manor
9.4 out of 10, Exceptional, (12)
"We loved our stay!!! Very comfortable beds, spacious layout and so clean. We will try to stay here everytime we come to visit family."
United States
Angela D.
$365 nightly
The price is $405
Dec 18 - Dec 19
Total with taxes and fees
Cheerful 4-bedroom with large and lush backyard

Coastal Bungalow ~ Firepit, Pool, Gazebo

Coastal Bungalow ~ Firepit, Pool, Gazebo
North Orange
9.4 out of 10, Exceptional, (3)
"Perfect 3 bedroom with fenced in backyard. "
United States
Beth A.
Coastal Bungalow ~ Firepit, Pool, Gazebo

Lake Front Home near Winter Park!

Lake Front Home near Winter Park!
Maitland
9.6 out of 10, Exceptional, (16)
"This was a very nice property. On a beautiful little lake, with a nice back porch."
United States
Dan W.
Lake Front Home near Winter Park!

Winter Park charm. Close to Park Ave

Winter Park charm. Close to Park Ave
Winter Park
9.8 out of 10, Exceptional, (46)
"Excellent communication and charming place to stay"
United States
Paul
Winter Park charm. Close to Park Ave

3-bedroom Bungalow in Welcoming Winter Park with WiFi, AC

3-bedroom Bungalow in Welcoming Winter Park with WiFi, AC
2.0 star property
Orwin Manor
10.0 out of 10, Exceptional, (1)
"Exactly as advertised. Great location. Like the off-street parking. Clean and quiet. Nicely remodeled. "
United States
John W.
3-bedroom Bungalow in Welcoming Winter Park with WiFi, AC

Modern, fabulous two-bedroom with parking in Winter Park

Modern, fabulous two-bedroom with parking in Winter Park
Winter Park
10.0 out of 10, Exceptional, (1)
"Great restaurants nearby & 5 min from Park Avenue! Kitchen & Laundry stocked really well."
United States
Shannon M.
Modern, fabulous two-bedroom with parking in Winter Park

Stroll to Park Avenue from Vintage Lake-View House

Stroll to Park Avenue from Vintage Lake-View House
Winter Park
9.6 out of 10, Exceptional, (30)
"had a very nice time"
United States
Susan H.
Stroll to Park Avenue from Vintage Lake-View House

Cute bungalow minutes walk from Park Avenue.

Cute bungalow minutes walk from Park Avenue.
Winter Park
9.6 out of 10, Exceptional, (10)
"Nice upgrades for the bathrooms and indoor living areas in a house 10 blocks from downtown Winter Park. Owner was very helpful and accommodating with questions. Outdoor space behind the house was lacking in space and comfortable furniture - no grill. House is directly off a main street / corner that makes it difficult for vehicle entrance or exit. "
United States
Dr Bruce D.
Cute bungalow minutes walk from Park Avenue.

LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!

LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!
Hannibal Square
10.0 out of 10, Exceptional, (3)
"I stayed here for just short of 3 months. The property is great! Clean, well appointed and a great central location. The pool is great, as well. Can’t wait to visit again!"
United States
Jennifer G.
LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!

Beautiful Mid Term Home in the Elegance of Winter Park!

Beautiful Mid Term Home in the Elegance of Winter Park!
Winter Park
10.0 out of 10, Exceptional, (1)
"Check in was easy and place was great "
United States
Jamie T.
Beautiful Mid Term Home in the Elegance of Winter Park!

THE CLOUD 9 SUITE

THE CLOUD 9 SUITE
Fairview Shores
THE CLOUD 9 SUITE

Home Away from Home- Winter Park

Home Away from Home- Winter Park
Winter Park
10.0 out of 10, Exceptional, (2)
"Very clean! Had all of the necessities. Easy to get in and out of. Great location. Owner was quick to respond to any questions."
United States
Sue B.
Home Away from Home- Winter Park

Charming 2BR/2BA Winter Park Cottage, steps from Park Ave

Charming 2BR/2BA Winter Park Cottage, steps from Park Ave
Winter Park
2.0 out of 10, (1)
"Don't book this property!! This host had our reservation for several days prior to arrival, yet waited until we arrived in her driveway to cancel the reservation saying the house was listed prematurely. She should never have listed if it wasn't ready, and certainly shouldn't have accepted a rental. We could have made other arrangements instead of traveling to her property to be turned away. VERY POOR MANAGEMENT and a huge disruption to our trip. VRBO put us up for one night in a hotel, which we...
United States
Joan A.
Charming 2BR/2BA Winter Park Cottage, steps from Park Ave

Cozy Comfort Just 2 Blocks From Park Ave!

Cozy Comfort Just 2 Blocks From Park Ave!
Hannibal Square
10.0 out of 10, Exceptional, (4)
"Very clean and comfy home. Perfect location overall an amazing stay. You’re walking distance to many shops and restaurants."
United States
Aryani E.
Cozy Comfort Just 2 Blocks From Park Ave!

Comfy Home in Winter Park, can accommodate up 6 guests!

Comfy Home in Winter Park, can accommodate up 6 guests!
Fairview Shores
9.0 out of 10, Wonderful, (8)
"My husband & I had our 2nd baby and rented this property for our parents given its proximity to our house. Check in was easy, the place was exactly as depicted in the description, and it was the perfect place for our family"
United States
Jennifer H.
Comfy Home in Winter Park, can accommodate up 6 guests!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winter Park Station Hotel Reviews

Find out more about Winter Park Station

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

At Expedia, you’ll find great Winter Park 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 Park 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 Park Station. While you’re making your decision, you can use our map facility to view your shortlisted properties and their distance from Winter Park Station, or nearby places of interest. There are great places to stay for every budget, so if you need cheap Vacation Homes in Winter Park Station, use our simple search function to help you secure a great deal.

How much do Vacation Homes cost in Winter Park Station?

The price per night for Winter Park 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 Park Station, to name just three. When there’s a high demand for rooms in Winter Park 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 Park Station, so you can sleep easy without going over your budget.

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

Expedia’s search function can help you find some of the best deals on Winter Park 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 Park 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 Park Station Vacation Homes?

Booking with Expedia allows you to browse a wide selection of places to stay in Winter Park 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 Park Station Vacation Homes?

At Expedia, we understand that plans change, and the good news is you can cancel many bookings for Winter Park 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 Park 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 

Explore a world of travel with Expedia