Winter Park Station Vacation Rentals

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Browse Select Winter Park Station Vacation Homes

Our top choices for Winter Park Station vacation homes

Coastal Bungalow ~ Firepit, Pool, Gazebo

9.4 out of 10, Exceptional, (3)
"Perfect 3 bedroom with fenced in backyard. "
Coastal Bungalow ~ Firepit, Pool, Gazebo

CHARMING - Cozy Retreat Near Lake Killarney in Winter Park

9.6 out of 10, Exceptional, (21)
"This was our 2nd stay in your cozy retreat near Lake Killarney. We enjoyed walks to the lake daily. Convenient, comfortable, and quaint. We will definitely book again.5 STARS"
CHARMING - Cozy Retreat Near Lake Killarney in Winter Park

Winter Park charm. Close to Park Ave

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

Winter Park Oasis

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!"
Winter Park Oasis

Lake Front Home near Winter Park!

9.6 out of 10, Exceptional, (16)
"My family and I stayed three nights and loved this home's location. It's close to all sorts of restaurants and stores. The house is very comfortable, and the host responded quickly to our questions. Definitely would stay again."
Lake Front Home near Winter Park!

Lakefront Paradise Near Attractions

2.5 star property
10.0 out of 10, Exceptional, (4)
"great house and location, perfect for our family."
Lakefront Paradise Near Attractions

Cheerful 4-bedroom with large and lush backyard

9.4 out of 10, Exceptional, (11)
"Great quiet neighborhood close to Winter Park and Downtown. Easy access to great food and entertainment (that is not Disney) In town to visit Rollins and tour Winter Park. The house was great for two families of 4 and the back yard was a nice spot to play while some people took their time getting ready. Wonderful hosts and will stay again. "
The price is CA $342
CA $678 total
includes taxes & fees
Sep 2 - Sep 3
Cheerful 4-bedroom with large and lush backyard

LUXURY 5/4 w Jacuzzi tub Winter Park/CP Orlando Gem

2.0 star property
10.0 out of 10, Exceptional, (1)
"The house was clean, spacious, close to downtown Winterpark, and the hosts were very responsive. Would stay again if in the area."
LUXURY 5/4 w Jacuzzi tub Winter Park/CP Orlando Gem

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

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

Mills House @WP. Sleeps 11 Renovated. Queen beds

10.0 out of 10, Exceptional, (1)
"This was a quaint little place with plenty of sleeping. The fenced in back yard with a canopy cover and chairs was a nice bonus. The kitchen was sufficiently stocked and newly remodeled. There were new smart TV ‘s in each room. There was a Publix right up the road as well as lots of great restaurants. We also enjoyed an antique mall (in the Publix plaza). We would highly recommend this place to others ."
The price is CA $187
CA $401 total
includes taxes & fees
Sep 2 - Sep 3
Mills House @WP. Sleeps 11 Renovated. Queen beds

6 Mi to Downtown Orlando: Quiet Home w/ Sunroom

10.0 out of 10, Exceptional, (3)
"This home is an old style Florida bungalow that the owner has renovated for VRBO rental. It has all the basics that are needed; plus extensive supplies, from cleaning products to coffee pods and a basket of snacks! The neighborhood was quiet and laid back. The owner lives nearby and was extremely responsive, doing her best to address our needs ASAP. "
6 Mi to Downtown Orlando: Quiet Home w/ Sunroom

Stroll to Park Avenue from Vintage Lake-View House

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

Cute bungalow minutes walk from Park Avenue.

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. "
Cute bungalow minutes walk from Park Avenue.

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

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

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

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

Modern, fabulous two-bedroom with parking in Winter Park

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

Home Away from Home- 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."
Home Away from Home- Winter Park

Beautiful Mid Term Home in the Elegance of Winter Park!

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

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

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

The beautiful Melrose Cottage - 25% monthly rental

The beautiful Melrose Cottage - 25% monthly rental
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 Park Station Hotel Reviews

Find out more about Winter Park Station

Find out more about Winter Park Station

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

When you’re looking for Winter Park Station Vacation Homes in 2025, you can use Expedia’s filters to find accommodation that’s family-friendly or business-friendly, and narrow down your search results by amenities, price per night, and much more. For example, you can search for Vacation Homes that welcome pets, or one with accessibility features. You’ll find a range of places to stay to suit every budget, so if you're looking for cheap Vacation Homes in Winter Park Station, use our simple search function to help you secure a good deal. If the exact location of Vacation Homes is important to you, try our map facility to view available places in relation to each other and to Winter Park Station.

How much do Vacation Homes cost in Winter Park Station?

Prices for Winter Park Station Vacation Homes can start from as little as * in 2025. The cost per night varies depending on several factors, including the amenities on offer at Vacation Homes, the exact location of Vacation Homes and how far they are from Winter Park Station, as well as how high the demand for accommodation is near Winter Park Station on the dates of your booking. At Expedia, we cater for every budget, so if you’re looking for cheap Vacation Homes in Winter Park Station, you can sleep easy knowing that we’ll help you to secure some of the very best deals on offer.

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

Expedia’s search function can help you find a great deal on Winter Park Station Vacation Homes. Changing the sort order of your search results can help you to find cheap Vacation Homes in Winter Park Station at a glance. If you have a specific price range in mind, try selecting minimum and maximum prices per night to narrow your results. You can also filter by guest ratings and star ratings to find some of the best offers for Vacation Homes within your budget. Don’t forget, if you’re an Expedia Rewards member, you can use the ‘Member Prices’ filter to make instant savings on your booking.

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

One of the many benefits of booking Winter Park Station Vacation Homes with Expedia is the clear and simple search function. When you use the many filters on offer, you can easily compile a shortlist of fantastic places to stay, and make comparisons between the different Vacation Homes so that you can choose exactly what you need. At Expedia, it’s possible to create your own customized package and make great savings by booking flights, car hire, and more at the same time as Winter Park Station Vacation Homes. And don’t forget that with free membership to Expedia Rewards, you can earn points on all eligible purchases, and build your points total to use towards future travel.

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

It’s often possible to change or cancel bookings at Winter Park Station Vacation Homes without a fee, but it depends on the rules and restrictions of the various Vacation Homes. Many booking options offer a window of flexibility, for example a full refund if you cancel more than 24 or 48 hours before Winter Park Station arrival dates. It’s best to check the policies of the individual Vacation Homes before making a booking, if flexibility is important to you. You can filter for the ‘Fully refundable’ payment type when you search for Vacation Homes. You can also view the terms of the different Vacation Homes at any time by checking the details of your booking at Expedia.

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

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