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Vacation rentals in Winter Park, United States

Carefully selected & verified rentals in Winter Park, United States

Check-in
15Jun
Check-out
16Jun
Rooms and Guests2 Guests, 1 Room
Winter Park features the scenic Chain of Lakes, plus the beautiful Mead Botanical Garden and the notable Charles Hosmer Morse Museum of American Art. You can stroll the park or enjoy water activities like kayaking at Lake Killarney. For accommodations, the city offers a variety of hotels. There are charming boutique inns like the Alfond Inn and family-friendly resorts with great amenities. This site features a curated list of Winter Park hotels, chosen for their excellent reviews and unique offerings, ensuring a pleasant stay. Book early, especially during events like the Winter Park Art Festival, and use local shuttles for easy transport.
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1-20 out of 315
Sort by: high popularity
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  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
Winter Haus, Winter Park 2 Bedrooms Corner Unit W Outdoor Patio Walking Distance To The Center Of Town
Winter Haus, Winter Park 2 Bedrooms Corner Unit W Outdoor Patio Walking Distance To The Center Of Town
Map2.7 mi from City Centre
FromUS$ 230 /nightSelect
Ski-In / Ski-Out Studio Condo At The Base Of Winter Park
Ski-In / Ski-Out Studio Condo At The Base Of Winter Park
Map900 yd from City Centre300 yd from Winter Park Resort
FromUS$ 161 /nightSelect
Ski-In / Ski-Out 1 Bedroom Condo Base Of Wp Resort
Ski-In / Ski-Out 1 Bedroom Condo Base Of Wp Resort
Map900 yd from City Centre300 yd from Zephyr Express
FromUS$ 171 /nightSelect
Iron Horse Building C Unit 1023
Iron Horse Building C Unit 1023
Map1400 yd from City Centre400 yd from Cabriolet
FromUS$ 258 /nightSelect
Great Location! Downtown Wp With Hot Tub! Sleeps 6!
Great Location! Downtown Wp With Hot Tub! Sleeps 6!
Map2.0 mi from City Centre
FromUS$ 263 /nightSelect
Ski-In/Ski-Out Winter Park Condo W/ Balcony
Ski-In/Ski-Out Winter Park Condo W/ Balcony
Map900 yd from City Centre300 yd from Winter Park Resort
FromUS$ 186 /nightSelect
Winter Park Condo W/ Mountain Views + Hot Tub
Winter Park Condo W/ Mountain Views + Hot Tub
Map800 yd from City Centre100 yd from Zephyr Express
FromUS$ 515 /nightSelect
Ski-In/Ski-Out Winter Park Condo W/ Hot Tub Access
Ski-In/Ski-Out Winter Park Condo W/ Hot Tub Access
Map900 yd from City Centre300 yd from Winter Park Resort
FromUS$ 249 /nightSelect
Condo On Fraser River < 4 Mi To Winter Park Resort
7.0
Very good
Condo On Fraser River < 4 Mi To Winter Park Resort
Map2.6 mi from City Centre
FromUS$ 160 /nightSelect
Ski-In/Ski-Out Zephyr 1 Bedroom Condo Winter Park
Ski-In/Ski-Out Zephyr 1 Bedroom Condo Winter Park
Map800 yd from City Centre100 yd from Zephyr Express
FromUS$ 538 /nightSelect
Beaver Village Unit #0724
Beaver Village Unit #0724
Map2.0 mi from City Centre
FromUS$ 214 /nightSelect
Cozy Downtown Condo With Jacuzzi 5 Min To Resort
Cozy Downtown Condo With Jacuzzi 5 Min To Resort
Map2.7 mi from City Centre
FromUS$ 144 /nightSelect
Guest Suite Downtown Winter Park Great Location
Guest Suite Downtown Winter Park Great Location
Map2.1 mi from City Centre
FromUS$ 179 /nightSelect
Beaver Village Unit #0332
Beaver Village Unit #0332
Map1.9 mi from City Centre
FromUS$ 335 /nightSelect
Crestview Place Unit 507
Crestview Place Unit 507
Map2.1 mi from City Centre
FromUS$ 472 /nightSelect
Cozy Winter Park Condo: Bike, Ski, & Hike!
Cozy Winter Park Condo: Bike, Ski, & Hike!
Map1.8 mi from City Centre
FromUS$ 65 /nightSelect
Hi Country Haus Unit 0309
Hi Country Haus Unit 0309
Map2.8 mi from City Centre
FromUS$ 195 /nightSelect
Snowblaze Condos Building E Unit 310 By Stay Winter Park
Snowblaze Condos Building E Unit 310 By Stay Winter Park
Map1.9 mi from City Centre
FromUS$ 196 /nightSelect
Cozy Ski-In/Out Winter Park Studio W/ Hot Tubs!
Cozy Ski-In/Out Winter Park Studio W/ Hot Tubs!
Map1400 yd from City Centre400 yd from Cabriolet
FromUS$ 749 /nightSelect
Snowblaze Condos Building C Unit 24
Snowblaze Condos Building C Unit 24
Map2.6 mi from City Centre
FromUS$ 472 /nightSelect
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Flexible Price Range for Vacation Homes in Winter Park

From cozy retreats to luxury villas – Find the ideal stay for every budget

⬆️ The highest price
USD 2 106
⬇️ The lowest price
USD 65
💸 Average price for
Apartments
USD 634

Top vacation homes in Winter Park

Based on guest reviews from the past 12 months

Convenient Downtown Escape:
Cozy Mountaintop Retreat:
Family Friendly Condo Stay:
Outdoor Adventure Base:
Relaxing Hot Tub Getaway:
Scenic Riverfront Stay:
Ski-In Ski-Out Luxury:
Tranquil Mountain Views:
Charming Rustic Vibe:

FAQs about Winter Park rentals

Get answers to common questions and plan your adventure smoothly

Which vacation rentals offer unique views or special amenities?
The Winter Park Condo with Hot Tub and Mountain Views! offers stunning scenery along with relaxing amenities. The Iron Horse Studio with Resort Amenities provides both convenient access to the area and beautiful sightings.
What are the top-rated vacation rentals in Winter Park based on guest reviews?
Top-rated properties based on guest satisfaction include the Ski-In / Ski-Out 1 Bedroom Condo and the Winter Park Ski-Inandski-Out Condo with Mountain Views. These properties are frequently praised for their location and quality of service.
Which vacation rentals are located near popular landmarks in Winter Park?
Several rentals are located close to key attractions. The Downtown Winter Park Condo is about 3 km from the Winter Park Resort, offering convenience for skiing and other outdoor activities. Other options like the Guest Suite Downtown Winter Park Great Location are ideally situated for easy access to local shops and restaurants.

Vacation Rentals Overview in Winter Park

This guide provides essential information on vacation rentals in Winter Park, evaluating around 100 properties to assist travelers in making informed accommodation choices.

Typical nightly rates range from $150-$400 USD.

Peak travel seasons are winter months and summer holidays.

Most properties impose a local tax of 12.8%.

Approximately 1-2 miles from Winter Park Resort and downtown.

Booking early can secure discounts and ensure availability.

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