183+ Luxury Vacation Rentals & Cabins in Winter Park |
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Winter Park Cabin Rentals

About Winter Park Vacation Rentals

There are more than 183 incredible getaway rentals that are available in Winter Park. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.ca and uncover great stays in Winter Park.

Cabinns.ca features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Cabinns.ca in Winter Park, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.ca vacation rentals, resorts, and Airbnb-style properties in Winter Park. Places to stay near Winter Park are 801.36 ft² on average, with prices averaging CA $311 a night.

Cabinns.ca helps you find the ideal holiday rental to create a lifetime of travel memories in Winter Park. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.

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Top Cabin Rentals, Cottages, and Holiday Home Rentals in Winter Park

Type Count
Vacation Homes 105
Holiday Apartments 44
Villas 5
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Winter Park

★ Pro Tip: Cabinns.ca is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Winter Park with Cabinns.ca.

Weather in Winter Park, FL

View the weather forecast for Winter Park before booking your Winter Park Vacation Rentals to confirm your best time to go.

December - February
High 38°F       Low 2°F
March - May
High 55°F       Low 18°F
June - August
High 75°F       Low 34°F
September - November
High 67°F       Low 19°F

Activities Winter Park Guest Reviews Local Attractions

A Large Selection of Cabins and Vacation Rentals from Around the World Winter Park. Discover Top Attractions For Your Next Outdoor Adventure.


Full Sail University
Rollins College
Winter Park Village
Kraft Azalea Gardens
Casa Feliz Historic Home Museum
Mead Garden
Lee Road Shopping Center
Morse Museum of American Art
Lake Virginia
Albin Polasek Museum and Sculpture Gardens
Crealde School of Art
All Fired Up
Winter Park Playhouse
Alfond Swimming Pool
Winter Park Country Club
Winter Park Corner Shopping Center
The Center of Winter Park Shopping Center
Virginia S. Nelson Rose Garden
Winter Pines Golf Club
Winter Park History Museum

Find Nearby Cabin Rentals in these Cities & Neighborhoods


Mead Garden 728 Properties
Hollie Anna Shopping Center 573 Properties
Lake Rose 514 Properties
Winter Park Playhouse 512 Properties
Lake Virginia 510 Properties
Alfond Swimming Pool 507 Properties
Lee Road Shopping Center 489 Properties
All Fired Up 469 Properties
Cahall Sandspur Field 460 Properties
Hannibal Square Heritage Center 458 Properties
Cornell Fine Arts Museum 456 Properties
Goldenrod 171 Properties

Complexes around Winter Park, FL


Orlandos Sunshine Orlando 3 Properties
Legacy Park 2 Properties

Frequently Asked Questions About Winter Park?

What are the top cabins, lake houses & summer homes in Winter Park?

We provide an array of great vacation destinations in Winter Park. If you are looking to stay in or around the Winter Park area, make sure to browse our options to find a premium cabin resort or rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Winter Park:

How many cabin rentals and resorts have private pools in Winter Park?

We have 15 cabins, luxury resorts, and holiday home rentals featuring a private pool in and near Winter Park. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which cabin rental, resort, or holiday home in Winter Park is best for families?

Searching for a family-friendly cabin in Winter Park? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfectly fit families of all sizes.

How many hotels, resorts, or cabin rentals are available in Winter Park?

Cabinns.ca offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.ca in 2026 is over 183 in the Winter Park area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.ca can provide you with a diverse amount of choices of the best luxury stays in Winter Park.

Nearby Neighborhood (6) 
Neighborhood Property Count
Northeast Orlando Rental Cabins and Private Getaways in Orlando, Florida 568
College Park Rental Cabins and Private Getaways in Orlando, Florida 44
Goldenrod Rental Cabins and Private Getaways in Orlando, Florida 171
Baldwin Park Rental Cabins and Private Getaways in Orlando, Florida 544
North Orange Rental Cabins and Private Getaways in Orlando, Florida 863
Orwin Manor Rental Cabins and Private Getaways in Orlando, Florida 842

People Also Ask

There are 17 hotels in Winter Park and 154 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Winter Park