Compare Cottages, Resorts, & Rentals in Winter Park, Florida, USA
About Winter Park Vacation Rentals
There are over 183 amazing vacation rentals available in Winter Park. Choose from a variety of options including villas, hotels, and other rental properties. Explore a vast selection of luxury amenities at unbeatable prices, providing you with the ideal spot for your next getaway. Life is Better at the Cottage with Vacation Cottage, where you can discover fantastic stays in Winter Park.
Vacation Cottage offers numerous last-minute deals on villas, hotels, and rentals, both near you and across the globe. Whether you need accommodations for a group or event, such as a hotel or vacation rental (including cabins and private luxury villas), let us assist you. With Vacation Cottage in Winter Park, you can easily compare options from multiple suppliers with just a click to find the perfect price point, amenities, and style of stay for you. Whether you're seeking group discounts, private pools, hot tubs, pet-friendly options, or spacious master suite bedrooms with open-air showers, you can find it all with Vacation Cottage vacation rentals, resorts, and Airbnb-style properties in Winter Park. The average size of places to stay near Winter Park is approximately 808.76 ft², with prices averaging US $227 per night.
Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in Winter Park. Prices listed often feature discounts compared to rack rates. Simply search for your destination and secure your ideal place to stay today.
Find Vacation Cottage Rentals in these Cities and Neighborhoods Winter Park, FL
Frequently Asked Questions About Winter Park?
What are the top cottages, summer homes, and lake houses in Winter Park?
- A curated stay in the Historic College Quarter
- Great Family Home
- GREAT LOCATION 🏡
- Amazing lakefront mid-modern 3-bed Winter Park home surrounded by Natural Beauty
- Winter Park Pool home close to Lake Virginia, Rollins College & Park Ave.
- Just 3 Blocks to Park Ave Shops/Restaurants, 2 From The Winter Park Village!
- Home away from home in the heart of charming Winter Park!
- LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!
- Cozy Comfort Just 2 Blocks From Park Ave!
- 6 Mi to Downtown Orlando: Quiet Home w/Sunroom
How many rentals, hotels, or resorts are available in Winter Park?
Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 183 properties listed by Vacation Cottage in the Winter Park area for the year 2026, with this number increasing daily. By aggregating listings from various websites and travel providers, Vacation Cottage ensures a diverse array of choices for the best luxury stays in Winter Park.
Nearby Neighborhood (6)
| Neighborhood | Property Count |
|---|---|
| Northeast Orlando Rental Cottages and Private Getaways in Orlando, Florida | 558 |
| College Park Rental Cottages and Private Getaways in Orlando, Florida | 44 |
| Goldenrod Rental Cottages and Private Getaways in Orlando, Florida | 171 |
| Baldwin Park Rental Cottages and Private Getaways in Orlando, Florida | 544 |
| North Orange Rental Cottages and Private Getaways in Orlando, Florida | 863 |
| Orwin Manor Rental Cottages and Private Getaways in Orlando, Florida | 842 |
