Fall Getaway deals

Book today for the upcoming fall season! Still great events, outdoor activities and ways to view the changing leaves.

We've made it easy for you - book now for the best pricing on all of our properties - no promo code needed!

This offer is valid for new reservations.  Valid dates of stay are 9/1/2024-10/31/2024. 

Call us at 1-800-215-6535book online, or email us at info@staywinterpark.com to book your Winter Park Getaway!


Properties Available 204 properties available
Luxurious sofas will envelop you as you relax with a game or movie on the television, while also taking pleasure in the gas fireplace within the delightful two bedroom condominium. The spacious layout also provides entry to the private balcony showcasing a view of the Winter Park Ski Resort from the building’s second floor; as well as a dining spa
Hot HOT 20
Beaver Village Unit #0322
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 1
A spacious 1,200 square feet, this unit is on the first floor and has a living room decorated in with a southwestern decor, gas fireplace, TV, VCR, a queen sofa sleeper, free Wi-Fi access and no air conditioning.Next to the living room is the dining area with large table and chair setting for 6 people. Guests can also access the private deck with m
Timber Run Dogwood Unit 2
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
This is a 2 bedroom 2 bathroom unit on the first floor of the building and has 1,200 interior square feet.In the living room guests will enjoy a gas fireplace, TV with VCR, modern comfortable furnishings and a queen sofa sleeper, free Wi-Fi access and no air conditioning.Adjacent to the living room, the dining area offers a solid wood table with ch
Timber Run Evergreen Unit 1
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
This inviting two-story townhome rental features a spacious open floor plan in the living room, which is equipped with a TV, VCR, and a wood burning fireplace. Additionally, it includes a queen sofa sleeper and provides access to a small private patio. The dining area, which accommodates six individuals with its table and chairs, is located next
Hot HOT 36
Hideaway Village Alpine 4
Townhome -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.5 7
This studio unit, encompassing 443 square feet, has been thoughtfully renovated and features new flooring and furnishings. Situated on the fifth floor, it offers stunning views of the Winter Park Resort and is conveniently located just a 150-yard walk from the slopes and the village. The kitchenette is equipped with granite countertops and stainles
Hot HOT 25
Fraser Crossing 3518
Condo -
Bathrooms 1 baths
Guests 2 guests
Rating 4.7 13
A spacious unit 1,128 square feet, this 3-bedroom condo is on the second floor of the building and offers free Wi-Fi access. In the living room, the decor has a country theme and gas fireplace, flat screen TV, DVD, Blue Ray disk player and telephone. No air conditioning. A solid wood table and chairs in the dining area provide seating for 8 people
Hot HOT 17
Lion's Gate Pines Unit 109
Condo
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
The hardwood flooring enhances the elegance of the kitchen, which features new wood cabinets, stainless steel appliances and countertops that include a breakfast bar accommodating four individuals. In the dining area, a spacious table can comfortably seat up to six people and is complemented by a large window that provides a scenic view. Situated
Hot HOT 41
Beaver Village Unit #1734R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4 2
This well-appointed and recently renovated one bedroom one bathroom unit is conveniently situated near the town of Winter Park and is accessible via the complimentary town shuttle to Winter Park Resort. The rental is equipped with all essential amenities for a pleasant vacation, including a fully equipped kitchen complete with dishware and cookwar
Hot HOT 21
Beaver Village Unit #0931R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4 1
Explore our brand new exquisite 2-bedroom, 2-bathroom condominium located in the center of downtown Winter Park! This flawless residence showcases top-notch contemporary aesthetics and comes fully furnished, perfect for your own use or as a vacation rental. Conveniently located near the main street, this unit provides easy access to Winter Park's d
Hot HOT 33
Arrow at Winter Park Unit 202
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 4
The renovated kitchen features tiled flooring, modern appliances, and updated cabinets and countertops. The compact center island serves as an excellent workspace or additional seating areas during meals. The unit is located on the ground floor, providing convenient access to the outdoor space.The dining area, located next to the kitchen, offers an
Hot HOT 25
Hi Country Haus Unit 2201
Condo -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 4.3 10
A comfortable studio apartment situated on the ski access level, providing convenient entry to the slopes of the Winter Park Resort.The kitchen exudes a contemporary aesthetic, featuring newly installed cabinets, granite countertops, tiled flooring and modern appliances. The sightline from the kitchen to the open-concept living area creates an ide
Hot HOT 32
Iron Horse Building D Unit 5054
Condo -
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 6
Reserve your upcoming Winter Park getaway in this recently renovated one bedroom unit at Beaver Village Condos, conveniently located near the clubhouse facilities, a short walk from town and the complimentary shuttle service.The updated kitchen appliances and lighting enhance the evening ambiance for cooking your preferred dish. The dining area off
Hot HOT 20
Beaver Village Unit #0332
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.6 13

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