Condos - Rating 5 (10)

Trailhead Lodges 131


Bedroom 3 bedrooms
Bathroom 2 baths
Guests 9 guests
Pets Allowed Pets Allowed

  • Address: 101 Trailhead Cir #131
  • Location: Downtown Winter Park
  • Type: Condos

Location Location

Description Description
This charming and expansive pet friendly three bedroom unit is located in the very center of downtown Winter Park.  The Trailhead Lodge unit offers a stunning view from the back deck overlooking the Winter Park Ski Resort and downtown area.  It serves as an excellent location for enjoying morning coffee, featuring an outdoor dining area and provides a perfect vantage point for appreciating the evening sunsets.
Families or small groups will appreciate the additional bedding and contemporary ambiance.  The main great room features hardwood flooring throughout, complemented by a fully equipped gourmet kitchen that includes granite countertops, stainless steel appliances and an island with seating for four. The main dining area boasts a spacious table with bench seating and seamlessly connects to the living area, which is adorned with numerous windows to take in the view, a flat screen TV, a gas fireplace, access to a private balcony and vaulted ceilings. Please note that there is no air conditioning.
The master bedroom features a King-sized bed.  The second bedroom is equipped with a Queen and a twin daybed, while the third bedroom contains two twin beds arranged as custom bunks along with a futon.  The unit includes two full bathrooms, both of which are accessible from the main hallway and have been renovated to include granite vanity countertops and tiled shower/tub combinations. 
Situated on the third floor of the building, guests may utilize the shared elevator for convenient access. PARKING: Only two designated spots are available. 
The complex is ideally situated adjacent to the Rendezvous Event Center, which hosts a variety of music, culinary, and fitness events throughout the summer. In the winter, the Rendezvous Event Center transforms into a sledding hill suitable for individuals of all ages. Guests can conveniently stroll the half block to Main Street in the downtown area or utilize the complimentary town shuttle, making it an excellent ski getaway or summer retreat for couples or small families.
Kindly be advised that construction activities are currently taking place in proximity to the complex, and guests may experience noise and visual disturbances related to this work.
The Trailhead Lodge clubhouse offers a variety of on-site amenities, including an outdoor grilling area, a game room, a fitness room, a hot tub and an outdoor pool, available throughout the year. 
Smoking is prohibited.  The regulations set forth by the Homeowner Association explicitly forbids guests from smoking on the premises. These regulations are rigorously enforced.  Any guests found smoking on the property will incur a fine of $200 for each day of violation.
WPSTR license: STR#17898

Specials Specials Tag
Location May lodging deals

Spring is finally here and summer is just around the corner!

Book your lodging direct with StayWinterPark and save on your lodging - we've made it easy - no promo or booking codes needed for the best price!

You can also book for your next summer adventure!

This offer is valid for new reservations only and cannot be combined with any other offers.  Valid dates of stay are 5/1/2025-9/30/2025.  All reservations must be booked by 5/31/25. 

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


*Offer expires 05/31/2025 and you must book your vacation between 05/01/2025 and 09/30/2025.


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Bedding Bedding
Master bedroom
King bed

Toilet,Combo Tub Shower

Second bedroom
Queen bed,Twin bed

Third bedroom
Twin bunk bed,Queen futon


Amenities 46 Amenities
  • Coffee Maker
  • Communal Pool
  • Dishwasher
  • Dryer
  • Elevator
  • Elevator in the building
  • Extra Pillows And Blankets
  • Fireplace
  • Fishing
  • Free Parking
  • Free parking outdoor
  • Game Room
  • Golf
  • Heated outdoor pool
  • Heating
  • Hiking
  • Hot tub - common area outdoor
  • Hot Water
  • Kitchen
  • Living Room
  • Microwave
  • Mountain View
  • Mountain views
  • Oven
  • Parking pass required
  • Patio Or Balcony
  • Pool Table
  • Private Entrance
  • Private Living Room
  • Refrigerator
  • Satellite or Cable
  • Shampoo
  • Shopping
  • Smoke Detector
  • Snowmobiling
  • Stove
  • Television
  • Toaster
  • Towels
  • Washer
  • Bed Linens
  • Carbon Monoxide Detector
  • Dishes & Silverware
  • Entire Property Non Smoking
  • Pet Friendly
  • Wireless Internet

Reviews Rating 5 (10) Reviews
Rating 5
We love Winter Park
We had a great ski vacation and were lucky to arrive just to lots of fresh powder and more throughout our stay. The condo was well appointed and the location is great. We had 3 teenagers and they had a hard time fitting in the bunk beds We didn’t anticipate enjoying the massage chair as much as we did but we had to reserve time to use it. Overall we enjoyed our stay.
Jennifer H from Asheville NC - Posted: 3/6/2025
Thank you for your review and we're very happy to hear that your family had a good stay with us and enjoyed the fresh powder and the massage chair
Stay Winter Park staff
Posted: 3/6/2025
Rating 5
Christmas
Family friendly home perfect for Christmas vacation. Great location!
Caroline H from Saint Helena Island SC - Posted: 1/31/2025
Thank you for your review and we are very happy our condo was a great spot for you to enjoy the holidays.
Stay Winter Park staff
Posted: 1/31/2025
Rating 5
Stay Winter Park
This residence was perfect and couldn't recommend it any more then we already have!
Mack N from Denver CO - Posted: 1/30/2025
Thank you for your 5 star review and we appreciate your recommendation to others!
Stay Winter Park staff
Posted: 1/30/2025
Rating 5
Beautiful, Comfortable Condo
Highly recommend this gorgeous condo! It exceeded our expectations- such as super comfortable beds, heated wood floors and massage chair! Excellent location, beautiful views from window. Can’t recommend enough!
Pam M from Claremont CA - Posted: 1/13/2025
Thank you for your review and we love to hear that you had such a wonderful stay with us and appreciate your recommendations!
Stay Winter Park staff
Posted: 1/13/2025
Rating 5
Great condition inside and the patio was lovely
Only downside was the elevator sometimes got stuck on the 3rd floor. Kind of odd
Jake B from Boulder CO - Posted: 10/14/2024
Thank you for your review and glad you had a good stay. We will share your feedback on the elevator with the HOA Management office to investigate.
Stay Winter Park staff
Posted: 10/14/2024
Rating 5
Perfect location
Close to shops, restaurants, etc. bus to Winter Park resort was 500 feet away.
Kartik S from Winter Park FL - Posted: 4/11/2024
Thank you for your review and we are very happy that you enjoyed your stay with us.
Stay Winter Park staff
Posted: 4/11/2024
Rating 5
Winter Park Christmas
Well appointed rental with everything we needed for our Christmas Holiday vacation! The massage chair was a welcomed surprise after a day of skiing/snowboarding!
Thomas R from Shamong, NJ - Posted: 1/2/2024
Thank you for your review and it is wonderful to hear you enjoyed your stay and the massage chair!
Stay Winter Park staff
Posted: 1/3/2024
Rating 5
Nice spot
Actually bigger than we anticipated!
Julie S from Denver CO - Posted: 10/23/2023
Thank you for your 5 star review!
Stay Winter Park staff
Posted: 10/23/2023
Rating 5
Great 30th bday
Came with my son and his friends.. They rode mountain bikes at Tressle. We had an awesome dinner at Dinos. Great location, lots of fun!
Sheri C from Indianapolis IN - Posted: 10/9/2023
Thank you for your review and we love to hear that you had such a great birthday and enjoyed the area.
Stay Winter Park staff
Posted: 10/9/2023
Rating 5
Excellent
Great location and really nice place
Brian L from Boulder CO - Posted: 3/27/2023
Thank you for your review
Stay Winter Park staff
Posted: 3/27/2023
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