Trailhead 812 Pet Friendly Downtown Winter Park

Trailhead Lodges – Downtown Winter Park Condo with Hot Tub, Pool & Event Access

Welcome to Trailhead Lodges, a stylish two-bedroom, two-bath condo located in the heart of downtown Winter Park. Perfect for families, couples, or groups, this ground-level unit offers convenient access to Hideaway Park and the Rendezvous event stage, home to world-class summer music festivals, including the Winter Park Jazz Festival. Relax after a day of skiing, hiking, or walking home from live events in a space designed for comfort and convenience.

Why You’ll Love It
Sleeps up to 7 guests with a King bedroom and bunk room with trundle
Ground-level condo with two private patios for relaxing outdoors
Gas fireplace and cozy living area for après-ski or evening downtime
Access to clubhouse amenities including BBQ grills, communal hot tub, heated pool, pool table, workout room, and sitting areas (please note the HOA manages the clubhouse not us)
Fully equipped kitchen for family meals or casual cooking

Inside the Home
This condo features a large primary suite with a King bed and oversized soaking tub, plus a second bedroom with a queen-over-queen bunk bed and trundle, ideal for families or friends. The open living area includes a gas fireplace, cable TV, and a soundbar for entertainment. Step outside to your two patios and enjoy mountain air while relaxing or dining al fresco.

Sleeping Arrangements
Primary Bedroom – King bed, en suite bath with oversized soaking tub
Second Bedroom – Queen-over-Queen bunk bed with pull-out trundle (lower bunk has limited clearance and is best suited for children).

Amenities Include
Free Wi-Fi
Cable TV + soundbar
Gas fireplace
Private washer & dryer
Two patios with outdoor seating
Smart lock for easy check-in
Ground-level access
Clubhouse access with pool table, kitchen, sitting area, workout room
Communal outdoor hot tub & heated swimming pool

Location Highlights
Steps from Hideaway Park & Rendezvous event stage
Downtown Winter Park restaurants, shops, and festivals within walking distance
Skiing and hiking trails nearby
Easy access to summer music festivals and community events

Good to Know
Town of Winter Park Registration Number: 005888
Pets allowed: Two medium dogs with $100 fee
No smoking in the condo
No shoes indoors
Quiet hours: 10 PM – 7 AM
Parking: Two cars only; RVs and trailers prohibited during holiday and festival weekends
The HOA manages the clubhouse, pool or hot tub - please note we are not in control of open/closing of these items.


Visit Winter Park Lodging is locally owned and operated. We live in the community full time and enjoy playing and working in our wonderful mountain community. We would be honored for you to stay in one of our vacation homes on your next visit to Winter Park and the surrounding areas.

Please remember you’re staying in a home, not a hotel. Please treat the space with respect. If any problems arise, we will do our best to take action ASAP, but there is no one living on-site 24/7.