Condo - Rating 4.9 (37)

Trailhead Lodges | Ground-Level, Pet-Friendly


Bedroom 2 bedrooms
Bathroom 2 baths
Guests 8 guests
Pets Allowed Pets Allowed

  • Address: 201 Trailhead Circle
  • Location: Winter Park
  • Type: Condo

Location Location

Description Description
Welcome

This ground-level Trailhead Lodges condo sits in the heart of downtown Winter Park, just across from Hideaway Park, home to summer music festivals including the Winter Park Jazz Festival. With two king bedrooms, two bathrooms, and a bonus bunk room, it sleeps up to 8 guests, making it a great fit for a large family or two families traveling with kids. A gas fireplace, private patio, and access to the Trailhead clubhouse with its hot tub and heated pool make it an easy home base for a ski trip or summer vacation.

Why You’ll Love It

Two king bedrooms plus a bonus bunk room for the kids

Across from Hideaway Park in downtown Winter Park

Ground-level unit with a private patio

Gas fireplace and a 60" TV in the living room

Dog-friendly: up to two medium dogs

Across from the Trailhead clubhouse: shared hot tub, heated pool, workout room, and grills

Ski locker and 24-hour keyless check-in

Inside the Home

The living room has comfortable seating, a gas fireplace, and a 60" flat-screen TV, perfect for a movie night after a day on the slopes. The kitchen has granite countertops, stainless steel appliances, and a gas stovetop, with everything you need to cook at home. A private washer and dryer are in the unit, and the private patio looks out toward the clubhouse.

We also stock the home with essentials so you can settle in right away:

Coffee and creamer for your first morning

Linens, towels, washcloths, and hand towels

Bar soap, hand soap, shampoo, conditioner, tissues, and toilet paper

Laundry detergent and fabric softener

Sleeping Arrangements

Primary bedroom: King bed, 50" flat-screen TV, and a full bathroom with a walk-in shower

Second bedroom: King bed and 35" flat-screen TV

Bonus bunk room: Two twin-over-twin bunk beds in a sleeping nook

Bathrooms: 2

Maximum occupancy: 8 guests

Amenities Include

In the condo

Free high-speed Wi-Fi

Gas fireplace

Cable TV and flat-screen TVs in the living room and both bedrooms

Fully equipped kitchen with gas stovetop

Private washer and dryer

Private patio

Ground-level access

Keypad lock with 24-hour check-in

Ski locker outside the unit

Shared clubhouse amenities

Outdoor hot tub

Heated outdoor swimming pool

Workout room

BBQ grills

Pool table, kitchen, and sitting area

Location Highlights

Across from Hideaway Park and its summer music festivals

Walk to downtown Winter Park restaurants, shops, and events

Across from the Trailhead Lodges clubhouse

Good to Know

Bunk room: The bonus bunk room is a sleeping nook rather than a separate bedroom, best suited for kids.

Ground level: The condo is on the ground floor, with no stairs to the unit.

Skis and bikes: Skis and bikes are not allowed inside. Please lock skis in the ski locker outside the unit.

Parking: Parking is for two cars only. RVs and trailers are not permitted during holiday and music festival weekends.

Shared amenities: The clubhouse, pool, and hot tub are shared with other Trailhead Lodges guests and residents. They’re managed by the HOA, which controls their hours, maintenance, and any closures, so we can’t guarantee they’ll be open during your stay.

Event weekends: Summer festivals across the street at Hideaway Park can bring crowds and music to the area.

Group stays: We manage several units at Trailhead Lodges, including the unit across from this one, so it’s easy to book multiple condos for a larger group.

House Rules

Up to two medium dogs allowed with a $100 pet fee

No smoking of any kind in the home

No shoes indoors

No parties or events

Quiet hours are 10 pm to 7 am

Skis and bikes are not allowed in the home

Parking for two cars only

No RVs or trailers during holiday and music festival weekends

Maximum occupancy is 8 guests

STR #: 009316

Guest Experience

This condo is built for families, with two king bedrooms for the adults and a bunk nook for the kids, all steps from downtown Winter Park and the summer concerts at Hideaway Park. Spend the day on the slopes, swim at the clubhouse, and come back to a movie by the fireplace. 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.


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Swipe Swipe for Availability

Bedding Bedding
Room Beds Baths TVs Comments
Room 10 King
Room 11 King

Amenities 40 Amenities
  • Bathtub
  • BBQ grill
  • Bed linen
  • Carbon monoxide alarm
  • Coffee maker
  • Cooking basics
  • Dedicated workspace
  • Dishes and silverware
  • Dishwasher
  • Dryer
  • Essentials
  • Extra pillows and blankets
  • Fire extinguisher
  • First aid kit
  • Free on-street parking
  • Free parking on premises
  • Freezer
  • Gym
  • Hair dryer
  • Hangers
  • Heating
  • Hot tub
  • Hot water
  • Indoor fireplace
  • Kitchen
  • Microwave
  • Oven
  • Pool
  • Pool table
  • Private entrance
  • Private living room
  • Refrigerator
  • Shampoo
  • Single level home
  • Smoke alarm
  • Stove
  • Toaster
  • TV
  • Washer
  • Wifi

Reviews Rating 4.9 (37) Reviews
Rating 5
We had 3 adults, 3 kids, and a dog and felt we
We had 3 adults, 3 kids, and a dog and felt we had plenty of space, fun activities nearby, and an overall fantastic time in Winter Park and from this rental! I would definitely recommend anyone looking for a place to stay to look here when staying in Winter Park. The rooms are spacious, the beds are adequate, and the amenities of the grills and pool were perfect for our group of energetic and busy kids. Walking distance to the main drag and vicinity to Rendezvous Park and Confluence Park provided a lot of relaxed enjoyment. The place was clean, and the kitchen while somewhat sparse provided what we needed over 2-3 days. The management company is fairly quick to respond though some automated messages contradicted what a live person was communicating. Nothing that caused any noteworthy difficulty. Thanks again for the great stay!
Duncan - Posted: 7/31/2026
Rating 5
We had a great time! Will stay here again!
We had a great time! Will stay here again!
Jenna - Posted: 7/6/2026
Thank you for your kind review! We're delighted you enjoyed your stay and truly appreciate your feedback. It was a pleasure hosting you, and we look forward to welcoming you back. We'll continue striving to provide a 5-star experience every time you visit!
Stay Vara staff
Rating 5
Great location,close to the park.
Great location,close to the park.
Mike - Posted: 6/29/2026
Thank you for your kind review!
Stay Vara staff
Rating 4
This was our second time staying in this condo.
This was our second time staying in this condo. The location can’t be beat and having access to a pool and hot tub is wonderful. The only area we found lacking a bit was the kitchen dishes and utensils. Pots and pans are well used and the unit could use new wine glasses and cups. Other than that, we thoroughly enjoyed our stay and would love to come back,
Lauren - Posted: 6/22/2026
Rating 5
Have stayed in this complex multiple times. This
Have stayed in this complex multiple times. This particular condo was the most up to date. We loved our time and will be back again.
Jon - Posted: 4/7/2026
Thanks so much for the kinds words!
Stay Vara staff
Rating 5
This was great stay in a prime location. We will
This was great stay in a prime location. We will be back.
Nicole - Posted: 4/3/2026
Thanks for the great review! We look forward to hosting you again!
Stay Vara staff
Rating 5
We had a great stay. The location is great -
We had a great stay. The location is great - walking distance to breweries and restaurants with a short drive to the ski area. There was a little trouble with the lock when we arrived but thanks to some great communication there was a quick solution. Highly recommend.
Clay - Posted: 1/26/2026
Thank you so much for the great review!
Stay Vara staff
Rating 5
What a wonderful property! This is the perfect
What a wonderful property! This is the perfect place to rent in winter park! So close to everything and a beautiful home. Spacious yet cozy, we were obsessed!
Kacey - Posted: 1/13/2026
Thank you so much for the great review!
Stay Vara staff
Rating 5
Would stay again!
Would stay again!
Melissa - Posted: 2/17/2025
Rating 5
Awesome weekend getaway right across the lot from
Awesome weekend getaway right across the lot from the pool, short walk to hideaway park and restaurants. Trails right out the door. Very comfortable beds and unit. Highly recommend.
Chase - Posted: 9/2/2024
Thanks Chase for leaving a great review! Cheers to all your future adventures.
Stay Vara staff
Rating 5
Perfect location, huge clean space. No complaints!
Perfect location, huge clean space. No complaints!
Josh - Posted: 3/4/2024
Rating 5
Good to stay. Convenient to Mountain.
Good to stay. Convenient to Mountain.
Nicholas - Posted: 2/9/2024
Thanks Nicholas!
Stay Vara staff
Rating 5
awesome place
awesome place
John - Posted: 12/20/2023
We think so too! Glad you enjoyed!
Stay Vara staff
Rating 5
Great location! What we needed
Great location! What we needed
Mark - Posted: 8/23/2023
Rating 5
Great location within walking distance of all the
Great location within walking distance of all the shops and restaurants in Winter Park!
Kelsey - Posted: 8/7/2023
We are so glad you enjoyed your stay Kelsey! Thanks for staying with us and taking time to leave a review.
Stay Vara staff
Rating 5
Overall great place, no complaints at all. Had
Overall great place, no complaints at all. Had everything we needed, awesome location, clean, affordable, great communication. A+++
Zachary - Posted: 7/11/2023
Wow! Thanks for leaving a fantastic review! We appreciate it! Cheers to all your future adventures!
Stay Vara staff
Rating 5
Excellent location in the center of town and
Excellent location in the center of town and place was exactly like the photos. thx
Alec - Posted: 4/12/2023
Thanks Alec for taking the time to leave a great review! So glad you guys enjoyed your stay, it was a pleasure to host you all.
Stay Vara staff
Rating 5
Everything was great I will book again!
Everything was great I will book again!
Emilio - Posted: 3/13/2023
Emillio, we're glad you enjoyed your stay! We hope to see you again in the future. The Visit Winter Park Lodging Team
Stay Vara staff
Rating 5
Great stay! Exactly as described and felt clean.
Great stay! Exactly as described and felt clean. Can't complain about a thing with the unit itself. Some noise from people going up and down the stairs outside, but to be expected with a condo building and nothing too disruptive.
Jessica - Posted: 2/23/2023
Rating 4
Winter Park Lodging is great. Communication and
Winter Park Lodging is great. Communication and service tops. They even provided local pool passes when the condo pool closed!
Mark - Posted: 8/15/2022
Thanks Mark for being such a great guest & taking the time to leave a review! It was a pleasure hosting you guys and come back and visit soon!
Stay Vara staff
Rating 5
The condo is a great space. We had no complaints.
The condo is a great space. We had no complaints. Very spacious and everything is in very good condition. The kitchen is well stocked to prepare meals. We could have used a potato peeler and masher but those are not things you will find in most Air-BnBs. There was a nice snack bag provided at checkin. Water pressure was a little lacking in the smaller bathroom but was great in the master bath. My nieces and nephew appreciated the proximity to the community pool and Hideaway Park.
Ami - Posted: 7/31/2022
Rating 4
Good stay, as described. Good location
Good stay, as described. Good location convenient to downtown shops. We would stay again as it fit all of our needs.
Justin - Posted: 7/25/2022
Rating 5
Loved this rental! Location, pool, hot tub,
Loved this rental! Location, pool, hot tub, cleanliness I could go on and on but myself and family really enjoyed our stay and would highly recommend.
Anna - Posted: 7/16/2022
Thanks for staying with us! Hope to have you back in the future. The Visit Winter Park Lodging Team
Stay Vara staff
Rating 5
fantastic place to stay and be at the right spot
fantastic place to stay and be at the right spot to visit the towns Great value for Monday our families enjoy it very much
Laura - Posted: 3/30/2022
We are so glad you guys enjoyed your stay! Thanks for staying with us and leaving a great review!
Stay Vara staff
Rating 5
Great space and great location!!
Great space and great location!!
Shawna - Posted: 2/11/2022
Thanks Shawna for a great review! It was a pleasure hosting you guys :)
Stay Vara staff
Rating 5
Great place, plenty of room and close to slopes.
Great place, plenty of room and close to slopes. We just took the free public bus everyday. The heated pool and hot tub in the community were nice after a long day snowboarding.
Cj - Posted: 2/10/2022
Rating 5
Relaxing condo that’s next to the hot tubs!
Relaxing condo that’s next to the hot tubs! Seamless checking and the condo was clean with all the basic amenities. Beds are comfy with heated floors throughout. We had a great ski trip!
Julie - Posted: 1/18/2022
We are so glad you guys enjoyed your ski trip Julie! Thanks for visiting & a great review! Come back and visit anytime :)
Stay Vara staff
Rating 5
Lots and lots of snow right now!
Lots and lots of snow right now!
Chelsea - Posted: 12/29/2021
Rating 5
This location is central to most of Winter Park.
This location is central to most of Winter Park. The place was large enough to host our family/extended family, was super clean, easy check in/check out. All of the amenities were a huge plus! We really enjoyed time here and would definitely book again!
Meghanne - Posted: 12/6/2021
We are so glad you enjoyed your stay and all the perks of the property! Come back and visit again :)
Stay Vara staff
Rating 5
The pictures don’t do this Airbnb any justice.
The pictures don’t do this Airbnb any justice. Both bedrooms were incredibly spacious. Couches were much more comfortable than expected. The space was spotless and had all necessary kitchenware for all of your cooking needs. The resort itself was very cute and right next to an event center! I would recommend this stay to anyone and would stay again!
Jenny - Posted: 9/12/2021
Rating 5
This house has everything and is very homey!
This house has everything and is very homey!
Adelle - Posted: 8/25/2021
Rating 5
We enjoyed our stay here. The unit had plenty of
We enjoyed our stay here. The unit had plenty of space for our family of 5. The location right across from the pool and Hideaway Park was enjoyed by all.
Arye - Posted: 8/13/2021
Rating 5
The place was perfect for our little group. IT
The place was perfect for our little group. IT was very clean and updated and it had all the basics for the kitchen. The location is superb if you plan to do snowboarding/skiing at Winter Park. The location is super close so you don't have to wake up too early to get some decent parking. Great value for the cost of the stay.
Jacqueline - Posted: 3/31/2021
Rating 5
great place!
great place!
John - Posted: 3/26/2021
Rating 5
Great location and space. Clean.
Great location and space. Clean.
Matt - Posted: 3/18/2021
Rating 5
Great location, Great space, Great price!
Great location, Great space, Great price! Beautiful condo with lots of room. Very comfortable and updated.
Jackie - Posted: 1/17/2021
Rating 5
I booked this stay the morning after checking
I booked this stay the morning after checking into Winter Park Mountain Lodge which did not accommodate us well. Myself My wife my 3 kids ages 7, 3, 5months old, and my 2 parents. Visit Winter Park’s accommodation was great and they communicate in a professional and timely manner. Walking into the home there is sitting area as soon as you walk in to take off your footwear so you don’t track snow mud water etc into the home there is also closet next to the sitting area to store your gear coats etc. The kitchen has everything you need to prepare your meals, seasonings included, just bring your groceries. The living room area with the fire place was comfortable and is able to be filled with natural light in the day time, the fire place was the selling point for my 7yr old. Both bedrooms with king size beds were comfortable. The bunk area/room is a nice touch and my kids loved it, I even laid down in there at one time to put my 3yr old to sleep. Both bedrooms and the living room / kitchen have their own temperature control which heats from the floor, which I did not realize until I took my slippers off. The host also provides laundry detergent fabric softener and dryer sheets if you choose to wash your clothes. Club house/communal pool hot tub etc areas were closed due to COVID. The pictures are what you see no bait and switch. The location is great, being between Winter Park Ski Resort and the town of Fraser which is where we went for snow tubing.
Dexter - Posted: 1/4/2021
Thank You Dexter for staying at our home, I'm glad we were able to accommodate you. Hope to have you and the family back in the future.
Stay Vara staff
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