Condo - Rating 4.8 (29)

Trailhead 232 pool, hot tub, clubhouse


Bedroom 2 bedrooms
Bathroom 2 baths
Guests 4 guests
Pets Not Allowed Pets Not Allowed

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

Location Location

Description Description
This oversized one-bedroom condo features a large primary bedroom with a King bed and a sleeping den with a Queen bed, sleeping up to 4 adults, perfect for families or couples!

This unit is located on the top floor and you’ll need to be able to navigate two flights of stairs to the condo.

Trailhead Lodges is conveniently located downtown Winter Park, just across from Hideaway Park which hosts world-class music festivals all summer long, including the Winter Park Jazz Festival and many more. This top-floor unit is located across from the clubhouse which features BBQ grills, a shared outdoor hot tub and heated swimming pool and an expansive clubhouse with pool table, kitchen, sitting area, workout room, and many more amenities. This unit also has a private balcony, a fully stocked kitchen, high-end appliances, and a gas fireplace.

County Permit 023010​​​​​​​

Amenities:

Private Patio

Free High-Speed Wifi

Free Clubhouse Access

Shared Outdoor Hot Tub

Shared outdoor heated swimming pool

Private washer and dryer

Gas fireplace

Smart lock for easy check In

Sleeping arrangements:

Primary bedroom – King Bed

Den – Queen bed

House Rules:

- No Pets are allowed

- No shoes are worn indoors

- No smoking of any kind in the home

- Quiet hours 10:00 pm till 7:00 am

-Parking for ONE car only

-Rv's and trailers are prohibited from parking at this site during holiday and music festival weekends.

Town of Winter Park Registration Number: 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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Bedding Bedding
Room Beds Baths TVs Comments
Room 1 Queen
Room 7 King

Amenities 42 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 parking on premises
  • Freezer
  • Gym
  • Hair dryer
  • Hangers
  • Heating
  • Hot tub
  • Hot water
  • Hot water kettle
  • Indoor fireplace
  • Iron
  • Kitchen
  • Microwave
  • Oven
  • Pack 'n Play/travel crib.
  • Pocket wifi
  • Pool
  • Pool table
  • Private entrance
  • Private living room
  • Refrigerator
  • Shampoo
  • Smoke alarm
  • Stove
  • Toaster
  • TV
  • Washer
  • Wifi

Reviews Rating 4.8 (29) Reviews
Rating 5
Great location and amenities for an on-the-go
Great location and amenities for an on-the-go family. The place had everything we needed and made it easy to enjoy our stay!
Callen - Posted: 8/17/2026
Rating 5
Great condo! Really nicely furnished and super
Great condo! Really nicely furnished and super clean. Very satisfied!
[email protected] - Posted: 8/10/2026
Rating 5
Incredible location for easy Winter Park trails,
Incredible location for easy Winter Park trails, parks, and good food. Great place to stay when traveling with a young kid. The pool and hot tub were also nice!
Monica - Posted: 6/21/2026
Rating 5
Great stay!
Great stay!
Colin - Posted: 3/29/2026
Thanks for the review!
Stay Vara staff
Rating 5
Great rental, would book again.
Great rental, would book again.
Luke - Posted: 12/10/2025
Thank you! Come back again soon.
Stay Vara staff
Rating 5
This was an excellent place to stay. It’s very
This was an excellent place to stay. It’s very close to most of the main stretch of Winter Park. It is directly across from Hideaway Park which is a really nice little park that our 3 year-old loved. The pool is also a plus. We came in the summer and fair warning there is no air conditioning, but that is very common in Winter Park and they have fans available to use and windows that can provide plenty of air in the evening. Check-in was a breeze, parking was easy, the place was very clean and had toys available for my son to play with, which was a big plus. The bathroom had all the essentials. Beds were comfortable. The elevator was not working when we were there, and I reached out to the host who immediately responded explaining that it goes out sometimes and they’ve notified the HOA about it since the HOA is in charge of that, not the host. Overall, it was a great apartment, very responsive host, and an excellent experience. Highly recommended.
Jacob - Posted: 8/10/2025
Thank you for such a great review, and so many highlights! We hope to host you again soon!
Stay Vara staff
Rating 5
We really enjoyed our stay in this beautiful
We really enjoyed our stay in this beautiful condo! The location was perfect and the host was responsive and helpful!
Mary - Posted: 4/23/2025
Thanks for the kind review.
Stay Vara staff
Rating 5
Great stay and will stay here again! Check in was
Great stay and will stay here again! Check in was relatively easy. I was sent two codes to get in by accident - figured it out though. Great condo and well appointed kitchen. Closet space and storage is a little on the small side but once you utilize the coat rack to hang your ski jackets and pants on it really isn’t that bad at all. Could use some more hangers in the master bedroom closet. Smart tvs were all great. I feel like the renters are doing themselves a disservice by calling this a one bedroom! While the small den bedroom doesn’t have a window, my teenage daughter found it comfy and cozy - a great place to have 2 kids and a comfy queen bed! The heated pool and hot tub are clean and spacious and the whole amenities building is great. Wish there wasn’t a charge for an early check-in when there was no one in the unit before us - feels a little “nickel and dime-y” but the rental price was such a great deal, it was fine to pay. If you’re thinking about this unit, go for it!
Kelsie - Posted: 4/21/2025
Thanks so much for the feedback Kelsie. Just an FYI; bedroom has a legal definition which does not allow the den to be counted, or you bet we would! We will add some hangers and look forward to hosting you again in the future!
Stay Vara staff
Rating 5
Super convenient and spacious place to stay. Easy
Super convenient and spacious place to stay. Easy to catch the shuttle the mountain then enjoy the hot tub at the end of the day. Very walkable to town for shopping or dining out. The unit was clean and lovely to spend time in!
Skye - Posted: 3/30/2025
Thank you for the review Skye!
Stay Vara staff
Rating 5
This place was super well stocked, and the hosts
This place was super well stocked, and the hosts were very responsive! Perfect for a week skiing and hanging around.
Morgan - Posted: 3/29/2025
Thanks Morgan!
Stay Vara staff
Rating 5
Clean, comfortable, and well appointed condo.
Clean, comfortable, and well appointed condo. Extremely easy check-in/out. Location was perfect for walking to shops and restaurants and the free sledding/tubing hill / concert pavilion area. Also an easy 5 minute drive to the Mary Jane base parking lot which is where we like to post up for skiing. Guests could easily take the bus to main resort which I’m guessing is only a couple of minutes. The nice washer & dryer was used daily so that we could pack light. We would most definitely return to this property on a future visit if available.
Dave And Dawn - Posted: 3/13/2025
Thanks so much for the great review! We look forward to hosting you again in the future!
Stay Vara staff
Rating 4
Honestly, we loved this condo. Location let us
Honestly, we loved this condo. Location let us walk to dinner every night, short walk to buses as well, nice not to have to drive to the resort as we always did in the past. The apartment itself was great, new, clean, well appointed, tastefully and comfortably decorated. And really liked the heated floors and gas fireplace. Only negative was the non-functioning elevator. Hauling all our gear up to the third floor in the thin mountain air was a puffer. I realize this is not in the control of this specific condo, but would have been nice had it been working. Otherwise, great. We'd definitely stay here again.
Scott - Posted: 3/4/2025
Hi Scott, Thank you for taking the time to leave a review! We're delighted to hear that you enjoyed the condo. Unfortunately, we do not manage the elevators, but we would have been happy to reach out to the HOA regarding the issue. If you choose to stay with us again and encounter a similar situation, please don't hesitate to reach out—we would love to assist in finding a solution. Thanks again!
Stay Vara staff
Rating 5
Super helpful and proactive communication! I
Super helpful and proactive communication! I forgot something behind 🙃 and they reached out and went out of their way to make sure I got my belongings. Place was awesome and hot tub was a great amenity. Close to the resort for a ski weekend. We’ll be back!!!
Mary Pierce - Posted: 2/16/2025
Thanks Mary for leaving a great review! Please come back and visit us, we would love to have you!
Stay Vara staff
Rating 5
This place should be rated 10 out of 5. Very nice
This place should be rated 10 out of 5. Very nice vacation suites for family. Pristine everywhere. High-end appliances and decoration. I want to come back every time when I’m in WP.
Yumeng - Posted: 12/11/2024
Thank you for such a great review Yumeng! We'd love to have you back anytime
Stay Vara staff
Rating 5
Great location and perfect Ski condo! Would
Great location and perfect Ski condo! Would definitely stay again.
Danielle - Posted: 12/6/2024
Come back again soon Danielle!
Stay Vara staff
Rating 5
Amazing location in laid back village. We rented
Amazing location in laid back village. We rented bikes and rode to Fraser for the afternoon. Walked everywhere in WP from the condo - shops, bakery, cocktails, fancy dinner. Loved our stay!! Bed was super comfy!!
Karmin - Posted: 9/29/2024
Glad you loved the location as much as we do! Would be happy to host you again in the future.
Stay Vara staff
Rating 5
Amazing Airbnb steps away from Rendezvous Event
Amazing Airbnb steps away from Rendezvous Event Center! Great hot tub, pool, and pool house! Airbnb kitchen had all the things you could need and even has a grill on the porch!
Jade - Posted: 8/9/2024
Thanks Jade for leaving a great review, and most importantly we are so glad you guys enjoyed your stay! It was such a pleasure to host you, come back and visit!
Stay Vara staff
Rating 5
Great stay, awesome location, extremely
Great stay, awesome location, extremely communicative!
Terry - Posted: 7/16/2024
Rating 5
Had a great time staying here! Unit is very well
Had a great time staying here! Unit is very well finished and felt homey. Had a maintenance issue and rental management company did a great job communicating and making it right for us. Would definitely come back to this complex for a ski trip again
Jordan - Posted: 4/8/2024
Thank you for your communication as well! Come back again anytime!
Stay Vara staff
Rating 5
Condo was exactly as described. Hot tub was
Condo was exactly as described. Hot tub was great after day on the slopes. Shuttle service to/from mountain was so easy and convenient. Walking distance to restaurants too :)
Beth - Posted: 12/18/2023
So glad you enjoyed your stay! Come back again soon!
Stay Vara staff
Rating 5
Excellent place to stay for a family of 4. We
Excellent place to stay for a family of 4. We spent 10 days in the unit during our annual training camp and we felt that we had plenty of room. The outdoor pool and hot tub are very nice. The onsite property management company does a great job taking care of the needs of the guests. During our stay, they replaced the refrigerator lightbulb, delivered a broom/dustpan, and fixed our clubhouse RFID key. The gym in the Club House could use a few upgraded machines and the plowing of the parking lot could be better. It was very icy in spots that did not get direct sunlight. Lastly, the elevator was out of service and no one from the HOA communicated if or when it would be fixed. Hauling all of our gear and goods up to the 3rd floor was a bit taxing. It would have been beneficial to know that the HOA and Property Management Company were aware of the issue and had a plan in place. All and All, this was an excellent place, great location, and only 5 mins from WPR. 5 stars!
Steve - Posted: 12/6/2023
Thanks for leaving us a great review Steve! Unfortunately we only manage the room, and do our best to communicate further issues with the HOA. We have passed along your concerns regarding the elevator and poor snow plowing. Come back and stay with us again soon!
Stay Vara staff
Rating 4
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Scott - Posted: 7/30/2023
Rating 5
Definitely a great price for what we got! Love
Definitely a great price for what we got! Love these apartments and they are always easy to check in and out. They are clean and comfortable beds.
Bethany - Posted: 7/18/2023
Thanks Bethany!
Stay Vara staff
Rating 5
We had an incredible stay in Winter Park. The
We had an incredible stay in Winter Park. The location is great - just off the main street so we were able to walk to restaurants and bars. There are several hikes nearby so you aren't stuck in your car all day. The condo was incredibly clean, cute and had everything we needed. It was actually bigger than we expected. We would love to stay here again, in fact, we've already talked about it! The host was very responsive and helpful. Thanks so much for having us!
Lori - Posted: 7/17/2023
Thanks for staying with us! Come back anytime!
Stay Vara staff
Rating 5
Great location. The condo was very clean and
Great location. The condo was very clean and everything was as expected. We would definitely book again.
Marla - Posted: 6/26/2023
Thanks Marla for taking the time to leave a great review! It was a pleasure hosting you guys! Cheers!
Stay Vara staff
Rating 5
It's a beautiful unit, very clean and well
It's a beautiful unit, very clean and well maintained. The location and view is outstanding. Please note, if you are bringing bikes, they are not allowed in the unit and there is no storage available. There is a bike rack at the bottom of the stairs you can use with your own lock, however, it is not secure, at all.
Chris - Posted: 5/22/2023
Rating 4
This was a nice place. However, check in was not
This was a nice place. However, check in was not flexible, but some spots in the kitchen and stove were not fully cleaned. In addition, we booked the place specifically with a hot tub as an amenity in mind, but the hot tub was broken all three days. No notification was provided and check out/ check in was unfortunately not flexible
Jenny - Posted: 2/27/2023
Rating 5
This place was truly 🤩 perfect. The amenities,
This place was truly 🤩 perfect. The amenities, the cozy cabin feel, the thorough instructions provided from the time we checked in, their prompt responses to my inquiries and the list goes on! I was thoroughly impressed. The location is perfect and super convenient to restaurants, shopping and activities in the area. The property was pretty much immaculate! I’d highly recommend and would stay here again in a heartbeat 💓 .
Rebecca - Posted: 2/19/2023
Rating 5
Fantastic stay!!
Fantastic stay!!
Mike - Posted: 1/30/2023
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