New to STRs – Seeking Advice on Two Unique Properties (Naples + Aspen)

[Ryan S.]

Hello BiggerPockets!

I'm new to short-term rentals (STRs) and currently own two exciting properties that I believe have serious potential. Like everyone here, I’m looking to maximize profits — but I do feel these properties are uniquely positioned to outperform.

Here’s a quick overview:

1. Naples, Florida – 139 Seabreeze Ave

https://share.icloud.com/photos/0fevv6f9VhopkNVrtInLE20yg (Photos are a bit dated — I'm currently completing an update!)

• Approximately 5,800 sq ft under air

• Currently 3 bedrooms + office (being expanded to 5 bedrooms)

• 4 full bathrooms and 2 half bathrooms

• Will offer 10 beds, sleeping up to 20 guests comfortably once complete

• Waterfront property with BIG water views

• 500-foot walk to the beach and walking distance to beachfront restaurants

• Prime location near LaPlaya Beach & Golf Resort, a major wedding venue throughout the year

• Enhancing outdoor entertaining spaces and upgrading interior furnishings to a high-end luxury rental standard

After researching the Naples STR market, I found very few options combining this size, bedroom count, waterfront access, and proximity to the beach — creating what I believe is a rare and highly desirable offering.

2. Aspen, Colorado – 124 E Durant Ave Unit 7

https://share.icloud.com/photos/0acH8n4Owg-NjmQOg8BGx_3pQ

Just closed on this one through a 1031 exchange — extremely excited about it!

• Approximately 1,200 sq ft, spread across three levels

• Currently 2 bedrooms + office, planning to convert to 3 true bedrooms

• 2 full bathrooms

• Recently updated with high-end finishes, Venetian plaster walls, and Waterworks fixtures

• Flat walk to Ajax Mountain(ski slopes), downtown shopping, and restaurants

• Townhouse style — no neighbors above or below (a big plus compared to typical Aspen condos)

• Set up with a local team (property manager, handyman, housekeeper) for smooth absentee management

• Evaluating whether to pursue short-term rentals or monthly furnished rentals, depending on seasonal performance

Would love to hear any advice from experienced STR investors!
Particularly around maximizing nightly rates, enhancing guest experience, and best marketing/booking strategies for premium properties like these.

Thanks so much for any insight you’re willing to share — I really appreciate it!

[Ryan S.]

Thank you, Mark, for the reply! I’m definitely going to hire a professional photographer to take pictures of both properties.

For my Naples home, I was thinking of reaching out to local wedding planners. I’m hoping it could be a great option for bachelor or bachelorette parties, or even for larger groups who want to stay together instead of booking multiple rooms at LaPlaya. I’m planning to keep bikes at the house, and a nice bonus is that LaPlaya has a fleet of electric bikes available for rent just a short walk away. I also love the idea of offering a golf cart and boat charter—great suggestions! I’m not quite sure what to expect with this property since there’s really nothing else like it in the market.

It’s interesting that you think I’ll make more money with STRs. I did a quick search and noticed there’s a lot of competition in Aspen. My place does stand out a bit since it’s a townhouse, which offers more privacy and separation compared to the typical condo, and it’s in a prime location. It’s also nicely renovated. Still, Aspen has plenty of great options, so it’s not quite as unique as my Naples property. It also lacks some amenities like a pool or hot tub, but the location is A+.

I’ve reached out to management companies, but they’re quoting fees between 20% and 40%, which feels steep. I’d rather put in some sweat equity, rent it out myself, and possibly rent it a bit less frequently but still net about the same as I would using a management company. That approach would also give me the flexibility to enjoy the property personally from time to time. I have a great cleaner and a property manager who inspects the unit after each checkout for $90, and I plan to use Hospitable to handle bookings and guest communication.