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!

[Andrew Steffens]

Hey Ryan! Welcome (and best of luck)

I am primarily a little North of you in the Tampa area but do manage some as far south as Naples.  It is still a competitive market so pricing / marketing is of extreme importance to your success.  I have a few spectacular properties that are price leaders but the majority of my properties are "average" in size and amenity and I have been beating the market by 14-16% in ADR and overall revenue.  I attribute that success 80% to revenue management.

Feel free to reach out with any more questions about to FL property.  Good luck!