Hey, friend! It’s Wednesday and the short-term rental market is calling. Today’s finds are packed with charm, opportunity, and potential for serious returns.

On the list: a custom colonial farmhouse just under two hours from NYC, perfect for city dwellers craving a rustic escape; an exceptional waterfront property in Land Between the Lakes, KY, designed to host large groups and create unforgettable stays; and a spacious 5-bedroom retreat in the Poconos, perfectly positioned near ski resorts, shopping, dining, and water parks – a four-season moneymaker. All shared exclusively with Investor’s Edge readers.

Could one of these properties be your next income-generating star? Let’s dig in.

Love what you’re seeing? Share this newsletter with someone ready to make their next bold move in the STR market. It would mean the world to me!

INVESTOR’S EDGE EXCLUSIVE

If you’ve been watching Chicago’s short-term rental market, you know it’s booming—revenues in the Windy City grew by 12% last year, driven by travelers seeking a balance of urban flair and neighborhood charm. And for hosts, properties that combine location, luxury, and guest-friendly design are the golden ticket.

Today’s Investor’s Edge exclusive? Think white oak hardwood floors, cathedral ceilings, and a chef’s kitchen with a quartz waterfall island that practically screams, “Host a dinner party!” Add in the proximity to parks, transit, and a lineup of restaurants and shops that could make any guest’s itinerary write itself, and it’s no wonder this house is expected to do north of $125K in revenue.

Upgrade to Investor’s Edge to receive the details on this rental goldmine alongside:

• 8+ of my favorite handpicked properties to hit the market every single day… before everyone else.

• An additional 40-80 amazing properties that didn’t make the newsletter each day in a running Google sheet.

• The ‘Investment Analysis’ spreadsheet I use to evaluate my investment opportunities.

• The ‘Monthly Revenue Tracker’ I use to manage my Airbnb P&L.

• The ‘Mortgage Payoff & Amortization Schedule’ I use to monitor may pay down rate and property equity.

• Quarterly in-depth write-ups to deliver must know industry trends.

All for about fifty cents a day. And, I’m currently offering the next 20 people who to sign up receive Investor’s Edge 52% off the standard price for the life of their subscription. Let’s make this the year you get the property that changes your life. Sign up below 👇

TODAY’S TOP PROPERTIES

5105 W Country Club Dr, Sarasota, FL 34243

Turn-key short-term rental in a quiet neighborhood on a 0.5-acre lot across the street from Palm Aire Country Club. No HOA and zero rental restrictions. This 3-bedroom pool home was totally renovated in 2022. Open floor plan with a second family room. Large primary bedroom with private patio. Pool was refinished in 2023, including a new pool heater. This home is ready for you to continue on Airbnb or to move right in. Pool room next to the garage could be converted to a 4th bedroom. Nice, quiet neighborhood with 12 minutes to SRQ Airport and 7 minutes from all the shopping and dining options at UTC. All furnishings, linens, appliances and cleaning supplies included with sale. $82,000 in revenue in 2024 with several weeks blocked for personal use. Currently a vacation rental, so showings need to be scheduled around bookings.

• Price: $587,500

• BR/Bath: 3 Bedroom / 2 Bath

• Sq. Feet: 1,890

• Avg. Daily Rate: $288

• Expected Occupancy Rate: 72%

• Expected Annual Revenue: $76,212

• Expected Annual Cash Flow: $16,231

• Expected Cash on Cash: 10.54%

66 Maple Avenue, Hunter, NY 12442

Welcome to Maple Mountain Colonial. This colonial farmhouse, built in 2012, offers modern mountain living with timeless charm at the base of Hunter Mountain. Offered furnished and turnkey, the home's striking black cedar siding, metal roof, and classic white trim set it apart in the heart of a welcoming village setting. Relax on the rocking chair front porch or enjoy the expansive backyard, which includes a patio for picnics, a fire pit, a bocce ball court, illuminated trails, and a BBQ area.

Set on an oversized one-acre village lot with municipal water and sewer, the property offers exciting potential: subdivide for an additional building lot or create your dream outdoor space with an inground pool.

Inside, the thoughtfully designed kitchen and dining area provide the perfect space for gathering after a day of mountain adventures. The library-style living room, anchored by a clean-burning fireplace, invites you to unwind while watching the snowfall.

The primary suite on the main floor is a serene retreat featuring a luxurious king bed and a spa-like bathroom. Upstairs, three sunlit bedrooms and a complete bath offer comfort and privacy for family and guests. A convenient side entrance leads to the mudroom with laundry facilities, a half bath, and ample storage.

This home is within walking distance of the village, a serene stream, a picturesque lake, and tennis courts, making it ideal for enjoying nature and community. The area allows short-term rental, making it perfect for investment or a combination of personal use and investment. Take advantage of this immaculate home in a prime location.

• Price: $679,000

• BR/Bath: 4 Bedroom / 3 Bath

• Sq. Feet: 1,764

• Avg. Daily Rate: $480

• Expected Occupancy Rate: 50%

• Expected Annual Revenue: $87,808

• Expected Annual Cash Flow: $20,651

• Expected Cash on Cash: 11.88%

Subscribe to Investor’s Edge to read the rest.

By joining STR Daily Investor’s Edge you get to read the rest of this post and access to Premium Member only content like:

• 8+ of the best handpicked properties to hit the market every single day… before everyone else.

• An additional 40-80 quality properties that didn’t make the newsletter each day in a running Google sheet.

• The ‘Investment Analysis’ spreadsheet I use to evaluate my investment opportunities.

• The ‘Monthly Revenue Tracker’ I use to manage my Airbnb P&L.

• The ‘Mortgage Payoff & Amortization Schedule’ I use to monitor may pay down rate and property equity.

• Quarterly in-depth write-ups to deliver must know industry trends.

Do you follow STR Daily on Instagram? Check out the latest post and give a follow on IG for exclusive content and giveaways:

Disclaimer: The information provided on STR Daily is for informational purposes only and should not be considered financial advice. Short-term rental regulations change constantly, so please review local rules and regulations prior to any purchases. Projected cash-on-cash returns are based on a 20% down payment, estimated furnishing costs appropriate for the property size, and anticipated fees. Actual returns may vary. Please run the numbers yourself or consult a financial professional to assess risks and develop a strategy suited to your specific needs.