Issue No. 50 · The Deal Drop
4
Properties this drop
$329K
Top Revenue
25%
Top ROI
📋 What’s Inside This Drop
Four different angles, four different markets — here’s the quick read on what’s worth a deeper look this drop.
Property 1 — Fayetteville, AR: $375K turnkey STR opportunity generating projected ~$64K/year (~17% ROI) with a transferable Airbnb license, established rental operations, and prime access to the University of Arkansas and downtown Fayetteville.
Property 2 — Seminole, FL: $1.295M coastal estate STR opportunity generating projected ~$329K/year (~25% ROI) with a private guest house, resort-style outdoor amenities, and exceptional proximity to Florida’s Gulf Coast beaches.
Property 3 — St. Augustine, FL: $949K turnkey triplex STR opportunity generating projected ~$161K/year (~17% ROI) with proven income, historic charm, and a prime location in the heart of America’s oldest city.
Property 4 — Fairview, NC: $799K Asheville-area STR opportunity generating projected ~$160K/year (~20% ROI) with a resort-style backyard entertainment space, large-group accommodations, and prime access to Western North Carolina’s top tourism attractions.
🏠 The Properties
We pressure-tested hundreds of listings this week. Here’s the shortlist — ranked by projected ROI after expenses.
📋 3 Beds • 2 Baths • 1,140 sqft
🏷️ Price: $375,000
💵 Projected Annual: $64K
📈 Est. Gross ROI: 17%
Why it made the cut:
Fully licensed Airbnb with a transferable permit, providing a significant competitive advantage in a market with increasingly limited STR approvals
Offered fully furnished and operational, allowing investors to begin generating income immediately
Potential transfer of future bookings creates instant revenue continuity from day one
Minutes from the University of Arkansas, a major driver of year-round demand from visitors, alumni, prospective students, and event attendees
Convenient access to Downtown Fayetteville's restaurants, entertainment, nightlife, and cultural attractions
Near Centennial Park, a nationally recognized cycling destination that attracts outdoor recreation travelers
Strong appeal for Razorback game-day weekends, graduation events, university functions, and leisure travelers
Affordable entry price relative to projected revenue supports attractive cash-flow potential
Turnkey setup minimizes startup costs, furnishing expenses, and operational delays for new owners.
📋 5 Beds • 4 Baths • 4,139 sqft
🏷️ Price: $1,295,000
💵 Projected Annual: $329K
📈 Est. Gross ROI: 25%
Why it made the cut:
Less than a mile from Indian Shores and minutes from top Gulf Coast beaches
5-bedroom setup across a main home and separate guest house accommodates larger groups
Private pool and nearly one-acre lot create a resort-style guest experience
Guest house with full kitchen adds flexibility and booking appeal
Ample parking for vehicles, boats, and RVs
Unique recreation amenities including an MLB-standard pitching mound and catcher’s box
NO flood insurance requirement offers a major advantage in a coastal market
Strong appeal for family vacations, beach getaways, and group retreats
Rare combination of beach proximity, privacy, and large-group accommodations supporting strong STR demand and revenue potential.
📋 3 Beds • 3 Baths • 2,067 sqft
🏷️ Price: $949,000
💵 Projected Annual: $161K
📈 Est. Gross ROI: 17%
Why it made the cut:
Fully remodeled and fully furnished triplex ready to generate income from day one
Proven STR performance with strong revenue history and established guest demand
Located in the heart of Historic St. Augustine, within walking distance of top attractions, dining, and entertainment
Three-unit configuration provides diversified booking opportunities and revenue streams
Historic 1920s character paired with modern updates creates strong guest appeal
Strong track record of positive reviews and repeat visitors
Generous yard offers additional value-add and guest experience potential
Rare combination of turnkey operations, proven income history, and premier historic-district location supporting strong STR demand and revenue potential.
📋 4 Beds • 3 Baths • 3,092 sqft
🏷️ Price: $799,000
💵 Projected Annual: $160K
📈 Est. Gross ROI: 20%
Why it made the cut:
Massive outdoor entertainment area featuring a fire pit, outdoor kitchen, bar, stone patio, and expansive deck
Screened porch creates additional year-round gathering space and enhances guest experience
Large fenced backyard appeals to families, pet owners, and groups seeking private outdoor amenities
Open-concept design supports group stays, celebrations, and extended-family vacations
Located just 15 minutes from downtown Asheville’s restaurants, breweries, shopping, and events
Convenient access to the Blue Ridge Parkway, hiking, waterfalls, and other Western North Carolina attractions
Quiet cul-de-sac setting offers privacy while remaining close to major tourism demand drivers
Strong appeal for Asheville weekend getaways, wedding groups, outdoor enthusiasts, and family reunions
Rare combination of high-capacity accommodations, premium outdoor amenities, and proximity to Asheville supporting strong STR demand and revenue potential
Want the full deal packet on any of these? Reply “DEAL #” to this email and we’ll send the full numbers, photos, and market comps.
Prefer to skip the reply and get matched to deals like these on autopilot?
📍 Market of the Week: St. Augustine Beach, FL
Why St. Augustine Beach continues to attract STR investors: a strong blend of beach tourism and historic-district demand, healthy ADR growth, and a market size that remains manageable compared to Florida’s larger vacation destinations.
The three levers driving performance right now:
Dual-demand destination — St. Augustine Beach benefits from both beachfront tourism and proximity to historic downtown St. Augustine, creating multiple demand drivers beyond a traditional beach market.
Strong pricing power — ADR has climbed to approximately $282 per night (+2.9% YoY), supporting annual revenues above $51K per listing despite a modest decline in occupancy.
Balanced growth profile — Active listings have increased (+3.1%), yet revenue continues to grow (+2.7%), suggesting demand remains healthy even as competition gradually expands.
St. Augustine Beach is a high-ADR coastal STR market where beach access, historic tourism, and steady pricing growth continue to support solid long-term performance.
🎯 Your Shortcut: The Market Match Call
Skip the guesswork. Tell us your budget, risk tolerance, and the kind of returns you’re chasing — we’ll match you with markets and deals that actually fit, before they hit the wider market.
💡Vendor Spotlight
Short-Term Rental Insurance Policies Made Simple
If you're still running your STR under a standard homeowners policy, you're likely underinsured — and you won't find out until you file a claim. InsureSTR specializes exclusively in short-term rental coverage, matching hosts with carriers that actually understand the risks: guest liability, income loss, high-turnover wear, and more. They offer fast, custom quotes tailored to how you actually operate (not a generic homeowner template). Book a free discovery call to find out if your current coverage has gaps.
That’s the pulse for today. Hit reply and tell us which headline surprised you most — real humans read every response.
— The Deal Drop Team 💧