Issue No. 49 · The Deal Drop
4
Properties this drop
$360K
Top Revenue
20%
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 — Jamaica Beach, TX: $995K waterfront STR opportunity generating projected ~$210K/year (~21% ROI) with canal-front access, heated pool, and strong upside in a high-demand Galveston vacation rental market.
Property 2 — Kissimmee, FL: $790K turnkey 8-bedroom STR opportunity generating projected ~$136K/year (~17% ROI) in Storey Lake Resort with themed rooms, private pool, and strong proximity to Disney and Orlando attractions.
Property 3 — Sevierville, TN: $1.95M income-producing mountain STR powerhouse generating projected ~$360K/year (~18% ROI) with 8 ensuite bedrooms, a detached indoor heated pool house, and proven $270K+ booking momentum in the Smoky Mountains.
Property 4 — Fairview, NC: $1.5M mountain STR compound generating projected ~$226K/year (~15% ROI) with two separate residences, a seasonal pool, 4.6 private acres, and strong income potential just outside Asheville.
🏠 The Properties
We pressure-tested hundreds of listings this week. Here’s the shortlist — ranked by projected ROI after expenses.
📋 4 Beds • 3 Baths • 1,940 sqft
🏷️ Price: $995,000
💵 Projected Annual: $210K
📈 Est. Gross ROI: 20%
Why it made the cut:
True waterfront canal home with private backyard access for fishing, crabbing, and boating activities
Strong projected revenue of ~$210K annually supported by consistent Galveston-area vacation demand
Sleeps up to 12 guests, making it ideal for high-occupancy family and group bookings
Heated pool already in place, a top-tier amenity for year-round rental performance
Recently built construction reduces near-term maintenance and capital expenditure risk
Premium Jamaica Beach location with strong short-term rental appeal and beach proximity
High experiential value with direct water access creating standout guest memories and reviews
Clear value-add upside through hot tub addition, game room conversion, and outdoor amenity enhancements
Opportunity to differentiate from competing listings through curated “experience-driven” upgrades
Attractive negotiation potential due to extended time on market, improving investor entry position
📋 8 Beds • 5 Baths • 4,289 sqft
🏷️ Price: $790,000
💵 Projected Annual: $136K
📈 Est. Gross ROI: 17%
Why it made the cut:
Located in the highly sought-after Storey Lake Resort, one of Orlando’s strongest short-term rental communities
Spacious 8-bedroom, 5-bath layout designed for large-family and group vacation demand
Fully furnished and turnkey, reducing upfront setup costs and accelerating time to cash flow
Private pool with peaceful pond and conservation views and no rear neighbors for enhanced guest privacy
Strong entertainment features including private movie theater, game room, and virtual reality experience setup
Themed bedrooms that increase booking appeal and support higher nightly rates and occupancy
Prime location just minutes from Disney, Universal, dining, and major Orlando attractions
Proven STR-friendly layout built for high occupancy and repeat family vacation bookings
Resort community amenities further strengthen guest demand and listing competitiveness
Attractive entry price point relative to bedroom count and projected income for Orlando market performance
📋 8 Beds • 9 Baths • 5,792 sqft
🏷️ Price: $1,950,000
💵 Projected Annual: $360K
📈 Est. Gross ROI: 18%
Why it made the cut:
Proven high-performing STR with ~$274K+ gross revenue in 2025 and ~$270K already on the books for 2026
Prime Catons Chapel location just 15 minutes from Pigeon Forge, Gatlinburg, and Sevierville attractions
Massive 8-bedroom, 9-bath layout with all ensuite bedrooms, ideal for large-group bookings and premium occupancy rates
Sleeps up to ~22 guests with strong design for multi-family stays, retreats, and reunion-scale rentals
Detached pool house with indoor heated swimming pool, separating amenities from main living areas for guest comfort and safety
Vaulted cathedral ceilings and rustic-modern design aesthetic aligned with high-demand Smoky Mountain STR style
Large-scale entertainment setup including expansive game room and theater lounge
Dual-level outdoor decks and gazebo offering strong indoor-outdoor guest experience appeal
Strong traffic-avoidance access to major tourist hubs via back-road routes, increasing guest convenience value
High-certainty income profile supported by real historical performance and forward bookings rather than purely speculative projections
📋 3 Beds • 5 Baths • 4,123 sqft
🏷️ Price: $1,500,000
💵 Projected Annual: $226K
📈 Est. Gross ROI: 15%
Why it made the cut:
Rare multi-structure setup featuring a spacious main home and fully detached guest house
Approximately 4.6 acres of private mountain land with wooded surroundings and open lawn areas
Strong Asheville-area STR demand supporting projected ~$226K annual revenue
Main residence includes multiple gathering spaces, a double-sided fireplace, and dedicated game room
Detached guest house offers its own kitchen, living area, laundry, hot tub, fire pit, and private deck
Seasonal pool adds a highly desirable amenity for family and group bookings
Flexible occupancy options ideal for large groups, retreats, reunions, and extended stays
Existing bonus rooms provide additional versatility, with seller pursuing permit expansion from three to five bedrooms
Strong blend of privacy, guest experience, and diversified rental income potential
Attractive opportunity as either a high-performing STR investment or private mountain retreat compound
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: Orlando, FL
Why Orlando continues to dominate global STR demand: a 96 Market Score, exceptional rental demand, and one of the most resilient tourism-driven economies in the U.S., anchored by year-round theme park visitation and international travel flows.
The three levers driving performance right now:
World-class, year-round demand engine — With a 93 Rental Demand Score, Orlando benefits from consistent visitation driven by Disney, Universal, conventions, and international tourism, reducing reliance on seasonal peaks.
High-velocity STR ecosystem at scale — Over 43,000 active listings and ~62% occupancy reflect a deep, liquid market where demand is strong enough to sustain one of the largest STR inventories in the country.
Steady revenue expansion despite scale saturation — Annual revenue (~$48K per listing) continues to grow (+3.9%), supported by modest ADR gains and increasing occupancy (+2.1%), even in a highly competitive environment.
Orlando is a large-scale, demand-dominant STR market where consistent tourism flows support strong occupancy and steady revenue growth, but competition requires disciplined pricing and strong property positioning to outperform.
🎯 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
Your STR. Your Income. Your Loan - STR Home Loans
Financing your next STR doesn't have to mean stacks of tax returns and W-2s. STR Home Loans specializes in DSCR loans built for short-term rental investors — you qualify on the property's income, not yours. They close in as few as 21 days, lend up to $2M, and their team actually invests in STRs themselves. Whether you're buying your first Airbnb or pulling equity out of your existing portfolio, they've got a loan program for it.
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 💧