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Prospect analysis
173 Paradise Way #173
Asking$888,000
Islamorada, FL · 2 bd · 2 ba · 1,230 sq ft · Built 2022
Underwritten as a short-term rental
Newer 2-bedroom oceanview residence in a resort community with strong short-term rental income projections and zero property taxes due to land lease structure.
This 2022-built, fully furnished property in Islamorada offers high guest appeal and access to extensive resort amenities. Underwriting metrics indicate robust cash flow and cash-on-cash returns, though the land lease structure and premium pricing warrant careful diligence.
Est. ADR
$553
Est. occupancy
62%
Gross rev / mo
$10,429
Cash-on-cash
22.8%
Airfolio market estimates · 20% down · detail in the underwriting panel.
Investment thesis
This property presents a compelling opportunity for investors seeking a turnkey short-term rental in a high-demand Florida Keys market. The combination of modern construction, ocean views, and resort amenities positions it well for consistent guest demand and premium nightly rates. Underwriting outputs suggest strong income and cash-on-cash returns, supported by high occupancy assumptions. The land lease structure eliminates property taxes and HOA fees, enhancing net returns, but also introduces unique long-term considerations. The primary caveat is the need to confirm ongoing STR regulations and the specifics of the land lease agreement during diligence.
Highlights
- Built in 2022 with modern coastal finishes
- 2 bedrooms, 2 bathrooms, 1,230 sqft
- Fully furnished and move-in ready
- Ocean views and abundant natural light
- Located within Sun Outdoors Islamorada resort with pools, clubhouse, and marina access
- Zero property taxes and no HOA due to land lease
- Direct access to Founders Park and nearby amenities
- High-confidence underwriting with strong projected cash flow
Risks
STR permitting: verify local ordinance and zoning allow short-term rental at this address before offering. Not verified.
Land lease structure may impact long-term appreciation and resale flexibility
STR regulations and permitting should be verified for ongoing compliance
Returns are sensitive to occupancy and ADR assumptions
Premium pricing requires sustained high rental performance
Potential competition from newer or similarly positioned resort inventory
Operational complexity of managing a high-turnover STR in a resort setting
Market
Islamorada is a sought-after destination in the Florida Keys, known for its waterfront lifestyle and strong tourism-driven rental demand. The market supports premium nightly rates for well-located, modern properties, particularly those with resort amenities and ocean views. While the STR market is robust, ongoing regulatory compliance and competition from new inventory are important considerations for investors.
Neighborhood
The property is situated within a resort community offering extensive amenities and direct access to Founders Park, enhancing guest appeal for both leisure and family travelers. The surrounding area is characterized by a mix of vacation rentals and resort-style developments, supporting a vibrant short-term rental environment. Given the limited location-specific demand signals, conclusions about neighborhood performance are medium confidence but supported by the area's established tourism profile.
Underwriting notes
At a list price of $888,000, underwriting metrics project a monthly expected income of $10,429 and cash flow of $3,378, with a 22.8% expected cash-on-cash return based on a 20% down payment, 6.4% interest rate, and 25% expense ratio. These projections assume a $553 ADR and 62% occupancy, which are aggressive but plausible for a property of this caliber in Islamorada. The absence of property taxes and HOA fees due to the land lease structure materially boosts net returns, but investors should carefully review the lease terms and confirm all assumptions during diligence.
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