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View PropertiesAs of Apr, 27 2026
Rabbu ROI Score
Westport presents a competitive opportunity: investor interest and demand are strong, but higher prices or tighter competition may require more selective deal sourcing.
Westport, CT is a premium coastal Connecticut market where high home values and a relatively small supply of just 27 active Airbnb listings create a selective but potentially rewarding landscape for short-term rental investors. With an average daily rate of $606—well above the $373 state average—and average annual revenue of $51,961, the market rewards operators who can command top-tier nightly rates. However, the 24% average occupancy rate signals that success here depends on capitalizing on strong summer demand rather than year-round bookings, making deal selection and pricing strategy critical.
According to Rabbu market data, the Westport short-term rental market shows:
| Metric | Context | Value |
|---|---|---|
| Active Airbnb Listings | As of Apr, 27 2026 | 27 |
| Average Daily Rate (ADR) | vs. $373 state avg. | $606 |
| Average Occupancy Rate | vs. 37% state avg. | 24% |
| RevPAN | ADR * Occupancy Rate | $147 |
| Average Monthly Revenue | Historical 12-month average | $4,330 |
| Average Annual Revenue | Historical 12-month average | $51,961 |
Data sources: Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Apr, 27 2026.
Westport attracts STR investors seeking premium nightly rates in an affluent, supply-constrained Connecticut shoreline market with strong seasonal demand.
Key investment factors
"Westport represents a competitive opportunity where selective deal sourcing matters more than in broad-demand urban markets. The pronounced seasonality—July revenue of $7,251 versus a January low of $2,159—means investors should model conservatively for winter months while recognizing that summer performance can be exceptional. The combination of above-average growth trends and a healthy supply/demand balance suggests the market is gaining momentum, but the below-average revenue-to-price ratio (driven by home values averaging $3.4 million) means that cash-flow positive outcomes will depend heavily on property acquisition cost and operational efficiency. This is a market best suited for investors with access to high-end inventory who can deliver a differentiated guest experience."
— Rabbu Market Analysis Team
Westport exhibits strong seasonality, with July ($7,251) and August ($7,012) generating more than three times the revenue of the slowest months—January ($2,159) and February ($2,167). This roughly $5,000 spread between peak and trough months means investors should plan for a summer-weighted cash flow cycle, with shoulder months like September and October still performing respectably around $4,700.
| Month | Trend | Revenue |
|---|---|---|
| January |
|
$2,159 |
| February |
|
$2,167 |
| March |
|
$2,550 |
| April |
|
$3,005 |
| May |
|
$4,527 |
| June |
|
$5,881 |
| July |
|
$7,251 |
| August |
|
$7,012 |
| September |
|
$4,727 |
| October |
|
$4,734 |
| November |
|
$3,990 |
| December |
|
$3,953 |
The market's 27 active listings are concentrated among 1-bedroom (8 listings), 3-bedroom (6 listings), and 2-bedroom (5 listings) properties. The relatively even distribution suggests no single size dominates, though the slightly higher count of 1-bedrooms may indicate room for differentiation with larger, family-friendly properties that command premium rates.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
8 |
| 2 bedrooms |
|
5 |
| 3 bedrooms |
|
6 |
ADR escalates dramatically with property size in Westport: 1-bedrooms average $166 per night, 2-bedrooms jump to $290, and 3-bedrooms command $626—nearly four times the smallest units. The outsized premium on 3-bedroom properties suggests guests are willing to pay significantly more for space, making larger homes the most compelling option for rate-driven revenue strategies.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$166 |
| 2 bedrooms |
|
$290 |
| 3 bedrooms |
|
$626 |
Two-bedroom properties deliver the highest RevPAN at $122, narrowly beating 3-bedrooms at $114, while 1-bedroom units trail significantly at just $39. This suggests that 2-bedroom listings strike the best balance between occupancy and nightly rate, offering investors the most efficient revenue per available night.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$39 |
| 2 bedrooms |
|
$122 |
| 3 bedrooms |
|
$114 |
Occupancy rates vary widely by property size, with 2-bedroom listings leading at 42%—nearly double the market average—while 3-bedrooms lag at just 18% despite their high ADR. One-bedroom units sit at 24%, indicating that mid-sized properties fill most consistently and may offer more predictable cash flow for investors prioritizing occupancy stability.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
24% |
| 2 bedrooms |
|
42% |
| 3 bedrooms |
|
18% |
Three-bedroom properties generate the highest monthly revenue at $6,915, followed by 2-bedrooms at $4,593 and 1-bedrooms at $2,204. While 3-bedrooms lead on gross revenue thanks to their premium ADR, the gap between 2-bedroom and 3-bedroom earnings is relatively modest compared to the ADR difference, reflecting the occupancy advantage of smaller units.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$2,204 |
| 2 bedrooms |
|
$4,593 |
| 3 bedrooms |
|
$6,915 |
Annual revenue scales meaningfully with size: 3-bedroom properties earn approximately $82,990 per year, more than three times the $26,456 generated by 1-bedroom listings. Two-bedroom units land at $55,124 annually, offering a strong middle-ground option for investors seeking solid returns without the higher acquisition costs typically associated with larger Westport homes.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$26,456 |
| 2 bedrooms |
|
$55,124 |
| 3 bedrooms |
|
$82,990 |
Parking and a full kitchen are universal (100%) across Westport listings, reflecting the suburban, car-dependent nature of the market and guest expectations for home-like stays. Washer/dryer (78%), dedicated workspace (74%), and backyard access (74%) are also prevalent, signaling that guests expect comfortable, extended-stay-friendly amenities—while niche features like beach access (11%) and waterfront location (15%) could serve as strong differentiators for listings that offer them.
| Amenity | Trend | Value |
|---|---|---|
| Parking |
|
100% |
| Kitchen |
|
100% |
| Washer |
|
78% |
| Dryer |
|
78% |
| Workspace |
|
74% |
| Backyard |
|
74% |
| BBQ Grill |
|
63% |
| Self Check-in |
|
56% |
| Outdoor Furniture |
|
52% |
| Pets |
|
52% |
| Patio or Balcony |
|
48% |
| Waterfront |
|
15% |
| Gym |
|
11% |
| Beach Access |
|
11% |
Rabbu's ROI Score is a proprietary metric that evaluates short-term rental investment potential based on multiple factors.
| Factor | Westport Performance | Weight |
|---|---|---|
| Revenue-to-Price Ratio | Below average | 40% |
| Occupancy Stability | Average | 30% |
| Market Growth Trend | Above average | 15% |
| Supply/Demand Balance | Above average | 15% |
Westport's ROI score of 46 out of 100 places it in the 'Competitive Opportunity' band, meaning strong demand and investor interest exist but higher property prices create a challenging revenue-to-price ratio (rated below average). On the positive side, market growth trend and supply/demand balance both score above average, while occupancy stability is average—suggesting the market is expanding and not yet oversaturated. Investors should pair this data with thorough local regulatory research and conservative underwriting to identify deals where premium nightly rates can overcome the high cost of entry.
Understanding local STR regulations is essential before investing in Westport. Here's the current regulatory landscape:
Short-term rental operators in Westport, Connecticut may be required to obtain permits or register with local authorities before listing a property. Investors should verify current requirements directly with the Town of Westport and the State of Connecticut, as rules can evolve.
Common restrictions that may apply to STRs in this area include occupancy limits, minimum stay requirements, noise and parking regulations, and potential HOA restrictions for properties within managed communities. Some Connecticut municipalities also impose caps on the number of permits issued, so checking local availability early in the investment process is advisable.
Short-term rental hosts in Connecticut are generally subject to state room occupancy taxes and potentially local tourism-related assessments. Platforms like Airbnb often collect and remit some of these taxes automatically, but hosts should confirm their full obligations with a tax professional to ensure compliance.
Regulations subject to change. Always verify with local authorities before purchasing. A Rabbu partner agent specializing in Westport can provide current regulatory guidance.
Financing an Airbnb investment in Westport requires lenders who understand STR income. Rabbu partner lenders offer:
"Over the next 12–18 months, Westport's STR market is likely to see continued upward pressure on demand given its above-average market growth trend and favorable supply/demand balance. Summer months should remain the primary revenue driver, with July and August rates potentially pushing ADR even higher as listing growth (up 244% year-over-year) attracts more traveler awareness. Investors can reasonably expect occupancy in the 22–28% range on an annualized basis, though peak summer months may deliver significantly higher fill rates. ADR increases of 2–5% are plausible given the affluent guest profile, though new supply entering the market could moderate gains."
— Rabbu Market Analysis Team
Rabbu provides Airbnb and short-term rental market data and statistics across the United States. Our mission is to empower investors with accurate insights and easy-to-use tools, so they can confidently identify and act on the best opportunities in the Airbnb market.
Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Apr, 27 2026. Revenue projections are estimates based on comparable properties and do not guarantee future performance. Data reflects trailing 12-month averages as of April 2026 and may not capture very recent market shifts. Local regulations, HOA rules, and tax obligations vary and should be independently verified before investing.
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