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View PropertiesAs of Apr, 27 2026
Rabbu ROI Score
Oak Bluffs presents a competitive opportunity: investor interest and demand are strong, but higher prices or tighter competition may require more selective deal sourcing.
Oak Bluffs on Martha's Vineyard commands a premium average daily rate of $612—above the Massachusetts state average of $582—driven by its status as a sought-after island destination. With just 32 active Airbnb listings and average annual revenue of $79,550, this is a small, high-ADR market where selective deal sourcing matters. Home values averaging nearly $2 million mean the revenue-to-price ratio demands careful underwriting, but the extreme summer seasonality can deliver outsized monthly returns during peak months.
According to Rabbu market data, the Oak Bluffs short-term rental market shows:
| Metric | Context | Value |
|---|---|---|
| Active Airbnb Listings | As of Apr, 27 2026 | 32 |
| Average Daily Rate (ADR) | vs. $582 state avg. | $612 |
| Average Occupancy Rate | vs. 44% state avg. | 18% |
| RevPAN | ADR * Occupancy Rate | $111 |
| Average Monthly Revenue | Historical 12-month average | $6,629 |
| Average Annual Revenue | Historical 12-month average | $79,550 |
Data sources: Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Mar, 17 2026.
Investors are drawn to Oak Bluffs for its premium nightly rates, iconic Martha's Vineyard location, and naturally constrained supply on an island market.
Key investment factors
"Oak Bluffs presents a competitive but narrowly seasonal opportunity best suited for investors comfortable with a concentrated earning window. August ($21,669) and July ($20,290) deliver roughly half the year's revenue in just two months, while winter months dip below $1,100—creating a pronounced cash-flow cycle. The market's ROI score of 50 out of 100 reflects average revenue-to-price ratios and occupancy stability alongside below-average growth trends and supply/demand balance, underscoring that profitability here hinges on maximizing summer returns. Investors who can secure well-located, amenity-rich properties at a reasonable basis relative to the $1.98M average home value will find the strongest path to positive returns."
— Rabbu Market Analysis Team
Oak Bluffs exhibits extreme seasonality: August leads at $21,669 and July follows at $20,290, while February bottoms out at just $662—a roughly 33x spread between peak and trough. Investors should expect approximately 75% of annual revenue to land within the June-through-September window.
| Month | Trend | Revenue |
|---|---|---|
| January |
|
$915 |
| February |
|
$662 |
| March |
|
$1,073 |
| April |
|
$2,801 |
| May |
|
$5,897 |
| June |
|
$10,385 |
| July |
|
$20,290 |
| August |
|
$21,669 |
| September |
|
$8,860 |
| October |
|
$3,791 |
| November |
|
$1,596 |
| December |
|
$1,606 |
Two- and three-bedroom units each account for 9 listings, making them the most common configurations, while 1-bedroom (5 listings) and 4-bedroom (6 listings) properties are less represented. The relatively thin supply of larger 4-bedroom homes could present an opportunity given their significantly higher revenue potential.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
5 |
| 2 bedrooms |
|
9 |
| 3 bedrooms |
|
9 |
| 4 bedrooms |
|
6 |
ADR nearly triples from $254 for 1-bedroom units to $718 for 4-bedroom properties, reflecting strong group and family demand on the island. The jump from 2 bedrooms ($479) to 3 bedrooms ($640) is particularly notable, suggesting that mid-size properties offer a meaningful pricing premium without the acquisition cost of the largest homes.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$254 |
| 2 bedrooms |
|
$479 |
| 3 bedrooms |
|
$640 |
| 4 bedrooms |
|
$718 |
RevPAN climbs steadily from $26 for 1-bedroom listings to $159 for 4-bedroom properties, indicating that larger units not only charge more but also convert that pricing into stronger per-night revenue after accounting for occupancy. The gap between 1-bedroom and 2-bedroom RevPAN ($26 vs. $101) is especially stark, suggesting a minimum of 2 bedrooms for viable returns.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$26 |
| 2 bedrooms |
|
$101 |
| 3 bedrooms |
|
$139 |
| 4 bedrooms |
|
$159 |
Occupancy rates cluster at 21–22% for 2-, 3-, and 4-bedroom properties, while 1-bedroom units trail at just 11%, reflecting weaker demand for smaller accommodations in this vacation-oriented market. These rates are modest overall but consistent across the larger property sizes, reinforcing that revenue differentiation comes primarily through ADR rather than occupancy.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
11% |
| 2 bedrooms |
|
21% |
| 3 bedrooms |
|
22% |
| 4 bedrooms |
|
22% |
Four-bedroom properties lead at $12,878 per month on average, more than double the $5,981 earned by 2-bedroom listings. Three-bedroom units occupy a strong middle ground at $10,549 monthly, offering a compelling revenue profile that may come at a lower acquisition cost than the largest homes.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$6,173 |
| 2 bedrooms |
|
$5,981 |
| 3 bedrooms |
|
$10,549 |
| 4 bedrooms |
|
$12,878 |
Annual revenue ranges from $71,777 for 2-bedroom properties to $154,540 for 4-bedroom homes, with 3-bedroom units generating $126,594—a configuration that may offer the best return potential when weighed against purchase price. Even 1-bedroom listings earn $74,077 annually, though their low occupancy rate makes them riskier propositions.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$74,077 |
| 2 bedrooms |
|
$71,777 |
| 3 bedrooms |
|
$126,594 |
| 4 bedrooms |
|
$154,540 |
Parking is a universal amenity at 100% of listings—likely essential on an island with limited transit—while kitchen (84%), dryer (84%), and washer (75%) signal that guests expect full home comforts for extended vacation stays. Outdoor-oriented amenities like BBQ grills (69%), backyards (63%), and patios (63%) are also prevalent, confirming that properties with strong outdoor living spaces are best positioned for this market.
| Amenity | Trend | Value |
|---|---|---|
| Parking |
|
100% |
| Dryer |
|
84% |
| Kitchen |
|
84% |
| Washer |
|
75% |
| BBQ Grill |
|
69% |
| Self Check-in |
|
66% |
| Backyard |
|
63% |
| Patio or Balcony |
|
63% |
| Outdoor Furniture |
|
56% |
| Workspace |
|
34% |
| Pets |
|
25% |
| Beach Access |
|
22% |
| Lake Access |
|
9% |
| Hot Tub |
|
9% |
Rabbu's ROI Score is a proprietary metric that evaluates short-term rental investment potential based on multiple factors.
| Factor | Oak Bluffs Performance | Weight |
|---|---|---|
| Revenue-to-Price Ratio | Average | 40% |
| Occupancy Stability | Average | 30% |
| Market Growth Trend | Below average | 15% |
| Supply/Demand Balance | Below average | 15% |
Oak Bluffs earns an ROI score of 50 out of 100, placing it in the 'Competitive Opportunity' band where strong demand coexists with high entry costs. Revenue-to-price ratio and occupancy stability both rate as average, reflecting that the $79,550 average annual revenue faces a steep denominator in nearly $2M home values—while market growth trend and supply/demand balance score below average, suggesting rising competition from a 215% year-over-year increase in listings. Pairing this data with thorough local regulatory research and conservative financial modeling is essential before committing capital to this market.
Understanding local STR regulations is essential before investing in Oak Bluffs. Here's the current regulatory landscape:
Oak Bluffs, Massachusetts may require short-term rental operators to register or obtain a permit before listing a property—investors should verify current requirements directly with the Town of Oak Bluffs and the Massachusetts state regulatory framework.
Common restrictions in island and coastal Massachusetts communities can include occupancy limits, minimum stay requirements, noise and parking regulations, and potential caps on the number of permits issued. HOA or neighborhood covenants may add additional layers, so it's important to review property-specific restrictions before purchasing.
Massachusetts imposes a state room occupancy tax on short-term rentals, and local municipalities like Oak Bluffs may levy additional community impact fees or local excise taxes. Platforms such as Airbnb often collect and remit these taxes on behalf of hosts, but operators should confirm their full tax obligations with local authorities.
Regulations subject to change. Always verify with local authorities before purchasing. A Rabbu partner agent specializing in Oak Bluffs can provide current regulatory guidance.
Financing an Airbnb investment in Oak Bluffs requires lenders who understand STR income. Rabbu partner lenders offer:
"Over the next 12–18 months, Oak Bluffs is likely to see continued strong summer demand with July and August driving the lion's share of annual revenue. ADR may hold steady or edge up modestly by 1–3% given limited island supply, though occupancy could remain compressed outside the June-through-September window. The 215% year-over-year growth in active listings signals rising investor interest, which may tighten competition for bookings during shoulder months. Investors should plan conservatively around a 4–5 month earning season and treat off-peak revenue as supplemental rather than foundational."
— 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 Mar, 17 2026. Revenue projections are estimates based on comparable properties and do not guarantee future performance. Data reflects trailing 12-month historical performance and current market conditions as of April 2026; future results may differ due to regulatory changes, economic shifts, or competitive dynamics. Individual property performance depends on factors including location, condition, amenities, pricing strategy, and operational management.
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