Short-term rentals (STRs) have become one of the most attractive ways to build wealth in real estate. They can provide a steady stream of income, long-term appreciation, and the flexibility to enjoy the property yourself when it’s not booked. But not every home makes a great rental. The best investments have certain qualities that consistently attract guests and maximize returns.
Here’s a checklist of what to look for when evaluating a short-term rental property:
1. Location, Location, Location
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Proximity to attractions: Homes near beaches, trails, parks, or town centers consistently perform well.
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Accessibility: Easy access to highways, ferries, or airports makes it convenient for guests.
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Neighborhood vibe: Quiet streets close to amenities can offer the best of both worlds.
💡 Example: My property at 118 Bay Road in Eastham is steps from a private association bay beach which is exactly the type of location guests are searching for when booking a Cape Cod getaway.
2. Layout and Space
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Bedrooms & bathrooms: More bedrooms = higher occupancy potential. A 3-bedroom home typically appeals to families and groups.
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Open common areas: Open-concept living, dining, and kitchen spaces make it easier for groups to gather.
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Flexible bonus rooms: Finished basements, lofts, or enclosed porches can serve as playrooms, offices, or extra sleeping space.
💡 118 Bay Road has an inviting open layout plus screened porches that double as extra hangout spaces.
3. Amenities That Attract Bookings
Guests often filter their search by amenities and the right features can make your property stand out.
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Outdoor living: Decks, patios, fire pits, and outdoor showers are highly desirable.
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Views: Water views, sunset decks, or balconies can command higher nightly rates.
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Modern conveniences: Reliable WiFi, updated kitchens, and in-home laundry are essentials for today’s travelers.
💡 This home offers a rooftop deck with sunset views, screened porches, and an outdoor shower - all features that add to its rental appeal.
4. Local Rental Laws and Regulations
Before buying, it’s critical to understand the rules for short-term rentals in your target market.
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Permits: Many towns require a license or registration for STRs.
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Zoning & occupancy limits: Some communities restrict how many guests can stay or how many nights a property can be rented each year.
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Taxes & fees: Be aware of state or local lodging taxes and how they affect your bottom line.
5. Maintenance and Management
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Durability: Homes with easy-to-maintain finishes and systems are best for frequent guest turnover.
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Cleaning & turnovers: Factor in costs for professional cleaning between stays.
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Property management: If you don’t live nearby, a local property manager can handle guest communication, maintenance, and emergencies.
The Takeaway
The best short-term rental investments combine a prime location, guest-friendly layout, and desirable amenities all within the framework of local regulations.
Properties like 118 Bay Road in Eastham, with deeded beach access, screened porches, a rooftop deck, and an outdoor shower, show how the right features can both delight guests and generate strong returns.
If you’re thinking about investing in a short-term rental, use this checklist as a guide and don’t hesitate to reach out. I’d love to help you evaluate properties and find the one that checks all the right boxes.
Questions? Contact Alison Borrelli of Berkshire Hathaway HomeServices Commonwealth.
📞 (617) 257-3012 | 📧 [email protected]
