Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Shelter Island, New York
Shelter Island, New York, offers a diverse range of Airbnb accommodations that cater to various preferences and group sizes. Visitors can choose from charming waterfront cottages that provide stunning views of the surrounding bays, perfect for those seeking a tranquil retreat. There are also elegant historic homes that capture the island's rich heritage, offering a unique blend of old-world charm and modern amenities. For a more contemporary stay, guests can opt for stylish, newly renovated houses equipped with luxurious features such as private pools and expansive decks. Additionally, cozy guest suites and apartments are available for solo travelers or couples looking for a more intimate setting. Many of these properties emphasize outdoor living, with beautiful gardens, patios, and easy access to the island's natural attractions, making Shelter Island a delightful destination for a relaxing getaway.
In Shelter Island, New York, short-term rentals, including those listed on platforms like Airbnb, are subject to specific regulations to maintain the character of the community. Property owners must obtain a rental permit from the town, which requires compliance with safety and zoning standards. The permit process includes an application fee and may involve inspections to ensure the property meets local codes. Additionally, there are restrictions on the number of days a property can be rented out short-term, typically limiting rentals to a certain number of days per year to prevent the commercialization of residential neighborhoods. Hosts are also required to collect and remit applicable taxes, including the New York State sales tax and the Suffolk County hotel/motel tax, which contribute to local revenues. These regulations aim to balance the economic benefits of short-term rentals with the need to preserve the residential nature and quality of life on Shelter Island.
Managing an Airbnb property on Shelter Island, New York, involves several key tasks to ensure a successful operation. First, maintaining the property to a high standard is crucial, which includes regular cleaning, landscaping, and addressing any maintenance issues promptly. Given the island's appeal as a vacation destination, effective marketing strategies are essential to attract guests, such as optimizing the listing with high-quality photos and detailed descriptions. Additionally, managing bookings and guest communications efficiently is vital, ensuring a seamless check-in and check-out process. Compliance with local regulations and obtaining necessary permits is also important to avoid legal issues. Finally, providing exceptional guest experiences through personalized touches and local recommendations can lead to positive reviews and repeat bookings, enhancing the property's reputation and profitability.
Shelter Island, New York, offers a serene and picturesque getaway with several ideal areas for an Airbnb stay. Dering Harbor is a charming spot known for its historic homes and stunning waterfront views, perfect for those seeking a tranquil retreat. The Heights is another popular area, offering a blend of Victorian architecture and easy access to local shops and restaurants, making it ideal for visitors who enjoy a quaint village atmosphere. For nature enthusiasts, staying near Mashomack Preserve provides an opportunity to explore miles of hiking trails and observe diverse wildlife. Each of these areas offers a unique experience, ensuring a memorable stay on Shelter Island.
Shelter Island, New York, presents a promising Airbnb investment opportunity due to its unique blend of natural beauty, exclusivity, and proximity to popular tourist destinations. Nestled between the North and South Forks of Long Island, Shelter Island offers a serene escape with its pristine beaches, lush nature preserves, and charming small-town atmosphere. The island's limited accessibility, primarily via ferry, adds to its allure as a secluded getaway, attracting visitors seeking tranquility and a break from the bustling Hamptons scene. The demand for short-term rentals is bolstered by the island's appeal to affluent travelers and its seasonal influx of tourists, particularly during the summer months. Investors can capitalize on the high occupancy rates and premium rental prices, making Shelter Island a lucrative market for Airbnb ventures.
Shelter Island, New York, is a popular destination for Airbnb rentals, with hosts typically experiencing strong demand, especially during the summer months. The average Airbnb revenue in this area can vary significantly depending on factors such as location, property size, and amenities offered. Generally, hosts on Shelter Island can expect to earn a substantial income during peak tourist seasons, with some properties generating several thousand dollars per month. However, during the off-season, revenues may decrease as visitor numbers decline. Overall, the potential for Airbnb revenue on Shelter Island is promising, particularly for well-maintained and strategically marketed properties.
Shelter Island, New York, experiences a distinct seasonality in its Airbnb occupancy rates, primarily driven by its appeal as a summer destination. The occupancy rates tend to peak during the summer months, particularly from June to August, when tourists flock to the island to enjoy its beaches, outdoor activities, and serene environment. During this period, occupancy rates can reach upwards of 80-90%, reflecting the high demand for short-term rentals. In contrast, the off-peak months, especially from late fall through early spring, see a significant drop in occupancy, often falling below 50%, as the island's attractions are less accessible and the weather less inviting. This seasonal fluctuation is typical for vacation destinations like Shelter Island, where tourism is heavily influenced by weather and seasonal events.
Why Choose Checkmate Rentals?
![]() | Other Property Managers | |
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Cost | Starting at 15% fee | 25-40% fee |
Guest Communications | Guest response within 10 minutes, 24 hours a day | Sporadic guest communications |
Host Communications | Designated host call in phone line | Bot response assistants |
Insurance | Full damage protection for every reservation | Unreliable insurance coverage |
Contract | No annual agreements | Contract lock-ins |
Checkmate Rentals

Attract Guests
List on top booking sites
Optimize listings for SEO
Feature show-stopping photos
Competitive, dynamic pricing
Mangage Operations
Tailored pricing algorithms
24/7 guest service
Reliable, professional cleaning
Restocking & inventory management
Maintenance coordination


Host Care
Unlimited owner stays
Flexible contract options
East to use host portal
Set it and forget it billing
Exclusive insurance discounts via our partner network
Get in touch with us.

Checkmate Rentals is a full-service property manager. That means the Airbnb listing, the home, the guest and the work is our responsibility.
Local Team Support
Know that you have a friendly, accessible team right up the road to handle any property needs.
Guest Screenings
Book only the most qualified guests 25 and over who’ll enjoy your home the right way.
Unlimited Owner Use
Block off your vacation days with ease, and enjoy your home as often as you want.
Reliable Property Maintenance
Keep your home running smoothly around the clock with a fast, reliable maintenance team.
Transparent Finances
Transparent Finances Booking payouts get paid directly to you for full financial transparency. We never handle your money.
Fast 24/7 Guest Communication
Make every guest feel cared for with industry best response times of 1-15 minutes day and night.
Marketing
Target, attract & book qualified guests with photography, email marketing, and optimized listings.
Revenue Management
Get the competitive edge with dynamic pricing and rates optimized daily by your pricing manager.

Ready to make the jump?
Let's get started! Schedule a call today to learn more about Checkmate Rentals.