Luxury vacation rentals: beautifully furnished homes in Shelter Island
Why Visit Shelter Island?
Shelter Island is the East End distilled—protected woods, calm bays, and real privacy.
Mornings can start with laps in clear water, a shoreline walk, or a quiet biker ide beneath oaks and pines; afternoons slip to sandy crescents with gentle entry, kayaks on still coves, or a shaded deck that turns lunch into a linger.
As the light softens, it’s an easy glide on the Sound, oysters at golden hour, and dinner in a room that feels composed rather than crowded. Distances are short, ferries keep the mood intimate, and every alternate plan is close and just as good—trail if the sun is high, cove if the ocean’s lively, early seating when you want time together.
Rove's Featured Must-See: Mashomack Preserve
Discover the Mashomack Preserve, covering a third of the island with rich ecosystems, hiking, and bird watching, all highlighting Long Island's purest natural appeal. Walk along calming boardwalks and spot local wildlife, for a perfect calming afternoon. Visit Mashomack Preserve
What To Do in Shelter Island
Shelter Island History Museum
The Shelter Island Historical Society centers on the 1743 Havens House and a modern History Center, pairing an intimate historic home with galleries, research space, and year-round programs. Its collections are deep—over 100,000 maps, deeds, diaries, photographs, and artifacts spanning the 17th–21st centuries—alongside rotating exhibits, talks, and community events on the green. It’s a stop that brings the island’s story close, from maritime roots to village life. Visit Shelter Island History Museum
Rams Head Inn
A chic, historic hideaway on Ram Island—a hillside manor with sweeping bay views, gracious country rooms (Frette linens, modern comforts), and a dining to rave about. Built in 1929 and newly revitalized, it balances heritage with ease—quiet lawns, beachfront access, and an atmosphere fit for lingering over oysters and a martini. Notably, the inn has a full calendar of events, and even hosted the landmark 1947 Shelter Island Conference on quantum mechanics—proof it’s long been a retreat for serious taste and good conversation. Visit Ram's Head Inn
Sylvester Manor
Sylvester Manor on Shelter Island is a 236-acre historic site and working educational farm, set on the ancestral homelands of the Manhansett people and preserved as one of the most intact remnants of a Northern provisioning plantation. Today, guided house and grounds experiences, farm visits, and arts programs present a fuller story—Indigenous, African, and European—alongside quiet walks, fields, and waterfront views. It’s a thoughtful, beautifully kept place to engage with Long Island history. Visit Sylvester Manor
Outdoor Adventures in Shelter Island
Crescent Beach
Relax, swim, and sunbathe on soft sands and in calm waters. Then, sip a cocktail and watch the sunset from one of the lively beach bars. Visit Crescent Beach
Shelter Island Country Club
Play a round at "Goat Hill," a public golf course amid incredible views and rolling hills in relaxed island vibes. Visit Shelter Island Country Club
Shell Beach
For those who like to go off the beaten path, this is the perfect spot to collect seashells, windsurf, or take a gentle stroll on the narrow beach with waters on both sides and panoramic views. Visit Shell Beach
Our Favorite Restaurants in Shelter Island
Vine Street Café
Fresh, locally sourced ingredients and inventive culinary artistry in a cozy, welcoming setting with a focus on sustainability. Visit Vine Street Café
Stars Cafe
Take a coffee break or sit down for a delicious breakfast with quality baked goods in this community-driven coffee space with warm customer service and local charm. Visit Stars Cafe
The Eccentric Bagel
Eccentric Bagel is Shelter Island’s first dedicated bagel shop—a small, upbeat spot turning out fresh, handmade bagels, hefty breakfast sandwiches, good coffee, and its cult-favorite baked bagel chips (in flavors from everything to black-garlic–truffle). Swing by early and take a dozen for the house. Visit The Eccentric Bagel
48 Hours in Shelter Island
Get Rove's insider tips for spending a weekend in Shelter Island to make the best of your stay.
Day 1
- Morning: Coffee and pastries at Stars Cafe, then a shoreline stroll at Crescent Beach before the day warms.
- Afternoon: Long, unhurried hike at Mashomack Preserve—choose an easy loop for birding or stretch it to the water—then a late browse at Black Cat Books and Marika’s.
- Evening: Sunset cocktails and dinner on the marina at Salt Waterfront Bar & Grill, or linger over a meal at Vine Street Café; close with a harbor walk.
Stars Cafe
Take a coffee break or sit down for a delicious breakfast with quality baked goods in this community-driven coffee space with warm customer service and local charm. Visit Stars Cafe
Black Cat Books
Black Cat Books is a beloved Shelter Island institution (est. 1996), buying and selling fine used and rare books— vintage collectibles, signed first editions, and a deeply curated general selection. The shop boasts two floors and 20,000+ titles, making it as rewarding for a quick browse as it is for collectors on the hunt. Visit Black Cat Books
Salt Waterfront Bar & Grill
Salt Waterfront Bar & Grill sits on West Neck Harbor with dockside tables, marina views, and a breezy, boater-friendly rhythm—ideal for oysters at golden hour, sushi and raw bar, or a warm or chilled lobster roll. Family-owned and locally sourced, it’s an easy glide from boat to table. Visit Salt Waterfront Bar & Grill
Day 2
- Morning: Paddle the Coecles Harbor Marine Water Trail to quiet coves, or play nine with views at Shelter Island Country Club (Goat Hill). Have a pick-me-up espresso stop, then a stop at Shelter Island Florist.
- Afternoon: Step into the island’s story at the Shelter Island Historical Society, then slip to Shell Beach for a yoga stretch, and a gentle-entry swim.
- Evening: Time dinner to blue hour—return to Vine Street Café for a lingering meal, or book a table at the Rams Head Inn when there’s live music; finish with a quiet drive under big sky.
Shelter Island Florist
Admire gorgeous floral arrangements and charming gifts that reflect the island’s relaxed and elegant vibe. Visit Shelter Island Florist
Shell Beach
For those who like to go off the beaten path, this is the perfect spot to collect seashells, windsurf, or take a gentle stroll (or have a yoga session) on the narrow beach with waters on both sides and panoramic views. Visit Shell Beach
Ram's Head Inn
A chic, historic hideaway on Ram Island—a hillside manor with sweeping bay views, gracious country rooms (Frette linens, modern comforts), and a dining to rave about. Built in 1929 and newly revitalized, it balances heritage with ease—quiet lawns, beachfront access, and an atmosphere fit for lingering over oysters and a martini. Notably, the inn has a full calendar of events, and even hosted the landmark 1947 Shelter Island Conference on quantum mechanics—proof it’s long been a retreat for serious taste and good conversation. Visit Ram's Head Inn
Best Shops and Local Gems in Shelter Island
Marika’s
Shop for curated home décor items that capture the bohemian elegance of Shelter Island life. Visit Marika's
Cornucopia Gift Shop
Stop by and select the perfect gift for that special someone (or for yourself, we won't tell. Discover an array of tastefully selected trinkets to suit sophisticated tastes. Visit Cornucopia Gift Shop
Shelter Island Florist
Admire gorgeous floral arrangements and charming gifts that reflect the island’s relaxed and elegant vibe. Visit Shelter Island Florist
Why Stay in a Rove in Shelter Island
Find a secluded sanctuary on Shelter Island with Rove’s luxury vacation rentals, perfect for those seeking privacy and natural beauty. Accessible only by ferry, this serene escape provides a tranquil backdrop for relaxation. Rove’s luxury vacation homes offer spacious luxury vacation apartments with sophisticated design and luxurious amenities. Enjoy a seamless stay with Rove as you explore the island’s pristine beaches, lush nature reserves, and exclusive, peaceful ambiance.
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Luxury Furnished Rentals in The Hamptons: FAQs
Why stay with Rove in The Hamptons?
At Rove, we offer seamless short-term rental experiences with our furnished luxury vacation homes in the Hamptons.
Our expert team, with years of experience in the New York area, hand-selects all our vacation rentals, ensuring high-end luxury and comfort.
Our fully furnished properties are equipped with everything you need for a perfect summer getaway, including well-stocked kitchens, elegantly designed living spaces, and dedicated work areas for remote professionals.
Many Rove homes are pet friendly with an additional cleaning fee - our four-legged friends are family, too.
You can find our properties in desirable neighborhoods like Southampton, East Hampton, Sag Harbor, and more.
Whether you're looking for a relaxing beachfront retreat or an upscale workation destination, Rove ensures you experience the very best of the Hamptons.
At Rove, we offer seamless short-term rental experiences with our furnished luxury vacation homes in the Hamptons.
Our expert team, with years of experience in the New York area, hand-selects all our vacation rentals, ensuring high-end luxury and comfort.
Our fully furnished properties are equipped with everything you need for a perfect summer getaway, including well-stocked kitchens, elegantly designed living spaces, and dedicated work areas for remote professionals.
Many Rove homes are pet friendly with an additional cleaning fee - our four-legged friends are family, too.
You can find our properties in desirable neighborhoods like Southampton, East Hampton, Sag Harbor, and more.
Whether you're looking for a relaxing beachfront retreat or an upscale workation destination, Rove ensures you experience the very best of the Hamptons.
Do all your short term rentals come fully furnished?
Yes. All Rove homes come fully furnished with award-winning interior designs, providing you with a comfortable home away from home.
Our homes feature fully stocked kitchens and premium finishes, such as toiletries, linens and towels.
Yes. All Rove homes come fully furnished with award-winning interior designs, providing you with a comfortable home away from home.
Our homes feature fully stocked kitchens and premium finishes, such as toiletries, linens and towels.
Can I book a monthly rental or seasonal rental in The Hamptons?
Of course! We offer discounted rates for extended monthly rentals, with the discounts applied automatically on our website. You're welcome to stay as long as you like, whether it's for a month or a full season.
Of course! We offer discounted rates for extended monthly rentals, with the discounts applied automatically on our website. You're welcome to stay as long as you like, whether it's for a month or a full season.
What if I would like to extend my property rental?
Certainly! We'd be delighted to accommodate your extended stay in the Hamptons. Extensions are subject to availability and require at least 24 hours' notice before your original checkout time. Please send an email or message to our concierge team at concierge@rovetravel.com.
Certainly! We'd be delighted to accommodate your extended stay in the Hamptons. Extensions are subject to availability and require at least 24 hours' notice before your original checkout time. Please send an email or message to our concierge team at concierge@rovetravel.com.
Do your properties come with pools?
Several of our Hamptons house rentals feature private pools for you to enjoy during your stay. Our listings show all amenities to ensure you get exactly what you're looking for in a Rove home.
Several of our Hamptons house rentals feature private pools for you to enjoy during your stay. Our listings show all amenities to ensure you get exactly what you're looking for in a Rove home.
Do you offer last minute Hampton rentals?
While last-minute availability may be limited, we always make our inventory available after cancellations. For peak summer months (June-September), it's advisable to start booking as early as February.
While last-minute availability may be limited, we always make our inventory available after cancellations. For peak summer months (June-September), it's advisable to start booking as early as February.
What are some must-visit places in The Hamptons?
The Hamptons offer so many exciting places to explore, from beautiful beaches to charming villages. To discover the best places to visit in The Hamptons, check out our blog post: Discover the Best Places to Visit in The Hamptons.
The Hamptons offer so many exciting places to explore, from beautiful beaches to charming villages. To discover the best places to visit in The Hamptons, check out our blog post: Discover the Best Places to Visit in The Hamptons.
Does Rove offer corporate housing options?
Rove does indeed offer corporate housing solutions designed to meet the unique needs of your business travelers. If your business is interested in housing an employee in a Rove furnished rental, please reach out to our team at concierge@rovetravel.com.
For more insights into corporate housing, budgeting, and amenities, explore these informative blog posts:
What Is Corporate Housing? Discover the concept of corporate housing and how it can benefit your business travelers. Get insights into the advantages and features of corporate housing.
Furnished Corporate Housing: The Ideal Solution for Business Travelers Find out why furnished corporate housing is the perfect solution for business travelers. Learn about the convenience and comfort it offers, making it a top choice for corporate stays.
Rove does indeed offer corporate housing solutions designed to meet the unique needs of your business travelers. If your business is interested in housing an employee in a Rove furnished rental, please reach out to our team at concierge@rovetravel.com.
For more insights into corporate housing, budgeting, and amenities, explore these informative blog posts:
What Is Corporate Housing? Discover the concept of corporate housing and how it can benefit your business travelers. Get insights into the advantages and features of corporate housing.
Furnished Corporate Housing: The Ideal Solution for Business Travelers Find out why furnished corporate housing is the perfect solution for business travelers. Learn about the convenience and comfort it offers, making it a top choice for corporate stays.