12 guests
-
6 bedrooms, 7 beds
6 bathrooms
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Live the life of a film star amongst the vintage Hollywood memorabilia of this extraordinary, tropical island retreat. Housed on Shelter Island, this home is a far cry from high rise New York. Retro 80s diner, meet Copacabana. Let your hair down and turn up the volume as you sip a pina colada in the pool from atop an inflatable flamingo and gaze out over the sound and palms. Now that is the life we’re talking about. At your very own Club Tropicana, drinks are free with a stylish cocktail bar to kick start the evening (or the day – there’s no judgement here). Large windows and folding doors out onto balconies and a multi-levelled deck with fire pit and barbecue all draw your eyes to three-hundred feet of your very own private beachfront. Inviting you in for a surf or swim, the water’s call is hard to resist. But, inside, the activities are endless too. A racquetball court, gym, media room with Apple TV, lofted games room with pool and shuffleboard, as well as an indoor pool and spa will have you spoilt for choice. The stars of the screen haven’t got much on you here, and with no director to shout “cut” this life of luxury carries an endless running time, sunset after sunset.
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What to expect
Highlights
Take in the view of Shelter Island Sound
Swim and surf down on your private beachfront
Never miss a sunset with balconies and terraces galore
Shake and stir a few cocktails to start the evening
Carry on the party outside round the firepit
Screen your very own premiere in the home cinema
Work up a sweat on the racquetball court
Wake up well with a morning workout in the gym
Like what you see? Explore more of this home
Home truths
If you are staying here outside of the summer months, be sure to check with your host that pool facilities are still available due to the northeastern climate
Pets are not allowed here, but express approval can be provided by your hosts in certain circumstances
This home is available only for members of the same family
If you're planning on hiring a car, keep in mind that you will need to catch a boat to get to Shelter Island
About this stay
Amenities
Gym
Wi-fi
Air conditioning
Parking available
Washing machine
Dryer
Swimming pool
Hot tub
Bedrooms & bathrooms
6 bedrooms, 7 beds
6 bathrooms
Extras
VIP services
Airport pick up
Daily cleaning
Fridge fills
Additional fees
There may be some extra fees to pay here, such as charges for utilities, final cleaning fees, city tax and security deposits – all of which you may need to pay in cash to the homeowner. Please reach out during the booking process to confirm.
Additional fees subject to a 3.5% handling charge.
Extras are subject to availability. Please enquire with your host.
Local guide
About Shelter Island
Reachable only by ferries, private boats, or small seaplanes, getting to Shelter Island is something of an adventure. And once you’re there, its turn-of-the-century charm, historical buildings, relaxed attitude and endless nature preserves (that make up one-third of the island) captivate city escapees and year-round residents alike. This bucolic island has quaint restaurants that feel more like home kitchens, farmer’s markets at the island’s historical society and silky stretches of...
Explore the area
Local restaurants, cafes, museums, sites and activities, recommended by our community of hosts and travel experts
Paddle through Shelter Island with Venture Out
Venture Out Paddle Board Rentals offers an unforgettable experience exploring Shelter Island's waters. With knowledgeable guides, top-notch equipment, and excellent service, it's the perfect way to stay active and have fun on your holiday.
Stay at Shelter Island House
Quaint country inn with casual-chic rooms, outdoor lounge, bakery, pool, and friendly staff. Enjoy private beaches, biking, and good food nearby. A lovely weekend getaway.
Explore the Rich Political History of Shelter Island
Immerse yourself in the fascinating political history of Shelter Island, a locality known for its significant role in shaping the region's governance. Discover historical landmarks and gain a deeper understanding of the area's past.
Explore Mitchell Park & Marina
A perfect beach for families with little kids, featuring a delightful carousel ride and a picturesque boardwalk. Enjoy the vibrant atmosphere with concerts and dancing, or simply take a leisurely walk around the beautiful marina.
Dine at Noah's
Experience the best of New American cuisine with a focus on local ingredients at this modern restaurant and bar. Indulge in incredible seafood dishes, from lobster rolls to tuna poké bowls, and enjoy generous portions and stellar service.
Savour Fresh Oysters at Little Creek Oyster Farm & Market
Shucked oysters & local beers served in a snug harborside cottage with a market & outdoor seating. Great atmosphere, delicious drinks, and an A+ waterfront location.
Shop at The Weathered Barn
Discover a genuinely lovely store in the North Fork that offers unique, high-quality items at fair prices. From diffusers and candles to soaps and cookware, this is the go-to shop for gifts and personal indulgences.
Explore 67 Steps Beach
A cute little rocky beach with beautiful views and clear waters. Accessible only by wooden stairs, it offers an intimate and quiet place to enjoy the ocean on Long Island.
Savour the Scenic Views at Kontokosta Winery
Indulge in a delightful experience at Kontokosta Winery, offering breathtaking views of the sound. Sip on exquisite wines and relish delectable snacks amidst the stunning surroundings of this charming establishment.
Explore the Serene Ruth Oliva Preserve
Take a leisurely stroll along the red trail and be treated to stunning views of waterfront and woodlands. Spot deer, ospreys, and even eagles with fish in their talons.
Sail the Stunning Bays with Sag Harbor Sailing
Sag Harbor Sailing Inc. is a passionate team of experienced sailors offering boat rentals, sailing lessons, and overnight charters. With well-maintained boats and knowledgeable instructors, this is the perfect activity to explore the Hamptons from a new perspective.
Dine at Bell & Anchor
Upscale, seafood-centric New American cooking served in a bustling, nautical setting with bay views. Enjoy delicious drinks, incredible oysters, and stunning entrees. A great restaurant to explore in Southampton and Sag Harbor.
Booking policies
House Rules
Children welcome (1-12 years)
Infants welcome (under 12 months)
No pets
No smoking
No parties or events
Good to know
Arrival from 15:00
Departure before 11:00
Air con
Wifi
Cancellation policy
Up until
60
days
Cancel at least 60 days before your check-in date for a 50% refund.
Not eligible for a refund once your check-in date is under 60 days away.
Host
This home is managed by Bryan
This home is managed directly by a business. A member of their staff will be your point of contact before and during your stay. Bryan and his team are vacation experts, especially when it comes to The Hamptons and surrounding towns. With years of experience, they’re with you every step of the vacation rental process – and they take pride in giving their guests a personalised experience to remember.
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