Fitness-friendly holiday rentals in Shelter Island

Farmhouse Style Hamptons Beach Home, Quogue

The Surf Farmhouse is a beach oasis only 1.5 hours from NYC! Classic coastal living at its best, this sundrenched house has an open floor plan, 3/4 of an acre and tons of family-friendly amenities. The home is a quick 7-minute drive to the nearest beach, and has access to more than 10 area beaches! Enjoy the quiet charm of the Hamptons—close to restaurants, wineries, farm stands, family farms, and amazing ocean/bay beaches. Designed for comfort and style, we can't wait to have you visit!

East Hampton Village Fringe, Renovated with Pool

This remarkable East Hampton home, nestled along a quiet cul-de-sac, is just moments from shopping, restaurants, and ocean beaches. The residence features an abundance of natural light, crisp neutral color tones, and tall, pitched ceilings that enhance the sense of space. The calming, heated pool provides a perfect retreat for relaxation. Please review our disclosures and house manual to ensure this home meets your needs and expectations. We want to make sure it’s the perfect fit for you.

New Chic SH Villa with Pool Sauna Gym Firepit

This newly renovated Southampton home features 4 spacious bedrooms and 3.5 luxurious bathrooms over two floors. The open-concept living area boasts high ceilings and a stunning wall of glass that opens to a serene pool area. Indulge in the spa-like master bath and enjoy gourmet meals prepared in the kitchen equipped with high-end appliances. The seamless indoor-outdoor flow is perfect for entertaining or relaxing. Experience modern elegance and comfort in this exquisite getaway near town.

AMG- Fall retreat Pool heated thru Oct. Walk2Town

Sleek renovated Amagansett home. Large corner property with Heated Saltwater Pool (May to late October) & separate cottage/pool house w/with Peloton, Sonos surround sound, large screen TV, bar & foosball table. Open kitchen w/marble counters. 2 baths with glass showers & Jacuzzi tub. Master with Queen bed, second bedroom has two twin beds. There is also an oversized sleeping loft with two twin beds. Bluestone patio with BBQ, dining & lounge area. Walk to town & beaches. No Pets.

Elegant Greenport Victorian -Winter Harbor House

Winter Harbor House is a stylish Victorian walking distance from the best restaurants, bars and beaches in Greenport Village. Absolutely perfect location. Only a few hundred feet from the Mitchell Park/Marina, Waterfront Boardwalk/Beach and the North Ferry to Shelter Island. Enjoy gorgeous marina views and great people watching from the front porch. This 1890's Victorian has all the modern amenities you want while making you feel like you're experiencing a part of Greenport's history.

Stunning North Fork House • Heated Pool/ Wineries

Chic and luxurious farmhouse retreat in North Fork. Set on a private 1-acre lot with a pool, lounge areas, and ocean breeze. Family-friendly and perfect for couples or a friends' getaway. Just 1.5 hours from NYC and close to beaches, wineries, farm stands, hiking, seafood, and golf. Enjoy fast Wi-Fi, a full kitchen, stylish interiors, outdoor pool, and landscaped grounds. Ideal for a peaceful escape, remote work, or wine country retreat near the Hamptons, North Fork and Shelter Island.

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Chic, 5-bedroom, 3.5 half-bath home is close to the water and the village of Southampton. The sparkling pool has a beautiful backdrop of a lushly landscaped garden. Southern exposure in the backyard brings an abundance of sunshine inside and out. The home includes an outdoor sauna, fire pit and rock garden perched above the pool for your very own spa retreat. The inside of the home is thoughtfully designed with a relaxed, chic & luxury feel making it the perfect Hamptons getaway.

Beachside Escape from NYC

Topping Rose House has been standing on the same intersection of Montauk Highway in Bridgehampton since 1843. The hotel was renovated and reopened in 2012 and is now the preeminent place to feel like a Hamptonite. In the summer, relax by the pool or bike to the Atlantic. In the winter, enjoy the stunning landscape of the villages of the Northeast. The hotel has 22 rooms, and is only listing on AirBnB for a limited time. The specific room type is assigned on the day of arrival.

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

Welcome to nature's retreat, our secluded North Fork haven where 2+ acres of wild beauty and private beach access promise unparalleled relaxation. Delight in our hot tub's warmth under the stars, unwind on swings, or glide on bay waters with our kayak. With enchanting porch views, an invigorating outdoor shower, and nearby organic farms, our cabin is an idyllic escape. Experience the local charm with vineyard tours and return to a haven of comfort and adventure.