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Homes for Rent in Shelter Island, NY Between $32,000 and $54,000

(1 - 15 of 241)
  1. This beautiful 4 bedroom home in a special bayfront enclave in Sag Harbor is steps away from the residents-only beach. Spacious 4 bedrooms and 3.5 baths on an acre of manicured grounds, with immense outdoor space for summer entertaining - think po...
    Mala Sander ·2 hours ago on RealtyWW
  2. Experience the epitome of a quintessential Hamptons summer. Positioned perfectly in the coveted stretch between Sag Harbor Village and East Hampton Village, this exquisite 4-bedroom rental home offers unparalleled proximity to the finest shopping,...
    Brendan Connolly ·4 hours ago on RealtyWW
  3. Enjoy the summer in this beautifully furnished 3-bedroom waterfront townhome on Hayground Cove in Watermill South, with a community pool, tennis courts, and a dock. Downstairs features a spacious foyer, living/dining room with fireplace, open kitc...
    Lawrence Ingolia ·40 minutes ago on RealtyWW
  4. Welcome to your luxurious summer retreat in Southampton, where timeless elegance meets modern comfort! Nestled between the serene waters of Shinnecock Bay and Peconic Bay, this exquisite rental property offers a unique blend of tranquility and sop...
    Robert Canberg ·16 hours ago on RealtyWW
  5. South of the highway, down the street from the Sagaponack School, sited on shy two acres, is this spacious renovated barn. Most of the windows and doors in all rooms face East and South offering beautiful light. There are five bedrooms in the main...
    Jane Gill ·42 minutes ago on RealtyWW
  6. A new rental in the Dunes! This adorable beach cottage has a renovated kitchen and baths and backs up onto a reserve. Great layout with EIK, dining room, big bright living room, and primary separate from other bedrooms, but all on one floor. South...
    Victoria Thompson ·1 day ago on RealtyWW
  7. This restored 1890s Shelter Island Heights Victorian with covered wrap-around porch has beautiful water views overChase Creek, and Dering Harbor. Perfect spot for morning coffee, quiet afternoons relaxing with a book and outdoor dining under the s...
    M. Wein Realty Inc. ·18 hours ago on LinkuRealty
  8. THINKING ABOUT NEXT SUMMER?Make your plans now. Enjoy this water front property, with its own private beach, just steps away from the Shelter Island Yacht Club, relax watching the regatta's pass by. In close proximity to all the Heights has to off...
    M. Wein Realty Inc. ·18 hours ago on LinkuRealty
  9. Enjoy a beautiful airy and bright mint condition Bay Front Orient Contemporary home, perfect for relaxing and entertaining. This 4-bedroom 4.5 bath home has gourmet kitchen, fireplace, open common space for easy entertaining. First floor has acces...
    Janet Markarian ·1 day ago on RealtyWW
  10. Enjoy lounging by the pool from this timeless Village charmer! Features include a living room, eat in country kitchen, 3 bedrooms, 1 bath and inviting outdoor spaces. Located in the heart of the village with pool and hot tub, August will be magica...
    Angela Boyer-stump ·1 day ago on RealtyWW
  11. Beautiful Post and Beam located in sought after Landfall Association in Northwest Woods. This impressive four bedroom three bath home has soaring ceiling that spill in warm beams of light from the expansive windows. The bedrooms are cozy and restf...
    James L Blueweiss ·1 day ago on RealtyWW
  12. Treat yourself to a perfect getaway in the heart of Southampton Village.On this quiet street, you'll find three bedrooms, two baths, central air and pool.All amenities make it easy for you to come home and relax after a big day of shopping, sunnin...
    Pam Jackson ·1 day ago on RealtyWW
  13. Sparkling traditional on Fresh Pond provides a great summer vacation opportunity. Enjoy the heated pool, boating on Fresh Pond or just minutes away, bathing at Wades Beach. A welcoming home that offers living room, chef's kitchen and dining area w...
    M. Wein Realty Inc. ·1 day ago on LinkuRealty
  14. Explore this elegant custom-built traditional home, curated by a renowned designer, nestled opposite the picturesque Gardiner's Bay with a private pathway granting direct access to the water. Step into the impeccably crafted interior boasting thre...
    Lori Lambert ·4 days ago on RealtyWW
  15. This south of the highway Bridgehampton home is spacious and overlooks a farm field located on a quiet cul-de-sac neighborhood which is a quick bike ride to Main Street. This Hamptons home features two master bedrooms with one upstairs that has a ...
    Jake Sinacori ·4 days ago on RealtyWW
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