Alquileres vacacionales en Shelter Island

Shelter Island Home with Large Yard And Pool

This cedar-shingled ranch on a quiet street has an open floor plan and large deck for lounging and BBQing, along with a large pool, a big yard and access to Ice Pond Park. It's just a half-mile walk to Crescent/Sunset Beach, the ferry and to Marie Eiffel and other Shelter Island Heights restaurants. The house is fully stocked with beach chairs, lounge chairs, towels, linens, bikes, grill, espresso machine (plus a Keurig ) and all you need for great meals and great times. We now have central AC.

Private Shelter Island Escape | Huge Yard + Pool

*New 2026* Spend your summer on Shelter Island in a private, family home designed for relaxed weeks with kids and friends - featuring a large yard, easy beach access, and everything you need to unplug from the city. The house is designed for relaxed indoor–outdoor living, with a private pool, generous outdoor space, and a comfortable layout well suited to extended stays. We rent the home selectively to guests looking for a quiet, well-cared-for place to enjoy Shelter Island over the summer.

Cozy Shelter Island 2 Bedroom 1 Bath Cottage

This cozy cottage is perfect place to relax and unwind. Located in the center of the island about a mile from the beach and nature preserve. Sleeps up to 9 people - with queen size aero bed provided. Linens, dishes, utensils etc. included. Fridge has icemaker and filtered water feature. Outdoor covered dining area with table and 8 chairs. 2 person swing, BBQ & outdoor shower. 2/3 acre. Relax with the whole family at this peaceful place to stay. Read House Manual for more info.

Private Hay Beach Retreat with Heated Pool

Built in 2015, this airy 4-bedroom house sits on a private acre near Hay Beach and comes with a heated 16x38 gunite pool, well-equipped kitchen, gas grill and modern amenities. Contemporary furniture, uncluttered space; home office with a wired internet connection. Pool is open between 5/23/26 and 9/30/2026. Pricing inclusive of weekly cleaning, pool, yard, and garbage collection services as well as utilities. *Propane for pool heating charged separately for stays a week or longer*

Newly Renovated w/ Pool, Hot tub & Fireplace

Shelter Island Rental License #: 2025-L-0056 !!!PLEASE DO NOT PUT IN A BOOKING REQUEST UNTIL WE HAVE HAD A CONVERSATION VIA THIS SITE. THANK YOU!!!! Great for fall and winter! Perfect for families! 4 Adults Max. Newly renovated, light filled home! Heated pool and hot tub in summer in a private tree-filled yard. Fireplace and great sledding in the colder months. Mid-century modern style; close to Shelter Island Heights and beaches. **POOL & HOT TUB CLOSED MID OCTOBER UNTIL MAY**

Two bedroom bungalow

Bright open contemporary with a beautiful sunny living room, big master bedroom with doors to back deck, small second bedroom with one set of twin bunk beds. Recently renovated kitchen, and laundry room with brand new washer/dryer. Landscaped and fully fenced yard has a great back deck running the length of the house, outdoor shower, green lawns and a secluded fire pit area. 1 Mile from Crescent Beach and Shelter Island Heights for stores, restaurants and ferry

Hay Beach Family Home: Fire Pit, Playroom, Yard

Two blocks from Hay Beach, this family-and-dog-friendly 3BR sleeps 6 in a quiet Shelter Island neighborhood. Fenced yard, fire pit, playroom, crib, toddler toys, beach gear, and bikes included. The home was built for families: open living area with wood-burning fireplace, full kitchen, 2 full baths, basement playroom, and workout space. Outside: fully fenced yard, fire pit, sun loungers, propane grill, Big Green Egg. Winter stays: $0 cleaning fee Nov–Mar.

Beautiful beach home with pool & water views!

Perfectly situated just past the Island Boatyard and Salt in a blissful neighborhood surrounded by water on 3 sides. 4 town landings and beach access right across the street. Newly renovated gourmet kitchen with large island and beautiful quartz counters. Back deck offers full outdoor dining space with propane Weber grill, wicker seating area with beautiful propane Firepit for hours of evening enjoyment and chaise lounges by the pool.

Bayfront 1BR/2BR detached guesthouse with pool

Perfect relaxing getaway for a couple or family. Bayfront 1BR/2BR fully detached guest house with gorgeous morning views. Property has saltwater pool + hot tub (open May -October) and bay access via private dock. Central to both north & south forks (wineries + Hamptons or Montauk just short drive away). Down the road from famous Shelter Island Sunset Beach + golf course. Come explore the beauty of the Hamptons without the stress!

Shelter island retreat

Private Top-Floor Retreat on Shelter IslandPrivate two-bedroom top-floor apartment on a secluded one-acre property on Shelter Island. Please note that this is the top-floor apartment of a larger property Features a wood-burning fireplace, stainless steel kitchen, layered decks, private hot tub, outdoor sauna, and fire pit. Guests enjoy exclusive use of the hot tub, sauna, and fire pit. Long-term rentals available.

Hamptons - Shelter Island Farmhouse

Kid friendly! Perfect two family split! Come enjoy our island retreat. Relax with the whole family at this peaceful pad. You will be 2 min on bike from Wades Beach. You can also walk to the best BBQ/seafood in Shelter, Commander Codys. Features a large open kitchen/dining room plus also a spacious living room. 4 bedrooms with new mattresses, huge outdoor patio for family BBQs. No dogs please.

Laid Back Relaxation

Kick back and relax in this calm, stylish space. Nice newly updated home on a quiet street within walking distance to beaches, restaurants and a golf course. Great location near Shelter Island heights town, Crescent beach and Sunset beach. The location provides both privacy and relaxation at home with just a short walk or ride to popular Shelter Island spots.