Shelter Island Vacation Rentals

Name: Beautiful Private 4 BR, Heated Pool. Close to Everything.
Address: East Hampton

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Check dates for Shelter Island hotels

Vacation Rentals in Shelter Island

Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

Located in Montauk, this vacation home is by the sea, within a 5-minute drive of The Hamptons Beaches and Second House Museum.

Gorgeous private Hamptons house with pool and volleyball court

Located in Hampton Bays, this vacation home is a 4-minute drive from The Hamptons Beaches and 10 minutes from Meschutt Beach.

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

With a stay at this vacation home in Southampton, you'll be within a 5-minute drive of Southampton Golf Range and North Main Street Historic District.

Unobstructed Ocean Views ! A Beautiful Montauk Getaway

With a stay at this vacation home in Montauk, you'll be on the beach, just a 1-minute walk from The Hamptons Beaches and 10 minutes by foot from Second House Museum.

Village Fringe Available May 24th - October 31st. Family/Pet Friendly

Located in East Hampton (East Hampton North), this vacation home is within a 5-minute drive of East Hampton Historical Society and Hither Hills State Park.

Exquisite New Hampton Home in a Perfect Location

Located in East Hampton, this vacation home is by the ocean, a 1-minute drive from Three Mile Harbor and 5 minutes from Old Hook Mill.

COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach

With a stay at this vacation home in Amagansett (Beach Hampton), you'll be steps from The Hamptons Beaches and 14 minutes by foot from Amagansett Beach.

Fall in the🌅beautiful sunsets

With a stay at this vacation home, you'll be centrally located in Hampton Bays, within a 10-minute drive of The Hamptons Beaches and Ponquogue Beach.

Center of Town - Ideal for Beach, Golf & Tennis

With a stay at this vacation home in Montauk, you'll be next to a golf course, just a 2-minute walk from Montauk Downs State Park Golf Course and 7 minutes by foot from Lake Montauk.

Cozy Westbrook Vacation Rental - Walk to Beach!

With a stay at this vacation home in Westbrook (Westbrook Center), you'll be a 1-minute drive from Westbrook Town Beach and 6 minutes from Tanger Outlets.

Beautiful Hamptons home close to beaches, shopping, & restaurants!

Located in Hampton Bays, this vacation home is a 3-minute drive from The Hamptons Beaches and 10 minutes from Meschutt Beach.

Beautiful Private 4 BR, Heated Pool. Close to Everything.

When you stay at this vacation home in East Hampton, you'll be near the beach, within a 5-minute drive of Three Mile Harbor and Pollock-Krasner House and Study Center.

Don't see what you're looking for?

See all available properties in Shelter Island

View all properties

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.