Shelter Island Condo Rentals

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

Condo Rentals in Shelter Island

Driftwood Resort

2178 Montauk Highway Montauk NY

$401 nightly

$458 total

Jul 19 - Jul 20

Total with taxes and fees

When you stay at Driftwood Resort in Montauk, you'll be on the beach, within a 10-minute walk of The Hamptons Beaches and Hither Hills State Park.

Pool

Kitchen

Offshore Spa & Residences

79 S Emerson Ave Montauk NY

$1,120 nightly

$1,280 total

Aug 18 - Aug 19

Total with taxes and fees

With a stay at Offshore Spa & Residences in Montauk (Downtown Montauk), you'll be a 1-minute drive from The Hamptons Beaches and 10 minutes from Montauk Point Lighthouse.

Pool

Kitchen

Montauk Mansion INDOOR + OUTDOOR POOLS

Montauk NY

When you stay at this condo in Montauk, you'll be by the sea, within a 15-minute drive of The Hamptons Beaches and Montauk Point Lighthouse.

Pool

Hot Tub

Amazing Location 2-bedroom Townhouse - Sleeps 8

Montauk NY

With a stay at this condo in Montauk (Downtown Montauk), you'll be a 1-minute drive from The Hamptons Beaches and 9 minutes from Montauk Point Lighthouse.

Kitchen

Air conditioning

Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound

Montauk NY

$571 nightly

$652 total

Jul 19 - Jul 20

Total with taxes and fees

With a stay at this condo, you'll be centrally located in Montauk, a 2-minute drive from The Hamptons Beaches and 11 minutes from Montauk Point Lighthouse.

PERFECT, BEAUTIFULLY NEWLY DESIGNED 1,000 FT. MONTAUK OCEANFRT 3-LEVEL TOWNHOUSE

Montauk NY

$975 nightly

$1,114 total

Aug 3 - Aug 4

Total with taxes and fees

When you stay at this condo in Montauk, you'll be on the beach, a 1-minute drive from The Hamptons Beaches and 10 minutes from Montauk Point Lighthouse.

Cozy 2-bedroom condo with AC, fitness room in charming Westbrook. Oceanfront,

Westbrook CT

With a stay at this condo in Westbrook (Westbrook Center), you'll be within a 15-minute drive of Hammonasset Beach State Park and Tanger Outlets.

Washer

Air conditioning

Brand Newly Renovated Resort Style One Bedroom Luxury Suite Simplex

Montauk NY

Located in Montauk, this condo is within a 15-minute drive of The Hamptons Beaches and Montauk Point Lighthouse.

Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

Greenport NY

When you stay at this condo in Greenport, you'll be on the beach, within a 5-minute drive of Kontokosta Winery and 67 Steps Beach.

Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!

Montauk NY

When you stay at this condo in Montauk, you'll be on the beach, within a 15-minute drive of The Hamptons Beaches and Montauk Point Lighthouse.

Atlantic Bluffs Club

707 Old Montauk Hwy Montauk NY

$9,024 nightly

$10,306 total

Jul 31 - Aug 1

Total with taxes and fees

When you stay at Atlantic Bluffs Club in Montauk, you'll be near the beach, within a 15-minute drive of The Hamptons Beaches and Montauk Point Lighthouse.

Spectacular Montauk Sunset in Gated Community - Perfect for Families!

Montauk NY

When you stay at this condo in Montauk, you'll be on the beach, within a 15-minute drive of The Hamptons Beaches and Montauk Point Lighthouse.

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.