Photo by tom owens

Search Condos Rentals in Shelter Island from CA $341

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Shelter Island Condo Rentals

Driftwood Resort
Enjoy cooking in this well-equipped kitchen with a tiled backsplash and black refrigerator.

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (227)
"Phenomenal property and our room had a private sand patio. Service was extremely attentive and friendly. The beach was very spacious and pretty clean."
The price is CA $341
CA $435 total
includes taxes & fees
Sep 3 - Sep 4
Driftwood Resort
Updated Modern Waterfront condo with private beach, pool, tennis, pier & more.<br>
Relax in this stylish living room with a large sofa, armchair, and dining area.

Updated Modern Waterfront condo with private beach, pool, tennis, pier & more.<br>

10.0 out of 10, Exceptional, (53)
"Beautiful apartment ! We had such a great time. Everything was perfect."
Updated Modern Waterfront condo with private beach, pool, tennis, pier & more.<br>
Amazing Location 2-bedroom Townhouse - Sleeps 8
Enjoy a meal with a view from this dining area, featuring a fireplace and comfortable seating.

Amazing Location 2-bedroom Townhouse - Sleeps 8

10.0 out of 10, Exceptional, (24)
"Amazing location, wonderful and thoughtful hosts, and clean/beautiful beach condo. It was perfect for our family getaway!"
Amazing Location 2-bedroom Townhouse - Sleeps 8
Brand New Waterfront - Chic & Sophisticated
Step into a cozy outdoor space with a covered entrance and comfortable seating area.

Brand New Waterfront - Chic & Sophisticated

9.0 out of 10, Wonderful, (2)
"This condo was perfect for our Labor Day vacation. Great location. Easy access to beaches and restaurants. Clean and perfect size for our family of 4. We will certainly return. Steve the host was extremely responsive and answered all my questions."
Brand New Waterfront - Chic & Sophisticated
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
Guests can enjoy access to the beach from this property.

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

9.8 out of 10, Exceptional, (91)
"This unit is just gorgeous breathtaking views!!!"
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
10.0 out of 10, Exceptional, (1)
Canoe Place Waterfront Residences
PERFECT, BEAUTIFULLY NEWLY DESIGNED 1,000 FT. MONTAUK OCEANFRT 3-LEVEL TOWNHOUSE
Guests can enjoy surfing and beach activities in this coastal location.

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

9.8 out of 10, Exceptional, (70)
"Wonderful location and place to stay."
PERFECT, BEAUTIFULLY NEWLY DESIGNED 1,000 FT. MONTAUK OCEANFRT 3-LEVEL TOWNHOUSE
Ocean Breezes & Resort Comfort – Montauk 2BR Surf Club Condo
On the beach

Ocean Breezes & Resort Comfort – Montauk 2BR Surf Club Condo

10.0 out of 10, Exceptional, (2)
"Such a great property that was truly more than enough space. Very close to the beach and the community includes tons of perks such as free food, drinks, etc. 100% recommend"
The price is CA $620
CA $935 total
includes taxes & fees
Sep 4 - Sep 5
Ocean Breezes & Resort Comfort – Montauk 2BR Surf Club Condo
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Experience the grandeur of our lobby, featuring high ceilings, arched columns, and comfortable seating areas.

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

9.4 out of 10, Exceptional, (36)
"we had a lovely stay in this apartment! it was very spacious and comfortable. The pull out couch was also surprisingly very comfy! Mark and Nancy were very responsive and helpful. "
The price is CA $371
CA $800 total
includes taxes & fees
Aug 17 - Aug 18
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Montauk Mansion INDOOR + OUTDOOR POOLS
Experience the grandeur of this beautifully appointed space, featuring a high ceiling, ornate chandelier, and elegant arched columns.

Montauk Mansion INDOOR + OUTDOOR POOLS

9.6 out of 10, Exceptional, (95)
"This place was very nice. Would stay there again. Montauk Manor is always a nice getaway!"
Montauk Mansion INDOOR + OUTDOOR POOLS
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
Relax on a serene coastal deck with a view of the calm sea.

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

10.0 out of 10, Exceptional, (76)
"Property was amazing "
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
Newly renovated Waterfront condo with amazing views, private beach, pool & more
Relax by the serene pool surrounded by lounge chairs and umbrellas, amidst lush flowering plants.

Newly renovated Waterfront condo with amazing views, private beach, pool & more

10.0 out of 10, Exceptional, (28)
"We will definitely book again. The views, the location, everything was perfect."
Newly renovated Waterfront condo with amazing views, private beach, pool & more
Condo on the Sound w/Beautiful Sunsets!
Enjoy cooking in this well-equipped kitchen with stainless steel appliances, a sink, and a small island with stools.

Condo on the Sound w/Beautiful Sunsets!

10.0 out of 10, Exceptional, (2)
"The condo was great and perfect for a getaway! Erica was very responsive and this was a great waterfront stay. Thanks, Erica!"
Condo on the Sound w/Beautiful Sunsets!
Spectacular Montauk Sunset in Gated Community - Perfect for Families!
Relax in this inviting living room with a sofa, coffee table, and ocean views through the sliding glass door.

Spectacular Montauk Sunset in Gated Community - Perfect for Families!

3.5 star property
10.0 out of 10, Exceptional, (10)
"My son and I had a great time staying here. Very clean, close to the water and short drive to everything in Montauk"
Spectacular Montauk Sunset in Gated Community - Perfect for Families!
Serene Montauk Condo with Stunning Bay View and Pool
Relax by the pool surrounded by comfortable lounge chairs and shaded areas.

Serene Montauk Condo with Stunning Bay View and Pool

8.8 out of 10, Excellent, (17)
"Great location and even better view - Chris made the process easy from start to finish. "
Serene Montauk Condo with Stunning Bay View and Pool
Unit 5 Dbl Queen - Bungalows at Common Ground
Guests can enjoy a tranquil waterfront setting with access to the marina and its boats.

Unit 5 Dbl Queen - Bungalows at Common Ground

3.0 star property
Unit 5 Dbl Queen - Bungalows at Common Ground
Cozy waterfront condo with WiFi, AC in charming Montauk
Living area

Cozy waterfront condo with WiFi, AC in charming Montauk

Cozy waterfront condo with WiFi, AC in charming Montauk
Unit 2 Dbl Queen - Bungalows at Common Ground
Enjoy boating and fishing from the marina's wooden piers, offering easy access to the calm waters.

Unit 2 Dbl Queen - Bungalows at Common Ground

2.5 star property
Unit 2 Dbl Queen - Bungalows at Common Ground
Unit 12 Deluxe Dbl Queen - Bungalows at Common Ground
Relax in a serene space with a large sliding door to an outdoor area, a flat-screen TV, and a comfortable white bed.

Unit 12 Deluxe Dbl Queen - Bungalows at Common Ground

3.0 star property
Unit 12 Deluxe Dbl Queen - Bungalows at Common Ground
Shelter Island Waterview Villa
Relax in a serene outdoor space surrounded by lush greenery and framed by large windows.

Shelter Island Waterview Villa

Shelter Island Waterview Villa
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shelter Island Hotel Reviews

Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Reasonable accommodation in premium location. Great find"
Mark 3-night trip
Posted 12 hours ago
Beachcomber Resort at Montauk