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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Featured Condo Rentals in Shelter Island

Driftwood Resort
Apartment, 1 Bedroom | Private kitchen

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (223)
"The staff was very friendly I will definitely be back again 👍"
The price is NZ$648
includes taxes & fees
26 June - 27 June
Driftwood Resort
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
The price is NZ$3,846
includes taxes & fees
26 June - 27 June
Canoe Place Waterfront Residences
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
On the beach

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

9.8 out of 10, Exceptional, (87)
"This unit is just gorgeous breathtaking views!!!"
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
Brand New Waterfront - Chic & Sophisticated
Terrace/patio

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
PERFECT, BEAUTIFULLY NEWLY DESIGNED 1,000 FT. MONTAUK OCEANFRT 3-LEVEL TOWNHOUSE
On the beach, sun-loungers, beach towels

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

9.8 out of 10, Exceptional, (68)
"Wonderful location and place to stay."
PERFECT, BEAUTIFULLY NEWLY DESIGNED 1,000 FT. MONTAUK OCEANFRT 3-LEVEL TOWNHOUSE
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Interior

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

9.4 out of 10, Exceptional, (33)
"Great stay"
The price is NZ$1,121
includes taxes & fees
30 June - 1 July
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Beachside Bliss at Montauk's Surf Club - 2BR Condo with Resort Amenities!
Outdoor dining

Beachside Bliss at Montauk's Surf Club - 2BR Condo with Resort Amenities!

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 NZ$1,237
includes taxes & fees
30 June - 1 July
Beachside Bliss at Montauk's Surf Club - 2BR Condo with Resort Amenities!
Montauk Mansion INDOOR + OUTDOOR POOLS
Interior

Montauk Mansion INDOOR + OUTDOOR POOLS

9.6 out of 10, Exceptional, (92)
"This place was very nice. Would stay there again. Montauk Manor is always a nice getaway!"
Montauk Mansion INDOOR + OUTDOOR POOLS
Welcome to Our Beachfront Studio
Pool

Welcome to Our Beachfront Studio

2.0 star property
Welcome to Our Beachfront Studio
Updated Modern Waterfront condo with private beach, pool, tennis, pier & more.<br>
Smart TV, DVD player, books, stereo

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

10.0 out of 10, Exceptional, (51)
"Beautiful apartment ! We had such a great time. Everything was perfect."
Updated Modern Waterfront condo with private beach, pool, tennis, pier & more.<br>
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
Property grounds

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
Amazing Location 2-bedroom Townhouse - Sleeps 8
Dining

Amazing Location 2-bedroom Townhouse - Sleeps 8

10.0 out of 10, Exceptional, (22)
"Owners were quick to respond and rectify any issues that came up! Would definitely stay here again. Thank you!!"
Amazing Location 2-bedroom Townhouse - Sleeps 8
Condo on the Sound w/Beautiful Sunsets!
Fridge, microwave, oven, stovetop

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

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

10.0 out of 10, Exceptional, (27)
"We will definitely book again. The views, the location, everything was perfect."
Newly renovated Waterfront condo with amazing views, private beach, pool & more
Spectacular Montauk Sunset in Gated Community - Perfect for Families!
Smart TV, books

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
A heated pool

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
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 5 Dbl Queen - Bungalows at Common Ground
House, 2 Queen Beds (Unit 5 Dbl Queen - Bungalows at Commo) | Property grounds

Unit 5 Dbl Queen - Bungalows at Common Ground

3.0 star property
Unit 5 Dbl Queen - Bungalows at Common Ground
Unit 2 Dbl Queen - Bungalows at Common Ground
Marina

Unit 2 Dbl Queen - Bungalows at Common Ground

2.5 star property
Unit 2 Dbl Queen - Bungalows at Common Ground
Waterfront Condominium on Fort Pond Bay with beautiful Sunsets
Outdoor dining

Waterfront Condominium on Fort Pond Bay with beautiful Sunsets

Waterfront Condominium on Fort Pond Bay with beautiful Sunsets
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.
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