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Search Condo Rentals in Shelter Island

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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 45 Condo Rentals in Shelter Island with updated reviews, rates, and availability.

Montauk Mansion INDOOR + OUTDOOR POOLS
Interior

Montauk Mansion INDOOR + OUTDOOR POOLS

9.6 out of 10, Exceptional, (90)
"Beautiful location, resort and spotless."
Montauk Mansion INDOOR + OUTDOOR POOLS
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (216)
"Beautiful property would definitely stay there again. Loved the ease of communication via text and for check-in and check out. Perfectly clean, beautifully decorated accommodations. Will definitely stay here again."
The price is AED 452
AED 596 total
includes taxes & fees
7 May - 8 May
Driftwood Resort
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, (32)
"Great stay"
The price is AED 1,102
AED 2,241 total
includes taxes & fees
26 May - 27 May
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
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, (85)
"Phenomenal view of the sea shore and modern amenities. "
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
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, (73)
"Very clean, very cozy, very convenient location. Great view."
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
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, (1)
"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 AED 1,469
AED 2,224 total
includes taxes & fees
4 May - 5 May
Beachside Bliss at Montauk's Surf Club - 2BR Condo with Resort Amenities!
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)
"The place was a perfect size for our family of four - spacious living room to hang out in, and comfortable beds, wich is all we needed. All very clean, and a beautiful view to the bay. Beautiful area to visit in winter!"
Spectacular Montauk Sunset in Gated Community - Perfect for Families!
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
Amazing Location 2-bedroom Townhouse - Sleeps 8
Dining

Amazing Location 2-bedroom Townhouse - Sleeps 8

10.0 out of 10, Exceptional, (22)
"Had an amazing stay at this property, very clean and very close to the beach! Could walk into town and the check in process was seamless Definitely would come back"
Amazing Location 2-bedroom Townhouse - Sleeps 8
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>
Serene Montauk Condo with Stunning Bay View and Pool
Sun loungers, beach towels

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
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
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!
Chic 1 BR Condo with just steps to the beach & with Ocean Views in Montauk
Pool

Chic 1 BR Condo with just steps to the beach & with Ocean Views in Montauk

Chic 1 BR Condo with just steps to the beach & with Ocean Views in Montauk
1-bedroom timeshare at Waters Edge Resort & Spa available April 18-25, 2025
Exterior

1-bedroom timeshare at Waters Edge Resort & Spa available April 18-25, 2025

1-bedroom timeshare at Waters Edge Resort & Spa available April 18-25, 2025
Welcome to Our Beachfront Studio
Pool

Welcome to Our Beachfront Studio

2.0 star property
Welcome to Our Beachfront Studio
Shelter Island Waterview Villa
Property grounds

Shelter Island Waterview Villa

Shelter Island Waterview Villa
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
nice condo
Interior

nice condo

nice condo
Million Dollar Sunsets Overlooking Bayfront Beach
Outdoor pool, a heated pool

Million Dollar Sunsets Overlooking Bayfront Beach

Million Dollar Sunsets Overlooking Bayfront Beach
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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Other property types in Shelter Island

Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1170)
"excellent overall stay"
The price is AED 555
AED 706 total
includes taxes & fees
19 May - 20 May
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (374)
"Good for a short stay "
The price is AED 604
AED 730 total
includes taxes & fees
4 May - 5 May
Montauk Oceanside Suites
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (283)
"Love the ocean view from the balcony"
The price is AED 565
AED 725 total
includes taxes & fees
12 May - 13 May
Windward Shores Ocean Resort
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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