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Compare 37 Condo Rentals in Shelter Island with updated reviews, rates, and availability.

Driftwood Resort
Property grounds

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (212)
"We were visiting our so. And just needed an inexpensive..relatively..place to stay….. this was quite convenient…. We had a good night sleep…took a walk to beach..had a great chat with one of the ‘beach boys’ and thought it was lovely……"
Driftwood Resort
Montauk Mansion INDOOR + OUTDOOR POOLS
Montauk Manor

Montauk Mansion INDOOR + OUTDOOR POOLS

9.6 out of 10, Exceptional, (88)
"Well kept unit. Easy access. Very quiet. Pool and spa area beautiful "
Montauk Mansion INDOOR + OUTDOOR POOLS
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Hotel Lobby

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

9.4 out of 10, Exceptional, (31)
"A great corner condo in the Montauk Manor. Had a wonderful weekend. The condo was clean, and a great size for 3 adults. Got to use all the facilities at the manor. Indoor pool beautiful, sauna. Great restaurant and free shuttle bus to take you to town. Just a great weekend. "
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!
Property grounds

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

9.8 out of 10, Exceptional, (84)
"Everything about this condo is perfect! The views are breathtaking and condo is clean and modern. Would love to come back again. "
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
Updated Modern Waterfront condo with private beach, pool, tennis, pier & more.<br>
Nightly sunset from the deck

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

10.0 out of 10, Exceptional, (51)
"This is the third summer that my husband and I have visited Montauk and it was, by far, our best week. Debra was an amazing, gracious host who clearly wants the best for her guests. The condo lived up to our expectations, and the adjoining grounds offered some beautiful views of the sunset. The complex is well situated and an easy walk into town. We would definitely come back!"
Updated Modern Waterfront condo with private beach, pool, tennis, pier & more.<br>
Serene Montauk Condo with Stunning Bay View and Pool
Sunset on the dock

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
Brand New Waterfront - Chic & Sophisticated
Bathroom

Brand New Waterfront - Chic & Sophisticated

9.0 out of 10, Wonderful, (2)
"A few things wrong like no light in bathroom. Needed bulbs.Received them. One bedroom light not working. Handle fell of going out to deck. "
Brand New Waterfront - Chic & Sophisticated
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
Living area

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

10.0 out of 10, Exceptional, (73)
"The condo was clean and as advertised with an unbelievable view looking over the water with amazing sunsets. We were in Greenport for a Wedding and found the area full of things to do with many wineries and a fun downtown area with restaurants, bars and shopping. Highly recommend the Waterfront Condo for your next visit to Greenport. "
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
Condo on the Sound w/Beautiful Sunsets!
Beach

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

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

Beachside Bliss at Montauk's Surf Club - 2BR Condo with Resort Amenities!
Spectacular Montauk Sunset in Gated Community - Perfect for Families!
Property grounds

Spectacular Montauk Sunset in Gated Community - Perfect for Families!

3.5 star property
10.0 out of 10, Exceptional, (7)
"Had an incredible weekend in Montauk. The property was very nice and had amazing views. Highly recommend!"
Spectacular Montauk Sunset in Gated Community - Perfect for Families!
Relaxing water front newly renovated condo
Private kitchen

Relaxing water front newly renovated condo

Relaxing water front newly renovated condo
nice condo
Living area

nice condo

nice condo
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Pool

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Breathtaking Waterfront Greenport Village Condo, private beach, pool, tennis
Outdoor dining

Breathtaking Waterfront Greenport Village Condo, private beach, pool, tennis

Breathtaking Waterfront Greenport Village Condo, private beach, pool, tennis
Waterfront Condominium on Fort Pond Bay with beautiful Sunsets
Room

Waterfront Condominium on Fort Pond Bay with beautiful Sunsets

Waterfront Condominium on Fort Pond Bay with beautiful Sunsets
Historic courtyard in Montauk, 2 bedrooms, duplex, sunset views
Interior

Historic courtyard in Montauk, 2 bedrooms, duplex, sunset views

Historic courtyard in Montauk, 2 bedrooms, duplex, sunset views
Million Dollar Sunsets Overlooking Bayfront Beach
Pool

Million Dollar Sunsets Overlooking Bayfront Beach

Million Dollar Sunsets Overlooking Bayfront Beach
Shelter Island Waterview Villa
Living area

Shelter Island Waterview Villa

Shelter Island Waterview Villa
The Exclusive Resort in Montauk
Living area

The Exclusive Resort in Montauk

The Exclusive Resort in Montauk
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
Exterior

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1090)
"Best old hotel on Long Island "
The price is AED 481
AED 621 total
includes taxes & fees
16 Jan - 17 Jan
Montauk Manor
Montauk Oceanside Suites
Front of property

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very Good, (352)
"Location, location..."
The price is AED 500
AED 607 total
includes taxes & fees
12 Jan - 13 Jan
Montauk Oceanside Suites
Windward Shores Ocean Resort
Property grounds

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (266)
"I recently had a wonderful stay at this property, and I can't recommend it enough! Although it takes less than a 10-minute drive into Montauk, it's perfect. The room we stayed in was very clean and spacious, providing all the comforts we needed. The property is exceptionally well-maintained, and it's clear that the staff takes pride in their work. From the friendly service to the beautifully kept grounds, everything contributed to a very pleasant experience. One of the highlights was the...
The price is AED 412
AED 550 total
includes taxes & fees
22 Jan - 23 Jan
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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