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Search Condo Rentals in Shelter Island

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Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

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)
"This place was very nice. Would stay there again. Montauk Manor is always a nice getaway!"
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, (214)
"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……"
The price is SAR 556
SAR 717 total
includes taxes & fees
27 Apr - 28 Apr
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, (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!
Interior

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

9.8 out of 10, Exceptional, (85)
"This unit is just gorgeous breathtaking views!!!"
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)
"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
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!

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 SAR 1,314
SAR 2,054 total
includes taxes & fees
17 Apr - 18 Apr
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)
"We so enjoyed our stay! The view from the property is spectacular, so we were able to enjoy the beach even though we had bad weather. The size was great - we were four adults and fit comfortably. Tim was an excellent host, who promptly assisted us with any questions we had. We will be looking to stay here again!"
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)
"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
Amazing Location 2-bedroom Townhouse - Sleeps 8
Dining

Amazing Location 2-bedroom Townhouse - Sleeps 8

10.0 out of 10, Exceptional, (22)
"We have spent a lot of time over this years in this part of Montauk and really enjoyed the location and nearby amenities. The owners were very friendly and attentive to our needs. Pretty easy stay and the condo was great. Clean, updated and enjoyable."
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)
"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
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
PERFECT, BEAUTIFULLY NEWLY DESIGNED 1,000 FT. MONTAUK OCEANFRT 3-LEVEL TOWNHOUSE
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (68)
"Highly recommend!"
PERFECT, BEAUTIFULLY NEWLY DESIGNED 1,000 FT. MONTAUK OCEANFRT 3-LEVEL TOWNHOUSE
Condo on the Sound w/Beautiful Sunsets!
TV

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
Private kitchen

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
Private kitchen

Waterfront Condominium on Fort Pond Bay with beautiful Sunsets

Waterfront Condominium on Fort Pond Bay with beautiful Sunsets
nice condo
Living area

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

Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!
Outdoor pool, a heated pool

Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!

10.0 out of 10, Exceptional, (41)
"This is the most magical property with a gorgeous pool, beautiful large trees, a pond and a badmitten court. My two children loved it. The property was a 3-4 minute drive from everything and yet felt totally isolated and removed from everything. I will say that the house was more cozy than we expected as the bedrooms upstairs were a steep walk and there was only one bathroom for the entire house. But we made do and had a lovely time."
The price is SAR 3,002
SAR 5,389 total
includes taxes & fees
14 May - 15 May
Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!
Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1155)
"Beautiful hotel."
The price is SAR 557
SAR 710 total
includes taxes & fees
29 Apr - 30 Apr
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (369)
"We stayed for a night and it was great. It was great location and setting. Overall stay was fantastic. Bathtub was a bit old, could not hold the water and if you are more than 1 person, you have to space your baths so you can all enjoy warm water. "
The price is SAR 511
SAR 624 total
includes taxes & fees
17 Apr - 18 Apr
Montauk Oceanside Suites
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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