Photo by tom owens

Search Condo Rentals in Shelter Island

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

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, (89)
"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……"
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!
On the beach

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!
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 SAR 1,313
SAR 1,873 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, (8)
"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)
"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
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)
"Highly recommend!"
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.
Don't see what you're looking for?
See all available properties in Shelter Island
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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, (1147)
"the location is great and price is reasonable. "
The price is SAR 536
SAR 685 total
includes taxes & fees
31 Mar - 1 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, (367)
"Had a great stay here . Staff was friendly and check in and out was a breeze . Was very clean and comfortable. Only complaint was I couldn’t get a hot shower . Otherwise place is excellent. Shops , restaurants and bars are all a short walk . "
The price is SAR 510
SAR 624 total
includes taxes & fees
31 Mar - 1 Apr
Montauk Oceanside Suites
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (275)
"A great experience. Beautiful suite in a beautiful place."
The price is SAR 494
SAR 646 total
includes taxes & fees
31 Mar - 1 Apr
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.

Frequently asked questions

Why book your condo in Shelter Island with Expedia?
We think that vacations should be a piece of cake, so if you’re after condos at the perfect price, Expedia has got you covered. Save money and select something small and affordable, or splurge on a luxury condo and spoil the ones you love most. Take advantage of our search filters to secure a property in Shelter Island that fits your needs.
How can I find cheap condos in Shelter Island?
Expedia can help you track down cheap condos in Shelter Island. To book your perfect stay in a few quick clicks, simply use our handy filter tool to tailor your search results by star rating, budget and amenities.