Photo by Erisa Dilo

Search Condo Rentals in Shelter Island Heights

    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
    today icon
    Change your mind
    Book hotels with free cancellation
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
9.6 out of 10, Exceptional, (84)
"The Montauk Manor deserves its landmark designation but it is certainly updated and thoughtfully remodelled. The space is very well laid out and there are lovely vistas from every vantage point. My biggest complaint is the noise. Not necessarily the noise of other guests, but an unexplainable mechanical noise. It was a nuisance mostly just in the quiet of the night and the only détraction to an otherwise delightful stay. "
Montauk Mansion INDOOR + OUTDOOR POOLS
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
9.8 out of 10, Exceptional, (81)
"We loved having a short getaway here. It was a beautiful location with an amazing view. The condo is indeed newly renovated and gorgeous! I wish we came during a warmer time so we can enjoy more of the on water restaurants. Nonetheless, this was a great stay and was close to everything we needed or wanted to enjoy; will definitely be staying again!"
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
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
Beachside Bliss at Montauk's Surf Club - 2BR Condo with Resort Amenities!
The price is HK$6,801
HK$8,769 total
includes taxes & fees
6 Nov - 7 Nov
Beachside Bliss at Montauk's Surf Club - 2BR Condo with Resort Amenities!
Spectacular Montauk Sunset in Gated Community - Perfect for Families!
3.5 star property
10.0 out of 10, Exceptional, (6)
"Columbus Day weekend for myself and my daughter. Beautiful setting!!!"
Spectacular Montauk Sunset in Gated Community - Perfect for Families!
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
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
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
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
Beautiful Oceanfront views in the heart of Montauk. Sleeps up to 6.
Beautiful Oceanfront views in the heart of Montauk. Sleeps up to 6.
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!
Relaxing water front newly renovated condo
Relaxing water front newly renovated condo
nice condo
nice condo
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
Breathtaking Waterfront Greenport Village Condo, private beach, pool, tennis
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
Historic courtyard in Montauk, 2 bedrooms, duplex, sunset views
Million Dollar Sunsets Overlooking Bayfront Beach
Million Dollar Sunsets Overlooking Bayfront Beach
Shelter Island Waterview Villa
Shelter Island Waterview Villa
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 Heights
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Shelter Island Heights

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1062)
"Loved the old school character "
The price is HK$1,078
HK$1,382 total
includes taxes & fees
27 Nov - 28 Nov
Montauk Manor
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (258)
"Very private"
The price is HK$1,024
HK$1,338 total
includes taxes & fees
6 Nov - 7 Nov
Windward Shores Ocean Resort
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, (336)
"It was very clean and affordable price"
The price is HK$896
HK$1,100 total
includes taxes & fees
6 Nov - 7 Nov
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.

Frequently asked questions

Why book your condo in Shelter Island Heights with Expedia?
Expedia makes it easy to find your dream condo in Shelter Island Heights. On the lookout for an upmarket stay? Find your way to the filters to search for properties with a 5-star rating. If you’re sticking to a budget, choose how much you’d like to spend and then browse our amazing deals. We’ll help you find a suitable stay whatever your plans or style of travel.
How can I find cheap condos in Shelter Island Heights?
With Expedia’s helpful filter tool, booking cheap condos in Shelter Island Heights couldn’t be easier. To find stays that’ll make your wallet smile, fine-tune your search results by amenities, star rating and budget.
What is there to do in Shelter Island Heights near my condo?
If you’re eager to make the most of your time in Shelter Island Heights, check out Crescent Beach. It’s a winner among locals and tourists alike.