Photo by tom owens
Search Condo Rentals in Shelter Island
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 45 Condo Rentals in Shelter Island with updated reviews, rates, and availability.

Montauk Mansion INDOOR + OUTDOOR POOLS
Montauk Mansion INDOOR + OUTDOOR POOLS
9.6 out of 10, Exceptional, (90)

Driftwood Resort
Driftwood Resort
9.0 out of 10, Wonderful, (214)
The price is SAR 556
SAR 717 total
includes taxes & fees
27 Apr - 28 Apr

Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.4 out of 10, Exceptional, (31)

Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
9.8 out of 10, Exceptional, (85)

Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
10.0 out of 10, Exceptional, (73)

Beachside Bliss at Montauk's Surf Club - 2BR Condo with Resort Amenities!
Beachside Bliss at Montauk's Surf Club - 2BR Condo with Resort Amenities!
10.0 out of 10, Exceptional, (1)
The price is SAR 1,314
SAR 2,054 total
includes taxes & fees
17 Apr - 18 Apr

Spectacular Montauk Sunset in Gated Community - Perfect for Families!
Spectacular Montauk Sunset in Gated Community - Perfect for Families!
10.0 out of 10, Exceptional, (10)

Brand New Waterfront - Chic & Sophisticated
Brand New Waterfront - Chic & Sophisticated
9.0 out of 10, Wonderful, (2)
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Shelter Island

Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!
Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!
10.0 out of 10, Exceptional, (41)
The price is SAR 3,002
SAR 5,389 total
includes taxes & fees
14 May - 15 May

Montauk Manor
Montauk Manor
9.2 out of 10, Wonderful, (1155)
The price is SAR 557
SAR 710 total
includes taxes & fees
29 Apr - 30 Apr

Montauk Oceanside Suites
Montauk Oceanside Suites
8.6 out of 10, Excellent, (369)
The price is SAR 511
SAR 624 total
includes taxes & fees
17 Apr - 18 Apr
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.
Recent reviews of Shelter Island hotels
Recent reviews of Shelter Island hotels

The Harbor Front Inn
5/5 Excellent
2 day getaway
"The experience was very good. everything was what I expected. only thought was the $25 parking was a bit much"
A verified traveler stayed at The Harbor Front Inn
Posted 7 hours ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
Top Condo Rentals in Other Destinations
More Accommodation Types in Shelter Island
- Vacation Homes in Shelter Island
- Cottages in Shelter Island
- Apartments in Shelter Island
- Villas in Shelter Island
- B&B in Shelter Island
- Motels in Shelter Island
- Guest Houses in Shelter Island
- Aparthotels in Shelter Island
- Resorts in Shelter Island
- Farmstay in Shelter Island
- Inns in Shelter Island
- Houseboats in Shelter Island
- Cabin Rentals in Shelter Island
- Condo Resorts in Shelter Island
- Hostels in Shelter Island
- Residences in Shelter Island
- Hotels