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Search and Rent Shelter Island Condos

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Oct 3 - Oct 5
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Oct 17 - Oct 19
In two months
Nov 14 - Nov 16
In three months
Dec 12 - Dec 14

Condo Rentals in Shelter Island

Driftwood Resort
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (232)
"Great place to stay for small family "
$182 nightly
The price is $208
Sep 29 - Sep 30
Total with taxes and fees
Driftwood Resort
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, (55)
"Beautiful apartment ! We had such a great time. Everything was perfect."
Updated Modern Waterfront condo with private beach, pool, tennis, pier & more.<br>
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, (39)
"we had a lovely stay in this apartment! it was very spacious and comfortable. The pull out couch was also surprisingly very comfy! Mark and Nancy were very responsive and helpful. "
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
10.0 out of 10, Exceptional, (1)
Canoe Place Waterfront Residences
Offshore Residences
One Bedroom Condo King with Steam Shower | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

Offshore Residences

4.0 star property
$629 nightly
The price is $719
Oct 19 - Oct 20
Total with taxes and fees
Offshore Residences
Amazing Location 2-bedroom Townhouse - Sleeps 8
Dining

Amazing Location 2-bedroom Townhouse - Sleeps 8

10.0 out of 10, Exceptional, (26)
"Amazing location, wonderful and thoughtful hosts, and clean/beautiful beach condo. It was perfect for our family getaway!"
Amazing Location 2-bedroom Townhouse - Sleeps 8
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, (94)
"Very Nice stay there for business would go back for pleasure"
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
Montauk Mansion INDOOR + OUTDOOR POOLS
Interior

Montauk Mansion INDOOR + OUTDOOR POOLS

9.6 out of 10, Exceptional, (99)
"This place was very nice. Would stay there again. Montauk Manor is always a nice getaway!"
Montauk Mansion INDOOR + OUTDOOR POOLS
Brand New Waterfront - Chic & Sophisticated
Terrace/patio

Brand New Waterfront - Chic & Sophisticated

9.6 out of 10, Exceptional, (5)
"This condo was perfect for our Labor Day vacation. Great location. Easy access to beaches and restaurants. Clean and perfect size for our family of 4. We will certainly return. Steve the host was extremely responsive and answered all my questions."
Brand New Waterfront - Chic & Sophisticated
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, (71)
"Wonderful location and place to stay."
PERFECT, BEAUTIFULLY NEWLY DESIGNED 1,000 FT. MONTAUK OCEANFRT 3-LEVEL TOWNHOUSE
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, (79)
"Property was amazing "
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
Newly renovated Waterfront condo with amazing views, private beach, pool & more
A heated pool

Newly renovated Waterfront condo with amazing views, private beach, pool & more

10.0 out of 10, Exceptional, (30)
"We will definitely book again. The views, the location, everything was perfect."
Newly renovated Waterfront condo with amazing views, private beach, pool & more
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)
"My son and I had a great time staying here. Very clean, close to the water and short drive to everything in Montauk"
Spectacular Montauk Sunset in Gated Community - Perfect for Families!
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, (18)
"Great location and even better view - Chris made the process easy from start to finish. "
Serene Montauk Condo with Stunning Bay View and Pool
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!
Unit 5 Dbl Queen - Bungalows at Common Ground
House, 2 Queen Beds (Unit 5 Dbl Queen - Bungalows at Commo) | Property grounds

Unit 5 Dbl Queen - Bungalows at Common Ground

3.0 star property
Unit 5 Dbl Queen - Bungalows at Common Ground
Unit 2 Dbl Queen - Bungalows at Common Ground
Marina

Unit 2 Dbl Queen - Bungalows at Common Ground

2.5 star property
Unit 2 Dbl Queen - Bungalows at Common Ground
Cozy waterfront condo with WiFi, AC in charming Montauk
Living area

Cozy waterfront condo with WiFi, AC in charming Montauk

Cozy waterfront condo with WiFi, AC in charming Montauk
Unit 12 Deluxe Dbl Queen - Bungalows at Common Ground
House, 2 Queen Beds (Unit 12 Deluxe Dbl Queen - Bungalows ) | 1 bedroom, WiFi

Unit 12 Deluxe Dbl Queen - Bungalows at Common Ground

3.0 star property
Unit 12 Deluxe Dbl Queen - Bungalows at Common Ground
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
Indoor pool, outdoor 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
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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Top Shelter Island Hotel Reviews

The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Great water front hotel. Perfect location for a stay in greenport. Ask for water view rooms!"
Daniel 1-night trip
Posted 2 days ago
The Harbor Front Inn

Find out more about Shelter Island

Find out more about Shelter Island

Shelter Island Condo Rentals information

Number of reviews
702
Accommodation
49 Condo Rentals
Lowest Price
$208
Highest Price
$719

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