Holiday rentals near Shelter Island
We found 3,279 holiday rentals — enter your dates for availability
Scroll through and discover holiday rentals within easy reach of Shelter Island that provide the perfect home base for your trip. Whether you're travelling with a group or just with your pet, holiday homes have the amenities that you need and want for your stay, which might include a hot tub and a washer and dryer. At the end of the day, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Shelter Island
Showing deals for:14 Nov - 21 Nov
Image gallery for Top Floor Ocean Front Remodeled Condo
1010 out of 10 rating
Exceptional
(60 reviews)
Top Floor Ocean Front Remodeled Condo
San Diego, CA
8% off
Price is AU$5,019
AU$5,019
AU$717 per night
includes taxes & fees
Image gallery for Spacious Ocean Beach Studio w/ Parking - Short Walk to the Beach
9.29.2 out of 10 rating
Wonderful
(12 reviews)
Spacious Ocean Beach Studio w/ Parking - Short Walk to the Beach
San Diego, CA
8% off
Price is AU$2,503
AU$2,503
AU$358 per night
includes taxes & fees
Image gallery for Near Bay Home with A/C, Bikes, Parking, and Wi-Fi - Mins to Beach!
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Near Bay Home with A/C, Bikes, Parking, and Wi-Fi - Mins to Beach!
San Diego, CA
8% off
Price is AU$3,916
AU$3,916
AU$559 per night
includes taxes & fees
Image gallery for Ocean/Sunset Views, Modern, Sunset Cliffs/Point Loma near OB, PLNU, Thurs Club
1010 out of 10 rating
Exceptional
(57 reviews)
Ocean/Sunset Views, Modern, Sunset Cliffs/Point Loma near OB, PLNU, Thurs Club
San Diego, CA
8% off
Price is AU$2,769
AU$2,769
AU$396 per night
includes taxes & fees
Image gallery for Living the Ocean Front Dream
1010 out of 10 rating
Exceptional
(17 reviews)
Living the Ocean Front Dream
La Jolla, CA
6% off
Price is AU$30,862
AU$30,862
AU$4,409 per night
includes taxes & fees
Image gallery for Pacific Beach Studio #1973 Close to beach, bay and more!
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Pacific Beach Studio #1973 Close to beach, bay and more!
San Diego, CA
8% off
Price is AU$1,604
AU$1,604
AU$229 per night
includes taxes & fees
Image gallery for Beach Bungalow 1 with Private Outdoor yard
9.49.4 out of 10 rating
Exceptional
(101 reviews)
Beach Bungalow 1 with Private Outdoor yard
La Jolla, CA
7% off
Price is AU$3,516
AU$3,516
AU$502 per night
includes taxes & fees
Image gallery for Blue Heron Beach House - Near the Beach with a backyard and bikes!
1010 out of 10 rating
Exceptional
(43 reviews)
Blue Heron Beach House - Near the Beach with a backyard and bikes!
San Diego, CA
7% off
Price is AU$5,234
AU$5,234
AU$748 per night
includes taxes & fees
Image gallery for Amazing location with endless views and stunning sunsets.4/bed, 3/bath home
1010 out of 10 rating
Exceptional
(108 reviews)
Amazing location with endless views and stunning sunsets.4/bed, 3/bath home
La Jolla, CA
7% off
Price is AU$10,315
AU$10,315
AU$1,474 per night
includes taxes & fees
Image gallery for 2-Bedroom Coastal Gem, Just Steps to the Sand
8.08.0 out of 10 rating
Very good
(11 reviews)
2-Bedroom Coastal Gem, Just Steps to the Sand
San Diego, CA
8% off
Price is AU$4,998
AU$4,998
AU$714 per night
includes taxes & fees
Image gallery for The Key Lime Oasis, Gorgeous Second-Story Unit!
9.49.4 out of 10 rating
Exceptional
(94 reviews)
The Key Lime Oasis, Gorgeous Second-Story Unit!
San Diego, CA
8% off
Price is AU$6,149
AU$6,149
AU$878 per night
includes taxes & fees
Image gallery for Newly Updated Retro Beach Rental
9.89.8 out of 10 rating
Exceptional
(88 reviews)
Newly Updated Retro Beach Rental
San Diego, CA
12% off
Price is AU$2,788
AU$2,788
AU$398 per night
includes taxes & fees
Image gallery for Pacific Beach Urban Oasis w/ Outdoor Entertaining
1010 out of 10 rating
Exceptional
(33 reviews)
Pacific Beach Urban Oasis w/ Outdoor Entertaining
San Diego, CA
15% off
Price is AU$4,022
AU$4,022
AU$575 per night
includes taxes & fees
Image gallery for POOL * Remodeled Single Level House * Ocean & City Views
1010 out of 10 rating
Exceptional
(18 reviews)
POOL * Remodeled Single Level House * Ocean & City Views
San Diego, CA
7% off
Price is AU$3,568
AU$3,568
AU$510 per night
includes taxes & fees
Image gallery for You'll Love the Casita in Ocean Beach 1/2 Block to Santa Cruz Beach Cove
9.89.8 out of 10 rating
Exceptional
(109 reviews)
You'll Love the Casita in Ocean Beach 1/2 Block to Santa Cruz Beach Cove
San Diego, CA
7% off
Price is AU$2,200
AU$2,200
AU$314 per night
includes taxes & fees
Image gallery for Walk to the beach! Heart of Ocean Beach!
9.29.2 out of 10 rating
Wonderful
(84 reviews)
Walk to the beach! Heart of Ocean Beach!
San Diego, CA
8% off
Price is AU$1,841
AU$1,841
AU$263 per night
includes taxes & fees
Image gallery for Beautiful Modern La Jolla Beach House
9.69.6 out of 10 rating
Exceptional
(66 reviews)
Beautiful Modern La Jolla Beach House
La Jolla, CA
8% off
Price is AU$6,123
AU$6,123
AU$875 per night
includes taxes & fees
Image gallery for Retro Sea Cottage 180' Ocean Front Panoramic View
1010 out of 10 rating
Exceptional
(65 reviews)
Retro Sea Cottage 180' Ocean Front Panoramic View
La Jolla, CA
16% off
Price is AU$15,153
AU$15,153
AU$2,165 per night
includes taxes & fees
Image gallery for Bayfront | Ultimate Family Fun | AC | Parking
9.89.8 out of 10 rating
Exceptional
(107 reviews)
Bayfront | Ultimate Family Fun | AC | Parking
San Diego, CA
11% off
Price is AU$6,235
AU$6,235
AU$891 per night
includes taxes & fees
Image gallery for Blocks to the beach! Ocean Beach Oasis!
9.09.0 out of 10 rating
Wonderful
(47 reviews)
Blocks to the beach! Ocean Beach Oasis!
San Diego, CA
12% off
Price is AU$1,741
AU$1,741
AU$249 per night
includes taxes & fees
Image gallery for Large Single Family Home * Steps to Windansea Beach * Dog Ok
9.09.0 out of 10 rating
Wonderful
(14 reviews)
Large Single Family Home * Steps to Windansea Beach * Dog Ok
La Jolla, CA
7% off
Price is AU$5,649
AU$5,649
AU$807 per night
includes taxes & fees
Image gallery for 5 STAR LA JOLLA Bright & Charming HIDEAWAY! SPECIAL FALL AND WINTER RATES.
9.49.4 out of 10 rating
Exceptional
(141 reviews)
5 STAR LA JOLLA Bright & Charming HIDEAWAY! SPECIAL FALL AND WINTER RATES.
La Jolla, CA
8% off
Price is AU$2,357
AU$2,357
AU$337 per night
includes taxes & fees
Image gallery for Unbeatable Pacific Beach Retreat: Stunning Coastline & Skyline Views Await!
9.89.8 out of 10 rating
Exceptional
(117 reviews)
Unbeatable Pacific Beach Retreat: Stunning Coastline & Skyline Views Await!
San Diego, CA
8% off
Price is AU$4,598
AU$4,598
AU$657 per night
includes taxes & fees
Image gallery for Architectural Masterpiece on Windansea Beach - Family and Pet Friendly!
1010 out of 10 rating
Exceptional
(94 reviews)
Architectural Masterpiece on Windansea Beach - Family and Pet Friendly!
La Jolla, CA
8% off
Price is AU$17,165
AU$17,165
AU$2,452 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Shelter Island
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Find the best place to stay - Shelter Island
Oceanfront WhiteWater Views-Private Pool & Hot Tub--Best Sunset Cliffs Views
Sleeps 22 · 6 bedrooms · 6 bathrooms
9.69.6 out of 10
Exceptionalexceptional
83 reviews(83 reviews)
Gorgeous Bay View & Sunrise/Sunsets from Your Private, Sunny Deck in Point Loma!
Sleeps 3 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
254 reviews(254 reviews)
Adorable home with good space and breathtaking views of the city and ocean
Sleeps 6 · 3 bedrooms · 2+ bathrooms
8.28.2 out of 10
Very goodvery good
65 reviews(65 reviews)
Ocean Beach #2 ‘Garden’ Cozy Cottage - Walk to the beach!
Sleeps 2 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
158 reviews(158 reviews)
1BD on Ocean Beach Cliffs w. Hot Tub & Ocean-Facing Patio!
Sleeps 3 · 1 bedroom · 1 bathroom
7.07.0 out of 10
Goodgood
2 reviews(2 reviews)
Spectacular Custom Home with Pool/Jacuzzi in Bajamar Ocean Front Golf Resort
Sleeps 7 · 3 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
73 reviews(73 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value