
Holiday rentals near Shelter Island
We found 3,275 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:9 Jan - 16 Jan
Image gallery for Million Dollar Ocean Views! Central Location & Parking

9.89.8 out of 10, Exceptional, (25 reviews)
Exceptional
(25 reviews)
Million Dollar Ocean Views! Central Location & Parking
San Diego, CA
8% off
Price is NZ$3,452
NZ$3,452
for 7 nights, 1 apartment
NZ$493 per night
includes taxes & fees
Image gallery for Luxury 5 star resort like dream home new 2024 AC private pool spa close to beach

9.69.6 out of 10, Exceptional, (63 reviews)
Exceptional
(63 reviews)
Luxury 5 star resort like dream home new 2024 AC private pool spa close to beach
San Diego, CA
8% off
Price is NZ$25,712
NZ$25,712
for 7 nights, 1 home
NZ$3,673 per night
includes taxes & fees
Image gallery for Perfect Location to Beach/SD Attractions, Parking, Beach Chairs, Boogie Boards

9.89.8 out of 10, Exceptional, (318 reviews)
Exceptional
(318 reviews)
Perfect Location to Beach/SD Attractions, Parking, Beach Chairs, Boogie Boards
San Diego, CA
7% off
Price is NZ$3,032
NZ$3,032
for 7 nights, 1 home
NZ$433 per night
includes taxes & fees
Image gallery for OCEAN BEACH, #1 Amore, Retro/Cozy, Studio Cottage, only 3 blocks to Beach!🏖

9.69.6 out of 10, Exceptional, (41 reviews)
Exceptional
(41 reviews)
OCEAN BEACH, #1 Amore, Retro/Cozy, Studio Cottage, only 3 blocks to Beach!🏖
San Diego, CA
8% off
Price is NZ$1,858
NZ$1,858
for 7 nights, 1 apartment
NZ$265 per night
includes taxes & fees
Image gallery for Steps to the water on both sides!!

9.49.4 out of 10, Exceptional, (85 reviews)
Exceptional
(85 reviews)
Steps to the water on both sides!!
San Diego, CA
11% off
Price is NZ$2,001
NZ$2,001
for 7 nights, 1 apartment
NZ$286 per night
includes taxes & fees
Image gallery for La Jolla - Bird Rock Suite - Stay by the Sea

9.89.8 out of 10, Exceptional, (32 reviews)
Exceptional
(32 reviews)
La Jolla - Bird Rock Suite - Stay by the Sea
La Jolla, CA
7% off
Price is NZ$2,847
NZ$2,847
for 7 nights, 1 home
NZ$407 per night
includes taxes & fees
Image gallery for Stunning Spanish Villa with Gorgeous Pool

9.09.0 out of 10, Wonderful, (18 reviews)
Wonderful
(18 reviews)
Stunning Spanish Villa with Gorgeous Pool
La Jolla, CA
8% off
Price is NZ$14,647
NZ$14,647
for 7 nights, 1 villa
NZ$2,092 per night
includes taxes & fees
Image gallery for Steps to sand & ocean view from inside the unit!

9.69.6 out of 10, Exceptional, (35 reviews)
Exceptional
(35 reviews)
Steps to sand & ocean view from inside the unit!
San Diego, CA
5% off
Price is NZ$3,774
NZ$3,774
for 7 nights, 1 home
NZ$539 per night
includes taxes & fees
Image gallery for Pacific Beach Studio #1973 Close to beach, bay and more!

8.88.8 out of 10, Excellent, (10 reviews)
Excellent
(10 reviews)
Pacific Beach Studio #1973 Close to beach, bay and more!
San Diego, CA
8% off
Price is NZ$1,848
NZ$1,848
for 7 nights, 1 apartment
NZ$264 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, Exceptional, (112 reviews)
Exceptional
(112 reviews)
Amazing location with endless views and stunning sunsets.4/bed, 3/bath home
La Jolla, CA
7% off
Price is NZ$11,147
NZ$11,147
for 7 nights, 1 home
NZ$1,592 per night
includes taxes & fees
Image gallery for a 'Haven Away' with Spectacular Panoramic View/Newly Remodeled

9.89.8 out of 10, Exceptional, (168 reviews)
Exceptional
(168 reviews)
a 'Haven Away' with Spectacular Panoramic View/Newly Remodeled
San Diego, CA
8% off
Price is NZ$5,424
NZ$5,424
for 7 nights, 1 apartment
NZ$775 per night
includes taxes & fees
Image gallery for Ocean Views | Steps from the Beach | Family-Friendly Retreat

9.89.8 out of 10, Exceptional, (36 reviews)
Exceptional
(36 reviews)
Ocean Views | Steps from the Beach | Family-Friendly Retreat
San Diego, CA
10% off
Price is NZ$4,984
NZ$4,984
for 7 nights, 1 home
NZ$712 per night
includes taxes & fees
Image gallery for Classic Beach Cottage Steps to Sand + A/C & Garage

1010 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)
Classic Beach Cottage Steps to Sand + A/C & Garage
San Diego, CA
6% off
Price is NZ$3,600
NZ$3,600
for 7 nights, 1 cottage
NZ$514 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, Exceptional, (18 reviews)
Exceptional
(18 reviews)
Near Bay Home with A/C, Bikes, Parking, and Wi-Fi - Mins to Beach!
San Diego, CA
8% off
Price is NZ$3,941
NZ$3,941
for 7 nights, 1 home
NZ$563 per night
includes taxes & fees
Image gallery for Cozy private entrance studio in heart of Point Loma Beach community

9.69.6 out of 10, Exceptional, (227 reviews)
Exceptional
(227 reviews)
Cozy private entrance studio in heart of Point Loma Beach community
San Diego, CA
8% off
Price is NZ$1,902
NZ$1,902
for 7 nights, 1 apartment
NZ$272 per night
includes taxes & fees
Image gallery for ☀ BEACH IS FULLY OPEN! Huge Rare 3BR Beach House! 80% OFF!☀

9.69.6 out of 10, Exceptional, (58 reviews)
Exceptional
(58 reviews)
☀ BEACH IS FULLY OPEN! Huge Rare 3BR Beach House! 80% OFF!☀
San Diego, CA
12% off
Price is NZ$8,931
NZ$8,931
for 7 nights, 1 home
NZ$1,276 per night
includes taxes & fees
Image gallery for Ocean Beach Garden Cottage - Cozy Coastal Retreat

1010 out of 10, Exceptional, (139 reviews)
Exceptional
(139 reviews)
Ocean Beach Garden Cottage - Cozy Coastal Retreat
San Diego, CA
15% off
Price is NZ$3,598
NZ$3,598
for 7 nights, 1 cottage
NZ$514 per night
includes taxes & fees
Image gallery for La Jolla Cove Entire Renovated, Designed Home

1010 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
La Jolla Cove Entire Renovated, Designed Home
La Jolla, CA
12% off
Price is NZ$8,861
NZ$8,861
for 7 nights, 1 home
NZ$1,266 per night
includes taxes & fees
Image gallery for HOT TUB, Parking, A/C - Near SeaWorld, Beaches, MCRD, Barnes Tennis, PLNU!

1010 out of 10, Exceptional, (71 reviews)
Exceptional
(71 reviews)
HOT TUB, Parking, A/C - Near SeaWorld, Beaches, MCRD, Barnes Tennis, PLNU!
San Diego, CA
7% off
Price is NZ$2,621
NZ$2,621
for 7 nights, 1 apartment
NZ$374 per night
includes taxes & fees
Image gallery for Water View Penthouse just 1 House to Bay!

1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Water View Penthouse just 1 House to Bay!
San Diego, CA
7% off
Price is NZ$5,801
NZ$5,801
for 7 nights, 1 home
NZ$829 per night
includes taxes & fees
Image gallery for The Cozy Beach Nook, 150 Steps To The Sand

9.89.8 out of 10, Exceptional, (58 reviews)
Exceptional
(58 reviews)
The Cozy Beach Nook, 150 Steps To The Sand
San Diego, CA
7% off
Price is NZ$3,690
NZ$3,690
for 7 nights, 1 home
NZ$527 per night
includes taxes & fees
Image gallery for 1 House to Beach * Rare 3 Level Corner Townhouse * EV Charger

1010 out of 10, Exceptional, (38 reviews)
Exceptional
(38 reviews)
1 House to Beach * Rare 3 Level Corner Townhouse * EV Charger
San Diego, CA
7% off
Price is NZ$6,920
NZ$6,920
for 7 nights, 1 home
NZ$989 per night
includes taxes & fees
Image gallery for Outdoor Living | Clean, Central & Spacious

1010 out of 10, Exceptional, (45 reviews)
Exceptional
(45 reviews)
Outdoor Living | Clean, Central & Spacious
San Diego, CA
10% off
Price is NZ$5,977
NZ$5,977
for 7 nights, 1 home
NZ$854 per night
includes taxes & fees
Image gallery for TOP FLOOR BEACH CONDO WITH STUNNING VIEWS JUST STEPS TO THE SAND

9.89.8 out of 10, Exceptional, (305 reviews)
Exceptional
(305 reviews)
TOP FLOOR BEACH CONDO WITH STUNNING VIEWS JUST STEPS TO THE SAND
San Diego, CA
8% off
Price is NZ$3,882
NZ$3,882
for 7 nights, 1 apartment
NZ$555 per night
includes taxes & fees
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