Holiday rentals near Shelter Island
We found 3,249 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Shelter Island
Showing deals for:1 Aug - 8 Aug
Image gallery for Ocean View ☆Few Steps to Sand & Dining☆AC☆ Dogs OK
1010 out of 10 rating
Exceptional
(13 reviews)
Ocean View ☆Few Steps to Sand & Dining☆AC☆ Dogs OK
San Diego, CA
8% off
Price is £8,817
£8,817
£1,260 per night
includes taxes & fees
Image gallery for New Luxury Condo on Ocean Cliff, 2 Bedroom Suites, Full Kitchen, Living Room
1010 out of 10 rating
Exceptional
(10 reviews)
New Luxury Condo on Ocean Cliff, 2 Bedroom Suites, Full Kitchen, Living Room
San Diego, CA
8% off
Price is £3,031
£3,031
£433 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 rating
Exceptional
(58 reviews)
Luxury 5 star resort like dream home new 2024 AC private pool spa close to beach
San Diego, CA
8% off
Price is £10,879
£10,879
£1,554 per night
includes taxes & fees
Image gallery for Luxury S Oceanfront Unit with Rooftop & Hot Tub - AC
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Luxury S Oceanfront Unit with Rooftop & Hot Tub - AC
San Diego, California
9% off
Price is £15,300
£15,300
£2,186 per night
includes taxes & fees
Image gallery for Highly rated Best Beach!⛱️ 3Bd 2Ba AC Luxury KING Beds!
9.69.6 out of 10 rating
Exceptional
(55 reviews)
Highly rated Best Beach!⛱️ 3Bd 2Ba AC Luxury KING Beds!
San Diego, CA
8% off
Price is £5,068
£5,068
£724 per night
includes taxes & fees
Image gallery for WALLED GARDEN ESTATE LOCATED IN NORTH PACIFIC BEACH SLEEPS 8/9 plus kids mats
1010 out of 10 rating
Exceptional
(137 reviews)
WALLED GARDEN ESTATE LOCATED IN NORTH PACIFIC BEACH SLEEPS 8/9 plus kids mats
San Diego, CA
8% off
Price is £6,071
£6,071
£867 per night
includes taxes & fees
Image gallery for Ultimate San Diego Beach Escape; Steps to the Ocean and Bay
9.89.8 out of 10 rating
Exceptional
(46 reviews)
Ultimate San Diego Beach Escape; Steps to the Ocean and Bay
San Diego, CA
9% off
Price is £4,884
£4,884
£698 per night
includes taxes & fees
Image gallery for Catamaran by AvantStay | 50ft to Beach + Views
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Catamaran by AvantStay | 50ft to Beach + Views
San Diego, California
7% off
Price is £8,695
£8,695
£1,242 per night
includes taxes & fees
Image gallery for Dog Friendly Beach Cottage, Private Yard - one block to Water & Dog Beach
1010 out of 10 rating
Exceptional
(13 reviews)
Dog Friendly Beach Cottage, Private Yard - one block to Water & Dog Beach
San Diego, CA
8% off
Price is £2,467
£2,467
£352 per night
includes taxes & fees
Image gallery for OCEAN VIEW Family Beach House 4BR 3BA Open Concept just 4 block walk to beach!
1010 out of 10 rating
Exceptional
(101 reviews)
OCEAN VIEW Family Beach House 4BR 3BA Open Concept just 4 block walk to beach!
San Diego, CA
8% off
Price is £5,351
£5,351
£764 per night
includes taxes & fees
Image gallery for Luv Oceanside-1 House to Beach
1010 out of 10 rating
Exceptional
(22 reviews)
Luv Oceanside-1 House to Beach
San Diego, CA
8% off
Price is £7,405
£7,405
£1,058 per night
includes taxes & fees
Image gallery for Vista Del Mar by AvantStay | Stunning Spanish Inspired Home w/ Pool, Hot Tub
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Vista Del Mar by AvantStay | Stunning Spanish Inspired Home w/ Pool, Hot Tub
La Jolla, CA
7% off
Price is £13,272
£13,272
£1,896 per night
includes taxes & fees
Image gallery for Oceanfront Penthouse w/ Unlimited Views & AC
1010 out of 10 rating
Exceptional
(112 reviews)
Oceanfront Penthouse w/ Unlimited Views & AC
San Diego, CA
11% off
Price is £9,074
£9,074
£1,296 per night
includes taxes & fees
Image gallery for Near Bay w/ 12 Bikes, A/C, BBQ, Deck, Wi-Fi, Parking - Min to Beach!
1010 out of 10 rating
Exceptional
(5 reviews)
Near Bay w/ 12 Bikes, A/C, BBQ, Deck, Wi-Fi, Parking - Min to Beach!
San Diego, CA
8% off
Price is £6,821
£6,821
£974 per night
includes taxes & fees
Image gallery for 2 Story + Ocean Front + AC + Exclusive View Balcony
9.49.4 out of 10 rating
Exceptional
(104 reviews)
2 Story + Ocean Front + AC + Exclusive View Balcony
San Diego, CA
7% off
Price is £4,081
£4,081
£583 per night
includes taxes & fees
Image gallery for Wake Up to the Waves- Private Beach Home
1010 out of 10 rating
Exceptional
(90 reviews)
Wake Up to the Waves- Private Beach Home
San Diego, CA
11% off
Price is £6,499
£6,499
£928 per night
includes taxes & fees
Image gallery for WaterFront * Exclusive View Patio * Ground Level * A/C
9.69.6 out of 10 rating
Exceptional
(66 reviews)
WaterFront * Exclusive View Patio * Ground Level * A/C
San Diego, CA
7% off
Price is £2,674
£2,674
£382 per night
includes taxes & fees
Image gallery for 2 Houses to Beach * Exclusive Patio * Dog OK
9.89.8 out of 10 rating
Exceptional
(13 reviews)
2 Houses to Beach * Exclusive Patio * Dog OK
San Diego, CA
7% off
Price is £3,421
£3,421
£489 per night
includes taxes & fees
Image gallery for MISSION BEACH 2 BDRM, WITH PARKING in the HEART OF MISSION BEACH + MISSION BAY!!
9.89.8 out of 10 rating
Exceptional
(39 reviews)
MISSION BEACH 2 BDRM, WITH PARKING in the HEART OF MISSION BEACH + MISSION BAY!!
San Diego, CA
8% off
Price is £3,017
£3,017
£431 per night
includes taxes & fees
Image gallery for Las Olas by AvantStay | Panoramic Ocean Views in the ❤ of Point Loma
8.68.6 out of 10 rating
Excellent
(12 reviews)
Las Olas by AvantStay | Panoramic Ocean Views in the ❤ of Point Loma
San Diego, CA
6% off
Price is £4,835
£4,835
£691 per night
includes taxes & fees
Image gallery for Ocean Views w/ Private Ground Floor Patio | Fire Pit
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Ocean Views w/ Private Ground Floor Patio | Fire Pit
San Diego, CA
11% off
Price is £2,368
£2,368
£338 per night
includes taxes & fees
Image gallery for 4 Bed/3 Bath, Private Hot tub, patio Parking + 5 bikes Included! Families only..
9.89.8 out of 10 rating
Exceptional
(43 reviews)
4 Bed/3 Bath, Private Hot tub, patio Parking + 5 bikes Included! Families only..
San Diego, CA
8% off
Price is £5,537
£5,537
£791 per night
includes taxes & fees
Image gallery for Professionally Designed | Private Outdoor Patio w/ AC
9.49.4 out of 10 rating
Exceptional
(20 reviews)
Professionally Designed | Private Outdoor Patio w/ AC
San Diego, CA
11% off
Price is £2,757
£2,757
£394 per night
includes taxes & fees
Image gallery for Waterfront Condo | AC | Beach Toys | Walk to All!
1010 out of 10 rating
Exceptional
(42 reviews)
Waterfront Condo | AC | Beach Toys | Walk to All!
San Diego, CA
11% off
Price is £3,568
£3,568
£510 per night
includes taxes & fees
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Find properties near top attractions in Shelter Island
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Find the best place to stay - Shelter Island
Summer break 2 blocks to beach, pier, Newport Ave
Sleeps 7 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
8 reviews(8 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
246 reviews(246 reviews)
Beach Suite at San Diego Shelter
Sleeps 6 · 1 bedroom · 1 bathroom
4 bed/ 3 bath North PB/ La Jolla family home, central AC , pool and Peloton Bike
Sleeps 8 · 4 bedrooms · 3 bathrooms
9.49.4 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Point Loma Escape - Walk to the Harbor, Restaurants, & Shops! W/parking
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
Beach Bungalow, Free Parking, 2 blocks to the beach
Sleeps 5 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
59 reviews(59 reviews)
Top rated rentals - Shelter Island
First time visit to San Diego (not the last!)
1010 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
Beautiful cottage near the sea
1010 out of 10
Exceptionalexceptional
103 reviews(103 reviews)
Perfect location, great amenities.
1010 out of 10
Exceptionalexceptional
152 reviews(152 reviews)
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All the privacy of homeEnjoy full kitchens, pools, gardens and more
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