Family-Friendly Vacation Rentals in Shelter Island, CA: Compare 10+ Sites & Save

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1591 Best Family Vacation Rentals in Shelter Island (Starting from $136)

The Pool Side Hideaway with Golf Cart
The Pool Side Hideaway with Golf Cart
Apartment
San Diego, CA, USA
0.9k from Shelter Island center

Apartments, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Beach, Hot tubs

4 Bedrooms10 Guests
9.4

Superb

16 reviews

$1256
Average price / night
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San Diego Home w/ Deck & Yard - 2 Blocks to Bay!
San Diego Home w/ Deck & Yard - 2 Blocks to Bay!
House
San Diego, CA, 92106, United States
0.9k from Shelter Island center

Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom4 Guests
8.8

Fabulous

49 reviews

$277
Average price / night
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La Playa - Charming Bayside Bungalow
La Playa - Charming Bayside Bungalow
House
CA, USA
0.9k from Shelter Island center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Bungalows

3 Bedrooms6 Guests
New to Booking
$526
Average price / night
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Kellogg’s Beach Home with  washer/dryer,/full kitchen, kids backyard and parking
Kellogg’s Beach Home with washer/dryer,/full kitchen, kids backyard and parking
House
San Diego, CA, 92106, United States
1.0k from Shelter Island center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.4

Superb

8 reviews

$593
Average price / night
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La Playa Abode
La Playa Abode
House
San Diego, CA, USA
1.0k from Shelter Island center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
6.5

Good

4 reviews

$138
Average price / night
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PRIVATE LA PLAYA BEACH/SPACIOUS 1300 SQ FT VACATION IN POINT LOMA SHELTER ISLAND
PRIVATE LA PLAYA BEACH/SPACIOUS 1300 SQ FT VACATION IN POINT LOMA SHELTER ISLAND
Condo
San Diego, CA, 92106, United States
1.1k from Shelter Island center

AC, Balcony, Dryer, Elevator, Extra Bed, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
10.0

Exceptional

24 reviews

$169
Average price / night
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Serene San Diego Retreat with Deck - Walk to Bay!
Serene San Diego Retreat with Deck - Walk to Bay!
House
San Diego, CA, USA
1.0k from Shelter Island center

Cheap, Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$236
Average price / night
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Bay Views, Watch Sailboats Go By....
Bay Views, Watch Sailboats Go By....
Apartment
San Diego, CA, 92106, United States
1.1k from Shelter Island center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fireplace, Free Parking, Heater

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$614
Average price / night
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On The Beach Casa
On The Beach Casa
House
San Diego, CA, USA
1.0k from Shelter Island center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

2 Bedrooms5 Guests
8.0

Good

5 reviews

$397
Average price / night
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Spacious Family & Group Getaway in San Diego with EV Charger+Laundry+Balcony
Spacious Family & Group Getaway in San Diego with EV Charger+Laundry+Balcony
Apartment
San Diego, CA, 92106, United States
1.3k from Shelter Island center

AC, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet

4 Bedrooms16 Guests
New to Booking
$777
Average price / night
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On The Beach Casita
On The Beach Casita
House
San Diego, CA, USA
1.0k from Shelter Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
New to Booking
$624
Average price / night
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King Bed, EV Charger, Sleeps 8, Balcony, Laundry
King Bed, EV Charger, Sleeps 8, Balcony, Laundry
Apartment
San Diego, CA, 92106, United States
1.4k from Shelter Island center

AC, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet

2 Bedrooms8 Guests
8.0

Good

1 reviews

$355
Average price / night
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On The Beach Clubhouse
On The Beach Clubhouse
House
San Diego, CA, USA
1.0k from Shelter Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$810
Average price / night
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Modern Upstairs Apartment Walk to Harbor & Dining
Modern Upstairs Apartment Walk to Harbor & Dining
Apartment
San Diego, CA, 92106, United States
1.5k from Shelter Island center

Balcony, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

2 Bedrooms6 Guests
4.0

Review score

1 reviews

$375
Average price / night
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Point Loma Escape - Walk to the Harbor Restaurants & Shops with Parking!
Point Loma Escape - Walk to the Harbor Restaurants & Shops with Parking!
House
San Diego, CA, USA
1.2k from Shelter Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

2 Bedrooms6 Guests
7.8

Good

5 reviews

$369
Average price / night
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Newly Renovated Home Near Harbor Island
Newly Renovated Home Near Harbor Island
House
San Diego, CA, 92106, United States
1.5k from Shelter Island center

Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Patio

3 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$537
Average price / night
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Nautical Point Loma Getaway - 7 mins to airport
Nautical Point Loma Getaway - 7 mins to airport
House
San Diego, CA, USA
1.2k from Shelter Island center

Parking, Fireplace/Heating, Security/Safety, Pet Friendly, Internet, Air Conditioner, Child Friendly

2 Bedrooms6 Guests
7.8

Good

7 reviews

$272
Average price / night
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Updated 1BR in Point Loma – Near Harbor & Airport
Updated 1BR in Point Loma – Near Harbor & Airport
Apartment
San Diego, CA, 92106, United States
1.5k from Shelter Island center

Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom3 Guests
New to Booking
$259
Average price / night
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Seaside Point Loma Home with Outdoor Patio
Seaside Point Loma Home with Outdoor Patio
House
San Diego, CA, USA
1.2k from Shelter Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

1 Bedroom5 Guests
7.3

Good

4 reviews

$218
Average price / night
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King Bed, EV Charger, Pet-Friendly, Balcony, Near Airport & Beaches
King Bed, EV Charger, Pet-Friendly, Balcony, Near Airport & Beaches
Apartment
San Diego, CA, 92106, United States
1.7k from Shelter Island center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

2 Bedrooms8 Guests
New to Booking
$336
Average price / night
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Big Red Lodge Cottage
Big Red Lodge Cottage
Villa
San Diego, CA, USA
1.3k from Shelter Island center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cabins, Cottages, Lodgings, Places to stay

1 Bedroom2 Guests
8.6

Fabulous

26 reviews

$136
Average price / night
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VIEWS! VIEWS!  VIEWS! 4 Master Suites 5 Star Architectural  Designer with Spa
VIEWS! VIEWS! VIEWS! 4 Master Suites 5 Star Architectural Designer with Spa
House
San Diego, CA, 92106, United States
1.8k from Shelter Island center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub

4 Bedrooms9 Guests
10.0

Exceptional

199 reviews

$783
Average price / night
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🌟Breathtaking 180º Views | Family+Work | Hot Tub | 💖of San Diego🌴 |5⭐️reviews
🌟Breathtaking 180º Views | Family+Work | Hot Tub | 💖of San Diego🌴 |5⭐️reviews
House
San Diego, CA, 92106, United States
1.9k from Shelter Island center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

6 Bedrooms14 Guests
10.0

Exceptional

66 reviews

$1465
Average price / night
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Near Beach & Airport w/King Bed, EV Charger, Free Parking
Near Beach & Airport w/King Bed, EV Charger, Free Parking
Apartment
San Diego, CA, 92106, United States
2.0k from Shelter Island center

AC, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet

2 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$359
Average price / night
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Boho-Style Point Loma Retreat, Large Outdoor Deck
Boho-Style Point Loma Retreat, Large Outdoor Deck
House
San Diego, CA, 92106, United States
2.1k from Shelter Island center

Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$635
Average price / night
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Luxury 5BR Private Pool Home w/ Panoramic Ocean Bay & City Views – Sleeps 12+
Luxury 5BR Private Pool Home w/ Panoramic Ocean Bay & City Views – Sleeps 12+
House
San Diego, CA, 92106, United States
2.2k from Shelter Island center

Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms12 Guests
10.0

Exceptional

147 reviews

$1460
Average price / night
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10 Min to Mission Beach, Downtown & Sunset Cliffs!
10 Min to Mission Beach, Downtown & Sunset Cliffs!
House
San Diego, CA, 92107, United States
2.3k from Shelter Island center

Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area

3 Bedrooms6 Guests
New to Booking
$730
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in Shelter Island.

Where to stay in Shelter Island? Best neighborhoods & areas

Shelter Island Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 1591 verified family-friendly vacation rentals in Shelter Island. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Shelter Island vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $136 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Shelter Island offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Shelter Island are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Shelter Island often include amenities such as Child Friendly, Fireplace/Heating, and Laundry. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.