Pet-friendly holiday rentals in Shelter Island

PB Dream HOUSE Steps to Beach Bay ❤️Modern Private

Located in the heart of Pacific Beach, this modern beach house has been completely remodeled and re-imagined to make your stay unforgettable. Designed with the eye toward comfort and entertainment. *Private Outdoor Retreat w/ Kitchen, 6 Person Hot Tub, Fire Pit *AC w/ independent temp control in each room *Voice Controlled Sound System, 4K TVs in every room *Beautiful bathroom w/ dual showers *Bikes, boards, beach towels and toys *Walk to coffee, yoga & gyms, dining, entertainment, shopping!

Charming Ocean Beach Cottage minutes to Ocean w/AC

Renovated charming beach cottage just 2 blocks from the beach in Ocean Beach, California! French doors that open to private fenced paver patio to enjoy the outdoors. 5 min Walk to beach and great restaurants, bars, shops & all OB has to offer ! Brand New Heating and Air conditioning unit 1 car Garage parking onsite with laundry Fast Wifi Smart tv New memory foam mattresses on queen bed in private bedroom & queen sofa sleeper. Very comfortable! Come stay at the best beach in San Diego!

Bayview Paradise

Known as the Huguette House, this luxury private single-family two bedrooms two bathrooms home in La Playa the heart of Point Loma, San Diego offers 180-degree panoramic views of the world-famous San Diego Bay and Downtown Skyline. views of the San Diego bay, marina, and Coronado Island during the day and spectacular views of the Downtown San Diego skyline at night, fully equipped kitchen, and laundry room, 2 bedroom suites with queen beds .2 luxury bathrooms, HDTV, computer desk and WFI

5 Min > Convoy | King Bed | Parking | Private Yard

Experience the beauty of San Diego at prime location, and inviting home 5 min → All freeways 9 mins → Balboa Park 13 mins → Petco Park / Gaslamp Quarter 14 mins → Airport 15 mins → La Jolla Shores Park 16 mins → USS Midway Museum 18 mins → Beach / Coronado 25 mins → Lagoon Trails ⭐️ "One of the best stays in SD" ⭐️ • Extreme Privacy & Fully Fenced • 2 Vehicles Private Parking • Large Patio + BBQ • Stocked Kitchen • Washer + Dryer Add to your wishlist - click ❤️ in the upper-right corner

The Cozy Craftsman

Bright • Walkable • Charming 2BR Craftsman retreat in San Diego's University Heights neighborhood, perfectly located between Hillcrest and North Park.  Skylights and large windows fill the home with natural light, while the thoughtfully updated interior offers comfort and style.  Enjoy a private fenced yard with outdoor seating, and walk to restaurants, cafes, and a grocery store just two blocks away.  Perfect for couples, small groups, or business travelers exploring San Diego.

Upgraded Pt Loma Panoramic Views - 1 Bedroom Suite

Brand new full kitchen installed November 2025. Enjoy your home away from home and beautiful Pt Loma. With an expansive view of the gorgeous San Diego Bay & Shelter Island you can enjoy a comfortable space with luxury amenities. A spacious oasis to escape the hustle and bustle of the city, but close enough for a night out on the town. If you’d rather stay in and enjoy the views, relax on the patio, soak in the hot tub, or have a drink by the fire pit with your fur baby.

Dream 3BR HOUSE San Diego - Spa BBQ Playroom

Located in the heart of San Diego, this stylish house has been completely remodeled and re-imagined to make your stay unforgettable. Designed with the eye toward comfort and entertainment. *Private Outdoor Retreat w/ BBQ, 6 Person Hot Tub, Fire Pit *4K TVs in every room/ ceiling fans AC living room and playroom. *Walk to coffee, restaurants, entertainment, shopping with beautiful hiking trails!!Plus short drive to Downtown/ Old town/ beaches/ Sea world/ zoo and more.

Sunset Cliffs Hideaway

Kick back and relax in this peaceful, stylish space. Spacious Bedroom in private residence with private entrance, easy parking, located 1.5 blocks from beautiful Sunset Cliffs. Less than 15 min drive to all of the best San Diego has to offer. Walking distance to Ocean Beach (~1 mi), a funky beach town with its own casual style. Room is "hotel style" with private entrance, small patio, bed, bath, fridge and microwave; no access to main house.

OB Casita

Stay in a cozy Casita surrounded by a private garden. The inside space is petite, the yard is large. This in-law unit features a kitchenette, a private bathroom, a BBQ, and a fenced outdoor area perfect for pups! Sit under the avocado tree on the back deck and watch for the OB parrots. Or, take a short walk in this lively neighborhood to, beaches, dog beach, tennis courts, restaurants, bars, shopping, a playground, or a dog park.

Completely Remodeled OB Casita

This condo has been completely remodeled, it's stylish, comfortable, an upstairs unit with no one underneath you, that is just blocks from the beach, restaurants and so much more! It has air-conditioning for those warm summer nights and a heater for the chilly winter nights, although it's never too cold here in San Diego. King size bed in bedroom and a queen size sofa sleeper in the living room.

Beachy Bungalow, Adult Retreat, Outdoor Oasis!

Adults only retreat. Pups welcome :) Rooftop level deck with Beautiful Sunset View. Sparkling clean for your health. Oasis Bungalow, Eco-friendly green, equipped with everything you will need for a comfortable stay. Our home, your vacation. Chill vibe & unique - like the rest of OB :) Lots of outdoor living; dining area w/ grill, lounge area with fire-pit. Beach gear! Walk to Beach, in OB!

Family Stay Point Loma Style (Beach and Bay)

Enjoy the idyllic La Playa/ Wooded area of Point Loma in our bungalow style house. The house is a 15 min drive or less from Sea World, the Zoo, Balboa Park, Cabrillo National Monument, Tide Pools, Liberty Station, Historic Old Town, Downtown, Airport, Shelter Island, Harbor Island, Surfing, Sailing, Sportfishing, Kayaking, and the Best Beaches in San Diego!