Pet-friendly holiday rentals in Shelter Island

Sauna, Ice Bath, Jacuzzi & Firepit, Rest & Relax

*Quiet Neighborhood *Wellness Trio: Sauna, Cold Plunge, and Hot Tub *Expansive Secluded Backyard *Spacious 1,600 sqft Living Space *Generously Sized In and Outdoor Space *Individual TVs in Every Bedroom *Netflix, Hulu, Disney +, HBOmax, Espn + included *Cozy Firepit Area *Efficient Central Air Conditioning *A quick 10-minute drive to downtown *Kitchen Ready with All You Need *Washer and Dryer in Unit *A short stroll to cafes, yoga studios, fitness centers, eateries, entertainment, and shops!

Outdoor spaces · Pets · Hot tub

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

Pets · Outdoor spaces · Family

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

Walkability · Outdoor spaces · Quiet

Dune’s Desert Oasis

Enjoy access to everything in San Diego from this centrally located home. Located in the midway district only four blocks from Sports Arena. This brand new unit is equipped with everything you need and more. It has a fully equipped kitchen with tons of storage, large living area, large bedroom, super fast Wi-Fi, filtered shower, backlit vanity mirror, full-size washer and dryer in closet, dimmable lighting throughout, cozy bedding, thick towels, parking, and tons of natural light.

Walkability · Pets · Amenities

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.

Outdoor spaces · Walkability · Family

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.

Outdoor spaces · Pets · Access

Dream Penthouse! The Most Amazing Bath & Views

Stunning Zen Penthouse with The Most Amazing Bathroom you have ever seen. Located right by Little Italy, Balboa Park, the Bay, the Convention Center, within walking distance to amazing restaurants, coffee shops, bars and within minutes of all San Diego Beaches and attractions. The Zen Penthouse has a total European feel to it, it's like being in London with amazing weather and the best part, the breathtaking views of the Skyline and unreal Sunsets!

Outdoor spaces · Pets · Value

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.

Pets · Walkability · Air conditioning

Dream HOUSE Steps to Beach & Bay

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 *Central AV *Voice Controlled Sound System, 4K TVs in every room *Beautiful bathrooms *Bikes, boards, beach towels and toys *Walk to coffee, yoga & gyms, dining, entertainment, shopping!

Walkability · Outdoor spaces · Parks

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.

Walkability · Pets · Location

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.

Walkability · Pets · Wi-Fi

Forever View

Enjoy the views from the covered patio while the ocean breeze flows around you! This is a modern home with a fully stocked kitchen and attention to the smallest detail accounted for. Short drive to the airport, downtown, beaches, SeaWorld, La Jolla and most other attractions in San Diego. Owners live in a unit on-site, and there are no shared spaces or access between units.

Walkability · Pets · Checkout