Pet-friendly vacation rentals in Shelter Island

Coastal Guest House with Gorgeous Sundeck

✨ Welcome to Our Charming Guest House on Voltaire Street ✨ Just want to make sure you know that the whole unit is private for your use only. Our listing is exclusive for you. You will not share any space with anyone else. Enjoy a cozy and freshly renovated space designed for comfort and relaxation. create a cheerful atmosphere that feels just like home. Step on our beautiful wooden floors, enjoy the spacious open layout, and unwind on the large private deck — perfect for soaking up the sun.

East Watch- a private getaway

East Watch is a 740 sq ft, 1 bedroom private retreat that provides the comforts and amenities of home with the style of a high-end hotel. All 5 to 15 min from shopping, downtown, and the beach. It's a short walk from Mt. Helix Park which offers a 360* view, weekday yoga, and stunning sunrises and sunsets. We have EV high speed car charging, a full kitchen with all appliances, workspace with dedicated fast WIFI, a spa shower, and super comfortable beds and pillows. Stay and let us charm you!

Comfy Cottage Near the Beach

Bring the whole family to our stylish, comfy beach cottage! Walk to Ocean Beach and Dog Beach, then wander Newport Ave for great eats and drinks. Enjoy morning coffee in fenced front yard or fire up a sunset BBQ out back. End the day with a trip to Sunset Cliffs to watch a breathtaking sunset! Pets welcome (+$100 pet fee). Simple, clean, and close to everything—perfect for carefree beach days together. A/C and fast Wi-Fi keep everyone comfy, and roomy living room is great for movie night fun!!

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

Private space close to the heart of Ocean Beach

Enjoy two private bedrooms and a modern bath on the lower level of an Ocean Beach home. Your private side entrance opens to a relaxing gated outdoor space. Each bedroom features a queen bed, hardwood furniture, décor, TV, and Roku. One TV is 55'' and the other is 32''. Includes heating, cooling, and a kitchenette (no full kitchen). The owner lives on the upper floor—no shared spaces, locked door separation. Just blocks from historic Ocean Beach, Newport Avenue, and the famous Dog Beach!

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.

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.

Private Home, Pet Friendly ~Sasha's Bungalow in OB

Welcome to Sasha’s Bungalow, your perfect Ocean Beach escape! Just one block from the ocean, this 2-bedroom, 1-bath retreat is steps from Newport Ave., Voltaire St., and OB’s lively shops and restaurants. Relax in your private yard with a fire pit, BBQ, and cozy seating, or sip coffee on the front patio. Inside, enjoy a fully stocked kitchen, fast WiFi, streaming, and beach gear. Best of all, we’re pet-friendly—bring up to 2 pets ($45/pet fee) to join your beach adventure!

Mid-Century Bungalow Block to Beach & Downtown OB

Excellent location to explore Ocean Beach and San Diego. This is a very walkable neighborhood and you will find sand and water, coffee, breakfast, lunch, dinner, music, shops, within a few blocks. The community of Ocean Beach has always been celebrated for its eclectic vibe. People are kind, considerate, and friendly. SeaWorld is a 10 minute drive, SD Zoo is 15 minute, Downtown San Diego/Gaslamp/Padres Stadium is 20 minute.

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.

Luxe OB Home, Walk to Beach, Sauna, and Backyard

Welcome to OB Surfer’s Paradise by Salt & Sky Lodging Co—your stylish coastal getaway just steps from Ocean Beach and Dog Beach. Enjoy a private sauna, fenced in backyard, balcony sunset views, and a dreamy master suite. With a chef’s kitchen, beach gear, 5 bikes, fast Wi-Fi, and walkable access to OB’s best spots, this home is designed for surf, relaxation, and effortless San Diego living.

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!