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!

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

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 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!

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.

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!

Modern ❤️ of South Park, SD skyline, private patio

- Newly renovated home - Historical neighborhood - Spacious front deck patio facing Dog Park - Skyline view of downtown San Diego - Extra large shower - Cozy bedding - Safe street parking - Dog friendly! $75 (2 pets max) Key landmarks - Balboa Park - Balboa Golf Course - 10 min walk to local favorite spots - 10 min drive to downtown San Diego - 15 min drive to SAN Airport

Modern Luxury w/ EPIC Backyard and Jacuzzi

Welcome to our newly remodeled "modern coastal" house with an incredible backyard! No detail was overlooked in this home, with designer finishes, high end furniture, and an outdoor oasis to soak in the beautiful San Diego days. Highlights include an open floor plan, jacuzzi, outdoor games, pool table, grill, string lights, and so much more. We cannot wait to host you!

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!

Coastal, Elegant, Modern, King Bed

-Stylish custom-built coastal apartment in the heart of San Diego -Modern kitchen, living space, reading area, dining area, washer dryer, bathtub, skylights -Bright, Spacious, Family Friendly, Pet Friendly -King Bed - Best location - 5 minutes to everything!! Close to Beach, Liberty Station, Airport, Downtown, Zoo, Sea World, Cabrillo National Monument

Pet-Friendly Home w/Ocean Views Near Sunset Cliffs

Welcome to our Ocean Beach home. We've put a lot of care into creating a comfortable, relaxing space where guests can slow down and enjoy the ocean views, sea breezes, and sunsets from the deck. Located just 1 mile from OB's surf, restaurants, shops, and nightlife, and a short walk to Sunset Cliffs.