Holiday houses in Shelter Island

Savor Panoramic Harbor and Skyline Views near Shelter Island

The views in our house are absolutely spectacular! The location is central to great restaurants, downtown SD, SeaWorld, and bay beaches where you can kayak or paddle board. It is a ideal choice for vacations and for business travelers looking for a comfortable place to call home while traveling. Entire House, 3 Patios, and parking for car in garage and driveway We like to stay out of our guests way during their stay, but we will always be accessible either via phone call or text; but if you are so relaxed and you don't want to expend energy to text or call, merely ring the wifi doorbell and it will connect to our cell phone and we can address any questions you may have. The mid-century modern house sits on the side of a hill in the La Playa neighborhood of Point Loma, overlooking the harbor. It is a quiet neighborhood, within walking distance of the harbor, beach, nice restaurants, and amenities. Please note 24 hours before arrival, we will provide you a door code you can use to enter the home, the same code locks the home when you come and go during your stay.

Location · Value · Parking

Kellogg’s Beach Cozy Home

Have fun with the whole family at this stylish place just a block away from Kellogg's Beach of San Diego Bay. Relax in our cozy home with a spacious kitchen and peaceful deck and backyard with wonderful trees and lots of space to play or relax. Kellogg's beach is a hidden gem. Enjoy your vacation just a block away from the beach while enjoying our stylish home with a peaceful backyard with beautiful trees just below our deck. The property lot splits between this home and a detached small home

Family · Value · Condition

New! Stunning Retreat Steps from Sunset Cliffs

Experience the epitome of relaxation & luxury at our splendid seaside retreat, The Carter Cottage in beautiful San Diego. Indulge in the finer things as you step into our immaculate, brand new home, meticulously crafted with a keen eye for detail. Sip coffee on our sunset deck looking towards the pacific and wind down in the evening around the natural gas fire pit. Our Cottage is equipped with luxury bedding, chefs kitchen and plenty of indoor and outdoor living spaces, you won't want to leave!

Family · Value · Condition

Private Hideaway, Shelter Island, Beach & Bay

Spotless studio apartment with all amenities. Relax on the private patio enjoying a panoramic view of Downtown and San Diego Bay, or get cozy in a love-seat by the outdoor Chiminea. The unit has a full kitchen and an outdoor BBQ. Private parking right out front. Quiet neighborhood, but close to Downtown, Beaches, SeaWorld and the World Famous San Diego Zoo. Walk to local restaurants, bars, Eppig brewery, bay side trails, grocery store, & sports fishing. No dogs due to host health issues.

Value · Family · Cleanliness

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

Value · Location · Laundry

Gorgeous Bay Views, Private Comfy Deck & Much More

Relax on your large, private deck with beautiful views of San Diego Bay, downtown skyline, Coronado, nearby mountains, and the Pacific ocean. Watch the fighter jets take off from North Island and the Navy & cruise ships. You have lovely sunrises and can watch the sunset reflected off the skyline from the same deck chair! Our home is located less than 10 minutes from the airport, Shelter Island, and VERY EASY walking distance to restaurants, shops, yoga, the bay, and FREE pickleball/tennis.

Family · Location · Laundry

Beautiful New 2BR/2.5BA Coastal Home In Point Loma

*** Point Loma***Each Bedroom Has Its Own Bathroom**First Floor Patio & Second Story Balcony**10 ' Vaulted Ceilings***Washer/Dryer ***BBQ***Fountain***Kohler Black Matte Finished Hardware***Italian Marble Counter Tops***High End Luxury Finishes***European Porcelain Floors**8' Mahogany Solid Core Doors***Assigned Tandem Parking For Two Cars***Walk to Humphries By The Bay Concerts*** The Home Is In A Quiet Neighborhood With A Respectful 10:00 PM Quiet Hours In Place Policy. Not A Party Home.

Value · Location · Sleep quality

Point Loma Retreat - 4 Streets to the Bay

You are welcome to stay in this gorgeous Point Loma house with all considerate finishes, AC, floor, walls, windows, lights, paintings, kitchen cabinets, counters, appliance, full bath, walk in closet and new furniture! The space features 1 bedroom, 1 bathroom, 1 walk in storage. Living, dining, and kitchen are laid out in a welcoming open space. You'll enjoy incredible access to the scenic harbor front and marina in a calm and peaceful dead end street with no traffic, high end neighbor.

Location · Family · TV

La Playa | Charming Bayside Bungalow

Live like a local from this quaint bungalow in the heart of Point Loma. Designed for comfort and privacy, this home features three well appointed bedrooms, a spacious living room, and a full kitchen. The private backyard is the perfect retreat for dining al fresco, or soaking the rays in on a perfect San Diego day. Step outside the front door and you'll be just steps away from great local restaurants, cafe's, & coffee shops - making this home the perfect launch pad for any San Diego

Value · Family · Amenities

San Diego! Sleeps 12! Walk to Restaurants! 3 decks

Welcome to our modern 6-bed 4.5-bath house in San Diego. Right down town Point Loma, ideal for families or groups, this luxurious retreat offers sleek design, spacious living areas, and 2 fully equipped kitchens! Each bedroom is tastefully furnished for ultimate comfort! Relax on the 3 patios, grill your favorite meals, and enjoy the sunny California weather! With easy access to San Diego Zoo, and stunning beaches, this stylish home is the perfect base for your unforgettable stay!

Family · Value · Sleep quality

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.

Value · Location · Condition

On The Beach Casa- with private bay access.

On The Beach Casa This beautiful Spanish style adobe, with private front row bay access - combined with city and harbor views - is a great place to call “home” for your seaside vacation in San Diego. This home can also be rented with a 1-bedroom, 1-bath home next to it - which might be perfect for grandparents or grown adult children. Please see Sandy Pointe Beach Club if you might be interested in this configuration.

Family · Location · Air conditioning