Vacation rentals 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.

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

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.

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

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.

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

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.

Romantic Bay View Suite • Rooftop deck & jacuzzi

Luxury Romantic Gateway Experience. Wake up to breathtaking views of the San Diego skyline and bay from your private rooftop deck. Relax in a stylish suite with a king-size adjustable bed, spa-style indoor Jacuzzi for two, and exclusive access to a rooftop fire pit and garden corner—perfect for a romantic night under the stars. Nestled in Point Loma, one of San Diego’s most exclusive and quiet neighborhoods, just minutes from Little Italy, the airport, and the beach.

Ocean Views w Stunning Sunsets by the Firepit!

Welcome to our stunning 3-bedroom retreat in the heart of Sunset Cliffs, where panoramic ocean views and coastal luxury await you! ✨ Perched majestically on the hill overlooking the Pacific Ocean, this spacious and beautifully appointed home 🏡 offers the perfect blend of comfort and style for your San Diego getaway. Step inside and be greeted by an abundance of natural light streaming through the expansive windows, illuminating the open-concept living space 🌴

Tiki Hut - Hot Tub, Indoor-Outdoor Entertainment

Tropical paradise in Point Loma! Escape to this stunning 4-bedroom coastal home featuring a relaxing, "Jimmy Buffet" atmosphere. The exceptional outdoor entertaining space includes two grills, outdoor dining area, hot tub, fire pit, and convenient mini fridge. Perfect for gatherings, beach getaways, and unforgettable sunsets. Steps from Ocean Beach's best restaurants, shops, and the iconic pier. Your ultimate Point Loma retreat awaits!

On The Beach Casita - Bay front access

On The Beach Casita This beautifully modernized Spanish 1-bedroom, 1-bath, 1000 sq. ft. 1-story casita, 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 2-bedroom, 1.5-bath home that is right next to it. Please see "On The Beach Clubhouse" if you are interested in renting both homes.

Hilltop Villa Offering Uninterrupted Ocean Vistas

Welcome to Casa Con Vista! Entertain family and friends at this sumptuous villa offering spectacular ocean views in almost every rooms. The house is fully equipped with relaxed and sophisticated style that echoes throughout the home. Guests can unwind around the fire pit while making s'mores on balmy evenings, or have a family barbecue in the private backyard before heading to the beach for sunset....