Holiday houses in Shelter Island

Cozy Retro Home with Bay & City Views

Step back in time at this charming, vintage San Diego retreat—your perfect home base with unforgettable views! This lovingly maintained retro home offers cozy comfort, timeless character, and spectacular panoramas of the harbor, ocean, and downtown skyline. With three inviting bedrooms—a primary en-suite with a king bed, a second king bedroom, and a queen guest room—there’s plenty of space for families and groups. The thoughtfully designed interior feels open and airy, blending Old World charm with warm, welcoming comfort. Relax in the living room as you take in sweeping bay and ocean views through large picture windows. Outside is where this home truly shines. The expansive patio offers one of the best “sit-down” views in the entire area, overlooking the harbor channel, glittering city lights, and surrounding mountains. Enjoy peaceful mornings, golden sunrises, and breezy evenings surrounded by blooming camellias, wisteria, and bougainvillea. What’s Nearby: This location is hard to beat! You’re just moments from Shelter Island Pier, waterfront paths, and fantastic seafood and Italian restaurants. A short drive brings you to downtown San Diego (5.5 miles), Mission Bay (6.5 miles), the Gaslamp Quarter (6.5 miles), and SeaWorld (4 miles). Beaches, parks, boutiques, nightlife, and top attractions are all within easy reach. Things to Know: * This is a vintage, retro-style home with classic features and fewer modern amenities, but it is cozy, clean, and wonderfully maintained. * Free WiFi * Full kitchen (no dishwasher) * TV with HDTV antenna This is a vintage home full of character and charm. To help preserve and protect its unique features, we do have a few thoughtful rules in place. We kindly ask that you review and respect them during your stay. We truly hope you appreciate the special nature of the home, and that these guidelines enhance your experience rather than limit it. Thank you in advance for your understanding—and we hope you’ll still feel confident leaving a 5-star review based on what this one-of-a-kind property offers. Things to Know * Free WiFi * Full kitchen (no dishwasher) * TV with HDTV antenna - NO cable * Guests must be 25 years or older to rent this property If you love unique spaces with character, history, and unforgettable views, this Old World charmer is the perfect place to experience San Diego.

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

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

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.

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.

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.

Bayside Retreat

Relax and unwind on your getaway, family vacation, or retreat in a beautiful spacious Point Loma home. This 2 bed/2 bath house in the heart of Point Loma has plenty of room to decompress from the hustle and bustle of life. This is a quiet residential neighborhood that is five blocks from the water's edge of San Diego Bay. Very quiet block/neighborhood. We live on 3rd level. There are guests below this unit. Please observe our house rules of no parting/parties. Quiet hours 10pm. No pets.

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.

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.

Bright & Modern OB Getaway

This newly built, 2 bedroom/2 bath, is the bright & airy, modern & stylish beach getaway you've been looking for! You'll be located 2 blocks from the beach, and are walking distance to a variety of different restaurants, coffee shops, yoga studios, and nightlife options. The rooftop deck provides an amazing panoramic view for catching sunsets, and even the Sea World fireworks show. Bikes and beach gear ready for use!

Cozy remodeled 2 bed apt in Point Loma

Stay in this cute and cozy remodeled 2 bed 1 bath apartment stocked with everything you need for your San Diego visit! Located in a quiet neigborhood of Point Loma, you are just a quick drive from the airport and lots of San Diego attractions. The apartment is newly remodeled and ready to be enjoyed with lots of space in the back patio to enjoy food and games at the picnic table or relax around the fire pit.