Holiday rentals in Shelter Island

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Top-rated holiday rentals in Shelter Island

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Top guest favourite
A modern house with large glass windows is set against a clear blue sky. The exterior features a mix of stone and wood elements, surrounded by landscaped greenery and architectural plants, creating an inviting yet contemporary appearance.
Home in San Diego
4.91 out of 5 average rating, 294 reviews

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.

Top guest favourite
A curving staircase is visible, flanked by white walls and adorned with vibrant blue tiles. Handrails provide support along the ascent, leading to a bright upper space. A potted plant enhances the serene ambiance at the top of the stairs.
Guest house in San Diego
5 out of 5 average rating, 223 reviews

Santorini-Inspired Cottage w/ Hot Tub + Views

*CHECK OUT OUR OTHER AIRBNB* Travel 16 steps up a Greek-inspired curving stairway with 2-story high walls to your tucked-away cottage built into the hillside villa of Alta Colina.  With spectacular views, step onto the balcony to watch planes take off & boats sail around the harbor. End the night in front of your secluded back patio fireplace or climb the steps of your spiral staircase to the rooftop Jacuzzi. European-inspired design & details, it'll be hard to believe you’re still in San Diego!

Guest favourite
The view from the open French doors showcases a spacious outdoor deck with comfortable seating, framed by lush greenery. San Diego Bay, the downtown skyline, and distant mountains are visible against a clear blue sky, inviting relaxation and enjoyment of the scenic landscape.
Home in San Diego
4.9 out of 5 average rating, 174 reviews

Gorgeous Bay View, Private Deck & More, Point Loma

Relax on your large, private deck with beautiful views of San Diego Bay, the downtown skyline, Coronado, the 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 pickleball/tennis.

Top guest favourite
A well-equipped kitchen features wooden cabinets and a granite countertop, with a gas stove and refrigerator clearly visible. A small round table with two chairs is positioned in the corner, along with a microwave and other kitchen essentials on the shelves above.
Guest suite in San Diego
4.94 out of 5 average rating, 690 reviews

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.

Top guest favourite
The exterior of the Huguette House displays a modern design with multiple levels, featuring large windows that offer views of the surrounding area. A sleek driveway leads to a spacious garage, while a landscaped pathway guides to the entrance, framed by elegant railings.
Home in San Diego
4.99 out of 5 average rating, 139 reviews

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

Top guest favourite
The exterior of a contemporary two-story house is displayed, featuring a large garage door with modern glass panels. Lush greenery and tropical plants line the pathway, while large windows allow for natural light. The overall structure is well-maintained and inviting.
Guest suite in San Diego
4.98 out of 5 average rating, 147 reviews

Point Loma Retreat - Steps 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 dinning and kitchen are layed 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.

Top guest favourite
A bright studio is showcased with a spacious bed and a cozy seating area featuring a blue couch. Large windows framed by yellow curtains allow natural light to fill the room. Colorful artwork adorns the walls, adding to the inviting décor.
Holiday home in San Diego
4.93 out of 5 average rating, 192 reviews

Bright Studio in Ocean Beach | Short Walk to Beach

Enjoy this newly remodeled stylish studio in the heart of Ocean Beach. Light and bright with a refreshing ocean breeze from its large central window. It’s just over a half a mile to Dog Beach and a quick ride to Sunset Cliffs, with some of the best surfing and beaches in San Diego. This studio has its own private entrance, full bathroom with shower, and kitchenette. In addition, the studio includes a standing desk with a large second monitor to accommodate your remote working needs.

Superhost
A spacious sleeping area is presented with a king-sized bed topped with white linens and fluffy pillows. A wooden headboard adds a warm contrast, while a nightstand with a lamp is positioned nearby. Large windows allow natural light to fill the room, enhancing the minimalist decor.
Flat in San Diego
4.84 out of 5 average rating, 1,669 reviews

At Mine | Central Suite in the Gaslamp Quarter

This unit is a meticulously renovated historical hotel suite, designed by the renowned Italian firm Pininfarina, located in Downtown San Diego. Nestled in the vibrant Gaslamp Quarter, you'll find yourself in the midst of nightlife with an array of restaurants and bars in close proximity. The suite provides private and spacious accommodations catering to both vacationers and business travelers. Its features include a comfortable king-sized bed, a smart TV, central AC, and a mini-fridge

Guest favourite
A private studio apartment is showcased with a spacious bed adorned with colorful pillows and a blanket. A relaxing hanging chair is visible beside a window, while a kitchenette area and full bathroom are nearby. Warm light is provided by a woven pendant lamp.
Guest suite in San Diego
4.82 out of 5 average rating, 378 reviews

Boho Flat 1 block from exclusive beach!

Clean, stylish and beautiful private studio apartment located steps from Kellogg Beach in Point Loma. This cute and perfectly set up studio is a stone's throw from the water, and gets a great sea-breeze during the day. All the best restaurants and entertainment are nearby in one of San Diego's premier destinations. This serene apartment is just minutes to everything San Diego has to offer. We are only 5 minutes to the San Diego airport as well!

Top guest favourite
A sunset is captured over the ocean, with shades of orange, pink, and yellow in the sky. Silhouettes of palm trees frame the scene, while the distant pier is visible along the coastline. The tranquil atmosphere reflects a peaceful end to the day.
Guest suite in San Diego
4.95 out of 5 average rating, 758 reviews

Place to Stay with Private Entrance near Beach

The room has a private entrance. It's ideally located in a residential area of Ocean Beach. 5 blocks to the beach, OB pier, and 2 blocks to village life, shops & restaurants. It has a queen bed, a small private bathroom with a shower, a fridge, TV, Wifi, microwave, etc. Guests will love the location and privacy! Beach chairs, towels, umbrellas, etc. are available for your enjoyment. Enjoy the great ocean view from the backyard.

Guest favourite
The exterior of the house features a contemporary design with a combination of white siding and warm wood accents. A spacious patio area is highlighted, furnished with several chairs and a dining table. Soft lighting adds an inviting touch as the sky transitions to twilight.
Home in San Diego
4.96 out of 5 average rating, 247 reviews

2022 Brand New! Two Story Coastal Farmhouse

***Roseville Point Loma***10 ' Vaulted Ceilings***Washer/Dryer ***Kohler Black Matt 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, Kellogg Beach*** The Home Is In A Quiet Neighborhood With A Respectful 10:00 PM Quiet Hours In Place Policy. Not A Party Home.

Top guest favourite
A bright lounge area features a large wall mural with palm trees against a blue sky. A white couch with orange and yellow accent pillows sits next to a dark rectangular coffee table. A dining area with four black chairs and a metal table is positioned nearby.
Guest suite in San Diego
4.99 out of 5 average rating, 166 reviews

🌴Private Guest Suite in Pt. Loma Wooded Area🌞⛱

Located 2 miles from the beach and 1 mile from the bay! Your 2-bedroom private guest suite is the 1st floor of a luxury private residence in the upscale wooded area of Pt. Loma San Diego. Located in a quiet neighborhood, a private entrance opens to a kitchenette, charming lounge area, two well-appointed bedrooms, and one roomy bathroom. Enjoy a private deck and yard for dining, grilling or lounging.

Popular amenities for Shelter Island holiday rentals