Vacation rentals in Shelter Island

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Top-rated vacation rentals in Shelter Island

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Top guest favorite
A bright living room features a gray sofa and a chaise lounge with floral accents. A round table with two stools is situated near a window. Soft natural light illuminates the space, highlighting the neutral tones and contemporary design.
Apartment in San Diego
4.97 out of 5 average rating, 159 reviews

Go Fishing and Boating from an Apartment with a Marina View

See marina views from the living room and front entry deck! Just steps to the San Diego Bay. Fully furnished kitchen: Refrigerator Gas range Dishwasher Microwave Toaster Oven and much More! Bedroom: Fully furnished with all linens Sleeps up to 2 people Living Room has a queen sized sofa bed, is light and bright with flexible seating for your comfort. Host is not onsite. Host may be reached by phone/text message during your stay. The apartment is walking distance to San Diego Bay's Shelter Island and Point Loma Marinas. Sport fishing, boat charters, a concert venue, restaurants, shops, and beauty salons are just outside the door. In addition to the local amenities that are in walking distance, this apartment is also an easy bike ride to the Embarcadero, Seaport Village, Little Italy and downtown San Diego. Quarters B is just 2.3 miles from San Diego International Airport and in close proximity to many popular San Diego attractions such as: The Gaslamp Quarter - 5.25 miles Sunset Cliffs - 2.4 miles Cabrillo National Monument/Fort Rosecrans National Cemetery - 4 miles Seaport Village -5 mil Petco Park - 7 miles San Diego Convention Center - 5 miles Balboa Park & San Diego Zoo - 6.5 miles Sea World - 4.4 miles Central to all San Diego's Universities, this makes a perfect location for families in town to visit university students. Point Loma Nazarene University -1.7 miles University of San Diego - 6 miles UCSD - 12 miles SDSU - 14 miles Quarters B is up one flight of stairs. There is no elevator. Parking for maximum of 1 car on property. Please park additional cars on the street.

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Guest favorite
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, 316 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.

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Guest favorite
A wooden dining table is set with plates and glasses, featuring a bottle of wine at the center. A decorative bowl containing assorted textured orbs adds a vibrant touch. Natural light fills the space through glass walls, with greenery and outdoor seating visible in the background.
Home in San Diego
4.94 out of 5 average rating, 175 reviews

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

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Top guest favorite
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, 751 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.

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Top guest favorite
Home in San Diego
4.99 out of 5 average rating, 155 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

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Top guest favorite
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, 193 reviews

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.

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Top guest favorite
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
4.97 out of 5 average rating, 306 reviews

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.

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Guest favorite
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
4.97 out of 5 average rating, 153 reviews

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.

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Superhost
The spacious living room is furnished with two brown leather sofas and a wooden coffee table. A flat-screen TV is mounted on the wall, while soft lighting enhances the design. Large windows allow natural light to fill the room, offering views of the outdoors.
Home in San Diego
4.79 out of 5 average rating, 71 reviews

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

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Superhost
The dining area features a large black table surrounded by green chairs, paired with a light fixture resembling a starburst. Decorative wall art made of woven materials adds texture, while sliding glass doors open to a view of a patio with greenery.
Home in San Diego
4.75 out of 5 average rating, 24 reviews

Point Loma 3 Bedroom|Skyline Views + Family-Ready

Bright, spacious, and newly remodeled, this stunning home in Point Loma blends modern comfort with timeless charm. Natural light pours into its open, airy layout, creating an inviting space perfect for relaxation or entertaining. Located minutes from downtown, beaches, Sunset Cliffs, and Cabrillo National Monument, it offers easy access to San Diego’s best attractions. Explore the vibrant harbor, enjoy local dining, or unwind in this luxurious retreat after a day of adventure.

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Top guest favorite
Guest suite in San Diego
4.9 out of 5 average rating, 110 reviews

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.

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Superhost
Guest suite in San Diego
4.72 out of 5 average rating, 18 reviews

Luxury Point Loma Stay | Central, Coastal & Unique

Stay in the heart of Point Loma, one of San Diego’s most desirable and central neighborhoods. This unique, thoughtfully designed space offers the perfect balance of comfort, style, and location. You’re minutes from Ocean Beach, Shelter Island, Downtown San Diego, and the airport, making it easy to explore the city while enjoying a quiet place to unwind. Guests love the unbeatable location, character, and clean, comfortable stay.

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Popular amenities for Shelter Island vacation rentals