Vacation rentals in Shelter Island

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Top-rated vacation rentals in Shelter Island

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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, 704 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.

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
4.89 out of 5 average rating, 178 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.

Top guest favorite
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, 140 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 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, 265 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.

Top 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, 149 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, 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.

Top guest favorite
A scenic rooftop deck is featured with two stylish lounge chairs, where two guests are seen enjoying drinks. In the background, the expansive San Diego skyline and bay create a breathtaking view, enhancing the calming atmosphere of the space.
Guest suite in San Diego
4.93 out of 5 average rating, 231 reviews

Bay View Suite • Rooftop Deck + Indoor Jacuzzi

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. Ideal for romantic getaways or peaceful stays with a view.

Guest favorite
A charming two-story casita is shown surrounded by lush greenery and palm trees. A large outdoor deck is visible, featuring an umbrella and comfortable seating. The terracotta roof complements the white exterior, while the inviting balcony windows provide a welcoming touch.
Guesthouse in San Diego
4.93 out of 5 average rating, 131 reviews

Charming Casita with City and Bay Views

This Private Casita is ideal for those wishing to be close to everything when visiting San Diego. From the outdoor deck enjoy expansive views reaching the tip of Point Loma and bay, to the Downtown skyline. Views of the City continue as you relax inside the living area watching your favorite shows, in a serene and comfortable setting. We are located within 4 miles of many great places to visit, including beautiful beaches, restaurants, Sea World, and the famous San Diego Zoo.

Guest favorite
A spacious outdoor area is framed by tropical plants, featuring a red umbrella over a round table with chairs. A patio is laid with brick pavers, and a couple of blue lounge chairs add to the inviting atmosphere. A covered entryway to the bungalow is visible.
Home in San Diego
4.94 out of 5 average rating, 198 reviews

𖤓 OB Bungalow - Studio Close to all the Action!

This rustic Studio Bungalow is nestled among tropical plants behind a high fence with 2 other cottages. The feeling of privacy is so special right here in the heart of Ocean Beach. Ocean Beach Bungalow is situated just minutes from Newport Avenue with all the eclectic shops, antique stores and incredible restaurants. The neighborhood is quiet, family residential and you can walk just half a block to the end of the street for amazing ocean views from the Cliffs.

Top guest favorite
Loft in San Diego
4.98 out of 5 average rating, 175 reviews

Waterfront Loft | 1BR | Little Italy | Downtown

The local neighborhood is highly walk-able and perched along the San Diego Bay in Little Italy. Little Italy is the most vibrant neighborhood in downtown San Diego with a main street that abounds with restaurants, boutiques, craft beer, and wine bars all at your doorstep. This is a very urban location which brings a lot of urban noise. The unit sits adjacent the train and trolley line in the urban core. No parking provided, Ideal for guests without a car.

Guest favorite
A modern living area features a comfortable sectional sofa in deep blue, complemented by a round wooden coffee table. A stylish chair sits beside the window, which allows natural light to fill the space. A large TV is mounted on a dark wood media console against the wall.
Apartment in San Diego
4.94 out of 5 average rating, 204 reviews

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.

Top guest favorite
The image shows a landscaped exterior with well-maintained pathways and lush greenery. Several palm trees are set against a clear blue sky, with residential buildings visible in the background, indicating a pleasant coastal neighborhood.
Guest suite in San Diego
4.9 out of 5 average rating, 192 reviews

Sweet Private Suite near the Beach

Beautiful private guest suite less than a mile from San Diego’s beautiful Ocean Beach. Perfect for business, travel or a new remote work location! Minutes away from great surf, restaurants and bars or a quick hop to the freeway for easy access to downtown, La Jolla or other parts of San Diego. Close proximity to the airport - minutes away by car via highway or side street.

Guest favorite
A spacious garden studio features a vaulted ceiling and bright natural light. A large bed is adorned with a colorful quilt, while a round dining table is accompanied by two black chairs. A wooden wardrobe and a piece of wall art contribute to the room's inviting ambiance.
Cottage in San Diego
4.89 out of 5 average rating, 157 reviews

Sunset Cliffs Garden Studio

Located 1 block from Sunset Cliffs Natural Park. Watch amazing sunsets everyday & do yoga on the cliffs facing the ocean! The garden studio is cozy, cute, and we use natural products for cleaning, etc. We're kid/baby-friendly too. We are located 3 miles from Seaworld & close to Ocean Beach, Pt. Loma, Cabrillo Light House, downtown San Diego, Pt. Loma Nazarine University.

Popular amenities for Shelter Island vacation rentals