Holiday rentals in Shelter Island

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Top-rated holiday rentals in Shelter Island

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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
4.92 out of 5 average rating, 289 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, 216 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!

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

Be one of the first to stay in this gorgeous Point Loma brand new house with all new 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.

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, 172 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.

Guest favourite
Guest suite in San Diego
4.9 out of 5 average rating, 421 reviews

New cozy studio 2 queen beds kitchen walk to water

Beautiful cottage-studio, just remodeled, in a fantastic location! All is brand new! Just 5 minutes to the beach and bay in a relaxing and safe area. Walkable any hour of the day and night. Enjoy 2 really comfy queen size beds, a kitchenette with all you may need, wonderful 2 rainfall showers, large smart TV and working space. Walk to La Playa Beach, Shelter Island or Sunset Cliff to experience the most amazing sunsets in San Diego! 5 min drive to Liberty Station and just 10 min to the airport

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, 685 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, 136 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

Superhost
A light-filled living area features a spacious beige sectional couch, complemented by a wooden coffee table with decorative accents. A ladder-style shelf and potted plant add a touch of greenery, while doorways lead to other rooms, enhancing the homey atmosphere.
Guest suite in San Diego
4.89 out of 5 average rating, 176 reviews

Adorable place in Point Loma

You will be close to everything when you stay at this centrally-located place. The place is recently renovated with brand new appliances, countertops, and kitchen cabinets. The space is light and airy with private entrance and small fenced in side yard perfect for pets. Bedroom has a queen sized bed and futon. There are 2 queen size mattresses and a queen air mattress and pack n play as well. **Must be comfortable with stairs, there are two sets of stairs when accessing unit

Superhost
The open living space features a cozy sofa, a glass dining table with modern chairs, and a 40" Smart TV mounted on the wall. Bright, airy design is complemented by natural light from windows, while coastal-themed artwork adorns the walls, enhancing the warm environment.
Home in San Diego
4.88 out of 5 average rating, 169 reviews

Beach House 3 min walk to Ocean!

Your beach home away from home! Equipped with all the essentials for a comfortable, convenient & fun filled stay in Ocean Beach. This home is located just one short block from the beach and walking distance to downtown OB, the pier and more! Take advantage of the close proximity to everything San Diego has to offer! Visit Mission Beach, Pacific Beach & SeaWorld in 10 mins. 15 mins get to San Diego Zoo, Little Italy, Liberty Station, Downtown.

Superhost
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, 374 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
The living room features a comfortable sofa and inviting chairs arranged around a low coffee table. A large TV is positioned against a white wall, complementing the artistic decor. Natural light enters through the windows, creating a welcoming ambiance in the cozy space.
Cottage in San Diego
4.93 out of 5 average rating, 395 reviews

Fabulous Cottage at the Beach

Newly remodeled 1940's cottage just 50 steps to the sand with fabulous beach and ocean views. Enjoy the ocean breeze from your front porch and watch people walk by. Go sunbathing and swimming, take a bike ride or a stroll on the beach, have a glass of wine and witness the most beautiful sunsets. We are located in a quiet residential neighborhood of Ocean Beach. This bright and cozy cottage has everything you'll need to feel at home.

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, 740 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.

Popular amenities for Shelter Island holiday rentals