Vacation rentals in Shelter Island

4.92 out of 5 average rating, 289 reviews

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

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.

5 out of 5 average rating, 215 reviews

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.

Guesthouse in San Diego

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!

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.

4.98 out of 5 average rating, 146 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.

4.89 out of 5 average rating, 171 reviews

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

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.

4.9 out of 5 average rating, 419 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

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.

4.94 out of 5 average rating, 684 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.

4.99 out of 5 average rating, 136 reviews

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

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.

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

The sitting room features high ceilings and large windows that provide ample natural light. A dining table with chairs is positioned next to a wall, while a small coffee station is available. A lush green plant adds a touch of nature to the space.

4.94 out of 5 average rating, 570 reviews

Stylish & Spacious! Deck w/ Stellar Views

Charming top floor of a 2-story beach home, large master bedroom, Cal King bed, bathroom w/ double sinks, sitting room, high ceilings, mini fridge, Keurig & kettle (no kitchen). Private deck, ocean & long views. Ceiling fans, flat screen FireTV w/ Netflix, Hulu, WIFI, windows & ocean breeze. Keyless/private entry. Easy walk to downtown OB, beach, shops, restaurants, breweries & more! We are downstairs, available if needed, though your privacy is fully respected.

A spacious bedroom features a light blue bedding set on a large bed, complemented by decorative pillows. Natural light filters through the window with bamboo shades, while a mirror reflects the room's bright, neutral tones. A bedside table and lamp add functionality.

4.96 out of 5 average rating, 157 reviews

Sunset Cliffs Hideaway

Kick back and relax in this peaceful, stylish space. Spacious Bedroom in private residence with private entrance, easy parking, located 1.5 blocks from beautiful Sunset Cliffs. Less than 15 min drive to all of the best San Diego has to offer. Walking distance to Ocean Beach (~1 mi), a funky beach town with its own casual style. Room is "hotel style" with private entrance, small patio, bed, bath, fridge and microwave; no access to main house.

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.

4.82 out of 5 average rating, 373 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!

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.