Vacation rentals in Shelter Island

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.

4.91 out of 5 average rating, 303 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.

5 out of 5 average rating, 248 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!

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.

4.95 out of 5 average rating, 159 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

4.97 out of 5 average rating, 118 reviews

Ocean View + 2 Patios | Sunset Cliffs Point Loma

Welcome to Sunset Cliffs Cabana Suite, your private coastal oasis, where you can relax, unwind & enjoy ocean views Key features 🌅 10-min walk to Sunset Cliffs 🚪 Roll-up garage door for seamless indoor/outdoor living 🌿 2 private ocean/sunset view patios 🛏️ Spacious queen bedroom 💻 Portable desk, chair & fast fiber internet for work or streaming 🔥 Fire pit for unwinding under the stars 🏆 Top 1% of homes globally on Airbnb Perfect for couples, remote work, Thurs Club events, & PLNU visits

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, 718 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.

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.

4.89 out of 5 average rating, 181 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.

A modern dining area features a wooden table surrounded by two woven chairs. A built-in bench with ample cushions provides additional seating. A surfboard is displayed on the wall, while blue tiles in the kitchen backdrop complement the space's bright ambiance.

4.98 out of 5 average rating, 98 reviews

Sunset View home 2 min walk to beach parking

This freshly renovated seaside home exudes coastal charm, offering partial ocean and sunset views from its front porch. Every detail of this charming bungalow has undergone a recent renovation, emphasizing both functionality and style. The result is a clean, comfortable, and relaxed space inspired by surf culture. Whether you're unwinding after a day at the beach or planning a fun-filled holiday in San Diego, this home provides all the amenities you need for a memorable and enjoyable stay.

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.

4.99 out of 5 average rating, 144 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

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.

4.97 out of 5 average rating, 152 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.

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.

4.93 out of 5 average rating, 238 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.

A modern kitchen features white cabinetry and stainless steel appliances. A round wooden table is surrounded by four light-colored chairs. Natural light floods the space through a skylight and window, illuminating the wood-look flooring.

4.99 out of 5 average rating, 375 reviews

Charming 2 BR /2 BA Home In Beautiful Point Loma

***Turnkey Single Story Living***2BR/2BA*** 2018 Cape Code in Roseville Point Loma***Village Living***Just Three Blocks to Pont Loma Sea Food***Sport Fishing***Better Buzz***San Diego Bay Harbor***One of two Houses on One Lot. (2 on 1).***It's in the Back.***Vaulted Ceilings***Fiber Internet ***Washer/Dryer ***Your Own Exclusive Fenced Private Turf Grassy Yard***Two Car Tandem Driveway Parking***Sea Port Village, Gaslamp, Airport, In Minutes***Grocery Store /4 Restaurants/Pub 3 Blocks***

An outdoor patio features a modern fire pit surrounded by four seating chairs, with greenery and low shrubs creating a serene atmosphere. The sunset casts a warm glow over the space, while coastal views and palm trees are visible in the background.