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Holiday houses in Shelter Island

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Top-rated holiday rentals in Shelter Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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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
4.91 out of 5 average rating, 305 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.

Guest favourite
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
4.95 out of 5 average rating, 162 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

Top 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, 725 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 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
4.89 out of 5 average rating, 183 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.

Guest favourite
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.
Home in San Diego
4.98 out of 5 average rating, 104 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.

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, 146 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

Guest favourite
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, 245 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.

Top Guest favourite
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.
Home in San Diego
4.99 out of 5 average rating, 381 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***

Top Guest favourite
Home in San Diego
4.94 out of 5 average rating, 186 reviews

Luxe Point Loma Oasis w/ Pool, Spa & Fire Pit

The vacation of your dreams awaits at the luxury 3BR Point Loma oasis. Each of the posh bedrooms has an en-suite bathroom and access to the exquisite backyard oasis-which is complete with a pool, spa, outdoor kitchen, and fire pit area. Enjoy outdoor dining by the pool or the lovely succulent gardens throughout the property. Sleeps 8. Washer/dryer, complimentary Wi-Fi, Netflix and parking are included. Hotel quality sheets and fresh duvets are also included with your stay. No parties.

Top Guest favourite
An outdoor seating area features six chairs arranged around a stone fire pit, with a warm fire glowing in the center. The background displays a vibrant sunset sky, and lush greenery accents the space, creating an inviting atmosphere for gatherings.
Home in San Diego
4.95 out of 5 average rating, 106 reviews

Ocean Views w Stunning Sunsets by the Firepit!

Welcome to our stunning 3-bedroom retreat in the heart of Sunset Cliffs, where panoramic ocean views and coastal luxury await you! ✨ Perched majestically on the hill overlooking the Pacific Ocean, this spacious and beautifully appointed home 🏡 offers the perfect blend of comfort and style for your San Diego getaway. Step inside and be greeted by an abundance of natural light streaming through the expansive windows, illuminating the open-concept living space 🌴

Top Guest favourite
A bright lounge area features a large wall mural with palm trees against a blue sky. A white couch with orange and yellow accent pillows sits next to a dark rectangular coffee table. A dining area with four black chairs and a metal table is positioned nearby.
Guest suite in San Diego
4.99 out of 5 average rating, 175 reviews

🌴Private Guest Suite in Pt. Loma Wooded Area🌞⛱

Located 2 miles from the beach and 1 mile from the bay! Your 2-bedroom private guest suite is the 1st floor of a luxury private residence in the upscale wooded area of Pt. Loma San Diego. Located in a quiet neighborhood, a private entrance opens to a kitchenette, charming lounge area, two well-appointed bedrooms, and one roomy bathroom. Enjoy a private deck and yard for dining, grilling or lounging.

Guest favourite
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
4.83 out of 5 average rating, 401 reviews

Boho Flat 1 block from exclusive beach!

Escape to this bright and charming coastal flat, just minutes from the beach. Perfect for couples or solo travelers, this thoughtfully designed space features a plush king bed, cozy dining nook, relaxing living area with pull-out sofa, and a fresh, inviting bathroom. Enjoy peaceful mornings, stylish comfort, and an easy location close to everything Point Loma offers.

Popular amenities for Shelter Island holiday rentals