Vacation rentals in Shelter Island

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Top-rated vacation rentals in Shelter Island

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Top guest favorite
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, 298 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 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, 706 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
A charming cottage with a welcoming porch is showcased. A colorful red umbrella provides shade over a patio table surrounded by several chairs on the paved outdoor area. Lush greenery accents the space, contributing to a relaxed atmosphere.
Cottage in San Diego
4.97 out of 5 average rating, 118 reviews

It’s so Lovely on Larkspur Adorable Cottage in OB

Relax in our remodeled and sunshine filled 1 bed, 1 bath cottage with easy access to the beach, parks, restaurants, coffee shops, grocery and more. Uniquely away from the hustle and bustle, our charming neighborhood has limited through traffic and that friendly OB vibe you are looking for. We live next door and are Superhosts and ambassadors of Ocean Beach; to prove it, check out our reviews before our remodel by going to my profile or searching for "Charming OB Cottage with Private Patio".

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, 141 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 favorite
A comfortable living area features a plush gray sofa adorned with decorative pillows. Soft natural light filters in from nearby windows, illuminating a modern dining space and a well-equipped kitchen visible in the background. A wooden side table holds a table lamp, adding to the inviting ambiance.
Home in San Diego
4.91 out of 5 average rating, 139 reviews

Central Charmer in Unbeatable Old Town Location!

Experience the best of San Diego from this elegant, hidden gem tucked away within the beating heart of Old Town! Explore cobblestone streets, quaint cafes, and boutique stores all just steps away along the happening San Diego Avenue. You'll have easy access to Downtown, the Gaslamp Quarter, and stunning beaches with the Trolley only a 6 min walk away, then return to this elegant hideaway filled with all of life’s little luxuries, modern spaces, and a sunny outdoor area for you to enjoy.

Top guest favorite
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, 364 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 favorite
A spacious bed with plush pillows is featured in a softly lit room, where warm curtains frame a window allowing natural light to filter in. Two bedside lamps provide additional light, complementing a serene ambiance.
Bungalow in San Diego
4.91 out of 5 average rating, 523 reviews

Stylish Craftsman Bungalow in Heart of North Park

Come relax in our newly remodeled North Park craftsman located in a quiet neighborhood that is a foody, Millenial paradise! 7-minute walk to 30th street and 15-minute walk to University - each with a plethora of trendy coffee shops, breweries, and restaurants. Eight min drive to Balboa Park/San Diego Zoo and fifteen-minute drive to Coronado beach. Coffee and tea is provided, although you will probably prefer a five-minute stroll to Santos Coffee house for a cold brew and breakfast bagel.

Superhost
The living area features a comfortable gray sectional sofa, accented with blue and white pillows. A round coffee table sits on a textured area rug, while a light-filled corner includes a small dining table and chairs. A large wall-mounted TV provides entertainment.
Townhouse in San Diego
4.78 out of 5 average rating, 211 reviews

Ocean Beach Beautiful Bungalow!

You will stay in an adorable private Bungalow that is 1/2 of a duplex, boasting 3br/1bath all recently remodeled and ready to be enjoyed! The property has a wonderful private partially enclosed patio with lovely ambiance, table seating and a brand new Weber BBQ! It is located 1 mile from Ocean Beach and just minutes away from famous Sunset Cliffs, Grocery store, wonderful restaurants, and so much more! Located in Ocean Beach but away from it's craziness - you will love your stay!

Guest favorite
A living room features warm tones and hardwood flooring. A comfortable beige sofa and a red armchair are complemented by a decorative area rug. A wooden coffee table sits in the center, and a TV is mounted on the wall opposite a welcoming entryway with red French doors.
Cottage in San Diego
4.93 out of 5 average rating, 127 reviews

Ocean Beach Garden Cottage - Cozy Coastal Retreat

Unwind in Coastal Charm at the Garden Cottage Welcome to the Garden Cottage, your serene home base in the heart of Ocean Beach. Relax in the private courtyard hammock or take a short stroll to sandy beaches, local shops, restaurants, and the vibrant weekly Farmers’ Market (every Wednesday). Explore the longest concrete pier on the West Coast or venture out to world-famous attractions like the San Diego Zoo, SeaWorld, or thrilling whale-watching tours.

Guest favorite
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.
Guest suite in San Diego
4.95 out of 5 average rating, 183 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.

Top guest favorite
A modern kitchen features dark cabinetry and a large island with granite countertops, complemented by sleek bar stools. Pendant lights illuminate the space, while stainless steel appliances add a contemporary touch. Large windows provide natural light, enhancing the open layout shared with the living area.
Home in San Diego
4.92 out of 5 average rating, 145 reviews

Cozy 3 Bedroom in Ocean Beach

Enjoy a stylish experience at this centrally-located place. Recently remodeled large 1,700 square feet house with 3 bedrooms, 2 bathrooms, a wide open-concept floor plan, and a private backyard for your family gatherings. 5 minutes to the beaches, 7 minutes to the airport, less than 10 minutes to other attractions like Sea World, Cabrillo National Monument, and Sunset Cliffs Natural Park. Private driveway parking for 3 cars

Popular amenities for Shelter Island vacation rentals