Vacation rentals in Shelter Island

Cozy Retro Home with Bay & City Views

Step back in time at this charming, vintage San Diego retreat—your perfect home base with unforgettable views! This lovingly maintained retro home offers cozy comfort, timeless character, and spectacular panoramas of the harbor, ocean, and downtown skyline. With three inviting bedrooms—a primary en-suite with a king bed, a second king bedroom, and a queen guest room—there’s plenty of space for families and groups. The thoughtfully designed interior feels open and airy, blending Old World charm with warm, welcoming comfort. Relax in the living room as you take in sweeping bay and ocean views through large picture windows. Outside is where this home truly shines. The expansive patio offers one of the best “sit-down” views in the entire area, overlooking the harbor channel, glittering city lights, and surrounding mountains. Enjoy peaceful mornings, golden sunrises, and breezy evenings surrounded by blooming camellias, wisteria, and bougainvillea. What’s Nearby: This location is hard to beat! You’re just moments from Shelter Island Pier, waterfront paths, and fantastic seafood and Italian restaurants. A short drive brings you to downtown San Diego (5.5 miles), Mission Bay (6.5 miles), the Gaslamp Quarter (6.5 miles), and SeaWorld (4 miles). Beaches, parks, boutiques, nightlife, and top attractions are all within easy reach. Things to Know: * This is a vintage, retro-style home with classic features and fewer modern amenities, but it is cozy, clean, and wonderfully maintained. * Free WiFi * Full kitchen (no dishwasher) * TV with HDTV antenna This is a vintage home full of character and charm. To help preserve and protect its unique features, we do have a few thoughtful rules in place. We kindly ask that you review and respect them during your stay. We truly hope you appreciate the special nature of the home, and that these guidelines enhance your experience rather than limit it. Thank you in advance for your understanding—and we hope you’ll still feel confident leaving a 5-star review based on what this one-of-a-kind property offers. Things to Know * Free WiFi * Full kitchen (no dishwasher) * TV with HDTV antenna - NO cable * Guests must be 25 years or older to rent this property If you love unique spaces with character, history, and unforgettable views, this Old World charmer is the perfect place to experience San Diego.

Location · Family · Walkability

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.

Location · Family · Cleanliness

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

Family · Location · Bathroom

New! Stunning Retreat Steps from Sunset Cliffs

Experience the epitome of relaxation & luxury at our splendid seaside retreat, The Carter Cottage in beautiful San Diego. Indulge in the finer things as you step into our immaculate, brand new home, meticulously crafted with a keen eye for detail. Sip coffee on our sunset deck looking towards the pacific and wind down in the evening around the natural gas fire pit. Our Cottage is equipped with luxury bedding, chefs kitchen and plenty of indoor and outdoor living spaces, you won't want to leave!

Location · Family · Walkability

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.

Family · Location · Walkability

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

Value · Location · Air conditioning

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***

Value · Family · Beach

La Playa | Charming Bayside Bungalow

Live like a local from this quaint bungalow in the heart of Point Loma. Designed for comfort and privacy, this home features three well appointed bedrooms, a spacious living room, and a full kitchen. The private backyard is the perfect retreat for dining al fresco, or soaking the rays in on a perfect San Diego day. Step outside the front door and you'll be just steps away from great local restaurants, cafe's, & coffee shops - making this home the perfect launch pad for any San Diego

Location · Family · Solo travel

Cozy Mid-Century Haven • Private Suite & Spa Bath

Luxury Romantic Gateway Experience: Step into a bright, stylish suite where mid-century charm meets comfort. Just minutes from downtown and Pacific beaches, enjoy your own private yard with stunning views of San Diego’s skyline and bay. Inside: a plush king-size bed, large smart TV with streaming, and a cozy coffee station with microwave and fridge. The spa-style bath offers a soaking tub and walk-in shower—ideal after a day exploring the city. Private, peaceful, and unforgettable.

Location · Value · View

Point Loma 4 Bedroom|Skyline Views + Family-Ready

Bright, spacious, and newly remodeled, this stunning home in Point Loma blends modern comfort with timeless charm. Natural light pours into its open, airy layout, creating an inviting space perfect for relaxation or entertaining. Located minutes from downtown, beaches, Sunset Cliffs, and Cabrillo National Monument, it offers easy access to San Diego’s best attractions. Explore the vibrant harbor, enjoy local dining, or unwind in this luxurious retreat after a day of adventure.

Value · Family · Cleanliness

Upgraded Pt Loma Panoramic Views - 1 Bedroom Suite

Brand new full kitchen installed November 2025. Enjoy your home away from home and beautiful Pt Loma. With an expansive view of the gorgeous San Diego Bay & Shelter Island you can enjoy a comfortable space with luxury amenities. A spacious oasis to escape the hustle and bustle of the city, but close enough for a night out on the town. If you’d rather stay in and enjoy the views, relax on the patio, soak in the hot tub, or have a drink by the fire pit with your fur baby.

Family · Value · Quiet

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 🌴

Value · Location · Layout