Vacation rentals in Shelter Island

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Top-rated vacation rentals in Shelter Island

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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, 283 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

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.

Guest suite in San Diego

4.98 out of 5 average rating, 144 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.

Guest favorite

The spacious suite features a colorful bedspread on a sleek bed frame, complemented by hardwood flooring. A decorative wall art piece enhances the atmosphere, while natural light brightens the room. A sliding barn door leads to the bathroom, offering convenience and privacy.

Guest suite in San Diego

4.95 out of 5 average rating, 263 reviews

Bright Spacious Studio in Pt Loma, near beaches

This is a beautiful private Suite with full bathroom, 480 sq ft.+ SUPER CLEAN w/separate entrance. Like a studio apartment w/a small refrigerator, microwave & coffee maker. In a very exclusive neighborhood in Pt Loma, close to everything w/Liberty Station on 1 side (5 min walk) & Ocean Beach on the other side of the pennisula (2.5 mi). The Suite is on the back side of our home (connected but separate) with easy/free street parking. Last minute bookings are welcome! Easy Check in -late night too!

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, 168 reviews

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.

Top guest favorite

A bright living area features large windows allowing natural light and providing views of greenery outside. A modern black sofa is paired with colorful throw pillows, complemented by a round white ottoman. Artworks and decorative mirrors adorn the walls, enhancing the space's inviting feel.

Guesthouse in San Diego

4.99 out of 5 average rating, 136 reviews

Casita Hermosa - Close to everything in San Diego

Stay in the quiet beauty of your own guest house and private garden patio. Recently remodeled, Casita Hermosa will delight your senses and relax your soul. Features include a private bedroom, living room, dining area, fully equipped kitchen, and a full bathroom. The entire unit will immerse you in the southern California lifestyle as you marvel at the decorative touches featuring surf, ocean, sun, beaches, and all the best that San Diego has to offer plus a nod to our southern neighbor, Mexico!

Guest favorite

A compact kitchenette features modern appliances including a microwave and coffee maker. A round wooden table with three stools is placed in the center, while open shelves above display decorative plants and kitchen essentials. Light from the window enhances the clean and tidy space.

Guest suite in San Diego

4.9 out of 5 average rating, 408 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

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, 666 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.

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.

Guest suite in San Diego

4.9 out of 5 average rating, 164 reviews

Adorable place in Point Loma - no cleaning fee!

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. Living room couch has a queen sleeper sofa. There is a queen air mattress and pack n play as well. **Must be comfortable with stairs, there are two sets of stairs when accessing unit

Top guest favorite

A charming two-story casita is shown surrounded by lush greenery and palm trees. A large outdoor deck is visible, featuring an umbrella and comfortable seating. The terracotta roof complements the white exterior, while the inviting balcony windows provide a welcoming touch.

Guesthouse in San Diego

4.93 out of 5 average rating, 122 reviews

Charming Casita with City and Bay Views

This Private Casita is ideal for those wishing to be close to everything when visiting San Diego. From the outdoor deck enjoy expansive views reaching the tip of Point Loma and bay, to the Downtown skyline. Views of the City continue as you relax inside the living area watching your favorite shows, in a serene and comfortable setting. We are located within 4 miles of many great places to visit, including beautiful beaches, restaurants, Sea World, and the famous San Diego Zoo.

Guest favorite

The exterior of the studio showcases a two-story yellow structure, featuring a white door and multiple windows. The surrounding area includes a small fenced garden space with artificial grass and a pathway made of stones leading to the entrance.

Tiny home in San Diego

4.97 out of 5 average rating, 108 reviews

Cozy studio in OB

Stay in the cozy studio, tucked behind my main house. The studio has queen bed with memory foam on the mezzanine level. The ground floor is a living room with fold up desk, a garden view, small fridge and microwave, two single chairs. Next to studio is private bathroom, open air shower and sink area. Outside relax in the shaded garden area just for guests. Please respect the no smoking on the grounds. You can borrow a push bike with lock and helmet.

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.

Guest suite in San Diego

4.83 out of 5 average rating, 362 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!

Guest favorite

A classic beach house is outlined by a white picket fence, featuring a green patio umbrella and gas grill in the front yard. Solar panels rest on the roof, and large windows provide natural light. Nearby, a second multi-story building is partially visible.

Bungalow in San Diego

4.93 out of 5 average rating, 107 reviews

One Bedroom Classic Beach House 1/2 block to beach

1/1 Classic Beach House, 1 PARKING SPOT, a half block from the beach. This home has character with a fresh look, upgrades. Restaurants, Bars, and Shopping with in walking. One parking space in driveway. Sit in the front yard, you can be a part of beach life or watch it happen. We just added motion lights and a full Tonal home gym. This is a fun place to stay. We live here part-time and Love it! Copy of ID is required before check in.