Vacation rentals in Harbor Island

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Top-rated vacation rentals in Harbor Island

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Top guest favorite

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

5 out of 5 average rating, 211 reviews

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!

Guest favorite

A bright living area is adorned with large windows that offer expansive views of the cityscape. A modern sectional sofa in warm hues provides ample seating, while a glass coffee table sits at the center. Artwork and potted plants enhance the contemporary decor.

Loft in San Diego

4.95 out of 5 average rating, 88 reviews

Contemporary Loft with Harbor & City Views

Book this spectacular contemporary loft with 25-foot ceilings and views from every window! Located in the heart of Little Italy, an area with a walking score of 9.8/10, and near great restaurants, bars, and shops. The unit is meticulously designed with huge bright windows, electric shades & contemporary high-end furnishings, and artwork. Only steps from the waterfront, you can decide if you want to sip cocktails and sample cuisine in the night scene or relax all day walking along the waterfront.

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, 680 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.

Top guest favorite

A charming cottage is set within a lush garden, featuring a variety of tropical plants and vibrant flowers. The pathway leads to the entrance, framed by palm and cacti, inviting guests to explore the serene outdoor space.

Guest suite in San Diego

4.98 out of 5 average rating, 796 reviews

MIKE'S PLACE - A PRIVATE COTTAGE

The cottage features full amenities that include: Tempurpedic™ queen-size bed. Wi-Fi . Cable HDTV, air conditioning, refrigerator, microwave, wet bar, coffee maker, toaster, and iron. Window seat for sitting, reading or lounging. Private entrance and patio connecting to a courtyard and Japanese garden. Spacious bathroom with 12 foot high tiled shower. French doors open to a private sitting area. If the days are booked in the cottage we might have an opening at, Mikes House and Garden.

Top guest favorite

A bright studio is showcased with a spacious bed and a cozy seating area featuring a blue couch. Large windows framed by yellow curtains allow natural light to fill the room. Colorful artwork adorns the walls, adding to the inviting décor.

Vacation home in San Diego

4.93 out of 5 average rating, 182 reviews

Bright Studio in Ocean Beach | Short Walk to Beach

Enjoy this newly remodeled stylish studio in the heart of Ocean Beach. Light and bright with a refreshing ocean breeze from its large central window. It’s just over a half a mile to Dog Beach and a quick ride to Sunset Cliffs, with some of the best surfing and beaches in San Diego. This studio has its own private entrance, full bathroom with shower, and kitchenette. In addition, the studio includes a standing desk with a large second monitor to accommodate your remote working needs.

Top guest favorite

This open-concept living area features a modern kitchen with bar seating for four, a cozy seating arrangement around a round coffee table, and large windows providing natural light. A soft rug covers the floor, and a staircase leads to the upper level.

Apartment in San Diego

4.98 out of 5 average rating, 61 reviews

Beautiful Guest Space Close to Everything

Enjoy a comfortable and convenient experience at our centrally-located Point Loma apartment. Come stay with us in our newly remodeled one bedroom, one bath private apartment located in the Loma Portal section of Point Loma. Just a 10 minute drive or ride share away from almost all San Diego has to offer. If you prefer public transit Old Town transit center is just a mile away. Within just a few miles experience Sea World, Beaches, Downtown, Commercial Fishing Marinas and more!

Guest favorite

A spacious bed is featured with crisp white bedding and decorative pillows. Soft curtains frame the windows, allowing natural light to enhance the room's simplicity. A small round side table sits beside the bed, accompanied by a potted plant, contributing to the tranquil setting.

Home in San Diego

4.96 out of 5 average rating, 55 reviews

Quaint 1-Bed Suite Mission Hills

Located in the heart of Mission Hills and walkable to downtown area with local shops and cafes. Enjoy a cozy, tranquil retreat in this one-bedroom suite designed for two. Featuring a plush murphy king bed, with a flat-screen TV, and a kitchenette, it’s perfect for relaxation. While the suite is accessed via private entrance, please note it is attached to an office that may generate noise during weekdays until 5:00pm. We also live on the property in a separate house.

Guest favorite

The room includes a cozy seating area with a patterned sofa and a coffee table. A spacious bed is positioned against a wall adorned with art, complemented by a ceiling fan above. A work desk and storage cabinet are also present, offering functionality in the space.

Guesthouse in San Diego

4.89 out of 5 average rating, 45 reviews

Walk to Bay|Steps to Grocery, Transit, Restaurants

Keep it simple at this peaceful and centrally-located place. Full kitchen and a half block from a Ralph’s grocery store. Save tons of money by doing your own cooking! Residential area with easy parking. There is a bus stop at the grocery store as well for those who are traveling car-free. If you are looking for spacious, this is not your place. But, if you are looking for something adorable, sparking clean, efficient, and private, you found the perfect place!

Top guest favorite

A modern kitchen area features sleek cabinetry and stainless-steel appliances. A spacious island with bar seating provides ample space for dining. Large windows allow natural light to fill the room, with greenery visible beyond the sliding glass doors.

Loft in San Diego

4.99 out of 5 average rating, 144 reviews

Waterfront Loft | 1BR | Little Italy | Downtown

The local neighborhood is highly walk-able and perched along the San Diego Bay in Little Italy. Little Italy is the most vibrant neighborhood in downtown San Diego with a main street that abounds with restaurants, boutiques, craft beer, and wine bars all at your doorstep. This is a very urban location which brings a lot of urban noise. The unit sits adjacent the train and trolley line in the urban core. No parking provided, Ideal for guests without a car.

Guest favorite

A serene garden courtyard is depicted, featuring two wooden chairs adorned with floral cushions. A small table sits between the chairs on a grassy area, surrounded by lush greenery and climbing vines, creating a peaceful outdoor setting.

Guesthouse in San Diego

4.92 out of 5 average rating, 440 reviews

La Casita - Fully Updated Casita in Mission Hills

This well designed, fully updated detached studio casita is located in one of the most sought after neighborhoods in San Diego - Mission Hills. Surrounded by a serene garden courtyard with private entry and quiet patio. Close to great dining, grocery stores and shopping, and a mere 10 minutes or less to most of San Diego’s main attractions. If you are coming by car, there is plenty of free street parking - otherwise Ubers are plentiful and reasonably priced.

Guest favorite

A cozy living area features a unique wooden coffee table at its center, surrounded by comfortable seating. Large glass doors provide access to an outdoor space, allowing natural light to fill the room. A guitar is displayed on the wall, adding character to the decor.

Home in San Diego

4.98 out of 5 average rating, 109 reviews

King Comfort in New Home + Projector

Luxury 2BR home in vibrant North Park, San Diego. Enjoy top-notch king/queen beds, a 150" projector, fresh coffee from our pour over, and sun-soaked patios. Walk to local attractions or reach others like Seaworld & the Zoo in <15 min. Benefit from free parking, ensuite bathrooms, a fully stocked large kitchen, and meticulous cleaning. Experience comfort, style, and convenience in our 1350+ sqft property. Your San Diego dream starts here!"

Top guest favorite

A sunset is captured over the ocean, with shades of orange, pink, and yellow in the sky. Silhouettes of palm trees frame the scene, while the distant pier is visible along the coastline. The tranquil atmosphere reflects a peaceful end to the day.

Guest suite in San Diego

4.95 out of 5 average rating, 734 reviews

Place to Stay with Private Entrance near Beach

The room has a private entrance. It's ideally located in a residential area of Ocean Beach. 5 blocks to the beach, OB pier, and 2 blocks to village life, shops & restaurants. It has a queen bed, a small private bathroom with a shower, a fridge, TV, Wifi, microwave, etc. Guests will love the location and privacy! Beach chairs, towels, umbrellas, etc. are available for your enjoyment. Enjoy the great ocean view from the backyard.