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, 228 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!

Top guest favorite
A sunlit living area features two comfortable armchairs facing a glass coffee table with books and magazines. Large windows are adorned with light curtains, and a decorative lamp adds warmth. A dining table with chairs is positioned nearby, creating a cozy gathering space.
Bungalow in San Diego
4.97 out of 5 average rating, 404 reviews

Vintage Spanish Revival Home - Balboa Park - Alcazar Court

• 1924 Spanish Revival Bungalows - Alcazar Court - Nestled in the heart of the city in historic Hillcrest - with cafes, bars, and shops • Fully equipped 1 bd 1 ba bungalows complement shady olive tree-lined patios - guests can enjoy coffee in the morning - a glass of wine in the afternoon. Enjoy the charm and tranquility of a bygone era and convenience of modern amenities, • Explore nearby Balboa Park, home to 16 museums and performing arts venues, as well as the world-famous San Diego Zoo.

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, 696 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
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
4.92 out of 5 average rating, 222 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 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, 810 reviews

MIKE'S PLACE - A PRIVATE COTTAGE

The cottage features full amenities that include: Tempurpedic™ queen-size bed. Wi-Fi, Smart TV, 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 spacious bedroom is showcased with a large bed adorned in white bedding, complemented by an orange decorative pillow. Two bedside tables hold lamps, and natural light floods in through multiple windows, illuminating the neutral-toned walls and soft carpet.
Guest suite in San Diego
4.9 out of 5 average rating, 634 reviews

Guest Suite with Balcony, Views, and Close to Ocean

This quiet beautiful studio-style space is bright and welcoming. It features a soaker tub, walk-in shower, a comfortable king bed and balcony with bay views. Located in Point Loma, it is less than a mile from the beach and within 15-20 minutes of the most visited San Diego attractions. Rental is above our home. No smoking, parties or loud music. Please note the kitchenette only has a mini fridge, microwave, toaster, and coffee maker. No washer and dryer on sight. Above flight path.

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
4.94 out of 5 average rating, 129 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.

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
4.98 out of 5 average rating, 167 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.

Top guest favorite
Guesthouse in San Diego
4.92 out of 5 average rating, 452 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.

Top guest favorite
A spacious studio apartment features a large bed with soft linens and decorative pillows. A sitting area with a cushioned bench provides comfort, while a well-equipped kitchen with modern appliances is visible in the background. Natural light streams through the large window, complemented by stylish curtains.
Home in San Diego
4.96 out of 5 average rating, 176 reviews

Stunning Ocean Beach Gem - has everything!

Beautiful, brand new, completely renovated studio apartment two blocks from the beach. 2nd-floor unit, redone top to bottom, professionally designed. Perfect vacation spot, walk to the beach, local restaurants, and bars. The host is an established 5-star Airbnb host. Beach chairs, towels, and cooler. The unit is super quiet for this active beach location with enhanced acoustic insulation. Off-street parking is available exclusively for the Airbnb.

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, 768 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.

Top guest favorite
The exterior of the house features a contemporary design with a combination of white siding and warm wood accents. A spacious patio area is highlighted, furnished with several chairs and a dining table. Soft lighting adds an inviting touch as the sky transitions to twilight.
Home in San Diego
4.96 out of 5 average rating, 253 reviews

2022 Brand New! Two Story Coastal Farmhouse

***Roseville Point Loma***10 ' Vaulted Ceilings***Washer/Dryer ***Kohler Black Matt Finished Hardware***Italian Marble Counter Tops***High End Luxury Finishes***European Porcelain Floors**8' Mahogany Solid Core Doors***Assigned Tandem Parking For Two Cars***Walk to Humphries By The Bay Concerts, Kellogg Beach*** The Home Is In A Quiet Neighborhood With A Respectful 10:00 PM Quiet Hours In Place Policy. Not A Party Home.

Popular amenities for Harbor Island vacation rentals

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  2. United States
  3. California
  4. San Diego County
  5. San Diego
  6. Harbor Island