Vacation rentals in Harbor Island

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Top-rated vacation rentals in Harbor 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, 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.

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, 241 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 wooden dining table is set with plates and glasses, featuring a bottle of wine at the center. A decorative bowl containing assorted textured orbs adds a vibrant touch. Natural light fills the space through glass walls, with greenery and outdoor seating visible in the background.
Home in San Diego
4.95 out of 5 average rating, 156 reviews

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

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, 413 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.

Top 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, 709 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 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, 369 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
An expansive view is displayed featuring a vibrant sunset over the ocean, with gentle waves lapping at the sandy shore. The pier extends into the water, surrounded by palm trees. Soft clouds create an artistic backdrop against the colorful sky.
Home in Imperial Beach
4.99 out of 5 average rating, 444 reviews

Enjoy the Best Ocean Views and Sunsets in a Beach Front Home

Relax in our fully equipped, beautifully furnished, 3 br, 3 ba home in the center of laid-back Imperial Beach. Savor a glass of wine while watching the sunset from the private balcony overlooking the pier and ocean. Prepare a gourmet meal in the upscale, contemporary kitchen or walk to lively craft breweries and great restaurants. Easy access to downtown, just 20 minutes from the airport! Keypad entry, free private parking in gated garage, child friendly, hi speed WiFi.

Top guest favorite
A spacious living area is highlighted by a large sectional sofa, complemented by a wooden coffee table and a patterned area rug. Natural light fills the room through large windows, and a dining area with a table for six is visible in the background, alongside decorative elements such as potted plants and beach-themed art.
Home in San Diego
4.98 out of 5 average rating, 106 reviews

Ocean Views, Private Yard, Just Steps to the Sand

Have fun with the whole family for a classic OB stay. Primary bedroom has a king bed and the second bedroom is queen size bed. A freshly updated, air-conditioned, centrally-heated, non-smoking, family-friendly beach home. Perfect for your beach vacation, steps from the sand, private yard with turf, deck, and patio. Great for both day & nighttime adventures, walkable location just 100 ft from the sand, with a variety of stores & restaurants. Garage parking on site!

Guest favorite
An outdoor dining area features a wooden table surrounded by metal chairs, set on a wooden deck. A built-in bench lined with soft pillows offers additional seating. Lush greenery borders the space, creating a serene atmosphere for outdoor gatherings.
Bungalow in San Diego
4.89 out of 5 average rating, 355 reviews

Sunny Ocean Beach Home - 2b/1b

Relax at this beautifully remodeled Ocean Beach bungalow just blocks from the beach and Sunset Cliffs. Located in a quiet neighborhood, yet an easy walk to Ocean Beach’s restaurants, cafés, and shops. The home features 2 bedrooms and 1 bath, plus a private outdoor oasis with built-in lounge seating, a spacious dining patio, and a turf lawn surrounded by lush vines and trees—perfect for relaxing after a day at the beach.

Guest favorite
A well-furnished living room features a blue sectional sofa with decorative cushions. A wooden coffee table sits on a striped rug, and a potted plant adds a touch of greenery. Natural light enters through windows, with art pieces adorning the walls and cabinetry in the background.
Apartment in San Diego
4.82 out of 5 average rating, 148 reviews

Quiet, Comfortable Sunset Ocean Beach Apartment!

Comfortable, fully furnished apartment in the best location of San Diego. A block to the breathtaking Sunset Cliffs and just down the block to a sandy cove beach - some of the most beautiful oceans in Southern California, and only a four block walk to all of the fun, eclectic hippie beach town vibes and new, exciting gastronomy and microbreweries on Newport Ave. This is the place you want to be in San Diego.

Top guest favorite
A welcoming living area showcases a sectional sofa adorned with blue cushions. A wooden coffee table sits in the center, with a candle and a small plant. Natural light enters through large windows, illuminating the space. A dining table is positioned nearby, complemented by modern decor.
Home in San Diego
4.97 out of 5 average rating, 124 reviews

Completely Remodeled OB Casita

This condo has been completely remodeled, it's stylish, comfortable, an upstairs unit with no one underneath you, that is just blocks from the beach, restaurants and so much more! It has air-conditioning for those warm summer nights and a heater for the chilly winter nights, although it's never too cold here in San Diego. King size bed in bedroom and a queen size sofa sleeper in the living room.

Top guest favorite
A welcoming entryway is framed by green siding and decorative wall planters that hold seasonal plants. A narrow walkway leads to a door with a glass panel, allowing glimpses of the interior. Natural light filters in, highlighting the pebbled landscaping on either side.
Bungalow in San Diego
4.93 out of 5 average rating, 224 reviews

Beachy Bungalow, Adult Retreat, Outdoor Oasis!

Adults only retreat. Pups welcome :) Rooftop level deck with Beautiful Sunset View. Sparkling clean for your health. Oasis Bungalow, Eco-friendly green, equipped with everything you will need for a comfortable stay. Our home, your vacation. Chill vibe & unique - like the rest of OB :) Lots of outdoor living; dining area w/ grill, lounge area with fire-pit. Beach gear! Walk to Beach, in OB!

Popular amenities for Harbor Island vacation rentals

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