
Holiday houses in Harbor Island
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Top-rated holiday rentals in Harbor Island
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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!

Spanish Revival 1920s Bungalow - Patio - 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 - 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.

Sunny Studio in Little Italy | Walk Everywhere
Located within a great walkable neighborhood is this stylish boho studio with everything you could need for a relaxing, central stay. The studio features bright, open plan living with a fully equipped kitchen, an inviting bedroom area, a Smart TV with access to streaming apps, a sparkling bathroom and a handy laundry. Stay just 10-20 mins from San Diego’s top attractions or walk to the many mouth-watering restaurants, bakeries, piazzas & cafes in vibrant Little Italy right on your doorstep.

Sunset Cliffs Oceanfront Beach House - remodeled
NEWLY REMODELED KITCHEN AND FLOORS Front row seats of Sunset Cliffs OCEANFRONT 180deg unobstructed view (2BR/2.5BA) Beach-themed open floor plan, over sized kitchen and gorgeous floors. Fast internet (AT&T 1G). Equipped with a whole house fan for the few warm nights in San Diego. Absolutely NO PARTIES and be respectful. Please don’t try to sneak past the number of guests. Sorry no pets. We’ve had one bad experience that cost us a lot of wasted time and money. No access to the garage

Modern Sweet Studio Hillcrest, A/C Parking
This modern studio sits in a prime location of Hillcrest, a highly desirable area in San Diego. It is very quiet and private and sits directly behind our house(pictured) with a beautifully landscaped brick courtyard. You are within walking distance to "The Heart of Hillcrest" where you will discover many fabulous restaurants, coffee and boutique shops, and so much more. We are a short Uber drive to downtown and everywhere else San Diego has to offer. We hope you stay with us soon!

Cozy Home with Views! By Downtown/Airport/Gaslamp
This home is truly a rare find! Nestled in the most desirable heart of Midtown, this home is located minutes away from the best San Diego has to offer: -7 min to Airport (2.5 mi) - 6 min drive to MCRD -10 min to Sea World, the Zoo, and Gaslamp District!(within 4.0 mi) -10 min to the beach (5.5 mi) -Walking distance to Blue Water seafood restaurant and more! One of a kind experience with all the amenities you need! Perfect for families and couples traveling. Would love to host you!

Ocean Beach Beautiful Bungalow!
You will stay in an adorable private Bungalow that is 1/2 of a duplex, boasting 3br/1bath all recently remodeled and ready to be enjoyed! The property has a wonderful private partially enclosed patio with lovely ambiance, table seating and a brand new Weber BBQ! It is located 1 mile from Ocean Beach and just minutes away from famous Sunset Cliffs, Grocery store, wonderful restaurants, and so much more! Located in Ocean Beach but away from it's craziness - you will love your stay!

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.

Cozy Loft by Petco Park - Gaslamp
Steps to Petco Park, Convention Center, restaurants, bars and shops! The Unique Loft by Petco Park is located in the heart of downtown San Diego. Built by award winning architect Jonathan Segal, FAIA, my place is modern, simple and cozy. It is within walking distance to Petco Park, Gaslamp, and Convention Center. There are nearby restaurants, shops and nightclubs. My place is good for couples, solo adventurers, and business travelers. Note: No parking space is provided.

Private Floor to yourselves with game room
This house is a great way to relax when you taking a break from touring the city. The kitchenette has a microwave, Keurig coffee, plates and sink. The game room has a pool table. This is a quiet residential neighborhood with families and it's very safe. It's not an area you walk around in to visit coffee shops. All major attractions are 10-15 minutes away by car. Your private floor is on the lower level. I sleep/work on the upper level.

Cozy 3 Bedroom in Ocean Beach
Enjoy a stylish experience at this centrally-located place. Recently remodeled large 1,700 square feet house with 3 bedrooms, 2 bathrooms, a wide open-concept floor plan, and a private backyard for your family gatherings. 5 minutes to the beaches, 7 minutes to the airport, less than 10 minutes to other attractions like Sea World, Cabrillo National Monument, and Sunset Cliffs Natural Park. Private driveway parking for 3 cars

Ocean View Loft in Bird Rock La Jolla with Parking
Welcome to the prestigious Bird Rock neighborhood of La Jolla and this absolute gem, entire home getaway! We're so excited to host you in our professionally designed and renovated home. Enjoy your time here soaking in the sunshine on the large, balcony deck taking in the blue Pacific ocean views and outdoor living at its best with an open concept that leads you into the modern living room and fully equipped, modern kitchen.
Popular amenities for Harbor Island holiday rentals
Other great holiday rentals in Harbor Island

San Diego 2BD with Downtown Views, Deck & BBQ!

Perfect Place to be in Mission Beach!

New Luxury Studio • Best of Kensington

Peaceful Jungle Retreat In The Heart of San Diego

Work and Play La Jolla Getaway

Stunning and Convenient!

Oceanview Retreat Suite Hilltop w/EVCharger

Cozy Mid-Century Haven • Private Suite & Spa Bath
Destinations to explore
- Southern California Holiday rentals
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- San Diego Holiday rentals
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- Rosarito Beach
- LEGOLAND California
- SeaWorld San Diego
- Oceanside City Beach
- San Diego Convention Center E Ent
- University of California-San Diego
- San Diego Zoo Safari Park
- Petco Park
- Ocean Front Walk
- Torrey Pines State Beach
- Tijuana Beach
- Coronado Beach
- Pacific Beach
- Balboa Park
- San Diego Zoo
- Liberty Station
- Moonlight State Beach
- La Misión Beach
- San Onofre Beach
- Belmont Park
- Sesame Place San Diego
- Oceanside Harbor
- San Diego State University
- Coronado Shores Beach




