Holiday rentals in Harbor Island

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!

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.

Bayview Paradise

Known as the Huguette House, this luxury private single-family two bedrooms two bathrooms home in La Playa the heart of Point Loma, San Diego offers 180-degree panoramic views of the world-famous San Diego Bay and Downtown Skyline. views of the San Diego bay, marina, and Coronado Island during the day and spectacular views of the Downtown San Diego skyline at night, fully equipped kitchen, and laundry room, 2 bedroom suites with queen beds .2 luxury bathrooms, HDTV, computer desk and WFI

Oceanfront Merman Suite, 1400 ft with spa & bar

Our La Jolla 1400 ft oceanfront suite with floor to ceiling sliding doors opens to a private spa, dining table, bar area and kitchen facilities. A king bed, 85" TV and fireplace with a 260 sq. ft bathroom. Flaming sunsets and moonlight silvering the ocean are yours. Pristine tide pools are accessed from the park next door. Blocks away, Garnet nightlife is wild. Walk to Wayfarers bakery or Paradisea restaurant. Make pizza here. Watch the ospreys! No blinds yet, but no one can ever see you.

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV

Welcome to your personal resort! This is your private Guest House with a salt & heated pool + hot tub. Located in a very quiet & safe neighborhood in beautiful San Diego. Drive 15 minutes to the beach, downtown, La Jolla, Zoo, stadiums, Sea World, Convention Center + more. Hike next door at Cowell Mountain or Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo, top quality finishes & furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

Beautiful Historic Home and Gardens Near Downtown!

Location, Location, Location...Welcome to Union Street Gardens. We are dedicated to providing a peaceful, serene atmosphere in which our guests can relax after a long day of exploring beautiful, sunny San Diego. This unique historic craftsman bungalow is just minutes from downtown, Balboa Park, the Zoo, beaches, and includes a Chef's kitchen, outdoor deck, gardens, fire pit and spa! Perfect for a family of 4 or two couples. Sorry no parties or large groups and no external guests please.

Luxe Point Loma Oasis w/ Pool, Spa & Fire Pit

The vacation of your dreams awaits at the luxury 3BR Point Loma oasis. Each of the posh bedrooms has an en-suite bathroom and access to the exquisite backyard oasis-which is complete with a pool, spa, outdoor kitchen, and fire pit area. Enjoy outdoor dining by the pool or the lovely succulent gardens throughout the property. Sleeps 8. Washer/dryer, complimentary Wi-Fi, Netflix and parking are included. Hotel quality sheets and fresh duvets are also included with your stay. No parties.

Ocean Views w Stunning Sunsets by the Firepit!

Welcome to our stunning 3-bedroom retreat in the heart of Sunset Cliffs, where panoramic ocean views and coastal luxury await you! ✨ Perched majestically on the hill overlooking the Pacific Ocean, this spacious and beautifully appointed home 🏡 offers the perfect blend of comfort and style for your San Diego getaway. Step inside and be greeted by an abundance of natural light streaming through the expansive windows, illuminating the open-concept living space 🌴

State & Fir (Little Italy Loft, Free Parking)

Ultra Minimal, Sunlit Bi-Level Loft In The Heart Of Little Italy—A Bright, Aesthetic Escape For Slow Mornings And Cozy Evenings. Enjoy Exposed Brick, High Ceilings, Beautiful Art, And An Airy Open Floor Plan. Step Outside To Trendy Cafés, Restaurants, Wine Bars, Farmers Markets, And Waterfront Park. Just Minutes To The Convention Center, Concerts, And The Trolley. Includes One Free On-Site Parking Spot And Free Laundry. Live Like A Local.

New Luxury 3BR/3.5BA Point Loma Coastal One Story

*3BR 3.5BA*1,600 Sq Ft Single Story Living*Indoor Outdoor Living & Entertaining ** Three En Suite Bathrooms***3 Blocks To SD Bay***2 Sets Of W/D***6 TVS***High Speed Fiber Internet***Forced Air HVAC***Heated Outdoor Entertaining Area w BBQ***2 Assigned Parking Spots**EV Charger****10 Ft Ceilings**Italian Marble Counter Tops**8' Solid Core Mahogany Doors**Italian Porcelain Floors**Vaulted Ceilings**Kohler Black Hardware*Village Living***

Bright & Modern OB Getaway

This newly built, 2 bedroom/2 bath, is the bright & airy, modern & stylish beach getaway you've been looking for! You'll be located 2 blocks from the beach, and are walking distance to a variety of different restaurants, coffee shops, yoga studios, and nightlife options. The rooftop deck provides an amazing panoramic view for catching sunsets, and even the Sea World fireworks show. Bikes and beach gear ready for use!

At Mine | Spacious Suite in the Gaslamp Quarter

This meticulously renovated historical hotel suite, designed by Pininfarina, is located in Downtown San Diego’s vibrant Gaslamp Quarter, surrounded by restaurants and nightlife. It offers private, spacious accommodations for both business and leisure travelers, featuring a king bed, smart TV, central AC, and mini-fridge. Please note: an adjoining bar operates until midnight, and some noise is expected.