Vacation rentals in Harbor Island

Romantic Getaway With Endless Pacific Ocean Views!

Bright and breezy 1 bd/ 1 ba casita with outdoor balcony. The perfect place for a romantic getaway. Home is 5-10 mins to many attractions including Sea World, SD Zoo, Petco Park Ocean Beach, Pacific Beach, Liberty Station and the airport. World class shopping at Fashion Valley Mall, take a fishing trip from Shelter Island, or go surfing at the famous Ocean Beach! We also strive to always use 100% Vegan and Cruelty - Free soaps and other products in our houses and we're 100% solar! *NO PARTIES

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.

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.

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.

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.

Dream Penthouse! The Most Amazing Bath & Views

Stunning Zen Penthouse with The Most Amazing Bathroom you have ever seen. Located right by Little Italy, Balboa Park, the Bay, the Convention Center, within walking distance to amazing restaurants, coffee shops, bars and within minutes of all San Diego Beaches and attractions. The Zen Penthouse has a total European feel to it, it's like being in London with amazing weather and the best part, the breathtaking views of the Skyline and unreal Sunsets!

Relaxing Little Italy Studio Apt | Near The Bay

Welcome To Our Sunny And Serene Studio In The Heart Of Little Italy—A Soft, Romantic Retreat Filled With Natural Light And A Calm, Aesthetic Vibe. Enjoy Minimal, Tasteful Decor, High-Quality Linens, And Cozy Touches Throughout. Relax On The Plush Sofa, Sway In The Hammock Chair, Or Wind Down With Your Favorite Shows On The Smart TV. Perfect For Couples, Solo Travelers, And Anyone Seeking A Peaceful, Beautiful Escape In San Diego.

The Cozy Craftsman

Escape to this serene, stylish retreat. Built in 1935, this Craftsman-style home exudes timeless San Diego charm. Perfectly situated in University Heights, bordering Hillcrest and North Park, you’ll be close to restaurants, cafés, grocery stores, public transportation, the San Diego Zoo, and Balboa Park. This 650 sq ft home has been renovated inside and out, and equipped with everything you need for a comfortable stay!

Luxury Studio W/ Garden View in Heart of Hilcrest

Charming Hidden Gem Studio in the Heart of Hillcrest Discover this hidden gem – a cozy, French-inspired studio casita with elegant furnishings and a private, furnished patio. Enjoy a fully equipped kitchen, a spacious open living and sleeping area, and an attached deck overlooking the tranquil canyon. Perfect for a peaceful retreat just steps from the vibrant Hillcrest scene.

Designer Cottage in the Historical San Diego Area

Charming cottage, nestled deep in the backyard behind the main property in a quiet neighborhood, centrally located in the historical area and only 10 minutes from the airport and downtown San Diego. Recently rebuilt and modernized to fit a couple or a family of 4. It features a private deck for dining, reading, or simply enjoying the perfect San Diego weather.

Private beach guesthouse w/ private parking

Located in Ocean Beach area of San Diego just blocks from the beach. Enjoy this beautiful, beach retreat with your own living space, bathroom, and kitchen. The guesthouse has a private fenced in outside space, separate laundry, and two parking spaces. It is a quiet, peaceful, relaxing experience close to some of San Diego's main attractions.

Shelter Island Village - 1 Bedroom Apt.

Just steps to the Point Loma Marina in the heart of Shelter Island Village, we call this unit "Quarters C". It is a brand-new, well appointed 1 bedroom apartment equipped with all the comforts of a fine home. Located in the heart of the Point Loma Marina/Shelter Island.