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!

Private Entry | Crisp Sheets | Cozy Grotto Shower

Think of this like a hotel room or a minimalist studio. The entire unit is: - ONE compact room - Bathroom - Private entrance There is no kitchen or living room. It's attached to my house. The room has a velvet couch that converts into a full sized bed. The bed is extremely comfy with its 2" topper. It will be ready as a bed upon arrival & is easy to convert into a couch. There is a desk, fridge/freezer, coffee machine, coffee, mugs, utensils, plates, bowls, washer/dryer & laundry detergent.

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 Room with Beautiful Views

Welcome to our charming retreat nestled in San Diego. This private suite, attached to the main house, features its own bathroom, kitchenette, and a convenient private entrance with easy self-check-in. Just 10 minutes from Mission Beach, downtown San Diego, Balboa park, and SeaWorld. 5 min from Fashion Valley Mall, and only 2 minutes from the University of San Diego. You can either use the free parking space in front of the house or make use of the private driveway next to the house.

Room T at The Dutra Inn - Little Italy

“I thought about changing this whole thing to just read: Napoleon slept here. Room T is kind of like the little spoon of The Dutra. Or maybe like a precious package tucked under the building’s right arm? But no, despite popular opinion, the T doesn’t stand for tiny. Room T is big enough for your wildest ambitions and your coffee in the morning. There’s approximately 1,000 cupboards here—all presumably concealing tiny French dictators or perhaps, hidden treasures." IG: @the.dutra

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.

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.

Sunny and Affordable Studio W/private outdoor yard

This a great home base to explore San Diego ! It’s a small studio ideal for a one person or couple to get some rest after enjoying San Diego all day. 1 mile to Northpark restaurants/bars/breweries 10-15 mins to Gaslamp,Old town, Seaworld Ocean beach. Full kitchen , coffee corner , gas stove and comfy full size bed. Private entrance from alley. STEET PARKING ONLY - will be very hard to find at night. Used to be a garage decades ago

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.

Studio Oasis in Hillcrest

Take it easy at this unique and tranquil getaway. All the amenities of home in this peaceful studio. Comfortable queen size bed next to the gas fireplace, steps from a private patio and semi-private front porch, in a garden Bali-esque setting. Work space and fast wifi. All curtains are black-out. With a walkability score of 94% this home is a Walker's Paradise to all the neighborhood amenities!

Boho Flat 1 block from exclusive beach!

Escape to this bright and charming coastal flat, just minutes from the beach. Perfect for couples or solo travelers, this thoughtfully designed space features a plush king bed, cozy dining nook, relaxing living area with pull-out sofa, and a fresh, inviting bathroom. Enjoy peaceful mornings, stylish comfort, and an easy location close to everything Point Loma offers.