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.

East Watch- a private getaway

East Watch is a 740 sq ft, 1 bedroom private retreat that provides the comforts and amenities of home with the style of a high-end hotel. All 5 to 15 min from shopping, downtown, and the beach. It's a short walk from Mt. Helix Park which offers a 360* view, weekday yoga, and stunning sunrises and sunsets. We have EV high speed car charging, a full kitchen with all appliances, workspace with dedicated fast WIFI, a spa shower, and super comfortable beds and pillows. Stay and let us charm you!

Mike's House and Garden

The care taken to honor the atmosphere of the original 1910 house creates a feeling of another time and place. The house is secluded in a prize winning garden and approached through a stone pergola. The Craftsman furniture, lighting and antique Persian carpets reflect a distant and captivating sensibility. This house has been featured in three books and “American Bungalow” magazine. The garden was mentioned in Sunset Magazine and featured as one of the premier gardens of University Heights.

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.

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***

The Island View Penthouse

⸻ Welcome to our sophisticated three-bedroom, three-bath retreat in historic Bankers Hill. Enjoy sweeping views, a full modern kitchen, and spacious living areas perfect for relaxing or entertaining. Located just minutes from Balboa Park, downtown, and San Diego’s best dining, this home blends comfort, convenience, and classic neighborhood charm. All rooms feature luxury beds from Davenport Collection. We require minimum 2-night minimum per City code, and a $299 cleaning fee.

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.

Private Home, Pet Friendly ~Sasha's Bungalow in OB

Welcome to Sasha’s Bungalow, your perfect Ocean Beach escape! Just one block from the ocean, this 2-bedroom, 1-bath retreat is steps from Newport Ave., Voltaire St., and OB’s lively shops and restaurants. Relax in your private yard with a fire pit, BBQ, and cozy seating, or sip coffee on the front patio. Inside, enjoy a fully stocked kitchen, fast WiFi, streaming, and beach gear. Best of all, we’re pet-friendly—bring up to 2 pets ($45/pet fee) to join your beach adventure!

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!

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.

Cozy remodeled 2 bed apt in Point Loma

Stay in this cute and cozy remodeled 2 bed 1 bath apartment stocked with everything you need for your San Diego visit! Located in a quiet neigborhood of Point Loma, you are just a quick drive from the airport and lots of San Diego attractions. The apartment is newly remodeled and ready to be enjoyed with lots of space in the back patio to enjoy food and games at the picnic table or relax around the fire pit.