Family-friendly holiday rentals in Downtown San Diego

1920's Bungalow with Original Charm - 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.

Explore Little Italy from this Gorgeous Mini Villa

La Scala rises from the center of Villa Little Italy in the heart of San Diego’s most popular restaurant and entertainment district. Just one block from India Street, Farmer’s Market, and minutes from downtown, Balboa Park, airport, and harbor & beaches. This is a delightful neighborhood, steeped in local history and culture, and popular for dining and exploring. Little Italy Bungalows is perfect for couples, families, business travelers, convention-goers, single travelers and adventurers.

Family-friendly fun in the sun

You will be close to everything San Diego has to offer in our cozy 2 bedroom 1 bathroom home. Family-friendly fully-gated yard with playset, mini putting green, games and seating area. Crib, changing pad, pack and play, 2 high chairs, child baths and dinnerware. Have a relaxing and fun time with multiple indoor games, large living room and bedroom smart TVs. Fast wifi, separate office space with desk, central heat/AC for comfort, W/D, 2 car driveway, lux bathroom and fully-equipped kitchen.

Calm Luxury Penthouse Getaway With Panoramic Views

Welcome to the most relaxing and luxurious penthouse condo in Little Italy! Featuring 2 expansive balconies with sweeping views, my condo sleeps 4-6 comfortably and is situated right in the heart of San Diego's most desirable neighborhood, Little Italy. Enjoy an area that is rich in exquisite cuisine, boutiques, patio cafés, exciting bars and local breweries. Area amenities nearby feature the famous San Diego Zoo, beautiful Balboa Park, Waterfront Park, the Convention Center and much more!

Chic Inner City Pad w/ Balcony | Walk Everywhere!

Stay right in the heart of vibrant Little Italy in this contemporary, inner-city apt with quaint piazzas and upscale boutiques all right on your doorstep. Split over two levels the apt features a thoughtfully curated design with living/dining on the lower level and an open double bedroom upstairs which steps out onto a balcony. Leave the car behind and walk to cocktail bars, brewpubs and restaurants or drive with downtown, the Gaslamp Quarter and Mission Beach only a short Uber ride away.

Kettner Row | Staycation-Featured Icon

Welcome to Kettner Row, a rare architectural masterpiece featured on Staycation Sports, an Emmy-winning show on the Destination Channel! Located in the heart of Little Italy—one of San Diego’s most desirable neighborhoods—and designed by renowned architect Jonathan Segal, FAIA. This detached row home is situated in the award-winning Little Italy Neighborhood Developers block (LIND). This modern home features dual master suites, a high-end designer kitchen, and luxurious spa bathrooms.

NEW Stylish❤️ of Downtown Little Italy w Parking/AC

Located in the heart of Little Italy San Diego, this street level condo has been completely remodeled and re-imagined to make your stay unforgettable. Designed with the eye toward comfort and entertainment. *AC w/ independent temp control in each room *Voice Controlled Sound System, 4K TVs in every room *Beautiful bathroom w/ dual showers *Walk to coffee, yoga & gyms, dining, entertainment, shopping! 6 min to Zoo 5 min Airport 9 min to SeaWorld 6 min Petco Park 8 min to Coronado

Spacious Apartment in Gaslamp, Sleeps 5 w/ Parking

Please Read Entire Listing Before Booking Noise Warning Come stay at our mid century modern apartment inside of a stylish Historic building. Located in the heart of Gaslamp Quarter. This 800 sqft apartment is perfect for a couples vacation, friends night out, or traveling business people. The Gaslamp action is right downstairs. The loft is surrounded by restaurants, bars, nightclubs, and coffee shops. Within walking distance to the Convention Center, Petco Park. Sleeps up to 5.

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.

Modern Private Loft • Walk to Petco

Stay steps from Petco Park in a thoughtfully designed two-story loft in the heart of downtown San Diego. Designed by award-winning architect Jonathan Segal, this modern space features high ceilings, a calm open layout, and a private balcony with city views. Enjoy a queen bed upstairs and a sofa bed in the living room, plus a full kitchen, washer/dryer, and easy self check-in. A more spacious, private, and relaxed alternative to typical downtown hotel stays.

Stylish Downtown Loft | Free Parking Near Bay

Tucked into the heart of Little Italy, this sun-drenched architectural loft is a calm, beautiful place to land in the middle of everything. Exposed brick, tall ceilings, and a chic open layout create a warm, inspiring retreat. Walk to top restaurants, cafes, bars, and Waterfront Park. Includes a cozy raised bed with ladder access, a full kitchen, one free onsite parking spot, and optional dog stay with $50 fee.

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.