Vacation rentals in Little Italy

BEST LOCATION in all of Little Italy & downtown!

Location, location, location! Can't get any closer to the bustling Little Italy area in downtown San Diego. San Diego's best restaurants and nightlife in your backyard. One of the only houses in all of downtown! This modern luxury home is just blocks from the waterfront and a short Uber or walk to the Gaslamp, Convention Center & San Diego Zoo! All the frills: ++ Prime location! 98/100 Walker Score rating ++ High-speed internet, Netflix & smart TV ++ A/C ++ Super Host 5-star service

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!

Modern Central Gem w/ Patio | Steps to All!

Discover the heart of Little Italy with our inviting apartment. Bright and airy, the space features floor-to-ceiling glass doors that open to a shaded patio, letting the city sound in as you unwind on the lounge. Prepare meals in the modern kitchen and then retreat to the stylish, chic king bedroom. Explore nearby streets filled with cafes, gelato shops, and trattorias. Downtown, Balboa Park, and the Gaslamp Quarter are just a short 5/10-minute drive away. Your ideal urban getaway awaits!

Gorgeous 2Bd Corner Bungalow in Little Italy

Little Italy Bungalows are located in the heart of San Diego’s most popular restaurant and entertainment district, Little Italy. 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.

City View Banker's Hill

A beautifully renovated 2-bedroom, 1.5-bathroom craftsman-style duplex is perfectly situated in the heart of Bankers Hill. The perfect blend of classic craftsmanship and modern amenities in this beautifully restored home. Minutes away from San Diego's top attractions, including Balboa Park, Little Italy, and the vibrant Gaslamp Quarter. Two comfortable bedrooms provide a peaceful retreat. Fully equipped kitchen with new appliances. A perfect place to enjoy all that San Diego has to offer.

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

Oceanview Loft – Walk to Food & Nightlife

Stylish, modern loft in the heart of Little Italy! This bright, newly remodeled space is steps from top restaurants, cafés, the waterfront, and close to downtown, the Embarcadero, and beaches. Perfect for relaxing or exploring San Diego’s vibrant culture. Please note this is NOT a Party house!! Thank You!! PLEASE NOTE: Access to the Condo requires climbing 3-flights of stairs, as there is no elevator. However, a cart is available to assist guests with carrying items upstairs.

Piccola Italia with free parking & NEW A/C

Experience the very heart of San Diego like a local from this stylish retreat in vibrant Little Italy! Step out your door and into the heart of it all—this location puts you within walking distance or a short drive to the San Diego Bay & Waterfront Park, USS Midway Museum, Gaslamp Quarter, Seaport Village and the best of San Diego’s culinary scene. Conveniently located near San Diego International Airport, Trolley lines and the Amtrak station at Santa Fe Depot.

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!

Room D at The Dutra Inn - Little Italy

“This is the room that all the locals book. I couldn’t figure out why, so one day I decided to ask a guest. ‘I’ve walked past here a million times, and I just had to see what was behind these doors,’ he replied, as if it were obvious.” Our 20 ft., 100-year-old naval train station doors do seem like have a story to tell. Salvaged and repurposed here in our only street-level loft, they bring in the light and life of downtown San Diego. IG: @the.dutra

Little Italy King Suite

A luxurious 1b/1b condo . The spacious living area includes a flat screen TV and large courtyard viewing window laced with marble tile. The peaceful bedroom features a king sized bed, SMART flat screen TV, and ample storage space. Experience San Diego in this prime Little Italy location . Walking distance to Water Front Park, Seaport Village, Embarcadero, and all of Little Italy. *No Parking Available After September 1, 2026.