Family-friendly holiday rentals in Little Italy

Room R at The Dutra Inn - Little Italy

“This room always makes me nostalgic. It’s not like I’ve stayed here before—I mean, maybe in a past life. But every time I turn at the top of the steps, just like that, the nostalgia hits me hard, deep in the cerebellum. Room R will do that to you. It doesn’t matter if you’ve been to San Diego a billion times before, or never. I like to think it’s the pull of my grandpa (we called him Popo) from the photograph in the far corner. Head of the room he’s never been in. Leo on a white horse. Both o

Contemporary, Fully Renovated Loft in Little Italy

Book this spectacular contemporary loft with 25 foot ceilings & views! The loft is in an area with a 9.8/10 walk score & known for having the best restaurants, bars &shops. The unit is newly renovated & meticulously designed with bright windows, contemporary high-end furnishings & an everyday spa inspired bathroom. Only steps from the waterfront, you decide if you want to enjoy cocktails & cuisine in the night scene or relax all day walking along the harbor. Free parking spot with access to all.

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.

Trendy Studio, Natural Light - Heart of Downtown

Large studio with comfortable queen sized Murphy Bed, a love seat, private entrance and private bath. Located in Cortez Hill - walk to the nicest neighborhoods in downtown like Little Italy, Gaslamp, East Village, and the Embarcadero. There is no full kitchen, but there is a small refrigerator, small microwave, and a pot for heating water. This is an ideal space for solo travelers, couples, events at the Convention Center, Padres Games, great eateries, and the best of Downtown San Diego.

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!

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.

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.

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.

Sunny Stylish & Central - Luxe Little Italy Studio

Located right in the heart of vibrant Little Italy is this sparkling Downtown studio filled with light, airy boho vibes and all the amenities you could need for a cozy stay. Whip up meals in the fully-equipped kitchen, snooze in the luxe king bed, soak up the sun on the lounge or sip your coffee at the chic café-style dining table. Ready to explore? Little Italy's buzzing restaurants, bakeries, and cafes are just steps away or take a quick 10-15 min drive to San Diego's top sights.

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

Little Italy 2BR Loft Near Waterfront & Convention

Discover the heart of San Diego from our spacious loft in Little Italy, the culinary gem of downtown. Perfectly situated for both business and leisure travelers, you're steps away from the waterfront, convention center, and vibrant city life. Embrace the urban experience with convenience at your doorstep, including eclectic bars and restaurants. We provide a white noise machine and earplugs, though the lower floor offers a quieter retreat. Experience the best of city living!