Family-friendly holiday rentals in Little Italy

Admire Harbor Views from the Porch at a City Gem

Unwind in a cozy colorful casita in this light-filled 1920s Spanish bungalow decorated with Mexican folklorico. Take a walk into Little Italy for dinner. Or to a show at the Old Globe.What’s best, is how close you are to so much, all without needing a car. A very small single car garage is provided, think compact car. Street parking is free but challenging at times. The house is located directly below the incoming flight path. You are encouraged to read the reviews regarding this.Ideal for four.

Kitchen · Indoor spaces · Biking

Spacious + Sunny 3bd in the Heart of Little Italy!

Comes with two parking spots in a gated/covered parking garage within the complex. Two full bathrooms. Centrally located in Little Italy. Close to great restaurants and coffee shops and a private balcony for an awesome view for plane watching. Bird Rock Coffee Roasters is located in the apartment complex on the first floor (Kettner Blvd). The Crack Shack and Ballast Point Brewery are right across the street. The Main Street of Little Italy is 2 blocks away and Waterfront Park is about 3 blocks.

Kitchen · Family · Checkout

Little Italy Historical

This AirBNB residence is a recently fully renovated historical property in San Diego’s Little Italy community. Many say it’s one of the finest. It is only 3 short blocks from Little Italy’s vibrant India Street and its many restaurants, bars, cafes, and shops, and four from the Trolley. It’s also a short drive to San Diego’s beaches and attractions. The AirBNB unit is a ground floor private one bed/one bath suite with a living room and its own entrances. Pics and descriptions are enclosed.

Kitchen · Family · Quiet

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.

Kitchen · Indoor spaces · Parking

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!

Indoor spaces · Family · Outdoor spaces

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.

Kitchen · Indoor spaces · Accuracy

Beautiful Historic Home and Gardens Near Downtown!

Location, Location, Location...Welcome to Union Street Gardens. We are dedicated to providing a peaceful, serene atmosphere in which our guests can relax after a long day of exploring beautiful, sunny San Diego. This unique historic craftsman bungalow is just minutes from downtown, Balboa Park, the Zoo, beaches, and includes a Chef's kitchen, outdoor deck, gardens, fire pit and spa! Perfect for a family of 4 or two couples. Sorry no parties or large groups and no external guests please.

Indoor spaces · Family · Bathroom

#1 LOCATION - Rare Luxury Home in Downtown

***THE BEST RATED RENTAL IN DOWNTOWN SAN DIEGO*** Location doesn't get better than this! Right in the heart of the lively Little Italy area in downtown San Diego. San Diego's best restaurants and nightlife in your backyard. Just blocks from the waterfront and a short Uber or walk to the Gaslamp, Convention Center & Zoo! All the frills: + Prime location! 98/100 Walker Score rating + Private parking + Private Sundeck & Backyard Stay at this modern luxury home for your next trip!

Family · Kitchen · Beach

Penthouse Little Italy/2 Bay-View Balconies/Garage

Penthouse 2BR/2BA in Little Italy - 4th floor quiet retreat. 2 private west-facing balconies with bay sunset views, reserved garage that fits SUV, rooftop sun deck with BBQ & gym, central AC, in-unit washer/dryer, fast WiFi + dedicated workspace. 2 blocks to Mercato, 3 min to Waterfront Park, walkable to Gaslamp & Bay. Self check-in 4pm checkout 12pm. Perfect for two couples, families, remote workers, weekend escapes seeking sunset views, secure parking and prime Little Italy location

Family · Kitchen · Laundry

Elegant Little Italy Hideaway w/ Sky Deck & Views

Discover an inviting oasis in the heart of vibrant Little Italy! This luxurious penthouse apartment exudes modern boho charm and boasts a stunning balcony overlooking all of Little Italy. Ideal for both entertaining and basking in the sun on lazy days, this penthouse offers a perfect inner-city retreat filled with abundant natural light. You'll be just minutes away from downtown, beaches, and steps away from Little Italy's delightful offerings. Welcome to your short-term sanctuary!

Family · Kitchen · Sleep quality

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

Family · Kitchen · Condition

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.

Indoor spaces · Kitchen · Bathroom