Holiday rentals in Little Italy

4.96 out of 5 average rating, 470 reviews

A charming Spanish bungalow is framed by vibrant greenery and colorful flowers. A small staircase leads to the main entrance, which features a decorative security screen door. The exterior showcases white stucco walls, accentuated by terracotta details and surrounded by lush tropical plants.

Home in Bankers Hill

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.

4.96 out of 5 average rating, 91 reviews

A bright living area is adorned with large windows that offer expansive views of the cityscape. A modern sectional sofa in warm hues provides ample seating, while a glass coffee table sits at the center. Artwork and potted plants enhance the contemporary decor.

Loft in Little Italy

Contemporary Loft with Harbor & City Views

Book this spectacular contemporary loft with 25-foot ceilings and views from every window! Located in the heart of Little Italy, an area with a walking score of 9.8/10, and near great restaurants, bars, and shops. The unit is meticulously designed with huge bright windows, electric shades & contemporary high-end furnishings, and artwork. Only steps from the waterfront, you can decide if you want to sip cocktails and sample cuisine in the night scene or relax all day walking along the waterfront.

Townhouse in Little Italy

The living room features soaring ceilings and a wall of windows, allowing ample natural light to illuminate the space. Comfortable seating arrangements are complemented by modern art pieces on the walls. A sleek fireplace and stylish furniture create a welcoming ambiance, framed by elegant decor.

4.94 out of 5 average rating, 119 reviews

Luxury Home in Little Italy, San Diego w/Parking

Welcome to this rare designer masterpiece in Downtown’s most desirable neighborhood! Designed and built by renowned modern architect/developer Jonathan Segal. Located in the award-winning Little Italy Neighborhood Developers block (LIND). Home features 20 ft. floor to ceiling windows, designer kitchen, dual master suites, backyard patio. All the best restaurants, coffee shops, bars, Waterfront park just steps away. Or take a quick Uber or walk to Convention Center, Gaslamp, Petco Park and more.

The sleeping area features a spacious bed dressed in muted bedding and accented by decorative pillows. Two bedside tables with lamps provide soft lighting. An armchair with a throw blanket is positioned nearby, accompanied by artworks on the wall that complement the exposed brick backdrop.

4.91 out of 5 average rating, 192 reviews

State & Fir (Little Italy Loft, Free Parking)

Minimal Downtown Bi Level Loft In The Heart Little Italy. Experience What It's Like to Live In One Of The Most Popular Neighborhoods In San Diego For A Few Days. Exposed Brick, High Ceilings, Beautiful Art & Open Floor Plan. Walking Distance To Everything That The Neighborhood Has To Offer. Close To The Convention Center! Loads Of Amazing Restaurants, Cafes, Bars, Farmers Markets, 5 Min Walk To Trolley, Waterfront Park, Concerts. 1 Free On Site Parking Spot, Free Laundry. Live Like a Local!

4.95 out of 5 average rating, 337 reviews

A spacious living area is furnished with a floral-patterned love seat and two armchairs. Custom-built shelves house a collection of books, while a coffee table sits on a patterned rug. Bright yellow walls enhance the natural light streaming through the shuttered windows.

Flat in Downtown

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.

A modern living space features a soft leather sofa adorned with cushions, accompanied by a round coffee table. Large windows allow natural light to fill the area, which includes a dining table in the background. A stylish entertainment unit holds a television and minimal decor.

4.88 out of 5 average rating, 114 reviews

Luxe Little Italy 2BR Penthouse w/ Rooftop Balcony

Located right in the heart of Little Italy is this luxe penthouse apartment offering a modern boho-style retreat with a stunning balcony overlooking pizzerias, wine bars, and coffee shops. Ideal for entertaining and lazy days soaking up the sun, the penthouse gives you the perfect inner city oasis filled with natural light where you can relax, unwind, and live like a local. You’ll be only mins from downtown, the Gaslamp Qtr, beaches and only steps from everything Little Italy has to offer.

Top guest favourite

An expansive outdoor patio is showcased, featuring a comfortable sectional sofa with soft cushions and a stylish coffee table. Bi-folding doors connect to a modern kitchen area adorned with sleek cabinetry. The distant view reveals the San Diego coastline under a clear blue sky.

4.94 out of 5 average rating, 191 reviews

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!

4.94 out of 5 average rating, 371 reviews

An exterior view of a bungalow showcases a unique architectural style with smooth, rounded walls. Soft lighting highlights the inviting entrance, surrounded by potted plants. The paved pathway leads to a wooden fence, adding to the property's privacy, all under a clear evening sky.

Bungalow in Little Italy

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.

4.9 out of 5 average rating, 703 reviews

A spacious living area is characterized by high ceilings with exposed beams and large windows allowing natural light. A comfortable gray sofa, adorned with colorful cushions, is paired with a bright yellow accent chair. A modern coffee table and entertainment unit complete the inviting space.

Home in Little Italy

#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!

Top guest favourite

A spacious living area features large windows that fill the room with natural light. A plush white sofa and bright red chairs provide seating, while a round coffee table sits centrally on a red carpet. A wall-mounted TV is visible for entertainment.

Flat in Gaslamp Quarter

4.89 out of 5 average rating, 1,592 reviews

At Mine | Spacious Suite in the Gaslamp Quarter

This unit is a meticulously renovated historical hotel suite, designed by the renowned Italian firm Pininfarina, located in Downtown San Diego. Nestled in the vibrant Gaslamp Quarter, you'll find yourself in the midst of nightlife with an array of restaurants and bars in close proximity. The suite provides private and spacious accommodations catering to both vacationers and business travelers. Its features include a comfortable king-sized bed, a smart TV, central AC, and a mini-fridge

A modern living area features a comfortable dark sofa with light throw pillows, complemented by a coffee table and a small dining setup. Large windows allow natural light to fill the space, and a stylish area rug adds warmth to the hardwood floor.

4.77 out of 5 average rating, 196 reviews

Spacious Studio in Little Italy with Parking

Ground level unit. Comes with parking in a gated/covered parking garage within the complex. 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.

A bright studio space features a comfortable seating area with a dark blue sofa and a round wicker accent chair. A flat-screen television is mounted on the wall across from a spacious bed. Natural light filters through multiple windows, enhancing the inviting ambiance.

4.97 out of 5 average rating, 32 reviews

Little Italy Bungalows | Unit 1531

Step into San Diego's history with this beautifully restored 1920s bungalow in the vibrant Little Italy neighborhood. The studio apartment-style space combines loads of vintage charm with modern amenities including a comfortable queen-sized Murphy bed, fully equipped kitchen, living area with flat-screen TV, and fast free WiFi. You’ll be steps from Little Italy’s best dining and boutique shopping, with iconic San Diego attractions like Balboa Park and Mission Bay a short drive away.

Popular amenities for Little Italy holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Little Italy

The studio bedroom features a spacious bed with hotel-quality linens and an accent throw blanket. A small wooden dining table with two stools is positioned by a sunny window, with a green plant adding a touch of freshness. Light walls and natural light create an airy atmosphere.

4.91 out of 5 average rating, 155 reviews

Perfect Downtown Studio | Steps to Little Italy!

4.86 out of 5 average rating, 766 reviews

A spacious living area is presented with a light grey sofa adorned with decorative cushions. A wood coffee table sits in front, accompanied by a cozy area rug. An open kitchen area is visible in the background, featuring a mix of cabinetry and colorful backsplash tiles.

Loft in Little Italy

Sunny, Open 2 Story Apt Downtown w/ Parking

Townhouse in Little Italy

The living room features a spacious sectional sofa with orange and gray accent pillows. A modern coffee table sits in the center, complemented by a sleek television on a wooden stand. Natural light filters through large windows draped with sheer curtains, enhancing the airy atmosphere.

4.82 out of 5 average rating, 780 reviews

BEST LOCATION in all of Little Italy & downtown!

An aerial view displays the Urban Boutique Hotel's modern architecture alongside neighboring buildings. The blue facade contrasts with the surrounding structures, while palm trees line the street below, creating a vibrant urban landscape with views of the bay in the background.

Hotel room in Little Italy

4.58 out of 5 average rating, 468 reviews

Equipped with the essentials

4.84 out of 5 average rating, 186 reviews

A charming kitchen area is featured, showcasing a retro blue refrigerator and a round dining table. Two bowls are set on a woven placemat, ready for use. Light-colored cabinets provide storage, while a vibrant area rug leads to the adjoining space.

Cottage in Little Italy

Stylish, cozy studio in the heart of Little Italy

4.76 out of 5 average rating, 815 reviews

The lofted sleeping area features a full-size bed adorned with a handwoven blanket in soft pastel tones. A large window allows natural light to fill the space, and a modern pendant light hangs above. A piece of wall art adds an artistic touch to the exposed brick and concrete backdrop.

Loft in Little Italy

Good Vibe (Little Italy Loft, Free Parking)

A light-filled living area features three large windows draped with sheer curtains. A plush sofa is centered beside a circular coffee table, while a hanging hammock chair provides a cozy seating option. A wooden lounge chair is positioned to enhance the space's relaxing ambiance.

4.83 out of 5 average rating, 493 reviews

Relaxing Studio Apt in Little Italy

An open-concept living area showcases high ceilings and large windows offering abundant natural light. A plush sectional sofa and a woven chair are arranged around a round coffee table. A dining area with modern chairs is visible in the background, complemented by tasteful wall art.