Holiday houses in Little Italy

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Quick stats about holiday rentals in Little Italy

Total holiday rentals
Explore 560 holiday rentals in Little Italy
Nightly prices starting at
Little Italy holiday rentals start at $85 NZD per night before taxes and fees
Verified guest reviews
Over 38,490 verified reviews to help you choose
Family-friendly holiday rentals
180 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 210 rentals that welcome pets
Holiday rentals with a pool
130 properties feature pools
Rentals with dedicated workspaces
320 properties have a dedicated workspace
Wi-Fi availability
560 of Little Italy holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Little Italy rentals
4.7 Average rating
Little Italy stays receive an average rating of 4.7 out of 5 from guests

Top-rated holiday rentals in Little Italy

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

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 - Park West

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, 511 reviews

Superhost

A modern two-story bungalow with a clean white exterior is captured at dusk. Large windows allow for ample natural light, while a set of stairs leads to the entrance. The surrounding area features minimal greenery, enhancing the structure's architectural lines.

Bungalow in Little Italy

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.

4.88 out of 5 average rating, 340 reviews

Guest favourite

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.

Townhouse 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

4.82 out of 5 average rating, 827 reviews

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.

Apartment in Little Italy

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, 254 reviews

Guest favourite

A modern living area features a comfortable gray sofa adorned with a light throw. A round coffee table sits in front, flanked by green plants. The open kitchen displays stainless appliances and white cabinetry. Soft lighting is provided by pendant lights overhead, creating a welcoming ambiance.

Condo in Little Italy

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

4.83 out of 5 average rating, 152 reviews

Top Guest favourite

A light-filled living area features a cozy gray sectional sofa and a wooden coffee table. A large Smart TV is positioned on a low console. The space is separated from the kitchen by a green accent wall, enhancing the modern aesthetic of the loft.

Loft in Little Italy

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.

5.0 out of 5 average rating, 58 reviews

Top Guest favourite

A bright living area features a gray sofa with decorative pillows, accompanied by a round coffee table and a textured area rug. Natural light enters through the windows, illuminating the open layout that connects to a dining area with modern chairs and a stylish pendant light.

Home in Little Italy

Little Italy 3BD Home with Huge Patio + Backyard!

Come and enjoy our recently restored three bedroom, two bath charmer, located right in the heart of San Diego's famed Little Italy district. Inside you are going to feel right at home with the natural light pouring through this spacious house. There is plenty of space to hangout in the kitchen, living room, and our large deck/backyard. Spend days and nights relaxing on the outdoor patio and lawn areas that offer plenty of space for entertaining or hanging out with the family.

4.96 out of 5 average rating, 73 reviews

Guest favourite

A spacious living area is showcased with large, bright windows offering views of greenery. Comfortable leather couches are arranged around a wooden coffee table, while a wall-mounted television is visible. Modern art and a large mirror are featured, enhancing the open and airy ambiance.

Condo in Little Italy

Luxury-award winning loft Townhouse, top location

Unpack your bags and enter the vibrant, artsy scene in Little Italy. Towering ceilings-windows flood this home with light and accentuate the quintessential urban space. Wood floors all around. The wide open floor plan on the main level, master suites on top and first floor, private balcony and patio, attached private garage and unmistakable architecture are among the many highlights. Located steps away from some of the best dining, night life and shopping in Little Italy.

4.85 out of 5 average rating, 88 reviews

Superhost

A stylish outdoor patio features a bar table set with two glasses of wine and a bottle of champagne. The backdrop showcases a scenic sunset over the harbor, with palm trees and boats visible in the calm waters.

Loft in Little Italy

Waterfront Little Italy Loft

Welcome to this modern one-bedroom loft in the heart of Little Italy, San Diego's most iconic neighborhood. With its central location, you'll be just steps away from all the best restaurants in the area - making it the perfect choice for couples & friends looking to experience the vibrant energy of the city. Here are a few things you will find; 80-inch OLED TV, full kitchen, California king bed, panoramic ocean views, an outdoor patio, & high speed internet.

4.89 out of 5 average rating, 102 reviews

Top Guest favourite

A spacious lounge area features a modern green sofa and two stylish chairs arranged around a low coffee table. Large windows allow natural light to fill the space, complemented by an earthy area rug. The industrial-style decor highlights the room's character.

Loft in Little Italy

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

4.94 out of 5 average rating, 535 reviews

Top Guest favourite

Apartment in Little Italy

Little Italy Penthouse -2 Sunset Balconies +Garage

Penthouse 2BR/2BA, 800 sq ft, Little Italy. 2 private sunset balconies w/ bay views, reserved garage (fits SUV), AC, W/D, fast WiFi + workspace. Beds guests love: BR1 Queen Adjustable Posturepedic Elite Hybrid (electric) w/ blackout. BR2 Queen Plush Memory Foam - most complimented, super comfy. 3 min to Waterfront Park, 2 blocks to Mercato. Rooftop deck/BBQ + gym. Self check-in 3pm/out 12pm flexible. Local host - ask for happy hour list!

4.9 out of 5 average rating, 112 reviews

Top Guest favourite

A green sofa is positioned against a wall adorned with an eclectic gallery of framed artworks, including abstract designs, floral patterns, and clock. Textures vary with a plush, white throw pillow placed at the center, providing a cozy accent against the diverse art pieces.

Condo in Little Italy

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.

4.97 out of 5 average rating, 99 reviews