Vacation rentals in Little Italy

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Top-rated vacation rentals in Little Italy

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Top guest favorite

A curving staircase is visible, flanked by white walls and adorned with vibrant blue tiles. Handrails provide support along the ascent, leading to a bright upper space. A potted plant enhances the serene ambiance at the top of the stairs.

Guesthouse in Mission Hills

5 out of 5 average rating, 209 reviews

Santorini-Inspired Cottage w/ Hot Tub + Views

*CHECK OUT OUR OTHER AIRBNB* Travel 16 steps up a Greek-inspired curving stairway with 2-story high walls to your tucked-away cottage built into the hillside villa of Alta Colina. With spectacular views, step onto the balcony to watch planes take off & boats sail around the harbor. End the night in front of your secluded back patio fireplace or climb the steps of your spiral staircase to the rooftop Jacuzzi. European-inspired design & details, it'll be hard to believe you’re still in San Diego!

Guest favorite

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

4.95 out of 5 average rating, 464 reviews

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.

Guest favorite

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 Downtown

4.95 out of 5 average rating, 88 reviews

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.

Guest favorite

A modern living area features two tufted grey sofas arranged around a glass-top coffee table on a vibrant orange area rug. Large windows provide natural light and views, while a flat-screen television is mounted on the wall. A dining area with bar stools is visible in the background.

Apartment in Downtown

4.92 out of 5 average rating, 330 reviews

PENTHOUSE + VIEW DECK Urban Design in Little Italy

Cozy memory foam King-size bed with two additional sleeper sofas! This penthouse suite is located in the heart of San Diego's highest rated neighborhood, Little Italy! Quick and secure access. Boasting over 36 retail establishments within a two block radius! 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!

Guest favorite

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.

Townhouse in Downtown

4.94 out of 5 average rating, 117 reviews

Luxury Home in #1 Downtown Location 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.

Guest favorite

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.

Apartment in Downtown

4.92 out of 5 average rating, 182 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!

Guest favorite

A cozy living space showcases light hardwood floors and a comfortable gray armchair. A flat-screen TV is mounted on the wall, while a small wooden table provides a casual surface. Natural light streams through two windows, enhancing the welcoming atmosphere.

Apartment in Downtown

5 out of 5 average rating, 33 reviews

Little Italy Bungalows | Unit 1529

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, fast WiFi, and micro patio. 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.

Superhost

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 Downtown

4.82 out of 5 average rating, 776 reviews

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

Top guest favorite

A charming cottage is set within a lush garden, featuring a variety of tropical plants and vibrant flowers. The pathway leads to the entrance, framed by palm and cacti, inviting guests to explore the serene outdoor space.

Guest suite in Hillcrest

4.98 out of 5 average rating, 795 reviews

MIKE'S PLACE - A PRIVATE COTTAGE

The cottage features full amenities that include: Tempurpedic™ queen-size bed. Wi-Fi . Cable HDTV, air conditioning, refrigerator, microwave, wet bar, coffee maker, toaster, and iron. Window seat for sitting, reading or lounging. Private entrance and patio connecting to a courtyard and Japanese garden. Spacious bathroom with 12 foot high tiled shower. French doors open to a private sitting area. If the days are booked in the cottage we might have an opening at, Mikes House and Garden.

Guest favorite

A modern living area features a leather sofa adorned with decorative pillows and a cozy throw blanket. A stylish chair is positioned nearby, accompanied by a small, round coffee table. Natural light enters through floor-to-ceiling glass doors leading to a balcony, enhancing the bright atmosphere.

Apartment in Downtown

4.93 out of 5 average rating, 107 reviews

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!

Guest favorite

A modern kitchen with dark cabinetry and a stylish backsplash is complemented by a circular dining table surrounded by four metal chairs. Natural light floods the space through large windows, and the living area is visible in the background, featuring a comfortable couch and wall-mounted TV.

Condo in Bankers Hill

4.94 out of 5 average rating, 124 reviews

Gated Parking | Panoramic Views | Walkable

Welcome to our comfortable and conveniently located condo offers sweeping views of the city and ocean, centrally located for all your travel needs with less than a 5 min drive to Little Italy, Downtown, Gaslamp District and the airport. This getaway is perfect for a weekend trip or extended stay offering 2bd/2ba in a top corner unit, complete with 2 patios to enjoy the pink and orange soaked sunsets and city skyline. We can’t wait to host you, please feel free to ask us any question.

Guest favorite

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 Downtown

4.93 out of 5 average rating, 364 reviews

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.