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, 210 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 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 Downtown

4.86 out of 5 average rating, 762 reviews

Sunny, Open 2 Story Apt Downtown w/ Parking

Our Spacious 2 Story, Beautifully Decorated Apt is the Perfect Home Away From Home for Families, Couples, Digital Nomad, or Solo Traveler Looking for a Comfortable & Convenient Place to Stay. Located in One of the Most Vibrant Neighborhoods in SD Little Italy is Known For its Restaurants, Cafes, & Local Shops. So Many Attractions! the Waterfront Park, CRSSD Festival, USS Midway Museum., Balboa Park, Petco Park, The Convention Center, Running/Bike Paths, The County Building. 1 Free Parking Spot

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, 465 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, 332 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 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.

Guest favorite

A modern living area features a soft beige sofa adorned with decorative pillows, a round coffee table, and a patterned area rug. Floor-to-ceiling glass doors open to a small balcony, allowing natural light to brighten the space. A large flat-screen TV is mounted on the wall.

Apartment in Downtown

4.91 out of 5 average rating, 153 reviews

Modern Inner City Pad w/ Patio | Walk Everywhere!

Enjoy everything Little Italy has to offer right on your doorstep from this bright, light and inviting apt. Open the floor-to-ceiling glass doors and let the sounds of the city in as you relax on the lounge and shaded patio. Cook in the modern kitchen, feel pampered in the luxe bathroom, then retire to the chic, king bedroom. Explore quaint streets, cafes, gelato shops, and charming trattorias just steps away then discover downtown, Balboa Park, & the Gaslamp Qtr, an easy 5/10 min drive away!

Top guest favorite

A charming historical property features a teal-colored exterior with white trim and a covered front porch. Large windows allow natural light to enter, while the surrounding landscape includes lush greenery. A red vehicle is parked nearby, enhancing the welcoming environment.

Home in Downtown

5 out of 5 average rating, 56 reviews

Little Italy Historical

Take it easy at and enjoy this unique and tranquil getaway. It’s a recently fully restored and renovated registered historical property in San Diego’s Little Italy community. Many say it is one of the finest. It is only 3 short blocks from Little Italy’s vibrant India Street and its many popular restaurants, bars, coffee shops and boutiques. The Air B&B unit is a ground floor private one bed and one bath suite with a living room and its own entrances. Pics and descriptions are enclosed.

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, 796 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

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.

Guest favorite

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 Downtown

4.9 out of 5 average rating, 696 reviews

#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 favorite

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 Downtown

5 out of 5 average rating, 22 reviews

Ocean View Loft Steps to Dining & Nightlife

Enjoy a newly remodeled, stylish stay at this modern loft in Little Italy! Nestled in one of the city’s most vibrant neighborhoods, this bright and spacious retreat is just steps from top restaurants, cafés, and the waterfront. With easy access to downtown, the Embarcadero & San Diego’s best beaches. Whether you're here to explore, relax, or experience the local culture, this beautifully appointed space is the ideal home base! Please note this is NOT a Party house!! Thank You!!