Vacation rentals in Little Italy, San Diego

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Top-rated vacation rentals in Little Italy, San Diego

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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, 194 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!

Top 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

4.96 out of 5 average rating, 456 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 Little Italy

4.95 out of 5 average rating, 79 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 Little Italy

4.92 out of 5 average rating, 320 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

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 Little Italy

4.91 out of 5 average rating, 141 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!

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 Little Italy

4.82 out of 5 average rating, 762 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

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 Little Italy

4.94 out of 5 average rating, 358 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.

Superhost

A modern living area features a green sectional sofa with natural wood accents, arranged around a round coffee table. A large framed artwork is displayed on the wall, complemented by a decorative hanging element. Lush greenery from a tall potted plant adds a touch of nature.

Loft in Little Italy

4.83 out of 5 average rating, 328 reviews

Stylish Downtown Loft w/ Parking in Little Italy

Stylish Modern Loft In The Heart Of Little Italy. Immerse Yourself In San Diego's Trendiest Neighborhood With A Stay In This Elegant Loft. Featuring Exposed Brick, Tall Ceilings, A Cozy Loft Bed Accessed By A Ladder, And An Open Layout Adorned With Stunning Artwork, This Space Blends Charm And Sophistication. Enjoy Vibrant Culture, Renowned Dining, And Little Italy’s Lively Atmosphere—All Steps From Your Front Door. Includes 1 Free Onsite Parking Spot. 1 Dog Accepted With A $50 Pet Fee.

Superhost

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.

Apartment in San Diego

4.89 out of 5 average rating, 1,488 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

Superhost

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.

Apartment in Little Italy

4.76 out of 5 average rating, 186 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.

Guest favorite

The charming facade of the Crowell Home showcases intricate architectural details, with a black exterior enhanced by lush greenery and colorful tropical plants. The front porch features a decorative railing, while large windows invite natural light into the interior.

Home in Little Italy

4.92 out of 5 average rating, 110 reviews

*New* Renovated Historic Home in Little Italy

Step into the newly renovated Crowell Home, a historic 1888 gem in Little Italy. This luxury retreat blends timeless elegance with modern upgrades, offering an exclusive stay in San Diego’s trendiest neighborhood. ✨ Highlights: ✔ Landmark 1888 Crowell Home – Fully renovated. ✔ Prime Location – Steps from top dining & attractions. ✔ Modern Upgrades – Smart tech, WiFi, keyless entry. ✔ Outdoor Living – Private patio for relaxation. 🌟 Book now & experience the best of Little Italy!

Guest favorite

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

4.88 out of 5 average rating, 108 reviews

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