Holiday houses in Little Italy, San Diego

4.96 out of 5 average rating, 77 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.

4.92 out of 5 average rating, 317 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!

4.93 out of 5 average rating, 139 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!

4.93 out of 5 average rating, 73 reviews

Guesthouse in Downtown

Lower Suite on Ivy St - Walk to Little Italy!

Welcome to the Ivy Street Suites! Your gateway to the best San Diego has to offer -- conveniently located within the buzzing restaurant district of both Little Italy + Bankers Hill. Drop your bags + explore the San Diego Zoo, Balboa Park, USS Midway Museum + the infamous Little Italy Farmer's Market! All within a nice stroll from the space. Upper + Lower Suites which can be rented together or separately, with a shared courtyard + private deck/patio each. This listing is for the lower suite.

4.82 out of 5 average rating, 759 reviews

Townhouse in Downtown

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

4.94 out of 5 average rating, 357 reviews

Bungalow in Downtown

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.

4.83 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.

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.

5 out of 5 average rating, 12 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.

4.88 out of 5 average rating, 106 reviews

Condo in Downtown

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

4.86 out of 5 average rating, 387 reviews

Entire 2bd - Most Convenient Location of San Diego

Professionally cleaned apartment located in Beautiful Bankers Hill - prestigious neighborhood up the hill from Little Italy, perfectly situated in the epicenter of San Diego! Our spacious 2br/1ba is within such short reach of Little Italy, Balboa Park, Downtown, Waterfront Park, Harbor, Airport, etc! Your private apartment comes equipped with high end appliances, finishes, and breath taking views of the city skyline and San Diego Harbor surrounding the property.

4.84 out of 5 average rating, 139 reviews

Guest suite in Downtown

Little Italy + Downtown Close to Convention Center

This remodeled studio is a couple blocks away from shops, restaurants + bars in Little Italy/Downtown SD and is close to Convention Center. Centrally located & minutes from the airport w/ plenty of free street parking. Walking distance to: - Waterfront Park - USS Midway - Balboa Park (half a mile) - Little Italy - Seaport Village - Embarcadero Short drive to: - Petco Park - Beaches (PB, Coronado, Ocean Beach, La Jolla) - Liberty Station/Point Loma - North Par

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Other great holiday rentals in Little Italy, San Diego

4.92 out of 5 average rating, 163 reviews

State & Fir (Little Italy Loft, Free Parking)

ToddRating, 5 stars2 weeks ago

Rachel’s place was perfect. Quite spacious for a loft. Easy to get in. On site parking was extremely convenient. The place was clean and had everything we needed. Great host and location.

4.86 out of 5 average rating, 750 reviews

Sunny, Open 2 Story Apt Downtown w/ Parking

ChloeRating, 5 stars3 weeks ago

We loved our stay at Rachel’s place. The apartment is beautiful, light and spacious. A lovely central location in a sweet neighbourhood with lots of fab Italian restaurants on the doorstep. Important to note the parking is not onsite but was easy to find with clear instructions and only 5 mins walk from the apartment. We would come back if we visit San Diego again!

4.91 out of 5 average rating, 141 reviews

Perfect Downtown Studio | Steps to Little Italy!

DonnaRating, 5 stars2 weeks ago

LOCATION! LOCATION! LOCATION!!! My husband and I enjoyed our stay at Evan’s place! It was so convenient to everything in Little Italy, but still far enough away that the noise was greatly reduced. We very much appreciated Evan’s quick replies and the manual he provided for restaurants, entertainment, and points of interest. The one thing we missed was having a comfy chair or loveseat to sit on, but the location, cleanliness, affordability and Evan’s quick responses made up for it. Bonus - also conveniently located near both bus and rail transportation.

4.93 out of 5 average rating, 173 reviews

Calm Luxury Penthouse Getaway With Panoramic Views

GayRating, 5 stars1 day ago

Perfect location! Close to waterfront, restaurants, and coffee. Apartment is also well equipped to cook in as well. We walked everywhere, no car needed. Uber easy to get if venturing further. We lived on the balcony, fantastic views and lovely breeze. Communication with Jessica was excellent. Check out instructions easy - just gather towels. Would definitely stay again.

4.87 out of 5 average rating, 359 reviews

Bungalow in Downtown

La Giardino, a Stylish Mediterranean Bungalow

FranciscoRating, 5 stars3 weeks ago

Everything is great! Thank you

4.77 out of 5 average rating, 801 reviews

Good Vibe (Little Italy Loft, Free Parking)

KirstiRating, 5 stars2 weeks ago

This stay met all our needs for a quick weekend in San Diego! Place is a little small but location is great. Walkable to little Italy. Also very helpful that parking is provided.

4.92 out of 5 average rating, 119 reviews

Sunny Stylish & Central - Luxe Little Italy Studio

LisaRating, 5 stars1 week ago

Evan is an incredible host and the location is perfect! Walkable to so many things we wanted to do, and literally a block to Little Italy’s Farmers Market (a favorite of ours). Evan has a great San Diego Guide to restaurants in the area that we referenced for some ideas. We also really appreciated how easy it was to find parking (lots of close options). We will definitely be back again and have even talked about checking out some of his other properties. Thanks for being such a wonderful host!