
Holiday rentals in Little Italy
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Top-rated holiday rentals in Little Italy
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

Contemporary, Fully Renovated Loft in Little Italy
Book this spectacular contemporary loft with 25 foot ceilings & views! The loft is in an area with a 9.8/10 walk score & known for having the best restaurants, bars &shops. The unit is newly renovated & meticulously designed with bright windows, contemporary high-end furnishings & an everyday spa inspired bathroom. Only steps from the waterfront, you decide if you want to enjoy cocktails & cuisine in the night scene or relax all day walking along the harbor. Free parking spot with access to all.

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.

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!

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.

#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!

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.

Sunny Stylish & Central - Luxe Little Italy Studio
Located right in the heart of vibrant Little Italy is this sparkling Downtown studio filled with light, airy boho vibes and all the amenities you could need for a cozy stay. Whip up meals in the fully-equipped kitchen, snooze in the luxe king bed, soak up the sun on the lounge or sip your coffee at the chic café-style dining table. Ready to explore? Little Italy's buzzing restaurants, bakeries, and cafes are just steps away or take a quick 10-15 min drive to San Diego's top sights.

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

Modern Urban Row Home * Dog OK * AC
Welcome to this modern Studio+1ba row home located in the heart of the vibrant Little Italy neighborhood of Downtown San Diego. Designed for hip, urban living by award winning architect Jonathan Segal, this offering features high ceilings with full floor windows, beautiful polished concrete floors, living room with separate reading nook, 1 dog ok (unfortunately no cats), a/c, & sleeps 4 (2 adults max). NOTE no washer/dryer or parking, kitchenette only (no full kitchen)

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.

Penthouse, Parking & Panoramic Views Little Italy
Walk to restaurants, bars, and Waterfront Park. Bask in stunning sunsets, balcony views, and refreshing bay breezes. My long-time residence embodies the neighborhood's charm, with the harbor nearby. Enjoy Saturday's local farmer's market just two blocks away. Experience the best of San Diego in the city's most walkable neighborhood! Happy to set you up at local restaurants and provide reservations as well. Will give you the best HH spots as well ;)
Popular amenities for Little Italy holiday rentals
Other great holiday rentals in Little Italy

Skyline Hot Tub Deck • Harbor Views, Sleeps 8

Modern 2BR Near Zoo, Balboa Park & Little Italy

Deluxe King | Wyndham Bayside | Heated Pool

BEST LOCATION in all of Little Italy & downtown!

Explore Little Italy from this Gorgeous Mini Villa

Close to Airport | Dining. Balcony & Pet-Friendly

La Giardino, a Stylish Mediterranean Bungalow

Chic Inner City Pad w/ Balcony | Walk Everywhere!
When is the best time to visit Little Italy?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $205 SGD | $217 SGD | $218 SGD | $212 SGD | $221 SGD | $228 SGD | $277 SGD | $233 SGD | $217 SGD | $210 SGD | $206 SGD | $201 SGD |
| Avg. temp | 15°C | 15°C | 16°C | 17°C | 18°C | 20°C | 21°C | 22°C | 22°C | 20°C | 17°C | 14°C |
Quick stats about holiday rentals in Little Italy

Total holiday rentals
Explore 570 holiday rentals in Little Italy

Nightly prices starting at
Little Italy holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 34,400 verified reviews to help you choose

Family-friendly holiday rentals
220 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 220 rentals that welcome pets

Holiday rentals with a pool
130 properties feature pools

Rentals with dedicated workspaces
330 properties have a dedicated workspace

Wifi availability
560 of Little Italy holiday rentals include wifi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Little Italy rentals

4.8 Average rating
Little Italy stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Loft rentals Little Italy
- Hotel rooms Little Italy
- Apartment rentals Little Italy
- Waterfront rentals Little Italy
- Rentals with a sauna Little Italy
- Pet-friendly rentals Little Italy
- Rentals with beach access Little Italy
- Rentals with outdoor seating Little Italy
- Rentals with an EV charger Little Italy
- House rentals Little Italy
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- Flat rentals Little Italy
- Rentals with a patio Little Italy
- Rentals with breakfast Little Italy
- Rentals with a fireplace Little Italy
- Rentals with a hot tub Little Italy
- Rentals with a firepit Little Italy
- Rentals with pools Little Italy
- Family-friendly rentals Little Italy
- Rentals with a washing machine and dryer Little Italy
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