Family-friendly holiday rentals in Little Italy

Home in Bankers Hill - Park West

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.

4.96 out of 5 average rating, 498 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.

4.97 out of 5 average rating, 431 reviews

A sunlit living area features two comfortable armchairs facing a glass coffee table with books and magazines. Large windows are adorned with light curtains, and a decorative lamp adds warmth. A dining table with chairs is positioned nearby, creating a cozy gathering space.

Bungalow in Hillcrest

Vintage Spanish Revival Home - Balboa Park - Alcazar Court

• 1924 Spanish Revival Bungalows - Alcazar Court - Nestled in the heart of the city in historic Hillcrest - with cafes, bars, and shops • Fully equipped 1 bd 1 ba bungalows complement shady olive tree-lined patios - guests can enjoy coffee in the morning - a glass of wine in the afternoon. Enjoy the charm and tranquility of a bygone era and convenience of modern amenities, • Explore nearby Balboa Park, home to 16 museums and performing arts venues, as well as the world-famous San Diego Zoo.

An expansive outdoor patio is showcased, featuring a comfortable sectional sofa with soft cushions and a stylish coffee table. Bi-folding doors connect to a modern kitchen area adorned with sleek cabinetry. The distant view reveals the San Diego coastline under a clear blue sky.

4.94 out of 5 average rating, 241 reviews

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!

A contemporary living area features a soft leather sofa adorned with various patterned cushions, complemented by a wooden coffee table displaying a plant and decorative items. A light-toned armchair adds to the comfortable layout, alongside a stylish lamp and art piece on the wall.

4.93 out of 5 average rating, 168 reviews

Chic Inner City Pad w/ Balcony | Walk Everywhere!

Stay right in the heart of vibrant Little Italy in this contemporary, inner-city apt with quaint piazzas and upscale boutiques all right on your doorstep. Split over two levels the apt features a thoughtfully curated design with living/dining on the lower level and an open double bedroom upstairs which steps out onto a balcony. Leave the car behind and walk to cocktail bars, brewpubs and restaurants or drive with downtown, the Gaslamp Quarter and Mission Beach only a short Uber ride away.

Townhouse in Bankers Hill - Park West

An outdoor seating area features four white Adirondack chairs arranged around a circular concrete fire pit. Lush greenery surrounds the space, and the home's exterior showcases a blend of gray and blue siding under the evening sky.

4.92 out of 5 average rating, 101 reviews

City View Banker's Hill

A beautifully renovated 2-bedroom, 1.5-bathroom craftsman-style duplex is perfectly situated in the heart of Bankers Hill. The perfect blend of classic craftsmanship and modern amenities in this beautifully restored home. Minutes away from San Diego's top attractions, including Balboa Park, Little Italy, and the vibrant Gaslamp Quarter. Two comfortable bedrooms provide a peaceful retreat. Fully equipped kitchen with new appliances. A perfect place to enjoy all that San Diego has to offer.

4.9 out of 5 average rating, 749 reviews

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 Little Italy

#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!

Townhouse in Little Italy

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.

4.95 out of 5 average rating, 151 reviews

Kettner Row | Staycation-Featured Icon

Welcome to Kettner Row, a rare architectural masterpiece featured on Staycation Sports, an Emmy-winning show on the Destination Channel! Located in the heart of Little Italy—one of San Diego’s most desirable neighborhoods—and designed by renowned architect Jonathan Segal, FAIA. This detached row home is situated in the award-winning Little Italy Neighborhood Developers block (LIND). This modern home features dual master suites, a high-end designer kitchen, and luxurious spa bathrooms.

4.83 out of 5 average rating, 139 reviews

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

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

4.98 out of 5 average rating, 194 reviews

A modern kitchen area features sleek cabinetry and stainless-steel appliances. A spacious island with bar seating provides ample space for dining. Large windows allow natural light to fill the room, with greenery visible beyond the sliding glass doors.

Loft in Little Italy

Waterfront Loft | 1BR | Little Italy | Downtown

The local neighborhood is highly walk-able and perched along the San Diego Bay in Little Italy. Little Italy is the most vibrant neighborhood in downtown San Diego with a main street that abounds with restaurants, boutiques, craft beer, and wine bars all at your doorstep. This is a very urban location which brings a lot of urban noise. The unit sits adjacent the train and trolley line in the urban core. No parking provided, Ideal for guests without a car.

4.83 out of 5 average rating, 531 reviews

Relaxing Little Italy Studio Apt | Near The Bay

Welcome To Our Sunny And Serene Studio In The Heart Of Little Italy—A Soft, Romantic Retreat Filled With Natural Light And A Calm, Aesthetic Vibe. Enjoy Minimal, Tasteful Decor, High-Quality Linens, And Cozy Touches Throughout. Relax On The Plush Sofa, Sway In The Hammock Chair, Or Wind Down With Your Favorite Shows On The Smart TV. Perfect For Couples, Solo Travelers, And Anyone Seeking A Peaceful, Beautiful Escape In San Diego.

Apartment in Downtown San Diego

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.

4.88 out of 5 average rating, 1,835 reviews

At Mine | Spacious Suite in the Gaslamp Quarter

This meticulously renovated historical hotel suite, designed by Pininfarina, is located in Downtown San Diego’s vibrant Gaslamp Quarter, surrounded by restaurants and nightlife. It offers private, spacious accommodations for both business and leisure travelers, featuring a king bed, smart TV, central AC, and mini-fridge. Please note: an adjoining bar operates until midnight, and some noise is expected.

4.84 out of 5 average rating, 194 reviews

A charming kitchen area is featured, showcasing a retro blue refrigerator and a round dining table. Two bowls are set on a woven placemat, ready for use. Light-colored cabinets provide storage, while a vibrant area rug leads to the adjoining space.

Cottage in Little Italy

Stylish, cozy studio in the heart of Little Italy

La Cantuccio - "the nook" - is Villa Little Italy's cozy studio. Set in an original 1930's bungalow, this two room studio, this has a main room with a Murphy bed and stylish living area as well charming kitchen. Every effort has been made to make this small space both functional and exquisitely comfortable ... the perfect hideaway to launch your exploration of Little Italy, San Diego, and parts beyond!

Popular amenities for Little Italy family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in University Heights

A colorful living area features a vibrant blue couch adorned with decorative pillows. A round white coffee table sits prominently on a multi-colored rug, while a television is mounted above a red cabinet. Artwork and framed prints decorate the pink walls, enhancing the playful ambiance.

4.95 out of 5 average rating, 119 reviews

Casa De Colores

Guesthouse in Mission Hills

A spacious living area features a large sectional sofa adorned with decorative pillows, complemented by a wooden coffee table. A vibrant wall art piece with colorful surfboards is displayed above the couch, while natural light fills the room through expansive windows.

4.97 out of 5 average rating, 292 reviews

Beautiful Historic Home and Gardens Near Downtown!

Home in Greater North Park

A spacious backyard features lush green artificial grass, surrounded by various plants and trees. Red Adirondack chairs invite relaxation, while a BBQ grill is positioned nearby. A patio area with steps leads to the rear of the home, completing this welcoming outdoor space.

4.96 out of 5 average rating, 225 reviews

North Park Gem with expansive backyard.

4.85 out of 5 average rating, 100 reviews

Home in City Heights

California Dreaming l Hot tub l Private Backyard

4.93 out of 5 average rating, 365 reviews

The open living area features a dining table with modern chairs and a sectional sofa. Artwork adorns the walls, and large windows allow natural light to fill the space. A cozy bedroom is highlighted by a stylish chandelier and a plush bed, complemented by decorative tiles in the bathroom.

Home in Normal Heights

NEW❤️Special Deals/HotTub/Firepit/private yard/BBQ

4.96 out of 5 average rating, 204 reviews

A spacious outdoor area is framed by lush greenery and palm trees. Comfortable seating is arranged around a fire pit, while a covered patio offers shade. A hot tub is visible in the background, providing a relaxing retreat under clear blue skies.

Home in San Diego

Dream 3BR HOUSE San Diego - Spa BBQ Playroom

4.97 out of 5 average rating, 161 reviews

The poolside area features a well-maintained saltwater pool reflecting the colors of the sunset. Comfortable seating arrangements, including lounge chairs and a cozy fire pit, are visible. Large umbrellas provide shade, and lush greenery adds to the serene ambiance.

Guesthouse in La Mesa

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV

4.87 out of 5 average rating, 117 reviews

Home in Normal Heights

Spanish Casita w/ Hot Tub, Fire Pit, Private Yard

Family- and pet-friendly home rentals

4.88 out of 5 average rating, 164 reviews

A cozy living area features a yellow tufted sofa paired with two brown leather armchairs. A decorative mirror hangs above a white fireplace. Natural light pours in through multiple windows, accentuating the space's inviting atmosphere. A ceiling fan and wall-mounted air conditioning unit are present.

Home in Ocean Beach

OB Spanish beach cottage w/ AC- 2 blks to beach

4.84 out of 5 average rating, 218 reviews

A bright living area features large floor-to-ceiling windows allowing ample natural light. A light wood coffee table is situated in front of a comfortable sofa adorned with decorative pillows. A large television stands on a modern console, with a potted plant adding a touch of greenery.

Home in Little Italy

Little Italy 2BR Loft Near Waterfront & Convention

A spacious living area is highlighted by a large sectional sofa and a contemporary coffee table. Natural light fills the room through sliding glass doors, leading to a balcony. A flat-screen TV is mounted on the wall above a modern entertainment unit.

4.9 out of 5 average rating, 100 reviews

Penthouse, Parking & Panoramic Views Little Italy

The living room showcases a spacious sectional couch with a chaise, paired with a sleek armchair. Natural light is welcomed through large windows, highlighting the warm hardwood flooring. Decorative elements include a coffee table and a soft rug, enhancing the inviting ambiance.

4.86 out of 5 average rating, 359 reviews

Modern House In The Hills | Killer Location!

An outdoor patio area showcases a modern gas fire pit with flames reflecting off the smooth surface. A spacious bed is visible through large glass doors, framed by stylish curtains. The warm tones of the interior including a wooden accent wall create a cozy atmosphere.

4.97 out of 5 average rating, 278 reviews

Ventana Vista | Ocean View | EV Charger | Designer

4.91 out of 5 average rating, 260 reviews

An inviting outdoor space is featured, illuminated by string lights against a night sky. Comfortable seating areas are present, including a large daybed with a canopy and hammocks. Lush trees provide a natural backdrop, enhancing the relaxing atmosphere of the yard.

Home in San Diego

Brunch House 3bd/2 Amazing Baths. Private yard.

4.8 out of 5 average rating, 101 reviews

Quiet Oasis With Private Yard

Townhouse in Little Italy

A bright living area features a leather sofa and a rattan chair positioned beside a light-colored coffee table. Large windows allow natural light to fill the space, showcasing a minimalist decor style. A framed art piece and potted plants add a touch of greenery.

4.79 out of 5 average rating, 206 reviews

Contemporary, Fully Renovated Loft in Little Italy

Family-friendly home rentals with a pool

4.86 out of 5 average rating, 204 reviews

An aerial view captures the oceanfront condo alongside the sandy beach, with an expansive coastline stretching below. The surrounding neighborhood features a mix of residential and commercial structures, interconnected by roads and pathways, creating a vibrant coastal community.

Condo in Pacific Beach

Ocean front condo heart of pacific beach

5 out of 5 average rating, 227 reviews

A serene backyard is framed by colorful sunset skies, featuring a cozy hammock in the foreground and a comfortable seating area with grey couches. String lights add warmth to the outdoor space, complemented by lush greenery throughout the neatly landscaped yard.

Home in La Jolla

La Jolla Beach House-Family Focused-3min to Beach

4.99 out of 5 average rating, 170 reviews

Two red Adirondack chairs are positioned under a covered patio, facing a serene backyard with a pool. Lush greenery surrounds the area, creating a tranquil atmosphere. A BBQ room and various seating arrangements are visible beyond the pool, enhancing the outdoor retreat experience.

Guesthouse in La Mesa

Private 1 BR Paradise Retreat

A vibrant heated pool is surrounded by minimalistic landscaping, featuring tall cacti and a clean white fence. Soft lounge chairs are positioned nearby for relaxation. The clear water reflects the blue sky, creating a refreshing setting for leisure and enjoyment.

4.93 out of 5 average rating, 287 reviews

Lionhead - Private Boutique Home

Apartment in Downtown San Diego

A living area is presented with a vibrant yellow sofa complemented by decorative cushions. A circular table sits on a striped rug, surrounded by a leather armchair. A small potted plant adds a touch of greenery, and large glass doors lead to a balcony, offering natural light.

4.85 out of 5 average rating, 122 reviews

Downtown Dream 3

4.94 out of 5 average rating, 204 reviews

A swimming pool reflects sunlight under a clear blue sky, surrounded by a patio area. A colorful hammock is suspended near the pool, while potted plants add greenery. The adjoining building features large windows and a seating area.

Guest suite in La Mesa

Hacienda de las Campanas (Bell Hacienda)

4.94 out of 5 average rating, 140 reviews

A living room features a luxury hanging chair suspended from the ceiling. Natural light filters through sheer curtains, illuminating a cozy seating area with a plush sofa and wooden coffee table. A 50” television is mounted above an elegant fireplace, enhancing the room's comfort.

Home in City Heights

Designer Luxury Rental With Pool