Family-friendly vacation rentals in Little Italy

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.

Apartment in Downtown San Diego

A spacious living area is furnished with a floral-patterned love seat and two armchairs. Custom-built shelves house a collection of books, while a coffee table sits on a patterned rug. Bright yellow walls enhance the natural light streaming through the shuttered windows.

4.95 out of 5 average rating, 368 reviews

Trendy Studio, Natural Light - Heart of Downtown

Large studio with comfortable queen sized Murphy Bed, a love seat, private entrance and private bath. Located in Cortez Hill - walk to the nicest neighborhoods in downtown like Little Italy, Gaslamp, East Village, and the Embarcadero. There is no full kitchen, but there is a small refrigerator, small microwave, and a pot for heating water. This is an ideal space for solo travelers, couples, events at the Convention Center, Padres Games, great eateries, and the best of Downtown San Diego.

4.89 out of 5 average rating, 332 reviews

A modern two-story bungalow with a clean white exterior is captured at dusk. Large windows allow for ample natural light, while a set of stairs leads to the entrance. The surrounding area features minimal greenery, enhancing the structure's architectural lines.

Bungalow in Little Italy

Explore Little Italy from this Gorgeous Mini Villa

La Scala rises from the center of Villa Little Italy in the heart of San Diego’s most popular restaurant and entertainment district. 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.

Townhouse in Little Italy

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.

4.83 out of 5 average rating, 812 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

4.98 out of 5 average rating, 145 reviews

Home in Normal Heights

Family-friendly fun in the sun

You will be close to everything San Diego has to offer in our cozy 2 bedroom 1 bathroom home. Family-friendly fully-gated yard with playset, mini putting green, games and seating area. Crib, changing pad, pack and play, 2 high chairs, child baths and dinnerware. Have a relaxing and fun time with multiple indoor games, large living room and bedroom smart TVs. Fast wifi, separate office space with desk, central heat/AC for comfort, W/D, 2 car driveway, lux bathroom and fully-equipped kitchen.

Apartment in Little Italy

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!

Apartment in Little Italy

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 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.

Apartment in Little Italy

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, 1,833 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.

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

Guest suite in Greater North Park

A spacious guest suite is featured, showcasing a comfortable bed and a stylish seating area. Natural light illuminates the room, highlighting a modern sauna enclosed in glass. Elegant decor is complemented by a chandelier, adding a touch of sophistication to the inviting atmosphere.

5 out of 5 average rating, 110 reviews

Hidden Spa w/ Sauna and Hot Tub near Balboa Park

4.93 out of 5 average rating, 165 reviews

Cabin in Mission Hills

Designer Cottage in the Historical San Diego Area

4.89 out of 5 average rating, 144 reviews

An outdoor seating area is set on a lush green lawn, featuring a wooden coffee table surrounded by a rattan chair and two cushioned chairs. Warm ambient lighting highlights the nearby architectural details and creates a relaxed atmosphere as dusk settles in.

Condo in Hillcrest

Stunning Hillcrest Villa! Tub AC Parking Ping-Pong

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

4.91 out of 5 average rating, 384 reviews

An open living area features a large wooden dining table surrounded by six white chairs. A cozy sofa, adorned with neutral pillows and a blanket, overlooks expansive glass windows showcasing hillside views. A Christmas tree stands in the corner, adding a festive touch.

Home in Bonita

Glass Home with Views, Hot Tub, FREE EV Charging!

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, 290 reviews

Beautiful Historic Home and Gardens Near Downtown!

4.94 out of 5 average rating, 188 reviews

Home in San Diego

Luxe Point Loma Oasis w/ Pool, Spa & Fire Pit

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

Family- and pet-friendly home rentals

4.91 out of 5 average rating, 216 reviews

A spacious private patio is illuminated by string lights, creating a cozy outdoor setting. A fire pit sits at the center, surrounded by modern seating. Large glass doors open to the interior, allowing for an open transition between indoor and outdoor spaces.

Home in Golden Hill

Historic Golden Hill Post Office - 3 BR w fire pit

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

4.97 out of 5 average rating, 119 reviews

A serene pool area features a cascading waterfall illuminated in soft purple hues. The water flows gently into the heated pool, adding a calming effect to the ambiance. Wood paneling surrounds the pool, creating a private and tranquil atmosphere.

Villa in San Diego

Lux Villa: Heated Pool, Sauna, & Gym

Condo in Downtown San Diego

A spacious living area is highlighted by two large abstract paintings in warm gold tones. Comfortable seating is provided by a plush sofa and armchair, complemented by unique coffee tables. Hardwood flooring adds to the welcoming atmosphere, accented by soft lighting.

4.87 out of 5 average rating, 190 reviews

Stylish/Modern/Gaslamp/Spacious 1BR/1BA

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

4.86 out of 5 average rating, 358 reviews

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.

Home in Mission Hills

Modern House In The Hills | Killer Location!

4.97 out of 5 average rating, 117 reviews

A bright living area is visible, featuring a mix of modern furnishings including a cozy sofa, a smart TV, and a circular dining table with wooden chairs. Large windows allow natural light to fill the space, highlighting the warm wooden flooring and inviting decor.

Guesthouse in La Mesa

East Watch- a private getaway

Apartment in Bankers Hill - Park West

A clean, modern small apartment building is shown, with two structures connected by an open walkway. Palm trees line the entrance, and large windows provide natural light. A paved driveway leads into the courtyard, highlighting the building's airy design against a backdrop of clear blue skies.

4.84 out of 5 average rating, 151 reviews

Modern Bankers Hill Studio on Maple Canyon

Family-friendly home rentals with a pool

4.92 out of 5 average rating, 116 reviews

A spacious outdoor patio showcases a private pool and hot tub, surrounded by comfortable seating and a fire pit. An activity area features games such as foosball and cornhole, with lounge chairs positioned for relaxation. Lush green landscaping complements the inviting space.

Home in Bay Park

Modern Central SD Home w/ Pool & Spa Near Beach

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, 226 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

Apartment in Greater North Park

A serene bedroom features a queen bed with a light-colored quilt. Two bedside tables with lamps are positioned on either side. The walls are adorned with various framed artworks and a large mirror, reflecting natural light from the windows.

4.79 out of 5 average rating, 479 reviews

On park. 1 bed apt.has air & small kitchen+w&d

4.85 out of 5 average rating, 108 reviews

The private pool area is surrounded by palm trees and cacti, with lounge chairs positioned for relaxation. A shaded dining area is visible in the background, complemented by the warm glow of a sunset sky. The scene creates a serene outdoor retreat.

Home in San Diego

Surf Cottage w/Pool & Firepit 10min from the beach

4.93 out of 5 average rating, 287 reviews

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.

Home in Mission Hills

Lionhead - Private Boutique Home

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