Vacation rentals with a pool in Little Italy

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Little Italy

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

The private backyard features an inviting pool, surrounded by various seating areas and lush greenery. A shaded BBQ room is visible, along with an umbrella atop a dining table. The expansive landscape offers a mix of stone pathways and flourishing plants beneath a clear blue sky.

Guesthouse in La Mesa

4.99 out of 5 average rating, 133 reviews

Private 1 BR Paradise retreat

Private, yet central. It is your exclusive paradise retreat to enjoy from your spacious 1 bedroom guest house located on the lower level of our home. Hang out in the expansive and private backyard with pool, different sitting areas and covered BBQ room. Or maybe a workout in the gym. Centrally located in the Village of La mesa. Just a 1/4 mile jaunt into the quaint village with its numerous assortments of dining options, stores and trolley station. Freeway close to beaches, downtown and airport

Top guest favorite

A private pool glistens under the sun, bordered by a brick patio and greenery. A shaded seating area is visible in the background, along with colorful pool floats, including a flamingo. The tranquil setting invites relaxation and enjoyment.

Guesthouse in Mission Hills

4.94 out of 5 average rating, 177 reviews

Casita w/Private Pool, King Bed, Full Kitchen!

Perfect poolside retreat suitable for small families and couples! The pool house boasts a fully-equipped kitchen, a private pool, front patio and sunbathing deck! You'll enjoy a luxurious king-size bed and a convenient full-size fold-out couch, perfect for kids! Plus, all the amenities necessary for a memorable stay. Located in one of San Diego's most central neighborhoods of Mission Hills, you're just a stroll away from restaurants, Old Town, the light rail, and easy access to the I-5 highway!

Top guest favorite

Home in Hillcrest

4.99 out of 5 average rating, 165 reviews

Custom Guesthouse, Balboa Park/Zoo/Hillcrest& pool

2021 CUSTOM guest home with pool in Hillcrest/San Diego Zoo/Balboa Park area. Full kitchen, a queen bed, a queen sleeper sofa, and a crib. Full bath, indoor/outdoor dining, WiFi, smart TV, pool, AC/heating, BBQ& free parking. Walking to restaurants/bars/shops/stores (Trader Joe's, Ralph's & Whole Foods). Under a mile to Farmers Market Sprouts. Minutes' drive to San Diego beaches. No rent for children under 3, only $95/stay. High chair, Pack & Play/Crib, crib mattress, and cover are provided.

Guest favorite

A tranquil pool area features a clear blue swimming pool surrounded by lounge chairs and a shaded umbrella. Elegant outdoor curtains frame a seating space, enhancing the inviting atmosphere of the space, perfect for relaxation.

Guesthouse in Mission Hills

4.91 out of 5 average rating, 472 reviews

Mission Hills Charming suite, walkable to all.

Heart of Mission Hills, upscale area, this private suite, separate from the house, is perched above the pool (separate from main house), own entrance, room has walkin closet, small fridge, swivel TV, electric fireplace to warm you up. We are minutes from airport, walking distance to coffee & restaurants and central to all of SD. Please note this property is wiped down after each visit and steamed, as well as all linens washed. We also don’t rent back to back giving time for thorough cleaning.

Top guest favorite

A bright living room features large glass doors opening to breathtaking ocean views. A comfortable white sectional sofa is surrounded by two plush armchairs. Wall art and a round coffee table enhance the inviting atmosphere, while a potted plant adds a touch of greenery.

Condo in Pacific Beach

4.98 out of 5 average rating, 178 reviews

Luxury Oceanfront Condo with Unbelievable Views

Welcome to your oasis! Prepare to be awestruck by the breathtaking views at Sunset Pacifica. This fully renovated condo features two ensuite bedrooms with the beachy SoCal vibe you desire. Ideally located on the boardwalk, you're minutes from La Jolla, Downtown, the San Diego Zoo, Embarcadero, and top restaurants, bars, and entertainment spots. Whether you're in the mood for exploration or relaxation, you'll find it here- lounging poolside or on the sandy shores of the stunning Pacific Ocean.

Top guest favorite

A serene outdoor space features a solar heated pool surrounded by a patio. Comfortable seating is provided, with potted plants and greenery enhancing the atmosphere. The house is visible in the background, showcasing inviting exterior colors and landscaping.

Guesthouse in Talmadge

4.98 out of 5 average rating, 217 reviews

Lovely Guesthouse in garden setting

Centrally located guesthouse on quarter acre lot in a beautiful community 5 minutes drive from restaurants, pubs, shops, library, SDSU. 15 minute drive to beaches, downtown, military bases, zoo, Balboa Park. 800sq’ cottage with great outdoor space- patio, gas grill, salt water/solar heated pool & hot tub, fruit trees for sharing, gardens. Central A/C and heat. Books and games for fun down time. Relax w/SMORS and drinks in the evening around the fire pit table : ) Street parking available.

Guest favorite

A private patio area is visible, adorned with a wooden structure and comfortable seating arrangements. The sparkling pool is set at a distance, surrounded by greenery. Sunlight casts gentle shadows, highlighting the textured concrete and wooden elements in the outdoor space.

Guest suite in Hillcrest

4.88 out of 5 average rating, 118 reviews

Hillcrest canyon home casita with pool access

Stay in a private canyon home in Hillcrest with pool access -just a few miles to the airport, downtown and little Italy. Walk to your favorite bars and restaurants in Hillcrest and Mission Hills, or explore Balboa Park, the world famous San Diego Zoo, and many of the nearby beaches, which are only a 10 -20 minute drive away. You will be 3 miles away from the Convention Center. My home is centrally located within 2 miles from the airport and almost everything is a 10 minute drive away.

Top guest favorite

This open concept studio features a light-filled seating area with a plush sectional sofa adorned with decorative pillows. A well-equipped kitchenette and a dining area with bar stools are present. The spacious bed is positioned in the background, complemented by soft lighting and neutral decor.

Guesthouse in La Mesa

4.99 out of 5 average rating, 102 reviews

Private Balcony! Sunset & SunriseVIEWS!

~PANORAMIC VIEWS~ ~PEACEFUL & PRIVATE~ ~CENTRAL LOCATION~ ~XL BALCONY~ ~POOL/SPA ADD ON PACKAGE~ OCEAN, Mountain, Harbor, & Valley views~to Pt Loma & Coronado! Historic Mt Helix neighborhood. Balcony with panoramic views~ an outdoor living space! Private entrance, 1 Driveway parking space Ask about our POOL/SPA/LOUNGE-available as an ADD ON fee package only~Scroll down for details on EXTRA deposits/fees & approval terms that apply NON SMOKING/VAPING property indoor & out

Top guest favorite

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

4.96 out of 5 average rating, 124 reviews

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

This is the perfect Guest House with a salted & heated pool & hot tub. We are located in a super quiet & very safe neighborhood in beautiful San Diego, 15 minutes drive to Downtown, La Jolla, Beaches, Zoo, Sea World & Convention Center. Hike next door at Mission Trails & Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo and top quality finishes await you inside. Everything you need for memorable vacation! No smoking or vaping on the property.

Guest favorite

Guest suite in El Cajon

4.88 out of 5 average rating, 243 reviews

Tranquil Poolside Studio

Quiet Poolside Studio Suite! Perfect for visiting family in La Mesa or enjoying everything San Diego has to offer! Please note: this is not a party house. Private side entrance to a relaxing poolside studio. Very quiet with TV, and full kitchen. Comfortable queen size bed and sofa that can sleep one more person comfortably. We are 20 min to the beach, or relax and enjoy the pool! Close to SDSU and easy freeway access to anywhere in San Diego.

Guest favorite

A private swimming pool is set amidst natural landscaping, surrounded by stone pathways and decorative plants. The vibrant blue water reflects the sunlight, creating a serene ambiance. A rock formation is visible near the shallow end, adding to the pool's inviting design.

Guesthouse in Tierrasanta

4.87 out of 5 average rating, 169 reviews

Fig Tree Cottage

The private upstairs addition to our home was built new Spring of 2017. Sitting over our garage, it is a cozy 500 sqft & offers guests a quaint & quiet place to relax. With well appointed furnishings & thoughtful decor, Fig Tree Cottage offers everything you need to enjoy all the comforts of home. Just 15 min away enjoy the beautiful beaches of La Jolla along with some of the best restaurants and boutique shopping San Diego has to offer!

Guest favorite

A well-maintained swimming pool is surrounded by a tiled deck. Two lounge chairs are positioned for relaxation, and a stylish water feature adds a serene touch. Lush greenery provides privacy, while a staircase leads to an upper deck area with additional seating options.

Guesthouse in Ocean Beach

4.89 out of 5 average rating, 488 reviews

Pool house at Sunset Cliffs, Ocean Beach, Hot Tub!

This is a unique property at the top of Sunset Cliffs within a mile to Ocean Beach! Close to Downtown Gaslamp. The property has a phenomenal entertaining backyard, great for relaxing by the pool during the day, Hot Tub, or sitting by the fire or rooftop bar at night with a glass of wine! Walk down to the bottom of the street and you will find 2 miles of walking trails next to the ocean cliffs!