Vacation rentals with a pool in Little Italy, San Diego

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Little Italy, San Diego

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

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Guest favorite

Guest suite in San Diego

4.97 out of 5 average rating, 352 reviews

Groovy canyon studio pool & spa blocks from SDSU

It’s a groovy studio splashed with color :) Enjoy this slice of paradise hosted by Airbnb super hosts. You can splendor in their thrifty take on the San Diego stay. Bask in the blissful views, and spoil yourself in the spa! If it gets too hot, hop in the pool! No worries allowed at this groovy getaway. We have unique booking methods! Short term stays less than 28 days are available for booking 1 month in advance. If it's over a month before your visit, our calendar only allows longterm booking

Guest favorite

Guesthouse in Mission Hills

4.93 out of 5 average rating, 144 reviews

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

Perfect poolside retreat suitable for small families and couples! The suite 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, cocktail bars, the light rail, and easy access to the I-5 highway!

Guest favorite

Home in Hillcrest

5 out of 5 average rating, 121 reviews

Custom Guesthouse, Balboa Park/Zoo/Hillcrest& pool

2021 CUSTOM guest home with pool in the heart of Hillcrest/San Diego/Zoo/Balboa Park area. Full kitchen, a queen bed in the bedroom & a queen sleeper sofa in the living room. Full bath, indoor & outdoor dining, WiFi, smart TV, pool, AC/heating, BBQ& free parking. Short walk to restaurants, shops & stores (TraderJoe's, Ralph's & Whole Foods). Minutes drive to San Diego beaches & bay. It accommodates 1-4 guests. No rent for children under 3, but $75/stay. High chair and Pack&Play are available.

Superhost

Guesthouse in City Heights

4.91 out of 5 average rating, 283 reviews

Green Door Cottage

Enjoy our new, fully renovated (2021) tiny Cottage which holds a timeless charm and is also filled with a modern touch. Close to all the wonderful things San Diego has to offer - beaches, downtown, the zoo, Padres games, SeaWorld, SAN airport, Old Town, SDSU, you name it! Nice sized turf yard with total privacy and an amazing back deck! Outside table and fire pit are perfect for the cool nights of San Diego. If you need more space, check out our other listing, Pink Door Craftsman (sleeps 7)!

Guest favorite

Home in Mission Hills

4.93 out of 5 average rating, 224 reviews

Lionhead - Private Boutique Home

Heated pool, spa, cabana and views. Boutique hotel vibes in San Diego. Palm Springs meets South Beach with a splash of groovy. Location is perfect for Downtown, conventions, shows in town. Highway friendly. Private backyard for bbq, food, drinks and relaxing. Pool is heated with cozy spa to relax and watch the planes take off. Hi speed Wifi, smart TV's, HBO, NFL Package, record player with albums. 19 speakers in the ceilings with connected to your phone for optimal happiness. Plug and play!

Guest favorite

Guesthouse in La Jolla

4.98 out of 5 average rating, 169 reviews

Luxury Tropical Private Guesthouse in La Jolla

Beautiful private guesthouse on $5 million property with stunning views and luxury amenities. Take a dip in the tropical pool with waterslide, tiki bar, and hot tub grotto. Enjoy indoor or outdoor dining. Gated property, vaulted ceilings, marble bathroom, private balcony, parking, and trail for guests. Guesthouse has 1 bedroom with a queen bed and can accommodate an extra twin bed on the loft. House has closet, bathroom with beautiful stone shower, modern kitchen, two patios, WiFi, TV.

Superhost

Condo in North Ocean Beach

4.82 out of 5 average rating, 287 reviews

Swell Times Beach Studio

Need a cozy, affordable beachside getaway located steps from the sand in world famous Ocean Beach? Come chill at The Swell Times Beach Studio with sprawling beach views - just steps from the sand. Great for solo travelers, small families, or anyone looking to enjoy all OB has to offer. Ocean Beach is the closest beach area to the San Diego Airport, and there are tons of great restaurants, bars, coffee shops, and more within easy walking distance - totally pet friendly too :)

Guest favorite

Guesthouse in Mission Hills

4.91 out of 5 average rating, 433 reviews

Mission Hills Charming suite, walkable to all.

Heart of Mission Hills, upscale area, this private guest suite, separate from the house, is perched above the pool (separate building from main house), own entrance; sure to provide privacy. 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 with Clorox as well as all linens washed. We also don’t rent back to back giving time for thorough cleaning.

Guest favorite

Home in Serra Mesa

5 out of 5 average rating, 185 reviews

Midcentury Lux 4BR home w Pool/Spa/Cabana/Firepit

COMPLETELY renovated 4BR 3 Bath mid-century home with heated pool, hot tub and fire pit in totally private backyard retreat. We renovated the house top-to-bottom, inside and out and everything is brand new. The beds are top quality with very high quality 100% cotton sheets and bath towels. The house is centrally located in a safe, friendly neighborhood and has beautiful mountain views in the back. Additionally, we do not charge any fees for anything!

Superhost

Home in University Heights

4.93 out of 5 average rating, 117 reviews

Your Modern Lux Pool Resort in the Heart of SD

Welcome to our canyon front, mountain-modern home in Hillcrest & University Heights. Just 3 blocks from the adored Vermont St. Bridge, you'll be right in the heart of Hillcrest and able to escape the city when it's time to relax. Enjoy spa-like accommodations, modern amenities, premium linens & toiletries, and sprawling outdoor spaces. Whoever you are, we are committed that you LOVE your stay.

Guest favorite

Guest suite in Bonita

4.88 out of 5 average rating, 324 reviews

Resort-Style Living, Pool, Close to All San Diego

Large, private air-conditioned studio attached to beautiful ranch-styled, executive home with amazing pool. Resort-style living. Unwind & relax by the pool and gardens. Close to the Olympic Training Centre, downtown SD, Comic Con, major attractions, beaches, airport & Mexico. Coffee, tea and snacks are provided in the room for your enjoyment! Lots of off street parking. Safe neighborhood.

Guest favorite

Guesthouse in Allied Gardens

4.95 out of 5 average rating, 368 reviews

The BEST NEST Clean, peaceful, private, affordable

This lovely private & separate unit is comfortable, clean and convenient. Your completely private suite is accessible via your own entrance. Minutes from major attractions, away from the hustle and bustle. Full kitchen for easy meal preparation. Located in a nice usually quiet neighborhood, close to major freeways. Enjoy the gorgeous San Diego weather in the quaint outdoor patio area.