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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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Guesthouse in San Diego

4.91 out of 5 average rating, 247 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)!

Aug 25 – Sep 1

G$27,605 GYD per night

Guesthouse in San Diego

4.93 out of 5 average rating, 122 reviews

Modern Guest House with pool, steps to SDSU

Casita within easy walking distance to SDSU, Viejas Arena, Cal Coast Credit Union Open Air Theatre, shops, and transit. Casita includes Tempur-Pedic Queen bed and a love seat which converts to twin bed. Enjoy the peaceful canyon side garden, firetpit and pool, or relax in the hammock. Panoramic door opens completely to let in our wonderful weather and the view. Note: Pool is heated with a solar cover, comfy for swimming APR-OCT. Max 3 guests, no children/infants due to unfenced pool.

Aug 31 – Sep 7

G$25,153 GYD per night

Guesthouse in Mission Hills

4.94 out of 5 average rating, 118 reviews

Central Guesthouse w/ Private Pool & Full Kitchen

Perfect poolside retreat suitable for small families and couples! This 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 option, accompanied by many 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.

Oct 6 – 13

G$58,001 GYD per night

Home in Point Loma Peninsula

4.93 out of 5 average rating, 120 reviews

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

The vacation of your dreams awaits at the luxury 3BR Point Loma oasis. Each of the posh bedrooms has an en-suite bathroom and access to the exquisite backyard oasis-which is complete with a pool, spa, outdoor kitchen, and fire pit area. Enjoy outdoor dining by the pool or the lovely succulent gardens throughout the property. Sleeps 8. Washer/dryer, complimentary Wi-Fi, Netflix and parking are included. Hotel quality sheets and fresh duvets are also included with your stay. No parties.

Jun 1 – 8

G$216,089 GYD per night

Home in San Diego

4.98 out of 5 average rating, 241 reviews

Resort Style Living with Pool, Spa, and Bay Views!

Resort style home with a solar heated pool, hot tub, outdoor entertaining space, bay and ocean views, multiple patios, modern amenities, comfortable beds, and more. Convenient location to freeways, Seaworld, Mission Bay, Beaches, Downtown, Balboa Park, Airport, La Jolla and other attractions. Perfect for families and groups. Two car garage parking included. 2300 square feet of indoor living and much more outdoors. Your ideal home base for enjoying all that San Diego has to offer.

Jan 4 – 11

G$142,295 GYD per night

Condo in San Diego

4.99 out of 5 average rating, 108 reviews

Luxury Oceanfront Condo with Unbelievable Views

Welcome to your Oasis! You will be completely in awe of the breathtaking views that Sunset Pacifica has to offer. This fully renovated condo features two ensuite bedrooms decorated with the beachy SoCal vibe you are looking for. Centrally located on the boardwalk and just minutes to La Jolla, Downtown, the famous SD Zoo, Embarcadero, restaurants, bars and entertainment. There is so much to do here or just lounge around poolside or on the sandy shores of the beautiful Pacific Ocean.

Oct 20 – 27

G$129,443 GYD per night

Apartment in Spring Valley

4.86 out of 5 average rating, 139 reviews

Comfy, Cozy Flat With Pool & Spa!

Our flat has a patio that enjoys great sunsets. We are freeway close to all, easy in and easy out!! You’ll love the place because of the comfy bed, space, patio and access to pool and spa. Also, the yard can be enjoyed for relaxing, eating, bonfires, horseshoes and cornhole. An adjoining space is also an AIRBNB studio suite. Great for traveling friends or as an alternative place to consider for your stay. Look for Foemer man Cave with Pool And Spa.

Sep 10 – 17

G$24,558 GYD per night

Guesthouse in Mission Hills

4.91 out of 5 average rating, 415 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.

Oct 26 – Nov 2

G$21,012 GYD per night

Home in San Diego

4.94 out of 5 average rating, 204 reviews

Boutique home with view, heated pool, spa + cabana

Heated pool, spa, cabana and view. 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 audio hub plug in.

Feb 23 – Mar 2

G$117,558 GYD per night

Guesthouse in San Diego

4.94 out of 5 average rating, 333 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.

Feb 24 – Mar 3

G$23,126 GYD per night

Home in San Diego

5.0 out of 5 average rating, 140 reviews

Midcentury Lux 4BR home with Pool, Spa & Cabana

COMPLETELY renovated 4BR 3 Bath mid-century home with heated pool, hot tub and fire pit! We renovated the house top-to-bottom, inside and out and everything is brand new. The beds are top quality with 100% cotton sheets. 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.

Dec 7 – 14

G$184,593 GYD per night

Guest suite in Bonita

4.86 out of 5 average rating, 288 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 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.

Mar 23 – 28

G$22,414 GYD per night

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Popular amenities for Little Italy, San Diego rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in San Diego

4.93 out of 5 average rating, 127 reviews

Ocean Front at La Jolla Shores

Mar 31 – Apr 7

G$173,417 GYD per night

Home in Paradise Hills

4.87 out of 5 average rating, 144 reviews

*Luxury Home* Salt Water Pool* Hot Tub* Fire Pit*

Nov 2 – 9

G$106,174 GYD per night

Home in La Mesa

4.96 out of 5 average rating, 139 reviews

Heated pool, outdoor fire pits, chef's kitchen

Aug 29 – Sep 5

G$177,833 GYD per night

Home in Chula Vista

4.9 out of 5 average rating, 142 reviews

Oasis with ocean views/Pool/Hot tub! Sleeps 10!

Sep 21 – 28

G$84,826 GYD per night

Home in Pacific Beach

4.94 out of 5 average rating, 326 reviews

PB Dream HOUSE Steps to Beach Bay ❤️Modern Private

Jun 21 – 28

G$171,449 GYD per night

Home in San Carlos

4.87 out of 5 average rating, 143 reviews

Bright and spacious home with views, pool & spa.

Aug 18 – 25

G$161,875 GYD per night

Home in San Diego

4.95 out of 5 average rating, 159 reviews

Coastal Chill: Heated Pool, Spa & Chef’s Kitchen!

Mar 28 – Apr 4

G$102,615 GYD per night

Home in Pacific Beach

4.97 out of 5 average rating, 103 reviews

Pacific Beach-Amazing Panoramic View-Heated Pool

Sep 5 – 12

G$172,386 GYD per night

Condo rentals with a pool

Condo in San Diego

4.84 out of 5 average rating, 228 reviews

Swell Times Beach Studio

Aug 11 – 18

G$42,239 GYD per night

Condo in San Diego

4.87 out of 5 average rating, 126 reviews

Ocean front one bedroom condominium

Sep 12 – 19

G$86,313 GYD per night

Condo in San Diego

4.93 out of 5 average rating, 427 reviews

Oceanfront Elegant Condo - Remarkable Amenities

Aug 9 – 16

G$82,134 GYD per night

Condo in Pacific Beach

4.92 out of 5 average rating, 104 reviews

Enchanted Ocean Sunsets

Oct 17 – 24

G$135,662 GYD per night

Condo in San Diego

4.95 out of 5 average rating, 196 reviews

Centrally located n UCSD/ utc-laJolla

Oct 30 – Nov 6

G$42,859 GYD per night

Condo in San Diego

4.87 out of 5 average rating, 130 reviews

“Fire and Ice” OCEANFRONT Modern and Comfy Condo

Sep 2 – 9

G$57,624 GYD per night

Condo in San Diego

4.96 out of 5 average rating, 141 reviews

Beautifully remodeled 10th floor oceanfront condo

Jan 6 – 13

G$86,386 GYD per night

Condo in San Diego

4.86 out of 5 average rating, 185 reviews

The Seashell - OCEANFRONT home away from home!

Sep 28 – Oct 5

G$78,905 GYD per night

Home rentals with a private pool

Home in Solana Beach

4.9 out of 5 average rating, 103 reviews

Amazing Views with Heated Pool and Jacuzzi Near Beach

Sep 10 – 17

G$185,920 GYD per night

Apartment in Oceanside

4.96 out of 5 average rating, 224 reviews

Beach Apartment near Oceanside Pier

Mar 1 – 8

G$46,283 GYD per night

Home in San Diego

4.89 out of 5 average rating, 161 reviews

Eco-Friendly Mount Soledad Pad with Views and Heated Pool

Dec 9 – 16

G$62,456 GYD per night

Home in San Diego

4.91 out of 5 average rating, 75 reviews

Home with Sparkling Pool & Views of San Diego Bay

Aug 14 – 21

G$158,402 GYD per night

Home in Rancho Bernardo

5.0 out of 5 average rating, 3 reviews

Luxury Home with Heated Pool and Pickle Ball Court

Jul 19 – 26

G$239,409 GYD per night

Home in Carlsbad

Tamarack Resort

Jan 15 – 22

G$196,437 GYD per night

Quick stats about vacation rentals with a pool in Little Italy, San Diego

Total rentals
70 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
590 reviews
Nightly prices starting at
G$14,597 GYD before taxes and fees

Destinations to explore