
Holiday 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.

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

Custom Guesthouse, Balboa Park/Zoo/Hillcrest& pool
2021 CUSTOM guesthouse with pool in Hillcrest/San Diego Zoo/Balboa Park /Marston Hill area.Full kitchen , a queen bed, a queen sleeper sofa & 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. Minutes' drive to all San Diego beaches. No rent for children under 3, only $95/stay. High chair, Pack & Play Crib, crib mattress & cover are provided

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.

Designer Luxury Rental With Pool
Welcome to Wander Haven, a luxury central rental. With it’s on trend design, custom built stock tank pool, array of amenities and thoughtful touches throughout, you won’t ever want to leave. But when do you do decide to venture out and explore all that beautiful San Diego has to offer, you will find the central location gets you to anywhere you want to be in minutes. You’re 15 minutes or less from beaches, downtown, balboa park, sea world, the zoo and hundreds of amazing bars and restaurants.

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.

Beautifully remodeled 10th floor oceanfront condo
Located on the 10th floor of the beautiful Capri by the Sea in Pacific Beach, this beautifully remodeled one bedroom condo has unbelievable views through its floor to ceiling windows. All kitchen amenities, beach toys, big screen TV, Cable, WiFi, one parking spot in gated lot with option for more. Steps to beach, short walk to lots of restaurants and bars. Resort style complex offering 360 degree view roof deck, gas BBQ, secure private pool and spa, hot water beach shower, and 24-hr security.

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.

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.

Resort-Style Living, Pool, Close to All San Diego
Nestled in a quiet, discreet neighborhood, our private air-conditioned studio offers a safe & serene retreat. Attached to a stunning ranch-style executive home, it features an amazing pool for your relaxation. We are conveniently located a short distance away from the Gaylord Convention Center, the Olympic Training Center, downtown San Diego, Comic-Con, major attractions, concert venues, beaches, airport & Mexico. Enjoy a complimentary butler tray that includes coffee, tea & snacks.

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.

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, record player with albums. 19 speakers in the ceilings with connection to your phone for optimal happiness. Plug and play!

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV
This is your 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 beaches, Downtown, La Jolla, Zoo, Stadiums, Sea World, Convention Center + more. Hike next door at Mission Trails & Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo and top quality finishes and furniture. Everything you need for memorable vacation! No smoking or vaping on the property.
Popular amenities for Little Italy rentals with a pool
House rentals with a pool

3BR Urban Oasis with Pool and Hot Tub in San Diego

Casa Bahia Beautiful San Diego Home with Pool

Mid-Century Modern and Contemporary House

Modern Hilltop Home: Roomy, Views, Family-Friendly

San Diego Luxury Villa: 6-BR, Pool, Hot Tub, Patio

Vacation Getaway w/ Gas Grill, Hot Jacuzzi, Pool

Beach House w/ Private Pool & Spa mins to beach!

Heated Pool Renovated 3BR Oasis
Apartment rentals with a pool

Best Beach in seconds! AC Luxury KING Beds!

Bay View Condo in Pacific Beach

Centrally located n UCSD/ utc-laJolla

Luxury Living Near the Beach

One Bedroom Ocean Front Condo!

Comfortable & convenient accommodation @ San Diego

Amazing View, Excellent Location in Little Italy!

Sweet Little La Mesa Condo(pool+hot tub) NEAR SDSU
Other holiday rentals with a pool

Studio | Hot Tub, King Bed, Pool, AC, Attractions

Literal neighbor to Balboa Park!

NEW DT Luxe King Suite with Sauna & Pool Access

Bright 2BR | Views &Walkability

Airbnb Luxe: Designer Pool, Fitness and Office

Breathtaking Ocean, Bay, City & Petco Park Views

Casita Arroyo - 1 BR guesthouse with pool/hot tub

Downtown Dream 3
When is the best time to visit Little Italy?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $242 SGD | $321 SGD | $321 SGD | $292 SGD | $247 SGD | $233 SGD | $291 SGD | $297 SGD | $278 SGD | $289 SGD | $257 SGD | $240 SGD |
| Avg. temp | 15°C | 15°C | 16°C | 17°C | 18°C | 20°C | 21°C | 22°C | 22°C | 20°C | 17°C | 14°C |
Quick stats about holiday rentals with a pool in Little Italy

Total holiday rentals
Explore 140 holiday rentals in Little Italy

Nightly prices starting at
Little Italy holiday rentals start at $90 SGD per night before taxes and fees

Verified guest reviews
Over 940 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wifi availability
140 of Little Italy holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Little Italy rentals

4.8 Average rating
Little Italy stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
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