
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.

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.

Midcentury Lux 4BR home w Pool/Spa/Cabana/Firepit
VERY PRIVATE, COMPLETELY RENOVATED 4BR 3 Bath mid-century home with heated pool, hot tub and fire pit in totally private backyard retreat. The house was redone top-to-bottom, inside/out with everything new. The beds are top quality with very high quality 100% cotton sheets and bath towels. Conveniently we are centrally located in a safe, friendly neighborhood with beautiful mountain views in the back. We never charge any fees - as we want to provide the experience we hope to get when traveling.

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.

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.

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.

Heated Pool-Jacuzzi-King Bed-City Views-Chic Decor
⚜ Stunning wrap-around balcony with panoramic city views ⚜ Heated pool with jacuzzi ($100/day to heat — request in advance) ⚜ 2,500 sq-ft of interior space with vaulted ceilings & open floor plan ⚜ Chic modern décor throughout ⚜ Two fully stocked kitchens ⚜ 4 king beds, 1 sofa bed & 1 couch ⚜ Poolside sun loungers & outdoor lounge areas ⚜ Complimentary washer & dryer ⚜ Attached studio suite with private access (included) ⚜ Located in Historic Mission Hills, San Diego

University Heights Oasis Getaway
Tucked back in the peaceful neighborhood of University Heights, this home includes a lusciously landscaped yard with a: - Pool -Hottub - BBQ -Outdoor patio furniture Perfect for both families and professionals, our property also offers the ultimate in convenience: - Acclaimed restaurants and cafes are just minutes away - Close to the Airport, Zoo, Balboa Park, and Downtown - Close to many world-class beaches

La Jolla Beach House-Family Focused-3min to Beach
Escape to our boho-inspired Bird Rock/La Jolla beach house, perfect for families! This serene La Jolla retreat features a private pool, large hot tub, and cozy fire pit. Enjoy a private backyard oasis with hammocks and a BBQ. Recently upgraded with modern decor and new appliances, this home comfortably accommodates your group for the ultimate relaxing getaway just minutes from La Jolla Cove and famous beaches.
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

Bright and spacious home with views, pool & spa.

Mid-Century Modern and Contemporary House

Modern Hilltop Home: Roomy, Views, Family-Friendly

5m to Zoo & pool- The San Diego Poolside Paradise

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

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

Beach House w/ Private Pool & Spa mins to beach!
Condo rentals with a pool

Best Beach in seconds! AC Luxury KING Beds!

Ocean-Bay-Sunset View Condo in Pacific Beach!

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

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

Treehouse Retreat in Mission Hills

Bright 2BR | Views &Walkability

NEW 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 4

Stunning 2BR/2BA| Plunge Pool, AC, Private

Incredible Views Resort-Style Apt next to Petco Pk
When is the best time to visit Little Italy?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ690 | ﺩ.ﺇ918 | ﺩ.ﺇ918 | ﺩ.ﺇ834 | ﺩ.ﺇ705 | ﺩ.ﺇ665 | ﺩ.ﺇ830 | ﺩ.ﺇ848 | ﺩ.ﺇ793 | ﺩ.ﺇ826 | ﺩ.ﺇ735 | ﺩ.ﺇ687 |
| 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 vacation rentals with a pool in Little Italy

Total vacation rentals
Explore 140 vacation rentals in Little Italy

Nightly prices starting at
Little Italy vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

Verified guest reviews
Over 940 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wi-Fi availability
140 of Little Italy vacation rentals include wi-fi 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
- Family-friendly rentals Little Italy
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- Rentals with pools San Diego
- Rentals with pools San Diego County
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- Rentals with pools United States
- Rosarito Beach
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- Torrey Pines Golf Course
- USS Midway Museum
- Santa Monica Beach




