
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

On park. 1 bed apt.has air & small kitchen+w&d
Apt is UPSTAIRS on park side. Queen bed in bedroom. 2 XL twin beds in living room. OLD unit. NOT for those who want modern perfection. TIGHT parking for 1 small car. Walk to brewery, bars, restaurants &coffee shops. Close to zoo, downtown and Hillcrest. Dogs considered. Tempurpedic Bed and 2 Twin beds. Full kitchen, W&D, , WiFi and free smaller size car parking ..not big trucks yes limit 2 dogs and they must be sociable dogs visiting must be walked not left alone all day or all night

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.

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.

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.

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.

Luxury North Park Home I Near Dining, Shops + Zoo
Welcome to Casa Clandestino🎋 Located in North Park, this fully remodeled 1914 Craftsman offers the perfect blend of location, privacy, and style. Enjoy a stunning outdoor area with a new 30 ft. Trex deck, heated pool/hot tub, resort furniture, 65-inch outdoor TV, market lights, and a 6-burner gas grill. Inside, find 4 beds, 2.5 baths, a chef’s kitchen, Carrera marble bathrooms, original hardwood floors, and coffered ceilings.

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
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 Contemporary 5-Bedroom Oasis, Pool and Yard

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

Casa Bahia Beautiful San Diego Home with Pool

Bright and spacious home with views, pool & spa.

Mid-Century Modern and Contemporary House

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

Oasis with ocean views/Pool/Hot tub! Sleeps 10!
Condo rentals with a pool

Best Beach in seconds! AC Luxury KING Beds!

Bay View Condo in Pacific Beach

Ocean front condo heart of pacific beach

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

Spacious 2 BR w/ Free Parking & WiFi
Other vacation rentals with a pool

Luxury Pool Haven with Views and Fireworks

Treehouse Retreat in Mission Hills

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 3

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

1 BR Coronado Resort Pool D
When is the best time to visit Little Italy?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $259 CAD | $344 CAD | $344 CAD | $313 CAD | $265 CAD | $249 CAD | $311 CAD | $318 CAD | $298 CAD | $310 CAD | $276 CAD | $258 CAD |
| 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 $96Â CAD 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 and kid-friendly amenities

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wifi availability
140 of Little Italy vacation 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
- Rentals with a sauna Little Italy
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- Rentals with a fireplace Little Italy
- Pet-friendly rentals Little Italy
- Rentals with outdoor seating Little Italy
- Rentals with a firepit Little Italy
- Family-friendly rentals Little Italy
- Rentals with a hot tub Little Italy
- Rentals with an EV charger Little Italy
- House rentals Little Italy
- Apartment rentals Little Italy
- Rentals with a patio Little Italy
- Rentals with breakfast Little Italy
- Fitness-friendly rentals Little Italy
- Rentals with pools San Diego
- Rentals with pools San Diego County
- Rentals with pools California
- Rentals with pools United States
- Rosarito Beach
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- Torrey Pines State Beach
- Tijuana Beach
- SeaWorld San Diego
- LEGOLAND California
- Pacific Beach
- University of California San Diego
- San Diego Zoo Safari Park
- Coronado Beach
- Balboa Park
- La MisiĂłn Beach
- Oceanside Harbor
- Moonlight Beach
- Liberty Station
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- Belmont Park
- Sesame Place San Diego
- Black's Beach
- Law Street Beach
- Strand Beach
- Torrey Pines Golf Course
- USS Midway Museum
- Santa Monica Beach




