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.

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Top Guest favourite
A bright living space features a warm wooden ceiling and large windows. A comfortable orange sofa is paired with a wooden coffee table on a patterned area rug. The kitchen, visible in the background, includes modern appliances and white cabinetry, enhancing the cozy atmosphere.
Home in Hillcrest
4.99 out of 5 average rating, 172 reviews

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

Guest favourite
The property features a spacious backyard with a heated pool surrounded by lounge chairs. Palm trees line the perimeter, and soft lighting illuminates the outdoor area during sunset. The two-story house overlooks the pool, creating an inviting atmosphere for relaxation and gatherings.
Home in La Mesa
4.95 out of 5 average rating, 221 reviews

XTRA 10% OFF until Nov: Pool, outdoor fire pits, c

Find your family's dream spot in San Diego! Our cozy house sits on a quiet hill, offering privacy and amazing sunset views. Dive into our pool year-round (heating at an additional cost), roast marshmallows by the fire, and cook up fun meals together. With 3 bedrooms and 2 bathrooms, it’s perfect for families, accommodating up to 9 guests. Plus, we're close to all the best attractions. Want a vacation you'll always remember? Send us a message to make it happen! 🌅🏠 We have 3 comfy beds that can

Guest favourite
A cozy sleeping area features a spacious bed with a striped throw blanket adorned with decorative tassels. A flat-screen TV is mounted on the wall, and a small table is positioned beside the bed. Soft lighting is provided by wall sconces, creating a calm ambiance.
Guesthouse in Mission Hills
4.91 out of 5 average rating, 486 reviews

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.

Top Guest favourite
A private outdoor area features a heated pool surrounded by lush green grass and modern loungers. An inviting fire pit is centrally located, with two stylish chairs positioned nearby. The backdrop includes well-maintained shrubbery and tall trees, enhancing the tranquil ambiance.
Home in Serra Mesa
5 out of 5 average rating, 254 reviews

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

VERY PRIVATE, COMPLETELY RENOVATED 4BR 3 Bath mid-century home with heated saltwater pool, hot tub and fire pit in totally private backyard retreat. Redone top-to-bottom, inside/out with everything new. The beds are top of the line 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.

Top Guest favourite
A bright living room features large glass doors opening to breathtaking ocean views. A comfortable white sectional sofa is surrounded by two plush armchairs. Wall art and a round coffee table enhance the inviting atmosphere, while a potted plant adds a touch of greenery.
Condo in Pacific Beach
4.98 out of 5 average rating, 194 reviews

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.

Guest favourite
A private patio area is visible, adorned with a wooden structure and comfortable seating arrangements. The sparkling pool is set at a distance, surrounded by greenery. Sunlight casts gentle shadows, highlighting the textured concrete and wooden elements in the outdoor space.
Guest suite in Hillcrest
4.89 out of 5 average rating, 123 reviews

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.

Guest favourite
The tropical pool features gentle waterfalls cascading into vibrant blue water. Surrounding palm trees and lush greenery enhance the serene environment. A tiki bar and a hot tub grotto provide inviting leisure options. A second-story balcony overlooks this tranquil outdoor space, illuminated by soft evening lights.
Guesthouse in La Jolla
4.97 out of 5 average rating, 193 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.

Top Guest favourite
A vibrant heated pool is surrounded by minimalistic landscaping, featuring tall cacti and a clean white fence. Soft lounge chairs are positioned nearby for relaxation. The clear water reflects the blue sky, creating a refreshing setting for leisure and enjoyment.
Home in Mission Hills
4.93 out of 5 average rating, 272 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, record player with albums. 19 speakers in the ceilings with connection to your phone for optimal happiness. Plug and play!

Top Guest favourite
The poolside area features a well-maintained saltwater pool reflecting the colors of the sunset. Comfortable seating arrangements, including lounge chairs and a cozy fire pit, are visible. Large umbrellas provide shade, and lush greenery adds to the serene ambiance.
Guesthouse in Lake Murray
4.96 out of 5 average rating, 140 reviews

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.

Top Guest favourite
A tranquil pool area is surrounded by lush landscaping, featuring palm trees and various plants. Two lounge chairs with an umbrella are positioned beside the pool, reflecting a serene evening sky with hues of pink and purple.
Home in University Heights
4.97 out of 5 average rating, 155 reviews

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

Superhost
An aerial view captures the spacious outdoor area, featuring a rectangular pool surrounded by sun loungers and umbrellas. Lush greenery is visible alongside neatly arranged pathways and stone retaining walls, complementing the mountain-modern design of the home in the background.
Home in University Heights
4.89 out of 5 average rating, 162 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.

Top Guest favourite
A serene backyard oasis features a small spa surrounded by lush greenery and decorative plants. The space is framed by an open wooden structure with a sloped roof, providing a cozy seating area with soft cushions. Unique pendant lights hang above, adding a touch of elegance.
Home in Normal Heights
4.96 out of 5 average rating, 112 reviews

Luxe Home w. Serene Backyard Spa

Escape to the heart of San Diego in our chic and luxurious 3-bed oasis, where upscale meets laid-back California cool. Steps from vibrant eateries, buzzing bars, and unique boutiques, this retreat offers a serene backyard with a soothing spa. Experience local attractions, beaches, and the San Diego Zoo, all a short drive away. Your ultimate San Diego adventure awaits!

Popular amenities for Little Italy rentals with a pool

When is the best time to visit Little Italy?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$327 NZD$435 NZD$435 NZD$395 NZD$334 NZD$315 NZD$394 NZD$402 NZD$376 NZD$392 NZD$348 NZD$326 NZD
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Quick stats about holiday rentals with a pool in Little Italy

  • Total holiday rentals

    Explore 130 holiday rentals in Little Italy

  • Nightly prices starting at

    Little Italy holiday rentals start at $122 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,050 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Little Italy holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Little Italy rentals

  • 4.9 Average rating

    Little Italy stays are highly rated by guests—averaging 4.9 out of 5!