Holiday rentals with a pool in Little Italy

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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
Two red Adirondack chairs are positioned under a covered patio, facing a serene backyard with a pool. Lush greenery surrounds the area, creating a tranquil atmosphere. A BBQ room and various seating arrangements are visible beyond the pool, enhancing the outdoor retreat experience.
Guest house in La Mesa
4.99 out of 5 average rating, 149 reviews

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

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, 175 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
A serene bedroom features a queen bed with a light-colored quilt. Two bedside tables with lamps are positioned on either side. The walls are adorned with various framed artworks and a large mirror, reflecting natural light from the windows.
Flat in University Heights
4.79 out of 5 average rating, 468 reviews

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

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.
Guest house in Mission Hills
4.9 out of 5 average rating, 493 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, 264 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.

Guest favourite
A living room features a luxury hanging chair suspended from the ceiling. Natural light filters through sheer curtains, illuminating a cozy seating area with a plush sofa and wooden coffee table. A 50” television is mounted above an elegant fireplace, enhancing the room's comfort.
Home in City Heights
4.93 out of 5 average rating, 132 reviews

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.

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.
Apartment in Pacific Beach
4.98 out of 5 average rating, 197 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.

Top guest favourite
A colorful living area features a vibrant blue couch adorned with decorative pillows. A round white coffee table sits prominently on a multi-colored rug, while a television is mounted above a red cabinet. Artwork and framed prints decorate the pink walls, enhancing the playful ambiance.
Home in University Heights
4.94 out of 5 average rating, 105 reviews

Casa De Colores

Need some color in you life? Come stay in our one of a kind home- groovy wall mural, bright decor, rainbow speckled floors. Tucked back in the peaceful neighborhood of University Heights, this home includes a lusciously landscaped yard with a: - Pool -Hottub - BBQ -Outdoor patio furniture 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

Top guest favourite
A solar-heated pool glimmers in the sunlight, surrounded by inviting lounge chairs and a shaded umbrella. A cozy outdoor dining area with a table is visible in the background, framed by lush greenery and large eucalyptus trees.
Guest suite in Bonita
4.89 out of 5 average rating, 383 reviews

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.

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.

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.
Guest house in Lake Murray
4.97 out of 5 average rating, 144 reviews

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV

This is your perfect Guest House with a salt & 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.

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, 275 reviews

Lionhead - Private Boutique Home

Experience boutique hotel vibes where Palm Springs meets South Beach. This "plug-and-play" retreat features a private backyard resort with a heated pool ($50/day for stays 5 days or less), Jacuzzi, cabana, and BBQ—perfect for watching planes take off over the city. Enjoy high-speed Wi-Fi, Smart TVs, and a vintage record player, all minutes from Downtown, conventions, and easy highway access.

Popular amenities for Little Italy rentals with a pool

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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 £52 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    130 of Little Italy holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Little Italy rentals

  • 4.9 Average rating

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