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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
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, 151 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, 176 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

Top guest favourite
A bright and airy living room features large floor-to-ceiling windows showcasing expansive ocean views. Comfortable seating arrangements consist of a plush sofa and armchairs, accented by light decor. A coffee table sits at the center, complemented by side tables with lamps, fostering a relaxing atmosphere.
Apartment in Pacific Beach
5 out of 5 average rating, 111 reviews

The Endless Summer Condo!

Let your worries drift away at this 6th floor corner condo with panoramic ocean views! With floor to ceiling windows throughout, you'll feel like you're floating above the sea! Leave your toes in the sand or walk to PB's best restaurants and attractions in minutes! When you're done exploring, put on a Beach Boys record while having dinner with the family amid a golden sunset..ah the good life! Create cherished memories that will linger long after the sun sets, here, at The Endless Summer Condo!

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, 269 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.

Superhost
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 serene backyard features a heated pool surrounded by palm trees and lounge chairs. The space is designed for relaxation and outdoor enjoyment, showcasing a clean landscape with concrete pathways and decorative gravel.
Home in Normal Heights
4.98 out of 5 average rating, 109 reviews

Family Oasis w/ Heated Pool

A family-friendly SD home with a private heated pool and spacious backyard for relaxing and playing. The Home ⁘ 3 Bedrooms & 2 Bathrooms ⁘ Personal A/C & Heat in Every Room ⁘ Complimentary Washer & Dryer ⁘ 2 Rollaway Beds Available Upon Request Outdoor Space ⁘ Private Heated Pool (inquire about fee) ⁘ Outdoor Shower & Wood Burning Fire Pit ⁘ Fenced Backyard ⁘ Pool Toys, Loungers, & Umbrellas Family-Friendly ⁘ Pack n’ Play & Games ⁘ Pets Welcome upon Request ⁘ Quiet Residential Neighborhood

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, 124 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
Home in Fleetridge
4.94 out of 5 average rating, 177 reviews

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.

Guest favourite
Townhouse in University City
4.87 out of 5 average rating, 164 reviews

UTC Venetian 3 miles La Jolla Beach UCSD Scripps

Approx 3 miles from the most famous La Jolla beach! Only a mile away from UCSD with bus stop right outside the side gate. One of the nicest and most convenient locations in UTC/La jolla. Located right by the 5 and 805 freeway w/52 nearby! Walking distance to Wholefoods, Chase & Citi bank, CVS, Rubios, Nordstroms Rack, Starbucks, CPK, Trader Joes, Ralphs, Wells Fargo, Ross, Best Buy, AMC movie theater, and many restaurants ALSO Westfield Shopping Mall and so much more!

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
4.96 out of 5 average rating, 159 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, 164 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 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, 278 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

When is the best time to visit Little Italy?

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Avg. price£141£187£187£170£144£136£169£173£162£163£147£149
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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!