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Vacation rentals with a pool in Little Italy, San Diego

Find and book unique homes with a pool on Airbnb

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Popular amenities for Little Italy, San Diego rentals with a pool

House rentals with a pool

Guest favorite
An outdoor area features a clear saltwater pool surrounded by elegant lounge chairs. A shaded umbrella stands nearby, and the landscape includes rolling hills and a distant view of the mountains, providing a serene backdrop for relaxation.
Home in El Cajon
4.98 out of 5 average rating, 122 reviews

Fletcher Hills luxury, Sunset View, 4 BR, Pool/Spa

YvetteRating, 5 stars2 weeks ago
Our home away from home. The property was conveniently located to major stores. It is 30 minutes to the San Diego Zoo, Birch Aquarium, and Sesame Street. The house is very spacious and brings in light energy. Our family loved the beds and comfy pillows which can make or break a vacation. The bathrooms were spacious and worked conveniently with the needs of our family, especially the Bluetooth speaker😁. The backyard was our favorite! Beautiful space during the day with plenty of space for our 3 year old to run. Serene and chill views in the evening. We 100% recommend this property for your family. And would definitely stay again.
Guest favorite
A view of the inviting swimming pool surrounded by a spacious patio. Natural rock elements and vibrant landscaping enhance the outdoor area. The multi-level deck is visible, offering seating options and picturesque canyon surroundings under a clear blue sky.
Home in La Mesa
4.88 out of 5 average rating, 171 reviews

The Queen House

YvonneRating, 5 stars1 month ago
It was wonderful. The views from the deck were amazing. Every bed was comfortable. I loved the bowl of gummy’s they had for us 😁. It’s was perfect for our family reunion everyone had privacy and the family room’s furniture was perfect to cozy up by the fire and watch tv. I loved the weather there. I opened up the windows and we had perfect weather so we never had to turn on the air conditioner. Kelly allowed us to put the cover over the pool and it warmed up the pool and the grandkids had a blast. We had multiple generations at home ( 4 generations from 85?to 1 yr old 😁) and everyone was happy. Thank you for the opportunity to enjoy family together.
Top guest favorite
An aerial view highlights a spacious backyard featuring a solar heated pool, hot tub, and tropical landscaping. Lounge chairs are arranged around the pool, and a palapa style cabana with seating is visible, offering an inviting outdoor space for relaxation and entertainment.
Home in Bay Park
4.98 out of 5 average rating, 275 reviews

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

EricRating, 5 stars6 days ago
Great place to stay! Very clean and great pool for the family! Close to SeaWorld and Malls! Definately would stay here again and Brian was a great host and very responsive when we needed him.
Superhost
A serene outdoor space features a salt-water pool surrounded by a concrete patio and manicured grass. An umbrella provides shade over the poolside area, with lush greenery and mountains visible in the background under a partly cloudy sky.
Home in San Carlos
4.87 out of 5 average rating, 192 reviews

Bright and spacious home with views, pool & spa.

OmarRating, 5 stars1 week ago
We had an incredible stay at Miguel’s Airbnb! The highlight was definitely the pool – it was sparkling clean and well-maintained. Everything was exactly as described, and Miguel was a fantastic host, ensuring we had everything we needed for a perfect stay. Highly recommend this place to anyone looking for a relaxing, private and hassle-free getaway!
Guest favorite
The backyard features a heated pool surrounded by light stone tiles and lounge chairs with striped towels. A shaded seating area is visible, along with a gas grill nearby. The wall offers privacy, enhancing the outdoor retreat atmosphere.
Home in Kensington
4.94 out of 5 average rating, 109 reviews

Centrally located Home w/Guest House, Pool & Spa!

BrittanyRating, 5 stars2 weeks ago
We had a very fun and relaxing friends get together here. We could walk to get food, and driving to different parts of San Diego was super easy from here. Our group has done many trips and this by far was the best residence for us by far, not to mention two large tables for playing board games. Would stay here again!
Guest favorite
A light-filled living room features a suspended hanging chair, a modern grey sofa adorned with patterned pillows, and a circular coffee table. A large television is mounted on the wall, while a ceiling fan and floor lamp provide comfort. A warm area rug anchors the space.
Home in City Heights
4.93 out of 5 average rating, 105 reviews

Designer Luxury Rental With Pool

KellyRating, 5 stars6 days ago
They were able to respond right away. I had trouble with locking up the place but it was coming from my end. Their response was quick and fast. :)
Guest favorite
An outdoor dining area is highlighted by a large table surrounded by six black wicker chairs. French doors open to a spacious interior, while potted plants and greenery frame the setting, creating an inviting and open atmosphere for relaxation and gatherings.
Home in Pacific Beach
4.93 out of 5 average rating, 371 reviews

PB Dream HOUSE Steps to Beach Bay ❤️Modern Private

SamRating, 5 stars1 month ago
The location is a ten minute walk to the beach. There’s a sprouts three minutes away and numerous bars, restaurants, and shops. The house was clean and had everything we needed. Great location with a very great host. Very kind people. I would definitely stay again.
Guest favorite
A private pool is surrounded by natural stone and lush greenery. Palm trees provide shade, while a bamboo privacy fence enhances the secluded atmosphere. The clear blue water invites relaxation, showcasing gentle ripples under the sunlight.
Home in Chula Vista
4.9 out of 5 average rating, 186 reviews

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

PaulinaRating, 5 stars2 weeks ago
We have stayed in many different types of homes both good and bad. But, I’ve gotta say “This one has been BY FAR, THE BEST”!! The view as well as the house is absolutely amazing. The design of the home is gorgeous. The house was extremely clean and the beds were very comfortable. I must mention the squatty potties and bidet’s in the bathrooms… SUPERB!! Before booking my reservation, I asked Van if I could have my family and friends (about 10 people) come over after a graduation ceremony and he said yes. He even accommodated us with extra tables and chairs. My friends and family all loved the place. Van always replied to my messages no matter the time of day or night. There was a hiccup with the fire alarms in the house which was completely out of Van’s control, but he handled it well. He personally appeared to resolve the issue. Meeting Van in person did not disappoint. He is as nice in person as he is in messages. We are definitely going to come back.

Condo rentals with a pool

Guest favorite
Aerial view captures a vibrant sunset over the ocean, with golden hues reflecting on the water's surface. The beachfront is framed by palm trees and residential buildings, while a sandy shore gently meets the water. Nearby, grassy park areas and a parking lot are visible.
Condo in Mission Beach
4.88 out of 5 average rating, 124 reviews

Best Beach in seconds! Luxury 3Bd/2Ba KING Beds!

NatalieRating, 5 stars2 weeks ago
We had a great stay at Bill's place! It looked just like the pictures and was very clean and well-stocked! The location was perfect and was in a very walkable area. Bill was super responsive and accommodating, and we'd definitely stay at his place again!
Guest favorite
A serene swimming pool is surrounded by tropical palm trees, providing a refreshing atmosphere. Lounge chairs are positioned beside the pool, inviting relaxation. The building's balconies overlook the area, creating a blend of leisure and comfort in the outdoor space.
Condo in Pacific Beach
4.99 out of 5 average rating, 91 reviews

Ocean-Bay-Sunset View Condo in Pacific Beach!

SalahRating, 5 stars2 days ago
We loved our stay in Paolo’s cozy condo! The place is nicely designed, well furnished, and clean. It is in a great location, situated closely to everything San Diego has to offer. Paolo was also very communicative, friendly, and helpful.
Guest favorite
An arched window frames a serene view of palm trees and distant hills at dusk. The soft hues of a fading sunset create a calming atmosphere. Neighborhood rooftops are visible below, with twinkling lights in the distance hinting at urban life.
Condo in Pacific Beach
4.97 out of 5 average rating, 116 reviews

Bay View Condo in Pacific Beach

JustineRating, 5 stars1 month ago
We had a wonderful stay at Kim’s place in San Diego! The condo was clean, centrally located and very spacious. The gated garage was awesome, and we loved staying on an upper floor with great views. We arrived very late in the night, and Kim was kind enough to stay awake to meet us with the keys and codes. We had a great time staying there during the long weekend!
Superhost
An aerial view captures the oceanfront condo alongside the sandy beach, with an expansive coastline stretching below. The surrounding neighborhood features a mix of residential and commercial structures, interconnected by roads and pathways, creating a vibrant coastal community.
Condo in Pacific Beach
4.86 out of 5 average rating, 159 reviews

Ocean front condo heart of pacific beach

AdrianaRating, 5 stars3 days ago
My family and I fell in love with this beautiful place. We spent a few days relaxing listening to the waves of the sea 🌊 with incredible views and access on foot in front of the beach🏖️. The place is very quiet and the reception guard is very friendly. Maria, thank you very much for letting us stay in your beautiful apartment. This place is on our list of favorites!! See you soon!♥️🫶🏻
Guest favorite
A light-filled living area is depicted with a comfortable white sectional sofa and a cozy armchair. A dining table is visible in the background, accompanied by a well-equipped kitchen. Shelving units feature books and decorative baskets, contributing to a tidy and inviting space.
Condo in San Carlos
5 out of 5 average rating, 18 reviews

Gated community, parking, 250 Mbps. Save 10%/month

ElisabethRating, 5 stars1 month ago
Judith’s place was perfect for our stay. For the sample, we brought kitchen equipment from NJ with us because we usually need it when we stay at other places. But Judith’s place had everything plus more than we expected. We left all the equipment in our car!! lol.😆
Guest favorite
The living room displays a blend of modern decor and comfort, featuring a gray sofa, an orange accent chair, and a circular coffee table on a vibrant area rug. A large flat-screen television is mounted on the wall, while natural light filters in through sheer drapes.
Condo in Point Loma Peninsula
4.96 out of 5 average rating, 25 reviews

Luxury Living Near the Beach

ArunramRating, 5 stars1 month ago
Melanie's place was perfect, instructions clear and place very well maintained
Superhost
The condominium complex features a centrally located pool surrounded by landscaped areas. The building displays multiple balconies, with palm trees adding to the tropical ambiance. The sky above is partly cloudy, creating a serene atmosphere in the courtyard.
Condo in Pacific Beach
4.86 out of 5 average rating, 181 reviews

One Bedroom Ocean Front Condo!

JuliaRating, 5 stars2 months ago
The apartment was so close to all the restaurants and easy to get to anywhere within around 15 minutes drive. Tina was an amazing host and on hand to answer any questions.
Superhost
A spacious living area features large windows offering panoramic ocean views and allowing natural light to fill the room. A comfortable blue couch is positioned near a glass coffee table, with a television mounted above a dark wooden entertainment unit.
Condo in Pacific Beach
4.91 out of 5 average rating, 156 reviews

Enchanted Ocean Sunsets

CaraRating, 5 stars2 weeks ago
When we walked in, we instantly knew this was going to be a great weekend getaway. The location is fantastic and the views from the room are stunning. Just steps away from the beach, we'd definitely come here again. There are restaurants and shops within walking distance. Plenty of things to do. Highly recommend this spot for couples, solo travelers, or friends looking for an escape without needing to drive everywhere.

Home rentals with a private pool

Guest favorite
A heated saltwater pool is surrounded by well-maintained foliage and features lounge chairs for relaxation. The inviting water reflects clear blue skies, while nearby greenery adds to the serene atmosphere of the outdoor space.
Home in Point Loma Peninsula
4.92 out of 5 average rating, 86 reviews

Historic Home with Pool/ Views of San Diego Bay

DebraRating, 5 stars3 months ago
I booked this place last minute literally after checking into a nearby hotel that was subpar at best and not as advertised. First time in Point Loma. Reason for visit was seeing my kids who live in Cali and Hawaii. So we met halfway as I am from the east coast. The ease of the entire experience is unmatched. The communication with the host was great and the house was amazing. Perfectly appointed. They thought of literally everything. And it was spotless and pristine. This is a unique home and experience. The most comfortable and beautiful and up to date everything is this house. I can’t think of a single thing that wasn’t perfect. There are stairs to the lower bedrooms and laundry and pool area. But I’m in shape and they didn’t scare me. The neighbors are super friendly. And the parking lot as adequate. The view is knockout insanely beautiful. The beds are comfy the pillows and linens are just like at home. It’s a quiet neighborhood close to everything. And I can’t think of a negative
Guest favorite
An open-concept living space features a brown leather sectional sofa, providing comfortable seating against a backdrop of light wood ceilings. A dining table with wooden chairs is visible, complemented by a sleek kitchen equipped with modern appliances and bright white cabinetry.
Home in Pacific Beach
4.9 out of 5 average rating, 180 reviews

Eco-Friendly Mount Soledad Pad with Views and Heated Pool

JamesRating, 5 stars2 days ago
We had a great stay! The place was beautiful, clean, and exactly as pictured. Our host was incredibly informative and always quick to respond to any questions. He also gave us some great insight into the area, which really helped us make the most of our trip. Would definitely recommend staying here!
The outdoor area features a salt-water pool surrounded by lounge chairs and lush greenery, creating a calming environment. A stylish outdoor dining setup is visible, accompanied by an umbrella for shade. Various plants and trees offer a sense of privacy and tranquility.
Home in Torrey Hills
4.82 out of 5 average rating, 11 reviews

Luxury San Diego House: Beach, Pool & Pet-Friendly

RalphRating, 5 stars3 weeks ago
Great house in a great area. Pool and hot tub were a bonus. Nice shopping, restaurants and bars very close by. Shirley (host) was so helpful and responsive. Highly recommend!!
Guest favorite
A modern kitchen area is highlighted by a spacious granite countertop with a dual sink. Large windows provide a view of the landscape, allowing natural light to flood the space and connect the indoors with the serene outdoor scenery.
Home in Ramona
4.93 out of 5 average rating, 44 reviews

Vista Grande

BrentRating, 5 stars3 weeks ago
We stayed at the property to attend a wedding at Mt Woodson castle. it was the perfect place to stay to get ready and be close to the wedding venue. The property was incredible and the view was amazing. Staying at this property was one of the best things about the entire trip. We told many people about our experience and they asked us for the link to the listing so they can book on future trips. Even people local to the area for staycations.
A resort-style pool is surrounded by palm trees, featuring a natural stone deck with loungers arranged for relaxation. Sun umbrellas provide shade, while the calm water reflects the clear sky, creating a serene outdoor atmosphere ideal for unwinding.
Home in Carlsbad

Tamarack Resort

Martha LuciaRating, 5 stars13 months ago
Great space, room for everyone to share and to have alone time. Swimming pool and hot tub could be cleaner, some green spots and mold. Dryer wasn’t working properly, we did a load of laundry and weren’t able to dry it. For such an amazing house and the cost important to have everything working. Loved the game room and how neat the house is. Would definitely come back.

Quick stats about vacation rentals with a pool in Little Italy, San Diego

  • Total rentals

    140 properties

  • Nightly prices starting at

    G$14,636 GYD before taxes and fees

  • Total number of reviews

    730 reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

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