
Vacation rentals with a pool in Little Italy, San Diego
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Top-rated rentals with a pool in Little Italy, San Diego
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Popular amenities for Little Italy, San Diego rentals with a pool
House rentals with a pool

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

The Queen House
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.

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

Bright and spacious home with views, pool & spa.
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!

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

Designer Luxury Rental With Pool
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. :)

PB Dream HOUSE Steps to Beach Bay ❤️Modern Private
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.

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

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

Ocean-Bay-Sunset View Condo in Pacific Beach!
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.

Bay View Condo in Pacific Beach
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!

Ocean front condo heart of pacific beach
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!♥️🫶🏻

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

Luxury Living Near the Beach
Melanie's place was perfect, instructions clear and place very well maintained

One Bedroom Ocean Front Condo!
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.

Enchanted Ocean Sunsets
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

Historic Home with Pool/ Views of San Diego Bay
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

Eco-Friendly Mount Soledad Pad with Views and Heated Pool
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!

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

Vista Grande
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.

Tamarack Resort
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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- Rosarito Beach
- Oceanside City Beach
- Belmont Park
- Tijuana Beach
- Torrey Pines State Beach
- Pacific Beach
- Coronado Beach
- SeaWorld San Diego
- La Misión Beach
- Coronado Shores Beach
- Oceanside Harbor
- University of California San Diego
- LEGOLAND California
- Black's Beach
- San Diego Zoo Safari Park
- Balboa Park
- Liberty Station
- Sesame Place San Diego
- Moonlight Beach
- Playas Los Buenos
- USS Midway Museum
- Law Street Beach
- Hillcrest
- Torrey Pines Golf Course