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

Gorgeous Eccentric Home with Cowboy Pool!
We really enjoyed our stay at this historic San Diego home! The floors were spotless, as was the rest of the house, and our kids were thrilled with wonder when they discovered the secret kids’ spaces. We loved the beautiful garden, as well as the spacious kitchen, dining, and living rooms. The location is less than 10 mins from the airport, which was great for our quick trip. Given that we have three kids, we would otherwise need 2 hotel rooms, so the value for having this whole home to ourselves was definitely worth it. Thank you, Cassia, for a great stay!

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.

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. :)

Luxe Home w. Serene Backyard Spa
Schafer and Drew were super friendly and responsive from when I started looking at the property, immediately after I booked the property and all the way until I checked in. They were both super helpful in all the questions I had prior to booking and definitely made me feel comfortable I made the right decision for a girls weekend. Upon checking in, the house was PERFECTION! We walked into not only a super clean property but GORGEOUS! You can tell they poured their entire soul into this house. The house was beautifully decorated and we all immediately felt 1000% at home to the point we did NOT want to leave! The backyard was an amazing oasis and honestly, we all felt sad leaving when we checked out.

ModernCoastal I View I Pool ITub
Location was as described and photographed. I had a great stay and found the view from the kitchen/pool very nice. Definitely would return.
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.

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!♥️🫶🏻

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.

Comfortable & convenient accommodation @ San Diego
I had a great time staying at Thelma De La Paz’s place! The space was cozy, very clean, and exactly what I needed for a comfortable stay. Thelma was a wonderful host - polite, welcoming, and super responsive to any questions I had. Highly recommend!

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.

Penthouse Near Mission Beach USD Golf Balboa Park!
Has everything I need ! Ian was very quick to respond with any questions and the place was very clean and comfortable!
Home rentals with a private pool
Beach Apartment near Oceanside Pier
The location was great, close to many restaurants and shops, great ocean breeze, great ocean view from the room, beautiful grounds, and 5 minutes from my sons house on Camp Pendleton!

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!!
Amazing Views with Heated Pool and Jacuzzi Near Beach
This place felt like a home away from home.

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 Old Town, San Diego
Total rentals
20 properties
Nightly prices starting at
G$10,455 GYD before taxes and fees
Total number of reviews
640 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi
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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
- San Onofre Beach
- University of California San Diego
- LEGOLAND California
- Black's Beach
- San Diego Zoo Safari Park
- Balboa Park
- Trestles Beach
- Pechanga Resort Casino
- Liberty Station
- Sesame Place San Diego
- Moonlight Beach
- Playas Los Buenos
- USS Midway Museum