
Holiday rentals with a pool in Shelter Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Shelter Island
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Shelter Island rentals with a pool
House rentals with a pool

Modern Central SD Home w/ Pool & Spa Near Beach
We stayed at Mohsen’s home to celebrate our daughter’s graduation and enjoy the weekend in SD. The home is easy to find in a quiet neighborhood with plenty of parking. The home was very clean upon arrival and easy to access. The kitchen is well stocked for cooking adventuresome meals and plenty of coffee and tea for the mornings. We had food delivered a couple times and there was no issue finding the property. We had one minor issue with the bathrooms upon arrival that Mohsen was quick to respond to, but in the end resolved itself. The back yard and pool area was perfect for family relaxing although we did not use the bar-b-q or fireplace. The location makes for easy access to the park and ocean, ocean restaurants and downtown with short drives to each.

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.

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

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!

Prime Location: Lux 4BR w Pool/Spa/Cabana/Firepit
Loved staying at Su’s beautiful Airbnb! The kitchen was well stocked with everything you might think of from aluminium foil to a pressure cooker. Plenty of silver wear, plates, bowls, pots, pans, cups and mugs. There was a lot of towels and extra blankets and covers and plenty of extra space for people to lay on and sleep. The backyard is as beautiful as the picture but a bit smaller than I expected which isn’t that big of a deal but very beautiful! This is the best vacation I ever had and I think it’s because of this beautiful airbnb that felt like home. Su is extremely polite and responsive. I asked her to heat up the pool and she did right away. I also asked for propane and she provided the same day! I will definitely be coming back to Su’s Airbnb.

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.

5BR | Salt Water Pool | Hot Tub | Fire Pit| BBQ
The place was clean and well-kept. The 5 rooms had comfortable beds and individual A/C units, adding to the comfort. The backyard was great for hosting. The only minor criticism was the lack of instructions for the fire pit. I managed to turn it on successfully; it produced a strong fire, perfect for cozy nights. There was adequate seating for everyone. Inside, the house felt clean, including the bathrooms. The living room had a large couch and the dining area had a large table, accommodating our group's size. A small improvement would be to hang the towels in the bathrooms to avoid a scavenger hunt. The wifi was down upon arrival and never regained function despite troubleshooting, but my cellular service (T-mobile) was sufficient. The host was very communicative and responsive throughout my stay. I didn’t receive dining recommendations, but it was easy to find places to eat.
Apartment 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.

Amazing Views | Luxury Studio with Swimming Pool
I’ve stayed in a lot of AirBnbs and this was the cleanest! What a lovely stay. The view is spectacular as well.

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 favorites list!! 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.

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.

CoastalGlam 1Bd+Pool+HotTub+Parking by UCSD/beach
We had a great stay at Johnathan and Cindy's place. It felt like home for our almost two week stay. The kitchen was very well appointed with every cooking utensil you need, the bed very comfy, just everything you need. Our thoughtful hosts planned every detail, with little cute signs all over the appartment. We hope to be back, thank you for sharing your lovely place.
Destinations to explore
- San Diego Holiday rentals
- La Joya Holiday rentals
- Anaheim Holiday rentals
- Palm Springs Holiday rentals
- Stanton Holiday rentals
- Los Angeles Holiday rentals
- Santa Monica Holiday rentals
- San Fernando Valley Holiday rentals
- Channel Islands of California Holiday rentals
- Southern California Holiday rentals
- Las Vegas Strip Holiday rentals
- Henderson Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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
- Liberty Station
- Sesame Place San Diego
- Moonlight Beach
- Playas Los Buenos
- USS Midway Museum
- Law Street Beach
- Hillcrest