
Holiday rentals with a pool in Shelter Island
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Top-rated rentals with a pool in Shelter Island
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Popular amenities for Shelter Island rentals with a pool
House rentals with a pool

Heated Pool, XXL Spa, Mini-Golf & Chef’s Kitchen!
Great home and the hosts were very responsive to issues. We had a sink that backed up and we notified the host and they had it fixed while we were out sightseeing. Home was beautiful and very comfortable for my family during our trip!

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!

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.

Dream Vacation! Sunny 3 Bedroom Home!
Had a great stay! Everything we hoped it would be. Hoping to return soon!!

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.

Canyon House: Sunset View Tranquil Private Pool
Jessica’s home is beautiful and located in a lovely neighborhood that is close proximity to many things. We came to celebrate the graduation of my niece and Jessica’s home was a great place for the family to connect, rest between events and spend time together! Her home is beautifully appointed and was perfect for our stay. Jessica is a great host who communicates with her guests and is very responsive! Her home is filled with good energy and I would definitely book again! for future family events when visiting San Diego!
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 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.

SKYLINE VIEW 4U
Amazing views perfect place if you’re going to the ballgame. Had a couple of issues but Thomas was their to help. Appreciate it

Stylish & Spacious KingBed Apt in Prime Location!
My stay was very peaceful and comfortable. The hosts were always very responsive and communicated very proactively. I stayed in this Airbnb for few days with my parents while visiting San Diego and we indeed had a really comfortable stay.

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.
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- Rosarito Beach
- Oceanside City Beach
- Torrey Pines State Beach
- Tijuana Beach
- Pacific Beach
- Coronado Beach
- La Misión Beach
- SeaWorld San Diego
- 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
- Surf Beach
- Belmont Park
- Liberty Station
- Moonlight Beach
- Sesame Place San Diego
- Playas Los Buenos
- Playa Popotla
- USS Midway Museum