
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.
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Popular amenities for Shelter Island rentals with a pool
House rentals with a pool

3 BR Urban Oasis with Pool and Spa in Great Area
Our family loved our stay in this home. We used the backyard every afternoon, our boys had fun jumping from the hot tub to the pool (even though the pool was chilly in February). Everything was super clean, and the beds were super comfortable. We usually struggle with hotel beds and this bed was excellent. The neighborhood was a real highlight. There is a beautiful park with a playground just around the corner and the nearby business strip down Park Ave is perfect for walking to dinner. All star stay and experience.

Fletcher Hills luxury, Sunset View, 4 BR, Pool/Spa
We had a fantastic time at KC's place! He was very prompt with his responses and incredibly helpful throughout our stay. The pool area was spacious, private, and offered a stunning view. We requested the pool to be heated, and it was wonderfully warm—far better than other Airbnb experiences we've had. The house itself was spotless and equipped with everything we needed. We also felt very safe in the area. We would absolutely love to return to KC's house and highly recommend it

Pool, Hot Tub, 15Min To ZOO SeaWorld Sesame Place
I chose this home for my birthday and enjoyed it. The location was convenient to everything we planned to do! Easy access and clear instructions. Although the pool was not running, the hot tub was a plus! I would definitely come back to this location during the summer time.

Modern SD Oasis w/ Pool & HotTub
Linar and this home were absolutely perfect! My family and I were in town for a wedding. I message Linar a couple days before we were to be there to see if there was a pack and play for my son. He assured me he would have one there the next day courtesy of the house! AMAZING! if you have ever traveled with kids you know how much stuff you already have to bring that was such a relief. The location is near the freeway so it's very convenient! The backyard is so nice! it was a bit too cold to swim but the hot tub was perfect! Very clean inside. Thank you Linar my family had the best time in your home it was so cozy and comfortable we will definitely stay again!

5BR Oasis | Pool, Hot Tub & Luxe Outdoor Retreat!
This home has so much to do. we opted for staying in instead of leaving the house because it was fun. There are lots of bedrooms and only a couple bunk beds. It is spacious and newly redone. We enjoyed our time in the jacuzzi and heated pool.

Modern Oasis - Pool, Spa, Great Location 5BR/4BA
Another Perfect Stay! This was our second time staying at this Airbnb, and it was just as amazing as the first! The place is always spotless, cozy, and well-equipped with everything we need for a comfortable stay. The attention to detail and thoughtful touches make it feel like a home away from home. The hot tub and pool are always a favorite for our large group! The BlueWhale is a fantastic host, always responsive and accommodating, making the whole experience seamless. We already can’t wait to come back next year! Highly recommend this Airbnb to anyone looking for a top-notch stay. Thank you again!!

Palmeras House: Pool + outdoor BBQ
This place is very cozy and comfortable. We feel like home. Very clean and organized. I am highly recommend this place. She even prepared a crib for our infant. Very nice place to stay. Very peaceful place.

Family Home w/Pool, Hot Jacuzzi and Park Access
We loved the house! There was so much to do between the game room and the hot tub, we decided to extend our stay one more night. For being on a corner lot, across from a park, it was very quiet and private. The linens and towels were nice and clean. There's a few cosmetic things that could be cleaned or updated, but they didn't affect us at all. (Door jams needing repaired, paint chipping...) The hosts were very responsive everytime we reached out to them. We would definitely stay here again with our family.
Condo rentals with a pool

Bay View Condo in Pacific Beach
We had a great stay, wonderful views, it was very spacious inside, and walking distance to the ocean, and restaurants/groceries. It was as advertised

Amazing Views | Luxury Studio with Swimming Pool
This was my 2nd trip staying in this condo & remains #1 on my list of places to stay in Tijuana. Before I found Icon condos, I’d stayed at hotels that were not worth the price-most were so unlike the reviews & photos I felt catfished! There are enough recent photos in this listing that nothing is left out. The host was very responsive and thoughtful. I would like to note, that since my previous stay (only about a month ago), they had changed the code to the key lockbox. That reinforced my sense of safety. The apartment has a doorbell camera, there are a lot of exterior building cameras, & full-time security (who are excellent-nothing gets by them!). On my last day, the security guard opened the gate to let me drive out which made checkout even easier, since I did not have to make a second trip to leave the gate card. The condo is very clean and the views are lovely with afternoon light. I love the remote-operated blinds, and the kitchen is well stocked. I’ll absolutely be back again!

Ocean front condo heart of pacific beach
Maria was always available when I needed to speak to speak to her. She is a warm and professional person. The place was just beautiful. We had everything we needed and more. Parking was easy. The ocean view was magical.The place was quiet and restful. We are coming back in May for my birthday. I can’t wait to return. It is the ideal spot to vacation. I would recommend anyone to schedule a vacation with Maria.

Centrally located n UCSD/ utc-laJolla
We stayed at Jennifer's place for a few days and couldn't recommend it enough. The place is centrally located and easily accessible by car. The home is super clean and nicely decorated. On top of that, Jen is super responsive and has a lot of valuable recommendations for the area.

One Bedroom Ocean Front Condo!
The condo has spectacular views of the Pacific Ocean, the PB pier, dolphins (binocular provided), and the best boardwalk in San Diego. The boardwalk has a plethora of restaurants, coffee shops, charming beach houses, and gift shops and it stretches for miles along the ocean. The underground parking was fine for our RAV4 and there is plenty of street parking nearby. It was surprisingly quiet at night with respectful neighbors. The jacuzzi was decent with hot water, strong jets, and fits four comfortably. The bed was very comfortable and the firmness can be adjusted. We loved our stay there with the waves soothing us, surfers, sunsets, dolphins, and the best walks by the ocean.

KING bed: Gated COMM. Wash&dry. A/C. Pool. Parking
Love this team! They really care about their properties and their guest! They answer phones, solve problems, and they are real people!

Enchanted Ocean Sunsets
Really enjoyed staying at Kiran's place in Pacific Beach. The apartment was exactly as advertised on her AirBNB page. The apartment was very clean and well equipped with all essentials for a comfortable stay. The view from the apartment is breathtaking. You can listen to the sound of waves from the unit. The building is right on the Ocean Drive boardwalk which made for accessible morning and evening beach walks. Kiran and her partner were super responsive when I needed their assistance. I highly recommend Pacific Beach as a base to explore San Diego as well as Kiran's place as a place to stay at.

REJUVENATE @Ocean123 *Available Now,Just Send Msg*
ABSOLUTELY LOVEDDDD THIS PLACE ! WILL definitely return ! The place was super easy to find , easy to check in, and easy parking very safe lot. The view was immaculate.. definitely enjoyed the living room. My fiancé and I had a blast :) we loved sitting on the couch just watching movies with a beautiful view. We had good recommendations thanks to our Host !
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