
Vacation 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.
Vacation 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

Beautiful craftsman home in SD | Pool | Jacuzzi
We absolutely loved staying at Brenda’s house. It was very spacious, cozy and comfortable. The location is very serene but near enough to shops and restaurants. Brenda was amazingly communicative and generous. She was very accommodating of us on a short notice booking. I would absolutely love to stay here again. Thank you for the perfect getaway!

Fletcher Hills luxury, Sunset View, 4 BR, Pool/Spa
A Perfect Getaway in El Cajon! From the moment we arrived, this stunning Airbnb exceeded all expectations. Nestled in the scenic hills of El Cajon, the property is peaceful, beautifully maintained, and feels like a true retreat. The home itself is immaculate—thoughtfully decorated with a blend of modern touches and cozy charm. Every detail, from the plush linens to the fully stocked kitchen, made us feel pampered and at home. Waking up to the golden California sun streaming through the windows and enjoying coffee on the patio with panoramic views was a daily highlight. The outdoor space is a dream—lush landscaping, a relaxing seating area, and the kind of quiet that lets you truly unwind. Our host was incredibly welcoming and responsive. Whether you’re looking to explore San Diego or just relax in a serene setting, this is the perfect place. We left feeling refreshed, grateful, and already planning our next trip!

Pool, Hot Tub, 15Min To ZOO SeaWorld Sesame Place
Great stay. Very responsive host and house looked like the pictures!

Modern SD Oasis w/ Pool & HotTub
This house hosted our family, which included a baby. It was easy to get to, get into and had what we needed. The host was very responsive, easy to get ahold of, and very involved in making our stay as great as possible! We had a longer stay and it was exactly what we needed— if you’re looking for a great space, interactive and caring host while visiting SD, this is your spot! We would easily stay here 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 came down to Chula Vista with our Grandkids to take them to SeaWorld and hang out for a few days on their spring break. This home was perfect. There were 7 of us. Plenty of room for everyone. There is a game room that we all loved. We enjoyed the beautiful backyard swimming and going in the spa and there is a wonderful park right across the street. I would definitely recommend staying here. The host always responded very quickly and always helpful.

5BR | Salt Water Pool | Hot Tub | Fire Pit| BBQ
Brian was very nice and responsive no matter what time I had a question. The house was just as the photos pictured. Unfortunately, we couldn’t get the fir pit on but Brian was willing to come fix it right away. Weather wasn’t on our side so we didn’t rush him. We got a lot of compliments from family about how neat it was that Brian had a coffee bar and snack cart set up. Everyone had plenty of room to sleep and enjoyed their stay.

Tropical Oasis: spa, solar heated pool, waterslide
This house was amazing! It was comfortable, spacious and well stocked with everything we needed. Close to stores, restaurants and not far from sights. The yard was truly a tropical oasis! Wow, wow, wow! We spent the week with some extended family and had a wonderful time. Myrna was a fabulous host; very responsive and accommodating. Will definitely be back!
Condo rentals with a pool

Best Beach in seconds! Luxury 3Bd/2Ba KING Beds!
We had a wonderful stay! The place was comfy with lots of great touches. Bill was a wonderful host - great communicator and lots of great suggestions. Would love to stay again!

Bay View Condo in Pacific Beach
A great vacation has some important qualities. For us, safety and feeling secure is number one. A comfortable bed and a great shower come next. Throw in a modern, clean kitchen and you are all set. The parking garage is a real convenience as parking can be tight. Air conditioning puts this apartment above the rest. The building laundry rooms are close and reasonably priced. We have always loved San Diego. It’s a great walking city with every kind of restaurant and cuisine. The scenery is beautiful. Be sure to walk the Embarcadero, hit the beaches, and Balboa Park is a real treasure. They are all free to visit.

Centrally located n UCSD/ utc-laJolla
We loved our stay here! The place was well stocked, especially with items for the beach for the kids. We appreciated the clean rooms and clean sheets, as well as quiet neighborhood. Would definitely recommend and would stay here again next time we are in town.

One Bedroom Ocean Front Condo!
My family and I throughly enjoyed our stay at Tina’s place! Tina is a very helpful host and responded quickly to any questions. She was also accommodating to us traveling with kids. We appreciated the pack n play and all of the beach toys. :) The condo is a very short walk to the beach and the view out the window is gorgeous! Highly recommend staying here!

Comfortable & convenient accommodation @ San Diego
We were very pleased with the clean accommodations, easy accessibility to highways, grocery store and gas station. We would definitely stay here again.

Enchanted Ocean Sunsets
Amazing location! The apartment has floor to ceiling windows and the view of the ocean is spectacular. The beds and couches were comfortable. You can hear the waves crashing because you are so close to the beach. We enjoyed going to sleep to the sound of the waves and going for walks along the water in the mornings. The location was just 15-20 away from every sight we wanted to visit in the San Diego area. We appreciated that there were beach towels, beach chairs and a football to borrow. The laundry machines are down the hall, not in the apartment, if that matters to you. We had no trouble using them.

Luxury Oceanfront Condo with Unbelievable Views
We loved staying here. It is clean, well kept and the view is amazing. We loved that there are lots of extra towels, blankets and pillows too. Great neighborhood with good restaurants within walking distance. We would definitely stay here again.

Beautifully remodeled 10th floor oceanfront condo
We had an absolutely wonderful stay! The location was perfect—just a short walk to the beach, great coffee shops, and local stores, with an amazing view to enjoy each morning. The condo was spotless, well-maintained, and felt like a home away from home. Traveling with a child can be tricky, but the hosts were incredibly accommodating—they even provided a pack n play, which made things so much easier for us. We were warmly welcomed with a basket of fresh fruit and a bottle of Rosé, which was such a thoughtful touch and really set the tone for a relaxing trip. Parking was super convenient, which made coming and going a breeze. To top it all off, I accidentally left my AirPods behind and the host was so kind and honest—they promptly shipped them back to me, which I really appreciated. Highly recommend this place to anyone looking for comfort, convenience, and genuine hospitality. We’d absolutely stay here again!
Home rentals with a private pool

Historic Home with Amazing 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
Was just what we were looking for. Great location and view, quiet neighborhood. Beautiful home, responsive hosts, relaxing getaway. Would definitely stay again.

Luxury San Diego House: Beach, Pool & Pet-Friendly
This was the perfect place, a roomy and well stocked home for our family! It was clean and comfortable and had a lot of both indoor and outdoor games. We appreciated that all bedrooms were connected to a bathroom. The backyard was another wonderful living space, I only wish we would have had time to utilize the pool! The holiday dog with lights in the entry way was adorable and a fun welcome when we walked in. The owner was proactive in contacting me prior to check in and provided the code and any home instructions to me via text. We would definitely stay in this home again if we are in the area.

Vista Grande
This is one the most incredible property that I've ever been to. We had a wonderful stay — the view was breathtaking, and every detail showed real care and thought. Communication was excellent, and the space was both comfortable and welcoming. A definite 5/5 — highly recommended!
Destinations to explore
- San Diego Vacation rentals
- La Joya Vacation rentals
- Anaheim Vacation rentals
- Palm Springs Vacation rentals
- Stanton Vacation rentals
- Big Bear Lake Vacation rentals
- Los Angeles Vacation rentals
- Joshua Tree Vacation rentals
- Santa Monica Vacation rentals
- San Fernando Valley Vacation rentals
- Channel Islands of California Vacation rentals
- Southern California Vacation 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
- Windansea Beach
- Surf Beach
- SeaWorld San Diego
- Santa Monica Beach
- Playas Los Buenos
- University of California San Diego
- San Diego Zoo Safari Park
- Playa Popotla
- San Onofre State Beach
- Belmont Park
- LEGOLAND California
- Balboa Park
- South Mission Beach, San Diego
- Silver Strand State Beach
- Liberty Station
- Moonlight Beach
- Cuyamaca Rancho State Park
- Aviara Golf Club
- Morgan Run Club & Resort
- Mission Trails Regional Park
- Sesame Place San Diego
- USS Midway Museum
- Carlsbad State Beach
- Strand Beach