Vacation rentals with a pool in Shelter Island

Find and book unique homes with a pool on Airbnb

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Popular amenities for Shelter Island rentals with a pool

House rentals with a pool

Top guest favorite
Home in Bonita
5 out of 5 average rating, 36 reviews

Beautiful craftsman home in SD | Pool | Jacuzzi

PhilRating, 5 stars3 months ago
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!
Top guest favorite
Home in El Cajon
4.97 out of 5 average rating, 115 reviews

Fletcher Hills luxury, Sunset View, 4 BR, Pool/Spa

StephanieRating, 5 stars6 days ago
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!
Superhost
Home in National City
4.76 out of 5 average rating, 33 reviews

Pool, Hot Tub, 15Min To ZOO SeaWorld Sesame Place

SerenaRating, 5 stars2 weeks ago
Great stay. Very responsive host and house looked like the pictures!
Guest favorite
Home in San Diego
4.94 out of 5 average rating, 17 reviews

Modern SD Oasis w/ Pool & HotTub

TrianaRating, 5 stars4 weeks ago
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!!
Superhost
Home in El Cajon
4.72 out of 5 average rating, 65 reviews

Palmeras House: Pool + outdoor BBQ

FathimaRating, 5 stars7 months ago
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.
Superhost
Home in Chula Vista
4.8 out of 5 average rating, 140 reviews

Family Home w/Pool, Hot Jacuzzi and Park Access

SandiRating, 5 stars2 weeks ago
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.
Superhost
Home in San Diego
4.85 out of 5 average rating, 196 reviews

5BR | Salt Water Pool | Hot Tub | Fire Pit| BBQ

RosaliRating, 5 stars1 month ago
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.
Top guest favorite
Home in Spring Valley
4.97 out of 5 average rating, 76 reviews

Tropical Oasis: spa, solar heated pool, waterslide

ChristinaRating, 5 stars3 weeks ago
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

Guest favorite
Condo in San Diego
4.87 out of 5 average rating, 117 reviews

Best Beach in seconds! Luxury 3Bd/2Ba KING Beds!

LukeRating, 5 stars3 days ago
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!
Guest favorite
Condo in San Diego
4.97 out of 5 average rating, 114 reviews

Bay View Condo in Pacific Beach

BarbaraRating, 5 stars1 week ago
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.
Guest favorite
Condo in San Diego
4.95 out of 5 average rating, 230 reviews

Centrally located n UCSD/ utc-laJolla

FlorenceRating, 5 stars4 days ago
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.
Superhost
Condo in San Diego
4.86 out of 5 average rating, 178 reviews

One Bedroom Ocean Front Condo!

MadelineRating, 5 stars1 month ago
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!
Superhost
Condo in San Diego
4.8 out of 5 average rating, 200 reviews

Comfortable & convenient accommodation @ San Diego

JudithRating, 5 stars2 weeks ago
We were very pleased with the clean accommodations, easy accessibility to highways, grocery store and gas station. We would definitely stay here again.
Superhost
Condo in San Diego
4.91 out of 5 average rating, 150 reviews

Enchanted Ocean Sunsets

JenineRating, 5 stars2 weeks ago
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.
Guest favorite
Condo in San Diego
4.98 out of 5 average rating, 156 reviews

Luxury Oceanfront Condo with Unbelievable Views

HeatherRating, 5 stars1 week ago
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.
Guest favorite
Condo in San Diego
4.96 out of 5 average rating, 163 reviews

Beautifully remodeled 10th floor oceanfront condo

RichardRating, 5 stars2 weeks ago
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

Guest favorite
Home in San Diego
4.92 out of 5 average rating, 85 reviews

Historic Home with Amazing Views of San Diego Bay

DebraRating, 5 stars3 weeks ago
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
Guest favorite
Home in San Diego
4.9 out of 5 average rating, 177 reviews

Eco-Friendly Mount Soledad Pad with Views and Heated Pool

ZebRating, 5 stars1 month ago
Was just what we were looking for. Great location and view, quiet neighborhood. Beautiful home, responsive hosts, relaxing getaway. Would definitely stay again.
Home in San Diego
4.8 out of 5 average rating, 10 reviews

Luxury San Diego House: Beach, Pool & Pet-Friendly

SandraRating, 5 stars4 months ago
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.
Home in Ramona
4.92 out of 5 average rating, 39 reviews

Vista Grande

SuhaRating, 5 stars2 weeks ago
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!

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