Vacation rentals with a pool in Cayman Islands

Find and book unique homes with a pool on Airbnb

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Popular amenities for Cayman Islands rentals with a pool

House rentals with a pool

Guest favorite
Home in Rum Point
4.87 out of 5 average rating, 53 reviews

Luxury 3bd Beach Front, # 5 Yellow, Stunning Views

KelseyRating, 5 stars3 months ago
We really enjoyed our time here! The view is incredible and home is clean and spacious. It was great to have a small private beach area and access to the swimming pool.
Superhost
Home in Cayman Brac
4.74 out of 5 average rating, 53 reviews

Villa Villekulla - Relax Poolside

GailynRating, 5 stars4 weeks ago
Lovely spot, house was clean and comfortable. Outdoor furniture and awning would have been nice to have, but being a very small island, it takes a long time for replacement items to arrive. Kitchen implements were a bit lacking (no bowls big enough to make a salad, etc), but we made do and ate out a bit more than usual at the lovely local restaurants!
Top guest favorite
Home in George Town
5 out of 5 average rating, 8 reviews

Beautiful 4 BR/3 BA South Sound Home w/pool.

ChristinRating, 5 stars2 months ago
My family and I had a wonderful stay! The house was spotless and Julie was a wonderful host. Would recommend staying here to anyone. Looking forward to the next visit.
Guest favorite
Home in Grand Cayman
4.92 out of 5 average rating, 25 reviews

3 Bedroom Beach House with Pools

DanRating, 5 stars3 weeks ago
The place is perfect to get away from the crowds and unwind. For the first 3 days, we had all the pools to ourselves which the kids loved. Several restaurants and take out places within a few minutes drive, but the kitchen is fully stocked to cook if you choose to. There are kayaks, pool noddles and snorkel gear already stocked in the closet. Would definitely stay here again
Top guest favorite
Home in West Bay Road, George Town
5 out of 5 average rating, 10 reviews

Island Oasis

EllenRating, 5 stars2 months ago
The house was beautiful and well appointed. If we had a concern I messaged Cline and he was always very responsive. We asked for more chaise lounge chairs and towels and on Christmas Day a guy showed up with six new chaise loungers for the pool area and a pile of new towels. Cline met our grocery delivery and the liquor store delivery so we were well stocked going into the holidays when stores were closed. He recommended grocery stores and restaurants and we felt well taken care of. We made reservations for several island excursions based on his recommendations. All were excellent. Overall it was a wonderful eight days in Grand Cayman and I can say that it was in large part due to Clines help. And I have a flexible awesome family.
Guest favorite
Home in George Town
5 out of 5 average rating, 19 reviews

Villa Olea -

JeffRating, 5 stars5 months ago
Leslie was an amazing host. Home was spotless and in a great location. She was very responsive and very bubbly. Thank you opening your home to us. The whole experience was revitalizing. Highly recommend booking!
Top guest favorite
Home in Stake Bay
5 out of 5 average rating, 55 reviews

Modern Oceanfront, 2Primary Suites, sleeps 6, pool

DianneRating, 5 stars1 week ago
Tides End is a tranquil vacation spot that ticks all the boxes. It’s right on the ocean, has two king suites, single level floor plan, all the modern conveniences, well equipped kitchen, pristine pool, kayak, life vests, and assorted fins and snorkel gear. The Brac Scuba Shack has anything else you might need. Nearby Radar Reef was the best place we found to snorkel. The whole island is so chill and quiet with raw natural beauty. Hiking on the bluffs was breathtaking. Julia is very responsive, kind and gracious. We had a lovely time!
Top guest favorite
Home in Georgetown, Cayman Islands
5 out of 5 average rating, 8 reviews

Hidden Hideaway House -7 mile -2King/1Queen- Pool

ElizabethRating, 5 stars2 months ago
Monika's house was the perfect place to spend a week in Grand Cayman. The location was perfect and close to the grocery store, across the street from the beach and within walking distance to many restaurants including Camana Bay. We enjoyed the pool, large backyard and safety of the residential neighborhood. The house was "as described" and we felt that we had everything we needed for the week. Thanks again!

Condo rentals with a pool

Guest favorite
Condo in George Town
4.92 out of 5 average rating, 38 reviews

2 Bed Condo in the Heart of Seven Mile Beach

EmmaRating, 5 stars3 weeks ago
We had a great stay the condo is in a great location lots of places to eat and drink in walkable distance. The beach access is amazing will defo be back! Thank you
Superhost
Condo in Sister Islands
4.77 out of 5 average rating, 39 reviews

Brac Sea'renity - Coastal chic oceanfront condo

BillRating, 5 stars2 weeks ago
Nice place. Comfy bed. Nice TV. High-end washer/dryer made life easier for 2 divers on a 15 day dive trip with just a carry on bag of clothes!
Superhost
Condo in George Town
4.86 out of 5 average rating, 51 reviews

2BR Beach Front Paradise on SMB- Grand Cayman

DavidRating, 5 stars2 months ago
Kenesha’s place was completely as advertised. We loved the location away from the crowds but close enough to walk to restaurants, bars, and resorts. The place was spotless, with a well appointed kitchen and wonderful screened in deck facing the ocean. The pool and hot tub were right on the ocean and many times we had it to ourselves. We would definitely love to come back in the future!
Guest favorite
Condo in Seven Mile Beach
4.98 out of 5 average rating, 64 reviews

Seven Mile Beach Condo Ocean/Pool

CallieRating, 5 stars1 week ago
This is a great location. The pool and pool bar are fun and reasonably priced. There is some snorkeling right off the beach. We walked to several restaurants, camana bay, the cruise ship port, and the south half of 7 mile beach. The buses are inexpensive and easy to use right from the condo. The condo itself was very clean, had nice views, and a great balcony that we used frequently. We would definitely stay here again in the future.
Superhost
Condo in George Town
4.84 out of 5 average rating, 124 reviews

Cozy Condo near Seven Mile Beach!

Velvet Rating, 5 stars1 month ago
Everything looks just like the photos, and it's clean. The apartment has great air conditioning, and plenty of hot water. The host was kind enough to let me check in a bit early, and check out an hour later than check out time. The location is convenient for walking to the supermarket, and the beach. You can get a local bus easily from the roads nearby if you don't want to hire a car.
Guest favorite
Condo in George Town
4.95 out of 5 average rating, 41 reviews

Beach front condo, Seven Mile Beach Cayman Islands

AngelaRating, 5 stars1 month ago
The place actually was bigger and nicer than the photos. Amy was very responsive to any questions. The location was not bad. Large construction site right next door yet was not noisy or disruptive. Disappointed that the beach right outside the place was not really useable due to the rocks. The nicer beaches were a couple of miles away and easy to access via public busses. Public busses are great, only $2-3. Come frequently, flag them down anywhere and will let you off anywhere. In walking distance was Peppers Restaurant which was good and had live music. Kirk’s supermarket was also in walking distance.
Superhost
Condo in George Town
4.86 out of 5 average rating, 160 reviews

Beautiful Modern Condo on 7 Mile Beach

StevenRating, 5 stars1 month ago
We loved this condo and the location of it. It was very comfortable and had everything that we needed. Thank you!
Guest favorite
Condo in Grand Harbour
4.93 out of 5 average rating, 248 reviews

The Sanctuary serene Grand Harbour view 2Bed/2Bath

ShantaeRating, 5 stars2 days ago
I booked this last minute stay for my family while their home underwent emergency repairs. It was late evening and we were initially worried the request would take a while to be accepted, but Craig was incredibly responsive and accommodating. From the moment of booking to the end of the stay, communication was seamless, and we truly appreciated his attentiveness. The home itself was beautiful—well-maintained, and filled with thoughtful touches. The location is in a fantastic walkable area with lots nearby to explore, and the amenities provide everything needed for a comfortable stay. Overall, this was a wonderful experience during a very stressful time for my family, and we would highly recommend this Airbnb to anyone looking for a great place to stay with an attentive host!

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