
Vacation rentals with a pool in Cayman Islands
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Top-rated rentals with a pool in Cayman Islands
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Popular amenities for Cayman Islands rentals with a pool
House rentals with a pool

Luxury 3bd Beach Front, # 5 Yellow, Stunning Views
The home and location were really nice. The North Side of the island is pretty far from everything which is nice if you want quiet, you'll have the whole beach to yourself. There are a few decent restaurants within 10 minutes. Most activities are 30-45 minutes away. We really enjoyed our stay, but 1.5 hours of driving every day to and from activities got kinda old after a few days. If you plan to spend most of your time at the house/beach/pool this is a great place to stay.

Villa Villekulla - Relax Poolside
A beautiful spot on Cayman Brac. We watched the sunrise every morning. Very clean, accurate photos and description, comfortable beds, gorgeous views. The pool needed some attention while we were there and the host was super responsive. As previously mentioned in other comments, the pool area is very sunny during the afternoon. We had an amazing stay and would stay again when visiting Brac.

Beautiful 4 BR/3 BA South Sound Home w/pool.
Beautiful home! The place was spotless and had great amenities. The pool and backyard area was super nice. Julie was very responsive and accommodating. I would definitely stay again!

Oceanfront Oasis Home with cottage & private pool
We came for spring break and absolutely loved the place. First, the view is absolutely fantastic! Being able to wake up and enjoy our morning coffee with the views of the ocean were a great way to greet the day. The pool was well used on our trip and it was both warm and clean! Loved the built in seats in the pool. The place was located near some great restaurants and close enough to everything that we didn't spend a lot of time getting from place to place. Chelsea was extremely helpful and very responsive. We will be back for sure!

3 Bedroom Beach House with Pools
Everything as advertised! Beautiful, peaceful and far from the crowds. If you like driving around the island and having a great place to come back to, this is where you want to be!

Modern Oceanfront, 2Primary Suites, sleeps 6, pool
Our stay at Tides End, Cayman Brac was nothing short of spectacular. The home itself was absolutely stunning—beautifully designed, immaculately clean, and equipped with every amenity you could possibly need (and more!). The location couldn’t have been more perfect—peaceful, private, and surrounded by breathtaking views. From the moment we arrived, we felt completely at ease. The hosts were incredibly gracious and attentive, making sure we had everything we needed to enjoy our stay to the fullest. Their warm hospitality added a personal touch that made the experience even more special. Whether you’re looking for a relaxing escape or a base to explore all that Cayman Brac has to offer, Tides End is the ideal choice. We can’t wait to return!

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

Seabreezes-Your Oceanside Escape
Phillip’s place was perfect for our stay. It was close to groceries, restaurants, snorkel spots and Georgetown. His property is well equipped, very clean and comfortable. Bed was great, porch was fantastic spot to enjoy morning coffee and there was even a hose available to wash down our snorkel gear each day. Loved that beach chairs, beach towels and more were available for our use. Neighbors are very friendly, we typically had the pool to ourselves, loved the Oceanside boardwalk. Would definitely recommend to any group of 1 or 2 travelers.
Condo rentals with a pool

Regal Beach Club #114
We had a great trip. Starting with the welcome packet, that was very detailed. The location was outstanding. We were steps to the pool or ocean. The place is very laid back and all the quests are very respectful. There were so many options for food and shopping within an easy walking distance. We enjoyed Peppers and got take out from Chicken Chicken and even had a sunset dinner next door at the Marriott. All the communication with the host was so helpful.

Lovely Ocean Front Sea Palm Villa #2
Beautiful location free from overwhelming crowd and noise. It was easy to drive to local beaches, and explore other parts of island. This was the perfect center location geographically to either side of island.

Enjoy Sunsets at Cayman Reef Resort - 7 Mile Beach
This place was great! Soooo close to the beach, literally you go downstairs and take just a few steps. Pool was nice, too. Cabana Bay was easy walking distance along a nice footpath. Gabrielle was super friendly and helpful with any questions I had. To accommodate my flight times, I was able to check in early and check out late as well. Would highly recommend to stay here. I love the roosters and hens, too! I hope they always get to stay. They aren't a bother and no one should consider them as such. Although they can't be fed there, that is still their home. ❤️ 🐓

Beautiful Modern Condo on 7 Mile Beach
Condo was exactly as advertised. Large balcony was great for drying beach towels and snorkeling gear. AC worked great. Steps to pool and beach. Plenty of beach and pool lounge chairs and umbrellas. Can walk up or down the beach from the resort beach. Host was quickly responsive to our texts.

Seven Mile Beach Area, Kyle's Condo @ ONE Resort!
Great stay! The place was clean, comfortable, and exactly as described. Check-in was easy, and the host was responsive and helpful. Would definitely stay here again.

Condo-Sunset Cove-Ocean | Pool | Seven Mile Beach
The condo at Sunset Cove was just perfect for our family of 3! Our 8 year old loved swimming in the pool and the ocean. There were lots of kids to play with and everyone was so friendly! I would recommend bringing a float with you to use in the pool. Having the swim up bar/restaurant was so great. The food was delicious for bar food. It is walkable enough especially for the price. Super clean, quiet, beds are comfortable. We will be back!!

3 Bedroom 2 Bath Condo right on 7 Mile Beach
Gary and Shannon really thought of everything! Having traveled around the world, these hosts had way more things for their guests than most. For example, snorkel gear, beach toys for kids, sports and games, phone/table charger in every room. Stocked with plenty of items to get you in the door and your vacation started. Having been to the Cayman Islands in the past, I was pleasantly surprised to see the water and beach were as beautiful as ever ! Crystal clear and loaded with life. Had a great time with a bunch of family and we all couldn’t be happier with the accommodations. Gary and Shannon delivered the goods and I am hoping for a repeat visit in the near future.

Beautiful Beachfront 2BR Condo.
The condo was absolutely beautiful. We loved the view from the kitchen/living room right out to the ocean. It had everything we needed to be able to cook some meals at the condo during our stay. The pool was big with plenty of room for everyone who wanted to enjoy it. And we also enjoyed having access into the water right in front of the condo- we were able to snorkel the ship wreck a few times. The outdoor shared patio’s were also great to have access to and watch the sunset from. We appreciated having access to the washer and dryer as well. They also have beach chairs, small cooler and other beach supplies if you need them- which is great so you don’t have to travel with those items or rent them. There was construction going on at the large building beside the condos - it didn’t bother us too much because we were always out and about during the day exploring. Parking is tight, so a smaller car is best - we backed into the spot which was much easier to get in/out. Loved this place!
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