
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.

South Sound Home-pool-4BR/3BA near Smiths Cove
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.

Parrot-ise 4 Bedroom Oceanfront Villa in Cayman Ka
As advertised. Beautiful location near the quiet Rum Point side of the island. Our group had a blast and the property manager was a joy.

Avi House - Oceanside Oasis
What can I say other than this place is a slice of heaven for those looking to unwind and enjoy the island. It was clean, amazing location and views, very cozy and spacious … would highly recommend, and we will be coming again for sure. Everything about the house was absolutely perfect, and the hosts were amazing to deal with. We’re sad to leave !!

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!

Luxury Beachview Retreat, Cayman Island.
Our entire party was impressed from the moment we pulled up to the property. As visually pleasing as the outside is, the inside pales it in comparison. The interior design is absolutely breathtaking with the most stunning views from almost every room. Each space provides the guest with the opportunity to either have total privacy, or engage in meaningful group connection and activities. We were shocked at how much we enjoyed the water using the Kayaks provided and the min golf. We must have played for hours. We had an amazing group bbq, utilizing the highly equipped kitchen. The appliances are top notch. The laundry was clutch and the communication was exceptional. This house I a gem. We would absolutely return.

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!
Condo rentals with a pool

2 Bed Condo in the Heart of Seven Mile Beach
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

2BR Beach Front Paradise on SMB- Grand Cayman
Stayed as a group of four friends and everyone had a wonderful time. Quiet and peaceful and plenty to do with walkable restaurants. Felt safe and had fun. Nice beach with easy snorkeling. Saw many cool fish. Amenities were as described and super enjoyable.

Seven Mile Beach Condo Ocean/Pool
Highly recommend! We stayed in Ariel's condo for spring break and it was perfect for our family! Our three teenagers loved the pool and being able to snorkel right outside our door. We walked to many great restaurants or take a quick taxi/bus too! All of the guests in the complex were super nice and respectful. Hope to be back again soon!

*Beachfront* Coco Sands - 2 bed condo at Rum Point
This place was perfect for what we needed and wanted for our trip! We really enjoyed how secluded it was but also how close it was to Rum Point! The place was incredibly clean. Beach towels, chairs and cooler were used daily and it was nice to be able to wash and dry swimsuits and towels while there! Natalie was very responsive and helpful when we had questions and even had her husband drop off an extra blanket! Our kids loved the pool and we loved being able to walk out to the water each morning! My only complaint was the wind while we were there!

Cozy Condo near Seven Mile Beach!
This location is within 5-10 minutes to Seven Mile Beach, Georgetown and West Bay in Grand Cayman. It is located right next to a highway so you can't walk to and from these places. My friend and I rented a car, which is honestly the best way to get around the island so it did not matter to us. Krys supplied two pods for the laundry machine, and had two beach chairs, an umbrella, and a cooler in a closet which was unexpected and appreciated! Her place is reasonably priced for how expensive the whole island is. It is a safe condo complex and my friend and I had a great experience here. Highly recommend!

Beautiful Modern Condo on 7 Mile Beach
We went with a group and we all stayed at 3 different locations. Our place was the best of 3, the Lazy Lizard and all the girls bartending were the best. We will stay here again!

The Sanctuary Serene Grand Harbour view 2Bed/2Bath
Its our 2nd time staying at Craig’s place. He’s a great host. Everything always in immaculate condition. The sunrise at the condo on the patio is breath taking drinking coffee! We Love it.

Oceanview 2BR Condo w/ Big Balcony on 7 Mile Beach
Our family of four stayed in Cocoplum 10 and had an amazing week. The view is even more beautiful than the pictures. The location is great, with close access to Seven Mile Beach and lots of restaurants and activities in the area. We loved that we could go out for the morning and then come back and hit the pool and lay low at the condo complex for the afternoon/evening. The host was very responsive and friendly, and the unit was exactly as advertised. I hope we get the chance to come back!
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