Vacation 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

Guest favorite
A charming oceanfront home with a bright yellow exterior is set against a backdrop of lush greenery and palm trees. The sandy path leads to the beach, while a spacious balcony is visible on the upper level, offering a taste of coastal living.
Home in Rum Point
4.87 out of 5 average rating, 55 reviews

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

DustinRating, 5 stars1 month ago
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.
Superhost
Lounge chairs sit poolside, offering a view of the ocean waves. The bright sky contrasts with the tranquil water, while the surrounding deck features a patterned edge. The scene is designed for relaxation and enjoyment of the coastal ambiance.
Home in Cayman Brac
4.74 out of 5 average rating, 54 reviews

Villa Villekulla - Relax Poolside

GingerRating, 5 stars1 month ago
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.
Superhost
A brightly colored two-story villa features a spacious deck and a pool, surrounded by tropical greenery. The ocean is visible in the background, with sandy beach leading to the water. The building has a red roof and multiple seating areas for relaxation.
Home in KY
4.69 out of 5 average rating, 13 reviews

Parrot-ise 4 Bedroom Oceanfront Villa in Cayman Ka

SeanRating, 5 stars3 months ago
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.
Superhost
A clear blue pool is surrounded by lush greenery, featuring two lounge chairs positioned on the poolside. A small seating area with a bench is visible in the background, creating a tranquil outdoor space for relaxation.
Home in Grand cayman
5 out of 5 average rating, 3 reviews

3 Bed Brand New by 7 Mile Beach!

PaulRating, 5 stars2 months ago
All around great experience. Tanis is so helpful and accommodating. The unit is brand new and in pristine condition. Right next to the pool, and near some of the best beaches in Grand Cayman!
Top guest favorite
An outdoor dining area features a large wooden table surrounded by metal chairs, with panoramic views of the ocean framed by retractable glass doors. Sun loungers and a hammock are positioned on sandy ground, providing a serene connection to the beach and lush greenery.
Home in Bodden Town
5 out of 5 average rating, 45 reviews

Casa Avi - Beachfront Bliss

KevinRating, 5 stars3 weeks ago
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 !!
Guest favorite
A refreshing pool is framed by palm trees and offers a view of the ocean beyond. The surrounding area features colorful buildings and landscaped pathways, creating a serene environment for relaxation. The clear blue water invites enjoyment under a clear sky.
Home in Grand Cayman
4.92 out of 5 average rating, 26 reviews

3 Bedroom Beach House with Pools

LeeRating, 5 stars1 month ago
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!
Top guest favorite
Home in West Bay Road, George Town
5 out of 5 average rating, 14 reviews

Island Oasis

TaylorRating, 5 stars1 week ago
Wonderful stay with good walkability to grocery and liquor store. Lived BBQing on the enclosed (mosquito-free) patio and the pool was sublime!
Top guest favorite
Home in Stake Bay
5 out of 5 average rating, 58 reviews

Modern Oceanfront, 2Primary Suites, sleeps 6, pool

MelodyRating, 5 stars2 weeks ago
Julia’s home is amazing! A great place for relaxing! The island is so peaceful, and everyone is friendly! Julia has amazing recommendations! Everything was exactly as described and had everything we needed for a relaxing week! We would definitely come back again! Thank you Julia for all your helpful suggestions, and Derwin was great too!!

Condo rentals with a pool

Guest favorite
The image showcases a clear, inviting pool surrounded by lush palm trees and vibrant tropical landscaping. Lounge chairs are positioned around the deck, providing a relaxing space for sunbathing. A bright blue sky with scattered clouds complements the serene pool ambiance.
Condo in George Town
4.88 out of 5 average rating, 40 reviews

2 Bed Condo in the Heart of Seven Mile Beach

EmmaRating, 5 stars2 months 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
An expansive view of a sandy beach is captured, featuring lounge chairs arranged neatly under a large tree. The turquoise waters of the Caribbean Sea stretch into the horizon, with gentle waves lapping at the shoreline, creating a serene seaside atmosphere.
Condo in George Town
4.87 out of 5 average rating, 52 reviews

2BR Beach Front Paradise on SMB- Grand Cayman

DavidRating, 5 stars3 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
The image captures a tranquil pool area surrounded by lounge chairs and shaded umbrellas. Lush greenery and palm trees provide a refreshing backdrop. In the distance, a sandy beach meets the ocean under a partially cloudy sky, enhancing the serene atmosphere.
Condo in Seven Mile Beach
4.98 out of 5 average rating, 66 reviews

Seven Mile Beach Condo Ocean/Pool

AmyRating, 5 stars3 weeks ago
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!
Guest favorite
An aerial view captures the beachfront condo surrounded by lush greenery, with a clear swimming pool visible beside the unit. Sun loungers line the sandy shore, and a thatched gazebo is positioned near the water's edge, offering a tranquil setting.
Condo in North Side
4.96 out of 5 average rating, 25 reviews

*Beachfront* Coco Sands - 2 bed condo at Rum Point

LauranRating, 5 stars4 days ago
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!
Superhost
A clear blue swimming pool is surrounded by a well-maintained patio area. Two lounge chairs are positioned beside the pool, with lush greenery in the background. Bright, sunny skies and a modern building can be seen beyond the pool area.
Condo in George Town
4.84 out of 5 average rating, 128 reviews

Cozy Condo near Seven Mile Beach!

HaleyRating, 5 stars1 week ago
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!
Superhost
Condo in George Town
4.87 out of 5 average rating, 164 reviews

Beautiful Modern Condo on 7 Mile Beach

LisaRating, 5 stars2 weeks ago
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!
Guest favorite
A serene pool area is surrounded by a landscaped patio featuring palmy greenery. The pool is seamlessly integrated with the outdoor clubhouse, which is framed by tall columns and a light-colored roof. Lounge chairs are positioned nearby for relaxation.
Condo in Grand Harbour
4.92 out of 5 average rating, 253 reviews

The Sanctuary Serene Grand Harbour view 2Bed/2Bath

JenniferRating, 5 stars3 weeks ago
Would stay here again, great location. We split our time between Cemetery Beach and Starfish Point. Craig was very responsive and a pleasure to deal with. Nothing to do with Craig but we had a hard time finding the property. We didn’t plan ahead and had no Verizon service when we arrived on the island. I would recommend knowing if your cell service will be active or knowing exactly where the unit is before you leave home. Hope to visit again next year.
Top guest favorite
A private pool is surrounded by sun loungers and tropical palms, with a clear blue sky overhead. The pool features a gentle curve and steps leading in, offering a serene space for relaxation and enjoyment near the ocean.
Condo in George Town
4.99 out of 5 average rating, 67 reviews

Oceanview 2BR Condo w/ Big Balcony on 7 Mile Beach

KellyRating, 5 stars4 weeks ago
Beautiful spot at the South end of 7 mile. Beach is a little Shelly but just up the beach is a great spot to swim. Amazing snorkeling right out front including a ship wreck. Walkable to the grocery store and a dive shop as well as several restaurants which was so nice. Owners were so responsive any time we had questions. We really enjoyed the condo. It’s the perfect mix of quiet and semi-private setting right in the mix of everything you need. Beds were firm in a Good way. Linens were SO comfortable! Beautiful kitchen and bathrooms. We loved the condo. Thanks for having us!

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