Vacation rentals with a pool in Cayman Brac

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Popular amenities for Cayman Brac rentals with a pool

House rentals with a pool

A serene outdoor space features white lounge chairs positioned by a swimming pool, with gentle palm trees swaying in the breeze. A fabric shade extends above, providing protection from the sun, while the ocean glimmers in the background under a soft sunset light.
Home in Stake Bay
5 out of 5 average rating, 15 reviews

Sea Fan Meadows: Oceanfront w/ Pool

MatthewRating, 5 stars9 months ago
Have been wanting to vacation at Cha Che’s home for 15years! Finally made it - didn’t want to leave! Total privacy, peaceful, and tranquil. Watched sunrise and sunset from the pool every day. House was lovely. Ocean was a bit rough some days due to hurricane Beryl but great snorkeling on property. Pool was perfect. Kitchen was lovely. Bed was comfy. Couldn’t ask for better. Will definitely return on our next trip to Cayman as it felt like our home away from home!!!
Superhost
A clear blue pool lies adjacent to a private beach, surrounded by soft white sand. Palm trees gently sway in the breeze, and the tranquil ocean stretches towards the horizon under a bright blue sky with scattered clouds.
Home in Cayman Brac
5 out of 5 average rating, 16 reviews

Featherstone - Upstairs Beach Front Apartment

JeffRating, 5 stars1 month ago
Coralie was great. Proactive communication. Flexible on check-in and -out. Helped right away with a minor problem Place was great. Cottage vibe, nicely decorated, comfortable Mattresses were great/comfy Kitchen (very important for me cuz we cook) was stocked with basics - right spices, good amount of condiments in the fridge, pots, pans, etc. We would stay again.
A clear view of the ocean is framed by palm trees, with gentle waves lapping against the rocky shoreline. A compact swimming pool lies just outside a covered terrace, surrounded by a stone deck. Sunlight reflects off the water, creating a serene atmosphere.
Home in Cayman Brac
4.44 out of 5 average rating, 9 reviews

Southern Reach. "A Little Piece of Paradise

TristanRating, 5 stars39 months ago
Our second trip in only a few months - love the location for the nature and the pool is a big hit. Paul is very responsive. Looking forward to coming back soon!
Guest favorite
An aerial view captures the layout of the property, highlighting the main house and the private pool. Outdoor furniture is arranged around the pool, with shaded areas provided by umbrellas, surrounded by sandy terrain and green vegetation.
Home in Spot Bay
5 out of 5 average rating, 5 reviews

Dan's Dive Seaside Retreat in Spot Bay with Pool

DavidRating, 5 stars2 months ago
What a quiet, peaceful and beautiful place. After traveling around the island, Spot Bay is the best and quietest part of the island. Highly recommend this cottage. It has awesome views of the Carribean, everything you need for a comfortable vacation, would most definitely stay again!
Top guest favorite
The image showcases a newly constructed house adjacent to a semi-private pool. Sunlight reflects off the clear water, while lush greenery frames the surroundings. A patio area features tile flooring and planters, enhancing the outdoor space for relaxation and enjoyment.
Home in Little Cayman
4.96 out of 5 average rating, 168 reviews

Just Chillin in Little Cayman

SophiaRating, 5 stars1 week ago
Another brilliant stay. This will be my go to place when going to Little. Thank you for everything!
Superhost
A serene outdoor space is featured, showcasing a sparkling pool surrounded by lounge chairs and shaded by billowing fabric canopies. Lush palm trees frame the view, with the tranquil Caribbean waters visible in the background under a clear blue sky.
Home in West End
4.86 out of 5 average rating, 14 reviews

2-bdm tropical beach paradise w/ pool, cabana&more

TimothyRating, 5 stars3 weeks ago
Henry’s place was the perfect place for some deep relaxation! Right on the water, with beautiful grounds and hammocks that were perfect for drifting in and out of sleep, reading, and generally soothing the days away. The location too, was perfect. Just a few minutes from “downtown” and under ten minutes to the Brac Scuba Shack. The sea was a bit choppy right in front of the house, but on calm days, you could absolutely shore dive just out the front. While we were there, the other two units were unoccupied, which meant that we had the hammocks and pool to ourselves. The interior was perfectly appointed with a great kitchen and comfy couches. Communication was impeccable. We would absolutely return!
A private pool area features a sleek turquoise pool, surrounded by wooden decking and lush greenery. Two lounge chairs and a sun umbrella provide shaded seating, while a set of stairs leads into the pool. The inviting outdoor space is bathed in natural light.
Home in West End
4.6 out of 5 average rating, 5 reviews

Villa VanEl

AlexiaRating, 5 stars11 months ago
Such a great place! Looks just like the pictures and Derri was always very responsive and accommodating. Would love to go back again.
Guest favorite
A clear swimming pool is framed by wooden decking, with steps leading into the water. Palm trees provide shade along the pool's edge, and the beach and ocean are visible in the background under a partly cloudy sky.
Home in Cayman Brac
4.89 out of 5 average rating, 19 reviews

Featherstone - The Cottage

Jayda Rating, 5 stars7 months ago
My partner and I had a lovely and peaceful experience here at featherstone. The place was very cozy and felt like at home. The scenery was beautiful, very easy accessible. Our host was great as well, she was very helpful, responsive and friendly. We plan to come again in the near future! This place was the perfect fit for our vacation.

Condo rentals with a pool

A serene outdoor pool area is highlighted, featuring a shimmering blue pool and two shaded cabanas. Palm trees sway gently in the breeze, while a nearby hammock offers a relaxing spot. The expansive view of the ocean stretches into the distance under a bright blue sky.
Condo in Sister Islands
4.77 out of 5 average rating, 39 reviews

Brac Sea'renity - Coastal chic oceanfront condo

BillRating, 5 stars1 month 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!
Guest favorite
A serene outdoor view features a sandy area with tropical palm trees and a pathway leading to the pool. A glimpse of the ocean is visible in the background, with two hammocks set up near the water, inviting relaxation under the clear blue skies.
Condo in Cayman Brac
5 out of 5 average rating, 9 reviews

Cayman Brac, Carib Sands 221- "Stumble Inn"

BarbaraRating, 5 stars2 months ago
Really enjoyed our stay at the “Stumble Inn” . Karen was quick to respond to our inquiries and provided us with helpful suggestions - access was simple and straightforward, and the unit perfect for our visit. Great location with a nice pool and small beach - and great bird watching close by. Would definitely recommend contacting Karen if you plan on visiting Cayman Brac .
Superhost
The image showcases the Conch Club property with pastel yellow buildings lining a serene beach. A freshwater pool is visible in the foreground, surrounded by tropical greenery. Palm trees sway gently, and kayaks rest on the sandy shore, inviting outdoor activities.
Condo in Blossom Village
4.85 out of 5 average rating, 60 reviews

Conch Club 16, Little Cayman, Cayman Islands

LeslieRating, 5 stars2 months ago
We really loved staying in this condo. It was very quiet and comfortable. We loved the view from the top floor deck and being able to bring chairs to the beach right below the condo in the afternoon. Little Cayman is really different from other islands because not that many people live here. The plane rides between the islands were a blast and we felt safe with two pilots in the front of the plane. We loved all the red footed boobies nesting in trees right along the road. We had a great time diving the Bloody Bay Wall with Little Cayman Divers. We will be back!
A tranquil seascape showcases the gentle waves of the ocean lapping against a rocky shoreline. The sky is filled with soft clouds and pastel hues from the setting sun, creating a serene atmosphere. Coastal greenery is visible in the foreground.
Condo in Sister Islands
4.33 out of 5 average rating, 3 reviews

Charming, Ocean Front Condo with Pool & Bluff View

ArminRating, 5 stars14 months ago
lovely apartment!
A tranquil swimming pool is centered among the two-story villas, framed by palm trees and tropical vegetation. Lounge chairs are positioned around the pool area, offering spots for relaxation. The ocean is visible in the background, enhancing the peaceful resort atmosphere.
Condo in LITTLE CAYMAN
4.5 out of 5 average rating, 6 reviews

The Club at Little Cayman - Luxurious Living

JaydeRating, 5 stars30 months ago
Great stay - very quiet complex located just a short walk from LCBR. Easy check in and thanks for letting us in early! Pool and beach right there with a nice sea view from the balcony! We’ll be back!

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