Vacation rentals with a pool in Cayman Brac

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Top-rated rentals with a pool in Cayman Brac

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Superhost

A serene pool area is surrounded by swaying palm trees and shaded by large fabric canopies. The inviting pool is framed by wooden lounge chairs, offering a perfect spot for relaxation while enjoying views of the nearby water.

Home in West End

4.75 out of 5 average rating, 4 reviews

2-bd tropical beach apartm. w/ deck, pool, cabana

Truly amazing tropical beach paradise on the water with pool and the most stunning sunsets! Property has private entrances, fully equipped kitchen with open dining area, living room, 1 bedroom w/ 2 bed, 1 bathroom, closets, separate washing room. Beach cabana, hammocks, bikes, grill, kayaks, fire pit, private deck. Great snorkeling right out front. Sandy beach. Leeward side of the island so many days with calm waters. AC's, TV, linens, beach + bath towels, games, books & more. 1 of only 3 units.

Top guest favorite

The tranquil pool and spa are surrounded by a spacious deck, with views of the ocean and palm trees. The sunset casts a warm glow over the area, creating a serene atmosphere for relaxation by the water.

Villa in Stake Bay

5 out of 5 average rating, 12 reviews

Stellar Views Waterfront Luxury Private Villa

Travel insiders are discovering our property. Coral Beach Villa was recently selected as one of the top 17 insider picks by Savoteur online travel magazine, and the ONLY privately owned home in the Cayman Islands to be featured besides luxury hotels. Cayman Brac is a 30 minute flight from Grand Cayman, but a world away from the traffic and crowds of the main island. The villa comfortably sleeps 8 in 3 master king bedrooms, each with private ensuites. Delight your senses and rejuvenate your soul!

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

4.74 out of 5 average rating, 42 reviews

Brac Sea'renity - Coastal chic oceanfront condo

Indulge in the comfort and tranquility of this newly remodeled oceanfront condo located on Cayman Brac’s South Side East. The space features an open-concept layout with lots of natural light, bright sun-baked colors, tasteful furnishings and décor. Enjoy mesmerizing ocean views from the kitchen, living room & primary suite! Wake up to the best view of the sunrise over the sparkling Caribbean Sea, play by the pool, relax in the hammocks & fall asleep to the soothing sound of the ocean waves.

A private in-ground swimming pool is surrounded by colorful shade sails, providing protection from the sun. Lush greenery and tropical plants frame the pool area, creating a serene environment. A rocky feature is visible near the pool, complemented by light-colored decking.

Villa in West End

5 out of 5 average rating, 3 reviews

TROPICAL RUNaWAY, Cayman Brac

PRICES INCLUDE TAXES (13%), CLEANING. 2.5 acres with 500' of sandy beach and sheltered, private, in ground, swimming pool, shared between two houses that rent separately. There is a 4 bedroom house and a 1 bedroom house. The big house is ideal for 3 couples to share, or 3 couples with young children. It also suits 2 couples. Larger groups consider reserving the entire property, both houses. The 1 bedroom house is $255 /night fees and taxes included! Excellent privacy between the houses.

Top guest favorite

An outdoor seating area features modern furnishings with turquoise and white accents. A glass table is topped with a small vase of yellow flowers. In the background, a private pool reflects the sky, framed by palm trees and ocean views.

Home in Sister Islands

5 out of 5 average rating, 30 reviews

Bliss Beach House - Secluded, Oceanfront, Pool

Newly constructed, custom designed 1 bedroom waterfront home on just under an acre of land with 100 ft. of oceanfront. All the conveniences of home, located on a secluded south side east beach property with private pool. This beach house is very private, with no close neighbours. There is only one residence on our property, so you will not be sharing either the property or the pool with anyone else. We are located on Cayman Brac, a short 30 minute flight from Grand Cayman on Cayman Airways.

Superhost

A panoramic view from the patio features two stylish chairs overlooking the ocean waves. The sunlight reflects off the water, creating a serene atmosphere. The horizon is complemented by a sky filled with soft clouds, enhancing the coastal experience.

Apartment in Cayman Brac

4.88 out of 5 average rating, 8 reviews

Sunburst Bliss

Nestled along the coastline, this charming oceanfront condo offers an idyllic escape where the rhythmic waves become your daily soundtrack. Wake up to breathtaking sunrises that paint the sky in hues of blue and pink, and spend your days basking in the salty breeze as it whispers through the swaying palms. With panoramic views of the cerulean sea stretching to the horizon, the serene beauty of the ocean is just steps away, inviting you to explore, relax, or simply unwind in nature's embrace.

A view from a covered porch offers a glimpse of the freshwater pool and the ocean beyond. Palm trees provide greenery, while gentle waves can be seen lapping at the shoreline in the distance. The space exudes a relaxing atmosphere.

Home in Cayman Brac

5 out of 5 average rating, 15 reviews

Captain's Cove Luxury Private Beachhouse

Captain's Cove offers privacy with the conveniences of home. There are two bedrooms with Kingsize beds and bathrooms off each. Both bedrooms have french doors facing the ocean with access to the expansive front porch. The freshwater pool is only steps from the porch and allows for a refreshing private retreat. Oceanside is a cabana with hammocks for a relaxing nap in the breeze. There is a coral-stone shoreline with slight sandy beach. Diving or snorkeling can be done right from shore.

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

4.73 out of 5 average rating, 55 reviews

Villa Villekulla - Relax Poolside

Welcome to Villa Villekulla, a place where time slows down and complete relaxation is possible. It’s located on the quaint sister island, Cayman Brac. You can Relax poolside in a private pool with spectacular views of the waves hitting the shore. We now have Exclusive Car Rental and Boat Charter rates. Just ask us! We do more for you to enjoy! Ask us also about Massage and beauty treatments. This too is now exclusively provided to guests at a discounted rate!

Top guest favorite

Home in Stake Bay

5 out of 5 average rating, 64 reviews

Modern Oceanfront, 2Primary Suites, sleeps 6, pool

Only a short 35-minute flight from Grand Cayman, this newer home provides stunning oceanfront vistas with all modern amenities to enjoy barefoot luxury. Large windows and the open concept floor plan allow breathtaking views of the pool and sea and include a fully-equipped kitchen, dining, and living areas. Also overlooking the ocean are two primary king-size bed suites with tiled baths. A third bedroom has a queen bed and views of tropical foliage.

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

This home and property are legend on the island. Spacious rooms decorated by an art collector, showers so roomy a curtain isn't needed, a gourmet kitchen, a full top-tier entertainment system- these are just a few of the amenities awaiting you! Sea Fan Meadows is located on two acres of ocean front, parrot occupied secluded property. Located directly off shore from a reef, the location offers the best of Brac snorkeling right in your backyard.

Guest favorite

A cozy bedroom is equipped with a spacious bed dressed in a patterned gray coverlet. Two windows allow natural light to fill the space, complemented by light gray walls. A bedside lamp and a small nightstand are positioned beside the bed, enhancing the room's functionality.

Condo in Cayman Brac

5 out of 5 average rating, 10 reviews

Cayman Brac, Carib Sands 221- "Stumble Inn"

Take it easy at this unique and tranquil getaway. Carib Sands is a quiet and restful place with a pool and boat dock with hammocks on the upper deck. While relaxing or reading you can enjoy the breeze. Also you can watch the fish swim around down below. The Stumble Inn has been freshly painted and new flooring installed alone with a new Queen size Murphy bed in the living room. The balcony is a great place to watch the ocean and boats go by.

Guest favorite

A two-story building is set back from a sandy beach, surrounded by lush greenery. Bright blue adirondack chairs are arranged in a small group on the beach, inviting relaxation under the palm trees.

Apartment in Cayman Brac

4.91 out of 5 average rating, 23 reviews

Featherstone - Downstairs Beach Front Apartment

This apartment on the ground floor of the main building at Featherstone and has incredible panoramic views of the sea and direct access to the beautiful beach - one of Cayman Brac's nicest. The apartment is well appointed and shares the private beach & pool with the other 2 units. Other communal items include laundry room, games room, hammocks, bikes, kayak, ping pong table, BBQ area and fire pit. Featherstone is the perfect place to unwind.