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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Villa in Stake Bay

5 out of 5 average rating, 8 reviews

Hot Tub Stargazing 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!

Superhost

Condo in Sister Islands

4.83 out of 5 average rating, 35 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.

Guest favorite

Home in Stake Bay

5 out of 5 average rating, 47 reviews

Modern Oceanfront, 2Primary Suites, sleeps 6, pool

We offer a Hurricane Worry-free Guarantee. Only a short 25-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 for breathtaking views of the pool and sea and include a fully-equipped kitchen, dining, and living areas. Also overlooking the ocean are two master king-size bed suites with tiled baths. A third bedroom has a queen bed and views of tropical foliage.

Guest favorite

Home in Sister Islands

5 out of 5 average rating, 26 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.

Guest favorite

Bungalow in Cayman Brac

5 out of 5 average rating, 27 reviews

Brac Magic - magical oceanfront home with pool

"Brac Magic" truly lives up to its name. Built in 2017, this magical oceanfront home has 2 bedrooms and sleeps 6-8, with 2 1/2 baths. It's air conditioned and has all of the amenities, including washer/dryer, fully equipped kitchen, smart tv, wifi, BBQ, rinse station and drying rack for dive gear. Relax in the pool or in a hammock in the shade while listening to the waves crash. It's secluded and peaceful here, away from the populated areas but only a short drive to everything you need.

Guest favorite

Home in West End

5 out of 5 average rating, 15 reviews

POOL, sandy beach w/cabana, wi-fi, a/c, sunsets

Truly Amazing Tropical Beach Paradise on the Water w/Pool. Prop has private entrances, full kitchen (with everything), dining, living, full bathroom, beach cabana, hammocks, bikes available, grill, kayaks, fire pit. WiFi. Great snorkeling right out front. Great sunsets! One of the few rental places on the island with a sandy beach. Leeward side of the island so many days with calm waters. Local cell phone provided. Washer and Dryer, TV, Linens, beach and bath towels & more. 1 of only 3 units.

Guest favorite

Home in Cayman Brac

5 out of 5 average rating, 14 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

Home in Cayman Brac

4.74 out of 5 average rating, 50 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!

Home in Stake Bay

5 out of 5 average rating, 14 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

Condo in Cayman Brac

5 out of 5 average rating, 7 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

Rental unit in Tibbett's Turn

4.9 out of 5 average rating, 20 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.