Holiday rentals in Sister Islands

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Top-rated holiday rentals in Sister Islands

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Guest favourite
An aerial view captures the stunning turquoise waters surrounding Little Cayman. The cottage is marked and situated along the serene coastline, with lush greenery nearby and smaller islands visible in the distance. Boats can be seen dotting the water, highlighting the area's natural beauty.
Bungalow in Blossom Village
5 out of 5 average rating, 7 reviews

Conch Club Cottage

This quaint 600 sq ft detached vacation Cottage has everthing you a need to experience the charm of Little Cayman. Includes all amenities of Conch Club (2 pools, dock, spa, snorkeling, shore diving, largest beach, 2 kayaks for both ocean and Booby Pond Nature Reserve, and 3 bikes). Within 5-10 min walking distance to all that Blossom Village has to offer, including restaurants, bars, shopping, grocery and hardware store, liquor shop, museums and the Booby Birding Center this Cottage has it all.

Top guest favourite
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, 31 reviews

Bliss Beach House - Secluded, Oceanfront, Pool

Recently constructed, this one-bedroom waterfront home sits on approximately an acre of land with 100 feet of oceanfront. Our secluded south-side east beach property features a private pool and comfortable, shaded seating area. The house offers utmost privacy, as there are no close neighbours and with only one residence on the property, you will not share it with anyone else, nor will you share the pool. We are situated on Cayman Brac, a 30-minute flight from Grand Cayman via Cayman Airways.

A beachfront house is visible against a clear blue sky, surrounded by swaying palm trees. The structure features three large front-facing windows, with a porch that includes comfortable seating. The sandy beach extends towards the gentle waves lapping at the shore.
Home in Cayman Brac
4.81 out of 5 average rating, 90 reviews

Southern Exposure, Secluded Paradise, Cayman Brac

On the Beach! Divers paradise! Beautiful slice of heaven on the exclusive south side of Cayman Brac. Stunning views from the windows - 100 ft of beachfront to call your own. The sea on one side, and the stunning and majestic bluff across the road. Pristine with luxury features to ensure you are comfortable. Local rates available! We have a 5 night minimum but please request for shorter stays. We look forward to hosting you at our island beach home! Jen & Rick IG: southernexposurecb

Top guest favourite
A wooden dock extends into clear turquoise water, leading toward a beach lined with palm trees and a row of beachfront properties. Fluffy clouds above are set against a bright blue sky, creating a serene coastal atmosphere.
Townhouse in Blossom Village
4.98 out of 5 average rating, 52 reviews

Stunning Little Cayman 3 Bedroom Beach Townhouse

Conch Club is a short walk up or down the down the beach to two restaurants and bars and a short bike ride to Blossom Village. Conch Club has a lovely beach, two pools, hot tub, a dock and spectacular views to the reef, Owen Island and perfect sunsets. Our newly refurbished 3 bedroom, 3 bathroom end town house has new furniture throughout and will sleep 9 people and is fully equipped and even has pool table, two Kayaks a stand up / sitdown paddle board, four old bikes and a gas BBQ.

Guest favourite
A charming outdoor area features rocking chairs arranged around a circular table, surrounded by sandy grounds and shade from leafy trees. The cottage is visible in the background, showcasing its light-colored exterior and large windows that invite natural light.
Home in Cayman Brac
5 out of 5 average rating, 6 reviews

Breezy Bluff Cottage

Breezy Bluff Cottage is a piece of paradise nestled between the Caribbean Sea and the majestic Cayman Brac bluff. This traditional but modern Cayman cottage is situated on a private beach. Enjoy the outdoor barbeque area, drink under a seagrape tree, bike ride, glass bottom kayak or dive into a book in one of the rocking chairs in what are the stunning surrounds of Breezy Bluff Cottage. Beach Resort is located 2 miles away from the cottage where you can use a pool and beach chairs.

Guest favourite
A shaded veranda features a wooden dining table set with breakfast items and drinks, alongside a hammock. The view captures the horizon during sunrise, surrounded by vibrant greenery and coastal scenery.
Home in Blossom Village
4.95 out of 5 average rating, 40 reviews

Gorgeous Beach House in Little Cayman

Situated on 160ft of private beach, this rustic beach house is the perfect place to relax and unwind in beautiful Little Cayman. Watch the sunrise from the wraparound veranda and enjoy a lazy afternoon in the hammock. This spacious beach house has everything you need for the perfect vacation, including a comfy King bed, air conditioning, Wi-Fi, Sonos speaker, BBQ grill, paddleboards, and bikes. The perfect place to enjoy the simple magic of island life.

Guest favourite
A light blue building is seen, featuring a white door and two white chairs placed on a small patio area. Bougainvillea with vibrant pink flowers is visible near the entrance, enhancing the natural surroundings. Stone pathways and a sandy area are part of the landscape.
Flat in West End
4.94 out of 5 average rating, 18 reviews

Sonscape's Cozy 1-Bdr 1-Bath Private Beach Suite!

On the beautiful island of Cayman Brac, enjoy Sonscape's private and cozy 1-bedroom 1-bath suite that opens right onto the beach and is located 100 feet from the water, offering excellent snorkeling and diving. Relax in a hammock, enjoy magnificent sunsets and incredible stars. The West End is also where everything is located - the airport, stores, restaurants - you're centrally located but you're still in a very private place at the end of the street.

Top guest favourite
The outdoor area features a large swimming pool with a built-in jacuzzi, surrounded by lounge chairs and tropical vegetation. A shaded cabana is visible, providing an area for relaxation with ocean views beyond. The clear blue water and bright sky create a serene atmosphere.
Home in Stake Bay
5 out of 5 average rating, 70 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.

Superhost
Aerial view of a serene coastal landscape shows two blue houses situated near a rocky shoreline. Lush greenery surrounds the properties, with the turquoise waters of the ocean gently lapping at the rocks. A clear sky with scattered clouds completes the tranquil setting.
Home in Blossom Village
4.25 out of 5 average rating, 8 reviews

THE ROCK HOUSE with private beach on Little Cayman

This is absolutely a get-away-from-it-all vacation! On a remote island (Little Cayman), just like Gilligan's island, you will not be disturbed by anyone. A pristine "dive" destination, plenty of fishing and lobster hunts or simply relax in the hammock at the outdoor tiki bar It will feel like you are staying on your own private island - there are a few restaurants, dive resorts and fishing tours available. You will not regret this vacation!

Guest favourite
A cozy beachfront cottage is surrounded by palm trees and tropical greenery. Loungers are positioned on the sandy beach, inviting relaxation. The clear water reflects the blue sky, enhancing the tranquil atmosphere of this serene coastal setting.
Flat in Cayman Brac
4.9 out of 5 average rating, 41 reviews

Two Bed Beach Apt in Brac-Shops, Restaurants Close

Serenity On The Bay is located in peaceful and tranquil Cayman Brac. Cayman Brac is one of the three Cayman Islands. Imagine waking up to the most breathtaking view of the ocean, sound of the waves and tropical breeze. During the day enjoy the white sandy beach, excellent snorkeling and fishing right outside your door. In the evening enjoying a drink while watching a stunning sunset. Please view videos of our beach and Apt on You Tube.

Superhost
A wooden dock extends over azure waters, leading towards a beachfront villa surrounded by lush palm trees. A clear blue sky enhances the coastal setting, while soft clouds add depth to the serene atmosphere. The villa's inviting exterior complements the tropical landscape.
Villa in Sister Islands

Sir Turtle Beach Villas, Little Cayman - Blue Side

Sir Turtle Beach Villa defines Caribbean paradise. It sits on an exceptional stretch of private beachfront on small and quiet island of Little Cayman, with soft white sand to sink your feet into and an endless stretch of azure water to swim, kayak and snorkel. These two villas can be rented Individually or rented together. Base Price is per Villa for 1-6 people. Subject to extra person charges per person per day.

Top guest favourite
An aerial view captures the scenic coastline, showcasing a sandy beach gently meeting clear blue waters. Lush greenery surrounds a light-colored building, while a winding road and parked vehicles are visible in the distance.
Apartment in Stake Bay
4.98 out of 5 average rating, 45 reviews

Ocean Wave- 1 Bedroom 1 Bathroom Condo

Ocean Wave is a divers paradise with all the amenities. Just opposite the your condo is a 30 foot dock that allows for easy entry and exit to the best diving in Cayman Brac! Situated in the town center, it's a 5 minute walk to the museum and a 2 minute drive to the supermarket. Also, enjoy all the modern conveniences you would expect, strong Wifi and Netflix. Get wet or sit back and relax at Ocean Wave!

Popular amenities for Sister Islands holiday rentals