Vacation rentals in Little Cayman

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Top-rated vacation rentals in Little Cayman

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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.

Guest favorite

The image captures a serene beach scene at sunset, featuring two palm trees standing on sandy shores. A calm ocean reflects the orange and pink hues of the sky, while a wooden pier is visible in the distance. A kayak is gently positioned on the sand.

Apartment in Little Cayman

5 out of 5 average rating, 5 reviews

"A Shore Ting" Newest property to market in LCM!

New! The only beachfront unit available within the quaint and charming complex of Neptune's Berth, this ground floor unit boasts a 40' porch on THE most desirable strip of beach on Little Cayman. Enjoy morning coffee while you watch the sunrise on the porch, and a sundowner on the dock as you watch the sunset. Within walking distance to all stores, hotels, dive boats, restaurants and airport, yet it feels totally secluded and serine. We can’t wait to share the magic of this property with you!

Tall palm trees frame a serene beach scene, leading to clear turquoise waters. A wooden dock extends into the water, while lush green shrubs border the sandy shore. The bright blue sky enhances the tranquil atmosphere of the outdoor space.

Condo in Blossom Village

4.82 out of 5 average rating, 61 reviews

Conch Club 16, Little Cayman, Cayman Islands

Walk directly from your condo to the palm shaded beach or one of the pools on this very tranquil little island. Enjoy the best diving in the Cayman Islands, great fishing, long walks on the beach, explore the Island on a bike or simply feel the breeze while relaxing on your patio. Take a chance fishing from the wooden dock or a very short paddle in the kayak to Owen's Island - a real desert island. Conch Club is a lovely place to unwind, experience the underwater world and a life on the beach!

Superhost

A light blue two-story house is surrounded by lush greenery and features a flowering bougainvillea tree. A wooden staircase leads to the upper level, enhancing the home's coastal charm. Adjacent to the house, sandy beach and tropical foliage create a serene outdoor atmosphere.

Home in West End

4.85 out of 5 average rating, 13 reviews

The Ocean Odyssey Main Guest House - Sonscape

On the beautiful island of Cayman Brac, enjoy Sonscape's oceanfront home with amazing sunsets from the deck while being serenated by the surf and fanned by tropical breezes! Stroll our lovely beach and relax in a hammock under the palm trees. Locals claim this is the best natural sandy beach on the Brac to watch the sunsets. There is excellent snorkeling and diving right off our beach with small shallow reefs that have an assortment of colorful fish, sea fans, brain coral and soft corals.

Guest favorite

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, 49 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.

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

An aerial view captures the cottage nestled among lush greenery, with the Caribbean Sea visible in the background. The property features a private pool surrounded by sun loungers and is bordered by a sandy beach, creating a serene coastal environment.

Cottage in KY

5 out of 5 average rating, 13 reviews

Humble and Polite Little Cayman

Relax with the whole family at this peaceful oasis. Situated on private acreage in Preston Bay, on the West End of Little Cayman, this 3-bedroom cottage has absolutely everything you need. Unobstructed views of the Caribbean Sea with a one-of-a-kind edge salt water pool and hot tub set on a raised deck with cool-to-touch stone tiles, it’s easy to enjoy being surrounded by nature and comfortable breezes. Great for couples, families, or a small group retreat.

Guest favorite

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 favorite

An aerial view of the Featherstone Estate reveals a private beach with crystal-clear waters and lush greenery. Three units are nestled among palm trees, and a pool is seen adjacent to the beach. The shoreline is framed by rocky outcrops extending into the turquoise sea.

Place to stay in Cayman Brac

5 out of 5 average rating, 11 reviews

Featherstone - The Estate

Rent the entire Featherstone Estate for a secluded get away with family or friends. Comprising of 3 separate units on a beautiful private beach this is the perfect place to get away from it all. Featherstone can easily accommodate 3 families, each with their own private space, or groups of up to 15 people. All units are well appointed and there is a communal pool, laundry room, games room, hammocks, bikes, kayak, ping pong table, BBQ area and fire pit.

Top guest favorite

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, 65 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!

Superhost

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.

Apartment in Cayman Brac

4.9 out of 5 average rating, 40 reviews

Two Bed Beach Apt-Close to Shops, Restaurants

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.