Little Cayman vacation rentals

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Top-rated vacation rentals in Little Cayman

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Blossom Village

4.85 out of 5 average rating, 54 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!

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 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

4.86 out of 5 average rating, 74 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

Superhost

Rental unit in Blossom Village

5 out of 5 average rating, 3 reviews

Beachfront Relaxation - Beautiful Conch Club!

Conch Club is a fantastically relaxing and tranquil complex overlooking beautiful South Hole Sound on the south shore of one of the most amazing islands in the world, Little Cayman. This condo is within sight of and a short kayak away from Owen Island (a throwback to Gilligan's Island). Next door is Southern Cross Club, a 5 minute walk down the beach is Little Cayman Beach Resort, and across the street is the Booby Pond Nature Reserve, which teams with unique and beautiful bird species.

Superhost

Guesthouse in West End

4.92 out of 5 average rating, 13 reviews

The Sandy Beach Retreat Guest Suite - Sonscape

Enjoy Sonscape's beachfront guest suite and escape stress with swaying palms, tropical breezes and a private sandy beach. Relax in hammocks, enjoy magnificent sunsets and incredible stars. Guests say this is the nicest natural sand beach on the island and locals claim it is the best spot on Cayman Brac to watch the sunsets and catch a green flash. The guest apartment door is located 100 feet from the water and offers excellent snorkeling and diving right off the beach.

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!

Guest favorite

Cottage in KY

5 out of 5 average rating, 9 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

Home in Blossom Village

4.96 out of 5 average rating, 28 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

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.

Guest favorite

Condo in Stake Bay

4.96 out of 5 average rating, 28 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!