Vacation rentals in Sister Islands

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Top-rated vacation rentals in Sister Islands

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Superhost

Condo in Blossom Village

4.85 out of 5 average rating, 52 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!

Nov 9 – 16

$288 per night

Guest favorite

Home in Stake Bay

5.0 out of 5 average rating, 35 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.

Mar 11 – 18

$435 per night

Guest favorite

Home in West End

5.0 out of 5 average rating, 12 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.

Sep 14 – 21

$129 per night

Guest favorite

Home in Cayman Brac

4.86 out of 5 average rating, 72 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

Jul 7 – 14

$152 per night

Superhost

Guesthouse in Cayman Brac

4.94 out of 5 average rating, 18 reviews

Vista Del Mar Beach House#2

This Lovely new Beach House is located on the South Side, West End of Cayman Brac, Walking Distance to Restaurants and Bars, Dive Shop, Big daddy's Liquor Store. Our Guest House Features 2 separate Units each with one bedroom and a pull out Sofa bed. one Bathroom, and Kitchen. Amenities include Internet Wifi and Television Vista Del Mar Beach house is perfect for a Romantic Getaway with Beautiful Ocean views of the Sea. Open Porch at the Beach, Deck Chairs and Hammock. Perfect Relaxation.

Dec 11 – 18

$152 per night

Guest favorite

Townhouse in Blossom Village

4.97 out of 5 average rating, 30 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.

Oct 15 – 22

$402 per night

Guesthouse in West End

4.79 out of 5 average rating, 53 reviews

Ocean Retreat

Hear and see the ocean in this beautiful, newly remodeled 670 Sq. Ft, one bedroom ocean view cottage features an open floor plan enabling you to interact with others easily. It has free US/Canada phone calls, local cell, central air, living room areas, all new kitchen with gorgeous vanilla cabinetry and quartz countertop, new appliances, bottled water quality water through an iSpring 5 Stage water purifier, new furniture, new premium pillow top mattress and updated bathroom.

Sep 19 – 26

$143 per night

Guest favorite

Guesthouse in West End

4.92 out of 5 average rating, 12 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.

Jun 9 – 16

$158 per night

Guest favorite

Home in Blossom Village

4.94 out of 5 average rating, 17 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 in every room, Wi-Fi, Sonos speaker, BBQ grill, paddleboards, and bikes. The perfect place to enjoy the magic of island life.

Aug 7 – 14

$333 per night

Guest favorite

Home in Tibbett's Turn

5.0 out of 5 average rating, 5 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 laundry room, games room, hammocks, bikes, kayak, ping pong table, BBQ area and fire pit.

Jul 23 – 30

$800 per night

Condo in Cayman Brac

5.0 out of 5 average rating, 4 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.

Oct 21 – 28

$136 per night

Guest favorite

Home in Little Cayman

4.97 out of 5 average rating, 144 reviews

Just Chillin in Little Cayman

Just Chillin is a new 2 bedroom house that connects to a semi private pool, with queen size bed in both bedrooms, it is close to the airport, store and restaurants, the true Island life. Little Cayman is One mile wide and 10 miles long, we also provide bikes if you’re adventurous, our waters are blue and crystal clear for the divers and People that like to snorkel, it is Paradise, and tranquility for the people that just want to chill!

Aug 26 – Sep 2

$178 per night