Deadman's Cay Rentals

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19 Houses

2 Bedroom/1 Bath with Sea Views in Wemyss

Deadman's Cay apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$172

2 BD 2 BTH Ocean Front Villa - Vehicle Included!

Deadman's Cay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$298

Great rentals within 20 miles that match your search

1BD 1 BTH Ocean Front Villa - Vehicle Included!

Long Island villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$224

Beautiful Oceanside House on Secluded Protected Cove

Salt Pond house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$344

Grotto Bay - Affordable Luxury On A Private Beach!

Salt Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

“Awesome stay” We stayed at Grotto Bay for a week in May. Salt Pond offers easy access to both ends of the island which you should absolutely explore. We went to numerous beaches and never had other people on them. Long Island doesn't have much to do other than beaches. There are a few restaurants and local markets, but other than that any kind of commerce is non existent. We flew in and out of Deadman's Cay and rented a car from Mr. T. Definitely recommend having a car. I wouldn't recommend Southern air, flights were late and planes iffy. As for our accommodations and hosts we couldn't have been happier. Jeannie and Kris gave us great suggestions and were more than happy to help with car reservations and general questions. The beach at the Grotto Bay is pretty and the water gorgeous. They have kayaks and paddleboards for use with islands close by to paddle to. We definitely recommend Grotto Bay and would go back with no hesitations.

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$166

C Shells Guest Quarters

Salt Pond apartment

  • 1 bathroom
  • sleeps 2

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$115

Comfy 4 BED, 2 BATH Beach Home - AT THE BEACH

Long Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

“A true get-a-way!” From the moment we landed, to the moment we left, George took care of every detail! If you are looking for a true get-a-way - this is the place. A busy day at the beach might include seeing 1 or 2 other people, otherwise you have every beach to your self! There is plenty to enjoy on the beach in from of Wymmsicalwish or take a drive, there are secluded beaches down every dirt road, each with their own unique personality. This was our second (of many more to come)visit to Whymmsical Wish. We have stayed there with our grown children and it has been throughly enjoyed by all.The guest house comfortably slept all 6 adults and we enjoyed breakfast every morning in the screened it porch. The fully equiped kitchen allowed us to make lunches and snacks to enjoy at the beach. We all were greatful for the wireless access to make sure that things were running well back at the office!

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$315

2 BED, 2 BATH COTTAGE AT THE BEACH !

Long Island cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Perfect Getaway!!” The Cabin was perfect and equipped with everything my husband and I needed!! George was the perfect host, helping us arrange a rental car, fishing guide and great local sights, including an absolutely beautiful secluded beach that we had to ourselves for the day. We enjoyed taking the kayaks out to explore. He was there to answer any questions and meet our needs but we also had plenty of privacy. We plan to return (with our kids) this winter and stay in the larger house. Even though we were able to find most of the items we needed, We will send food ahead next time because it is so expensive on the island and the choice of meats is so limited.

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$315

The Cottage at Palmirage

Long Island cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Shangri La” This is a beautiful spot. The cottage itself was very clean and lovely. The sheets were excellent, and the kitchen had every cooking utensil needed, along with heavy bottomed cookware (excellent for cooking that cracked corn for grits!) Sara and Dan are very knowledgeable, and generous with said knowledge. The beach is a short walk and is gorgeous, and quiet. No complaints whatsoever!

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$229

Baywatch Cottage

Salt Pond cottage

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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$315

BEACHFRONT HOME w/STUNNING VIEWS SECLUDED QUIET

Clarence Town villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$295

LO LA MARI

Long Island house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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$287

House of Blues at Deans Blue Hole

Long Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$344

The Boathouse at Palmirage

Long Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$344

Grotto Bay Beach House

Salt Pond house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$373

Grotto Bay - Affordable Luxury On A Private Beach!

Salt Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$166

Palm Tree hideaway

Salt Pond house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$233

Whistling Duck

Clarence Town cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 21 minutes

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Price per night from

$229

Passionate Pelican

Clarence Town cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 21 minutes

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Price per night from

$229

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