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Cayman Islands Vacation Rentals & Condos - 107 Rentals Available

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107 Vacation rentals

(41)

1 / 41

Rum Point House

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$300

Excellent (41 reviews)

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from $300 / night

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(1)

1 / 53

Rum Point Villa

  • 3
  • 6
  • Min stay varies
  • Child friendly
  • Air conditioning

$1000

Excellent (1 reviews)

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from $1000 / night

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(1)

1 / 24

Rum Point Condo

  • 2
  • 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$180

Excellent (1 reviews)

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from $180 / night

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(14)

1 / 24

North Side Villa

  • 4
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

$625

Excellent (14 reviews)

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from $625 / night

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1 / 30

Rum Point Villa

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly

$199

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from $199 / night

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(2)

1 / 6

Cayman Brac Apartment

  • 1
  • 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden

$171

Excellent (2 reviews)

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from $171 / night

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(36)

1 / 16

North Side Villa

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$219

Excellent (36 reviews)

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from $219 / night

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(4)

1 / 8

North Side House

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$179

Very Good (4 reviews)

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from $179 / night

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1 / 30

Rum Point Villa

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$199

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from $199 / night

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(1)

1 / 11

Little Cayman Condo

  • 2
  • 6
  • Min stay varies
  • Ask about children
  • Air conditioning

$295

Excellent (1 reviews)

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from $295 / night

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(4)

1 / 29

Seven Mile Beach Apartment

  • 3
  • 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$360

Excellent (4 reviews)

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from $360 / night

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(25)

1 / 34

North Side Villa

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool

$500

Excellent (25 reviews)

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from $500 / night

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(3)

1 / 7

North Side Villa

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$219

Very Good (3 reviews)

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from $219 / night

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(7)

1 / 5

Cayman Brac Cottage

  • 1
  • 3
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
“We truly loved our vacation at this wonderful destination. Everything was perfect. My absolute favorite part was listing to the waves at night while going to sleep and feeling the soft sea breeze flow through our beautiful cottage. The mornings I...”
- Review left on 02/12/2015

$171

Very Good (7 reviews)

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from $171 / night

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1 / 22

George Town Condo

  • 3
  • 6
  • Min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Ask about children

$850

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from $850 / night

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(1)

1 / 19

Rum Point Condo

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Air conditioning
“The title says it all. A wonderful 3 week stay in this condo. The condo is very clean and has everything you need for a self-catering holiday. The location is a bit remote but well worth it. Beautiful views and a very quiet part of the island....”
- Review left on 02/04/2016

$200

Excellent (1 reviews)

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from $200 / night

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(3)

1 / 21

Rum Point Apartment

  • 1
  • 5
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Mi Casa, Su Casa does exactly what it says on the tin! This beautiful Caribbean hideaway has captured the perfect balance between the stunning tropical picture perfect location, luxurious accommodation and vacation activities. We loved this...”
- Review left on 08/10/2015

$200

Excellent (3 reviews)

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from $200 / night

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1 / 24

Seven Mile Beach Condo

  • 4
  • 8
  • Min stay varies
  • Child friendly
  • Air conditioning

$1200

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from $1200 / night

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(1)

1 / 37

George Town Villa

  • 6
  • 17
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“Seascape is everything a big group could want. An absolutely beautiful house, right on Seven Mile Beach. Yuri, the on site manager, is wonderful. You can walk to a beach bar, and some of the most wonderful restaurants are also within walking...”
- Review left on 07/14/2016

$1920

Excellent (1 reviews)

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from $1920 / night

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(38)

1 / 39

Seven Mile Beach Condo

  • 2
  • 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

$260

Excellent (38 reviews)

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from $260 / night

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1 / 16

Seven Mile Beach Condo

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$225

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from $225 / night

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(1)

1 / 20

West Bay Villa

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$399

Excellent (1 reviews)

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from $399 / night

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(1)

1 / 9

Cayman Brac Townhouse

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$200

Excellent (1 reviews)

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from $200 / night

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1 / 25

Seven Mile Beach Condo

  • 4
  • 8
  • 14 nights min
  • Child friendly
  • Air conditioning

$1200

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from $1200 / night

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(12)

1 / 100

Little Cayman House

  • 8
  • 20
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$400

Excellent (12 reviews)

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from $400 / night

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1 / 43

Cayman Brac Apartment

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$170

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from $170 / night

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(6)

1 / 24

Seven Mile Beach Condo

  • 4
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This was our fourth time to the island. We travelled with 4 other couples. This was one of the few places we could find where we could all stay together. This condo was beyond perfect for our group. Every detail of the condo was perfect. We enjoyed...”
- Review left on 10/22/2016

$858

Excellent (6 reviews)

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from $858 / night

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(1)

1 / 24

Seven Mile Beach Condo

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“Harbor Heights #6 was great for our January getaway. Updated, clean, well-equipped and the great property location added to the enjoyment of Cayman! The kitchen was so great that we cooked in all but one night! The owners considered all needs when...”
- Review left on 01/10/2017

$315

Very Good (1 reviews)

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from $315 / night

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1 / 20

Seven Mile Beach Condo

  • 4
  • 8
  • Min stay varies
  • Child friendly
  • Air conditioning

$1200

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from $1200 / night

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(1)

1 / 19

North Side Villa

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$375

Excellent (1 reviews)

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from $375 / night

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(1)

1 / 28

Bodden Town Villa

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly

$250

Excellent (1 reviews)

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from $250 / night

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1 / 20

Bodden Town Villa

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$155

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from $155 / night

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(5)

1 / 16

Little Cayman Villa

  • 3
  • 9
  • Min stay varies
  • Child friendly
  • Air conditioning

$270

Excellent (5 reviews)

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from $270 / night

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1 / 20

West Bay Apartment

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$155

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from $155 / night

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1 / 24

West Bay Apartment

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$190

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from $190 / night

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(5)

1 / 13

Little Cayman Villa

  • 3
  • 6
  • Min stay varies
  • Child friendly
  • Air conditioning

$225

Very Good (5 reviews)

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from $225 / night

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(10)

1 / 25

Cayman Islands Villa

  • 6
  • 15
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“The luxury furnishings and appointments of this home are exemplary, and far exceeds most rental properties on Cayman Kai for the price. You will want for nothing at Treasure Cove (outside of maybe a couple of bikes would've been nice). The master...”
- Review left on 04/04/2017

$750

Excellent (10 reviews)

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from $750 / night

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(1)

1 / 24

Grand Cayman Villa

  • 6
  • 15
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$400

Excellent (1 reviews)

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from $400 / night

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1 / 13

West Bay Apartment

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$155

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from $155 / night

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(14)

1 / 14

Grand Cayman Apartment

  • 1
  • 4
  • Min stay varies
  • Child friendly
  • Air conditioning

$145

Very Good (14 reviews)

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from $145 / night

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About Cayman Islands

Calm blue waters, white sand, and swaying palm trees are the hallmarks of the Cayman Islands. Located south of Cuba and west of Jamaica, the Caymans are becoming the place to vacation in the Caribbean. Cayman Islands vacation rentals are perfect for families who want the comforts of home as they explore this island paradise. The Cayman Islands have so much beauty and adventure to offer its visitors, and this destination can’t be missed.

Climate

The Caymans enjoy a tropical marine climate. Temperatures hold steady around 80 degrees Fahrenheit during the summer and hover around 70 degrees in the winter. Summer is the wet season for the Cayman Islands, and it lasts from May to October. Winters are relatively dry and cool by island standards. The best time to visit the Cayman Islands is between May and June when temperatures are at their best and the weather is calm and clear.

Areas within the Cayman Islands

The Caymans consist of three islands: Grand Cayman, Cayman Brac, and Little Cayman. Grand Cayman is the largest of the three islands. Historic George Town offers fine dining and duty-free shopping among traditional Caribbean-style buildings. Cayman Brac has the most spectacular landscape of the three islands. Book Cayman Island vacation rentals with wonderful views of the limestone outcropping, or “brac,” in the center of the island which gives Cayman Brac its name. Little Cayman is smaller and less developed than its sisters but is world famous for scuba diving and has more than 50 unique dive sights.

Things to Do

The Cayman Islands are a playground for seaside activities and entertainment. On Grand Cayman, enjoy the white sands and crystal waters of Seven Mile Beach, voted one of the world’s ultimate beaches. When you’re not cooling off in the water or strolling along the sand at Seven Mile Beach, you can get up close and personal with the local wildlife at Stingray City and interact year-round with the friendly southern stingray here. Offshore, scuba dive through the warm, cerulean waters, explore man-made reefs like the USS Kittiwake. Visit the South Hole Sound Lagoon or dive at Bloody Bay Wall Marine Park on Little Cayman to see the brilliant underwater landscape.

Away from the sandy beaches, visit the imposing, three-story Pedro St. James Castle in Savannah, learn about the maritime past of the Cayman Islands at East End Lighthouse Park and discover the history of the Cayman Islands at the National Museum. Take the kids to Booby Pond Nature Reserve on Little Cayman, and see red-footed boobies at the largest colony in the Western Hemisphere. Birdwatching is popular on Cayman Brac where visitors can catch a glimpse of more than 200 species that call the island home.

Food & Dining

The cuisine of the Cayman Island is a mix of Jamaican, British, and native culinary traditions often supplemented with international flair. Local dishes contain native fruits, such as coconuts, plantains, breadfruit, and cassava, and reflect the abundance of the islands. Seafood is also prevalent in a variety of chowders and stews that contain conch, lobster, shrimp, and fresh fish. These local and Caribbean ingredients can be found in the dishes served up Upstairs at Kaibo, a renowned restaurant overlooking the serene North Sound. For casual dining with a colorful, Caribbean flair, head to Sunshine Grill, a favorite of the locals in Grand Cayman. For fishing enthusiasts, some restaurants even have “you catch, we cook” options.

Whether you enjoy swimming, diving, learning or simply relaxing, the Cayman Islands have something for every vacationer. Cayman Islands vacation rentals offer the perfect home away from home during your getaway and will allow you to see the island through the eyes of a local. There’s no place quite like the Cayman Islands for an island retreat.

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