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Cayman Islands Vacation Rentals & Condos with Swimming Pool - 76 Rentals Available.

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76 Vacation rentals

Filters applied: Swimming pool

(24)

1 / 34

North Side Villa

  • 3
  • 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool

$500

Excellent (24 reviews)

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from $500 / night

(13)

1 / 24

North Side Villa

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

$625

Excellent (13 reviews)

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from $625 / night

(38)

1 / 39

Seven Mile Beach Condo

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

$271

Excellent (38 reviews)

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from $271 / night

(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

(4)

1 / 29

Seven Mile Beach Apartment

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

$516

Excellent (4 reviews)

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from $516 / night

(35)

1 / 16

North Side Villa

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

$229

Excellent (35 reviews)

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from $229 / night

(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

$857

Excellent (6 reviews)

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from $857 / night

(41)

1 / 41

Rum Point House

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

$300

Excellent (41 reviews)

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from $300 / night

(3)

1 / 7

North Side Villa

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

$229

Very Good (3 reviews)

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from $229 / night

(2)

1 / 6

Little Cayman Condo

  • 3
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We stayed at this idyllic beach cottage in Little Cayman. With two separate cottages there was enough room and privacy for all of us (4 adults). You stepped out every morning on to your own private beach. Walking distance from all amenities....”
- Review left on 12/13/2016

$400

Excellent (2 reviews)

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from $400 / night

1 / 20

West Bay Villa

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

from $400 / night

1 / 43

Cayman Brac Apartment

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

$171

Book

from $171 / night

1 / 19

Grand Cayman House

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

from $500 / night

1 / 12

West Bay Apartment

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

from $251 / night

1 / 28

Bodden Town Villa

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

from $251 / night

(3)

1 / 23

Grand Cayman Apartment

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

$180

Very Good (3 reviews)

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from $180 / night

1 / 13

West Bay Apartment

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

from $156 / night

1 / 22

Grand Cayman Villa

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $460 / night

(3)

1 / 18

Grand Cayman Apartment

  • 2
  • 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$300

Excellent (3 reviews)

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from $300 / night

(11)

1 / 14

Little Cayman Villa

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$360

Excellent (11 reviews)

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from $360 / night

(2)

1 / 13

Grand Cayman Villa

  • 2
  • 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$296

Very Good (2 reviews)

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from $296 / night

1 / 17

Grand Cayman Apartment

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

from $300 / night

1 / 19

North Side Villa

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

from $325 / night

(4)

1 / 22

Grand Cayman Villa

  • 4
  • 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$431

Excellent (4 reviews)

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from $431 / night

(2)

1 / 17

Grand Cayman Apartment

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

$300

Very Good (2 reviews)

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from $300 / night

(5)

1 / 27

Seven Mile Beach Apartment

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

$136

Very Good (5 reviews)

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from $136 / night

(15)

1 / 24

Grand Cayman Villa

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

$396

Excellent (15 reviews)

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from $396 / night

(1)

1 / 17

George Town Apartment

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

$300

Excellent (1 reviews)

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from $300 / night

(20)

1 / 20

Grand Cayman Apartment

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

$156

Very Good (20 reviews)

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from $156 / night

(13)

1 / 17

Grand Cayman Apartment

  • 2
  • 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$151

Very Good (13 reviews)

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from $151 / night

1 / 18

Grand Cayman Apartment

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

from $300 / night

1 / 21

West Bay Apartment

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

from $191 / night

(9)

1 / 23

Grand Cayman Apartment

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

$251

Very Good (9 reviews)

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from $251 / night

(9)

1 / 11

Grand Cayman Apartment

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

$171

Excellent (9 reviews)

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from $171 / night

(23)

1 / 12

Grand Cayman Apartment

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

$191

Excellent (23 reviews)

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from $191 / night

(1)

1 / 21

Grand Cayman Apartment

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

$500

Very Good (1 reviews)

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from $500 / night

1 / 25

Seven Mile Beach Apartment

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

from $500 / night

(1)

1 / 13

Grand Cayman Apartment

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

$185

Excellent (1 reviews)

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from $185 / night

(1)

1 / 17

Grand Cayman Apartment

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

$225

Excellent (1 reviews)

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from $225 / night

(8)

1 / 22

Grand Cayman Villa

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

$256

Very Good (8 reviews)

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from $256 / night