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Cayman Islands Vacation Rentals & Condos with Swimming Pool - 82 Rentals Available.

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82 Vacation rentals

Filters applied: Swimming pool

(43)

1 / 41

Rum Point House

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

$300.00

Excellent (43 reviews)

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from $300.00 / night

(16)

1 / 24

North Side Villa

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

$540.00

Excellent (16 reviews)

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from $540.00 / night

(4)

1 / 29

Seven Mile Beach Apartment

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

$515.00

Excellent (4 reviews)

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from $515.00 / night

(36)

1 / 16

North Side Villa

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

$259.00

Excellent (36 reviews)

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from $259.00 / night

(12)

1 / 100

Little Cayman House

  • 8
  • 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$400.00

Excellent (12 reviews)

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from $400.00 / night

(3)

1 / 7

North Side Villa

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

$259.00

Very Good (3 reviews)

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from $259.00 / night

(26)

1 / 34

North Side Villa

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

$500.00

Excellent (26 reviews)

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from $500.00 / night

(39)

1 / 39

Seven Mile Beach Condo

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

$280.00

Excellent (39 reviews)

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from $280.00 / night

(3)

1 / 24

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

$185.00

Excellent (3 reviews)

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from $185.00 / night

1 / 30

Rum Point Villa

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

$239.00

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from $239.00 / 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

$1,000.00

Excellent (6 reviews)

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from $1,000.00 / night

1 / 43

Cayman Brac Apartment

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

$170.00

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from $170.00 / night

(1)

1 / 9

Cayman Brac Townhouse

  • 2
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$200.00

Excellent (1 reviews)

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from $200.00 / night

(1)

1 / 24

Rum Point Condo

  • 2
  • 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$175.00

Excellent (1 reviews)

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from $175.00 / night

1 / 13

Seven Mile Beach Apartment

  • 2
  • 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$240.00

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from $240.00 / night

(15)

1 / 20

West Bay Apartment

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

$180.00

Very Good (15 reviews)

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from $180.00 / night

(24)

1 / 12

Seven Mile Beach Apartment

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

$190.00

Excellent (24 reviews)

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from $190.00 / night

(2)

1 / 21

Seven Mile Beach Apartment

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

$430.00

Excellent (2 reviews)

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from $430.00 / night

1 / 25

Seven Mile Beach Apartment

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

$500.00

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from $500.00 / night

1 / 20

West Bay Apartment

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

$200.00

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from $200.00 / night

1 / 13

West Bay Apartment

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$155.00

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from $155.00 / night

1 / 15

George Town Apartment

  • 2
  • 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$240.00

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from $240.00 / night

(14)

1 / 17

Seven Mile Beach Apartment

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

$150.00

Very Good (14 reviews)

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from $150.00 / night

1 / 17

West Bay Apartment

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

$250.00

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from $250.00 / night

1 / 24

West Bay Apartment

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

$190.00

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from $190.00 / night

1 / 23

Camana Bay Apartment

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

$150.00

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from $150.00 / night

1 / 15

Seven Mile Beach Apartment

  • 3
  • 7
  • Min stay varies
  • Swimming pool
  • Child friendly

$275.00

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from $275.00 / night

(2)

1 / 24

Seven Mile Beach Apartment

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

$500.00

Excellent (2 reviews)

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from $500.00 / night

1 / 20

North Side Villa

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

$340.00

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from $340.00 / night

1 / 20

Seven Mile Beach Apartment

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

$300.00

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from $300.00 / night

(10)

1 / 11

North Side Apartment

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

$170.00

Excellent (10 reviews)

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from $170.00 / night

(3)

1 / 17

Seven Mile Beach Apartment

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

$225.00

Excellent (3 reviews)

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from $225.00 / night

(3)

1 / 26

Bodden Town Villa

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$570.00

Excellent (3 reviews)

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from $570.00 / night

(9)

1 / 14

North Side Apartment

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

$170.00

Very Good (9 reviews)

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from $170.00 / night

(3)

1 / 23

Seven Mile Beach Apartment

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

$180.00

Very Good (3 reviews)

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from $180.00 / night

1 / 19

Seven Mile Beach Apartment

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$225.00

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from $225.00 / night

1 / 21

Seven Mile Beach Apartment

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

$300.00

Inquire

from $300.00 / night

(5)

1 / 11

North Side Apartment

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

$155.00

Very Good (5 reviews)

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from $155.00 / night

1 / 16

North Side Apartment

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

$160.00

Inquire

from $160.00 / night

(2)

1 / 16

North Side Villa

  • 2
  • 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$295.00

Excellent (2 reviews)

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from $295.00 / night