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Florida Keys Vacation Rentals & House Rentals with Swimming Pool - 130 Rentals Available.

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130 Vacation rentals

Filters applied: Swimming pool

(15)

1 / 16

Islamorada Condo

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$200

Excellent (15 reviews)

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from $200 / night

(122)

1 / 28

Key West Apartment

  • 2
  • 6
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly

$200

Excellent (122 reviews)

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from $200 / night

(13)

1 / 13

Tavernier House

  • 4
  • 12
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$300

Excellent (13 reviews)

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from $300 / night

(1)

1 / 23

Marathon Shores House

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

$358

Excellent (1 reviews)

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from $358 / night

1 / 23

Marathon Townhouse

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$245

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from $245 / night

(5)

1 / 15

Key West Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly

$228

Excellent (5 reviews)

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from $228 / night

1 / 24

Duck Key Villa

  • 3
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $535 / night

(5)

1 / 14

Key West Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly

$186

Very Good (5 reviews)

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from $186 / night

(7)

1 / 12

Key West Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$250

Very Good (7 reviews)

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from $250 / night

(9)

1 / 14

Islamorada House

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

$421

Excellent (9 reviews)

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from $421 / night

1 / 25

Marathon House

  • 4
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $320 / night

(3)

1 / 15

Tavernier House

  • 5
  • 10
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$167

Excellent (3 reviews)

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from $167 / night

1 / 24

Duck Key Villa

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $340 / night

(11)

1 / 16

Marathon House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$393

Excellent (11 reviews)

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from $393 / night

(48)

1 / 34

Cudjoe Key House

  • 6
  • 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$414

Very Good (48 reviews)

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from $414 / night

(1)

1 / 15

Key Largo Condo

  • 2
  • 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$145

Excellent (1 reviews)

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from $145 / night

(3)

1 / 33

Islamorada House

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$457

Excellent (3 reviews)

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from $457 / night

(3)

1 / 6

Key West Apartment

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

$295

Very Good (3 reviews)

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from $295 / night

(2)

1 / 16

Tavernier Condo

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

$175

Excellent (2 reviews)

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from $175 / night

(2)

1 / 23

Cudjoe Key House

  • 2
  • 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool

$157

Very Good (2 reviews)

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from $157 / night

(52)

1 / 36

Key West Condo

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

$209

Excellent (52 reviews)

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from $209 / night

(8)

1 / 8

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$243

Excellent (8 reviews)

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from $243 / night

(7)

1 / 9

Islamorada House

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

$429

Excellent (7 reviews)

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from $429 / night

(27)

1 / 16

Key Largo Villa

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$300

Very Good (27 reviews)

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from $300 / night

(3)

1 / 20

Summerland Key House

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

$233

Excellent (3 reviews)

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from $233 / night

(17)

1 / 17

Key West Townhouse

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Car not necessary

$200

Excellent (17 reviews)

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from $200 / night

(16)

1 / 15

Key Largo House

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$350

Very Good (16 reviews)

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from $350 / night

(20)

1 / 22

Key West B and B

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

$730

Excellent (20 reviews)

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from $730 / night

(17)

1 / 42

Key Largo Cottage

  • 1
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool

$100

Excellent (17 reviews)

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from $100 / night

1 / 16

Marathon House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$1000

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from $1000 / night

(2)

1 / 17

Key Largo Townhouse

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$250

Excellent (2 reviews)

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from $250 / night

(1)

1 / 20

Key Colony Beach Condo

  • 2
  • 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$103

Excellent (1 reviews)

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from $103 / night

(8)

1 / 10

Islamorada House

  • 3
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$500

Excellent (8 reviews)

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from $500 / night

(18)

1 / 26

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool

$372

Excellent (18 reviews)

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from $372 / night

(2)

1 / 18

Key West Condo

  • 3
  • 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$209

Excellent (2 reviews)

Book

from $209 / night

(11)

1 / 60

Key Largo Condo

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$128

Excellent (11 reviews)

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from $128 / night

(2)

1 / 73

Marathon House

  • 5
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$1071

Excellent (2 reviews)

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from $1071 / night

(28)

1 / 19

Marathon Villa

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$286

Excellent (28 reviews)

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from $286 / night

(1)

1 / 27

Key Largo House

  • 3
  • 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$160

Excellent (1 reviews)

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from $160 / night

(1)

1 / 34

Key Largo House

  • 4
  • 14
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$200

Excellent (1 reviews)

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from $200 / night