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Islamorada Vacation Rentals & House Rentals with Swimming Pool - 44 Rentals Available.

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44 Vacation rentals

Filters applied: Swimming pool

(19)

1 / 27

Islamorada House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 35 minutes

“This house is the best!!!!! We had two familys staying and was perfect. The separate living quarters made our trip very enjoyable and very roomy. The house upstairs is remarkable and very up to date as well as downstairs. The back yard is your own...”
- Review left on 08/09/2016

$429.00

Excellent (19 reviews)

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from $429.00 / night

(9)

1 / 14

Islamorada House

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Had a great time. Beautiful house. Very convenient to everything. We highly recommend this property...”
- Review left on 08/05/2016

$533.00

Excellent (9 reviews)

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from $533.00 / night

(5)

1 / 21

Islamorada Apartment

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children

$114.00

Excellent (5 reviews)

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from $114.00 / night

(1)

1 / 24

Islamorada House

  • 4
  • 10
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$262.00

Excellent (1 reviews)

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from $262.00 / night

(2)

1 / 25

Islamorada House

  • 2
  • 5
  • 30 nights min
  • Swimming pool
  • Ask about children

$86.00

Excellent (2 reviews)

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from $86.00 / night

(21)

1 / 25

Islamorada Apartment

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children

$211.00

Excellent (21 reviews)

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from $211.00 / night

(2)

1 / 24

Islamorada Apartment

  • 2
  • 5
  • 30 nights min
  • Swimming pool
  • Ask about children

$80.00

Excellent (2 reviews)

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from $80.00 / night

1 / 25

Islamorada Apartment

  • 2
  • 6
  • 30 nights min
  • Swimming pool
  • Ask about children

$120.00

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from $120.00 / night

(1)

1 / 20

Islamorada House

  • 2
  • 6
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$100.00

Excellent (1 reviews)

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from $100.00 / night

(2)

1 / 24

Islamorada House

  • 3
  • 8
  • 30 nights min
  • Swimming pool
  • Ask about children

$617.00

Excellent (2 reviews)

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from $617.00 / night

(2)

1 / 25

Islamorada Apartment

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children

$147.00

Excellent (2 reviews)

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from $147.00 / night

1 / 25

Islamorada Apartment

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children

$80.00

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from $80.00 / night

(3)

1 / 26

Islamorada House

  • 3
  • 8
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$184.00

Very Good (3 reviews)

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from $184.00 / night

(2)

1 / 25

Islamorada Apartment

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children

$110.00

Excellent (2 reviews)

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from $110.00 / night

(2)

1 / 25

Islamorada House

  • 3
  • 8
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$199.00

Excellent (2 reviews)

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from $199.00 / night

1 / 25

Islamorada Apartment

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children

$80.00

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from $80.00 / night

(1)

1 / 24

Islamorada Apartment

  • 1
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children

$70.00

Excellent (1 reviews)

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from $70.00 / night

(1)

1 / 24

Islamorada Apartment

  • 2
  • 6
  • 30 nights min
  • Swimming pool
  • Ask about children

$77.00

Very Good (1 reviews)

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from $77.00 / night

1 / 25

Islamorada Apartment

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children

$100.00

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from $100.00 / night

1 / 25

Islamorada Apartment

  • 1
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children

$64.00

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from $64.00 / night

1 / 28

Islamorada Condo

  • 2
  • 6
  • 30 nights min
  • Swimming pool
  • Ask about children

$77.00

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from $77.00 / night

Your search has been expanded 16.9 miles to include more rentals

(5)

1 / 17

Key Largo Townhouse - 11.4 miles away

  • 3
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.01 mi
  • Swimming pool
“Norm was thorough in the walk through of the property we stayed. Townhouse condo was clean and well stocked. Next to salt water lagoon and pool. All the water toys were made available like snorkels, fins, fishing rods, kayaks and paddleboards. Golf...”
- Review left on 03/25/2017

$287.00

Average (5 reviews)

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from $287.00 / night

(25)

1 / 30

Key Largo Condo - 11.5 miles away

  • 3
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“We have been coming to Key Largo for the past three years and by far this was our most enjoyable stay. We are looking forward to returning next year. You could not asked for a better host than Norman. Very accommodating. The location is excellent...”
- Review left on 05/15/2017

$287.00

Very Good (25 reviews)

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from $287.00 / night

(27)

1 / 16

Key Largo Villa - 11.2 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.01 mi
  • Swimming pool
“This place was awesome-everything included we had paddle boards, Kayaks, golf cart and bicycles. The host Norman couldn't have been more friendly and helpful. I recommend this getaway to anyone and it is pet friendly...”
- Review left on 01/19/2017

$401.00

Very Good (27 reviews)

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from $401.00 / night

(3)

1 / 28

Key Largo House - 11.7 miles away

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

$258.00

Excellent (3 reviews)

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from $258.00 / night

1 / 25

Key Largo House - 11.6 miles away

  • 3
  • 6
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$174.00

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from $174.00 / night

(2)

1 / 25

Matecumbe Key Condo - 3.7 miles away

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children

$147.00

Excellent (2 reviews)

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from $147.00 / night

(1)

1 / 25

Matecumbe Key Condo - 3.7 miles away

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children

$100.00

Excellent (1 reviews)

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from $100.00 / night

1 / 25

Key Largo House - 11.7 miles away

  • 4
  • 10
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$184.00

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from $184.00 / night

1 / 25

Tavernier House - 3.9 miles away

  • 4
  • 8
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$333.00

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from $333.00 / night

(2)

1 / 25

Key Largo Apartment - 11.6 miles away

  • 3
  • 6
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$140.00

Excellent (2 reviews)

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from $140.00 / night

1 / 25

Matecumbe Key Condo - 7 miles away

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children

$74.00

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from $74.00 / night

(3)

1 / 24

Tavernier House - 2.3 miles away

  • 4
  • 10
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$317.00

Very Good (3 reviews)

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from $317.00 / night

1 / 26

Key Largo House - 11.9 miles away

  • 4
  • 10
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$292.00

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from $292.00 / night

(3)

1 / 18

Key Largo Apartment - 16.9 miles away

  • 2
  • 6
  • 30 nights min
  • Swimming pool
  • Ask about children

$105.00

Excellent (3 reviews)

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from $105.00 / night

(1)

1 / 25

Tavernier House - 3.3 miles away

  • 4
  • 10
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$217.00

Excellent (1 reviews)

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from $217.00 / night

1 / 22

Tavernier Apartment - 3.8 miles away

  • 2
  • 4
  • 60 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$142.00

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from $142.00 / night

1 / 25

Matecumbe Key Condo - 3.7 miles away

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children

$117.00

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from $117.00 / night

1 / 25

Matecumbe Key Villa - 1.6 miles away

  • 4
  • 10
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$500.00

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from $500.00 / night

(2)

1 / 25

Key Largo House - 10.3 miles away

  • 2
  • 6
  • 30 nights min
  • Swimming pool
  • Ask about children

$100.00

Very Good (2 reviews)

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from $100.00 / night