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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

1 / 25

Islamorada House

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

$1,145.00

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from $1,145.00 / night

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(8)

1 / 22

Islamorada House

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“We had four couples on our summer fishing vacation that we do every year in Islamorada.Couldnt have been better,we had couple days at first to go feed tarpon at Robbies and relax till seas calmed down and we got out in flat waters to fish,we caught...”
- Review left on 05/29/2015

$429.00

Excellent (8 reviews)

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from $429.00 / night

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(19)

1 / 27

Islamorada House

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

$458.00

Excellent (19 reviews)

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from $458.00 / night

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(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

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(4)

1 / 21

Islamorada Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children

$110.00

Excellent (4 reviews)

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from $110.00 / night

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(2)

1 / 25

Islamorada House

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Ask about children

$85.00

Excellent (2 reviews)

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from $85.00 / night

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(2)

1 / 24

Islamorada Apartment

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Ask about children

$80.00

Excellent (2 reviews)

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from $80.00 / night

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(1)

1 / 24

Islamorada House

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$245.00

Excellent (1 reviews)

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from $245.00 / night

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(17)

1 / 25

Islamorada Apartment

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

$226.00

Excellent (17 reviews)

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from $226.00 / night

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(1)

1 / 24

Islamorada Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children

$76.00

Excellent (1 reviews)

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from $76.00 / night

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1 / 22

Islamorada House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$100.00

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from $100.00 / night

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1 / 25

Islamorada Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children

$103.00

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from $103.00 / night

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1 / 25

Islamorada Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children

$80.00

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from $80.00 / night

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(2)

1 / 24

Islamorada House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children

$616.00

Excellent (2 reviews)

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from $616.00 / night

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(2)

1 / 25

Islamorada Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children

$146.00

Excellent (2 reviews)

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from $146.00 / night

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(1)

1 / 25

Islamorada Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children

$110.00

Excellent (1 reviews)

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from $110.00 / night

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(1)

1 / 24

Islamorada Apartment

  • 1
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children

$70.00

Excellent (1 reviews)

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from $70.00 / night

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(3)

1 / 26

Islamorada House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$183.00

Very Good (3 reviews)

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from $183.00 / night

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(2)

1 / 25

Islamorada House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$198.00

Excellent (2 reviews)

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from $198.00 / night

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1 / 25

Islamorada Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children

$80.00

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from $80.00 / night

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(1)

1 / 24

Islamorada Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children

$76.00

Very Good (1 reviews)

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from $76.00 / night

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1 / 28

Islamorada Condo

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children

$76.00

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from $76.00 / night

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1 / 25

Islamorada Apartment

  • 1
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children

$64.00

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from $64.00 / night

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Your search has been expanded 16.9 miles to include more rentals

1 / 24

Key Largo Condo - 11.3 miles away

  • 2
  • 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

$201.00

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from $201.00 / night

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(4)

1 / 17

Tavernier Condo - 5.7 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“My family and I had a fabulous time. Enjoyed all the perks available. Close to a local shopping center which has everything you may need. We will be back...”
- Review left on 12/02/2016

$270.00

Excellent (4 reviews)

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from $270.00 / night

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(4)

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

$250.00

Average (4 reviews)

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from $250.00 / night

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(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

$300.00

Very Good (27 reviews)

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from $300.00 / night

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1 / 14

Key Largo House - 11.7 miles away

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

$300.00

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from $300.00 / night

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(18)

1 / 39

Key Largo Cottage - 14.2 miles away

  • 1
  • 5
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Our family of 4 stayed here over Thanksgiving week and had the best time. Penny is very organized and everything was perfect, love the ambiance. We love the old Florida feel and the tiki hut is the best. Our teenage boys had a fantastic time swimming...”
- Review left on 04/14/2016

$184.00

Excellent (18 reviews)

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from $184.00 / night

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1 / 26

Key Largo House - 11.9 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$291.00

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from $291.00 / night

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(3)

1 / 22

Key Largo Apartment - 11.5 miles away

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

$150.00

Very Good (3 reviews)

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from $150.00 / night

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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

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(2)

1 / 25

Matecumbe Key Condo - 3.7 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children

$146.00

Excellent (2 reviews)

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from $146.00 / night

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1 / 25

Tavernier House - 3.9 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$332.00

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from $332.00 / night

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1 / 27

Matecumbe Key Condo - 3.7 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children

$143.00

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from $143.00 / night

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(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

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(2)

1 / 24

Tavernier House - 2.3 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$316.00

Very Good (2 reviews)

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from $316.00 / night

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(3)

1 / 15

Key Largo Apartment - 16.9 miles away

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

$150.00

Excellent (3 reviews)

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from $150.00 / night

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(1)

1 / 25

Tavernier House - 3.3 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children

$217.00

Excellent (1 reviews)

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from $217.00 / night

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(2)

1 / 25

Key Largo House - 10.3 miles away

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children

$95.00

Very Good (2 reviews)

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from $95.00 / night

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