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Islamorada Vacation Rentals & House Rentals with Swimming Pool - 22 Rentals Available.

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22 Vacation rentals

Filters applied: Swimming pool

(7)

1 / 9

Islamorada House

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“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

$300

Excellent (7 reviews)

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from $300 / night

(9)

1 / 14

Islamorada House

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

$391

Excellent (9 reviews)

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from $391 / night

(12)

1 / 24

Islamorada House

  • 5
  • 15
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This is the second time we've rented this house and it was better than the first time. Beautiful views and easy access to the bay was exactly what we were looking for. The new ice maker and huge refrigerator were perfect for our large group. Amazing...”
- Review left on 07/11/2016

$572

Very Good (12 reviews)

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from $572 / night

(3)

1 / 33

Islamorada House

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We enjoy coming back, weather just great. Just so relaxing. Chiki bar, pool, private dock all a plus. Est place to vacation...”
- Review left on 10/17/2016

$457

Excellent (3 reviews)

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from $457 / night

(8)

1 / 10

Islamorada House

  • 3
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“What a lovely place. Immaculately clean and beautifully appointed. Everything as advertised and the pool and hot tub are beautiful. Nicely situated in Lower Metacumbe. The private beach was a gorgeous addition. We had a wonderful time and Capt....”
- Review left on 03/24/2016

$400

Excellent (8 reviews)

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from $400 / night

1 / 23

Islamorada House

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

from $83 / night

(1)

1 / 14

Islamorada Apartment

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

$75

Excellent (1 reviews)

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from $75 / night

1 / 16

Islamorada Apartment

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

from $75 / night

1 / 23

Islamorada Apartment

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

from $80 / night

1 / 25

Islamorada Apartment

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

from $100 / night

1 / 25

Islamorada House

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

from $200 / night

1 / 25

Islamorada Apartment

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

from $80 / night

(1)

1 / 25

Islamorada Apartment

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

$80

Excellent (1 reviews)

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from $80 / night

(8)

1 / 25

Islamorada Apartment

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

$225

Excellent (8 reviews)

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from $225 / night

1 / 24

Islamorada House

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

from $217 / night

(1)

1 / 25

Islamorada Apartment

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

$68

Excellent (1 reviews)

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from $68 / night

1 / 25

Islamorada Apartment

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

from $100 / night

1 / 17

Islamorada Apartment

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

from $148 / night

1 / 25

Islamorada Apartment

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

from $68 / night

1 / 25

Islamorada Apartment

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

from $108 / night

1 / 23

Islamorada Apartment

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

from $108 / night

(2)

1 / 26

Islamorada House

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

$176

Average (2 reviews)

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from $176 / night

Your search has been expanded 21.1 miles to include more rentals

(13)

1 / 17

Tavernier House - 1.7 miles away

  • 4
  • 12
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Comfortable home in a super-quiet neighborhood. Easily accommodated 8 adults. Plenty of room at the dining table for dining, cards, and games. Generous kitchen allowed milling about and food prep participation. Good beds and pillows; good bathrooms....”
- Review left on 02/07/2017

$300

Excellent (13 reviews)

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from $300 / night

(1)

1 / 27

Tavernier House - 1.7 miles away

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

$300

Very Good (1 reviews)

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from $300 / night

(19)

1 / 14

Tavernier Condo - 3 miles away

  • 2
  • 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Condo is quiet and private, large balcony and view was spectacular. Clean and well stocked. Plenty of room for 5. Owner easily available by text or email, Would highly recc for others”
- Review left on 08/15/2016

$129

Excellent (19 reviews)

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from $129 / night

(1)

1 / 25

Tavernier House - 3.2 miles away

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

$217

Excellent (1 reviews)

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from $217 / night

(2)

1 / 16

Tavernier Condo - 7.1 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“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

$176

Excellent (2 reviews)

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from $176 / night

(2)

1 / 15

Tavernier House - 8.1 miles away

  • 5
  • 10
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We have just returned from a month long celebration of retirement in the Keys. The lovely home we stayed in was perfectly located smack dab in the middle of everything there is to do in the Keys! The owner of this property was quick to respond to...”
- Review left on 02/05/2016

$168

Excellent (2 reviews)

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from $168 / night

(16)

1 / 15

Key Largo House - 15.8 miles away

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Great place for family who like boating, fishing, diving, snorkeling and have fun in the beautiful reef at John Penny Camp State under water park. I recommended to everyone I know. This place is awesome!! I am a HAPPY Camper...”
- Review left on 08/23/2016

$351

Very Good (16 reviews)

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from $351 / night

(25)

1 / 16

Key Largo Villa - 15.8 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“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

Very Good (25 reviews)

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from $300 / night

1 / 17

Key Largo Condo - 16 miles away

  • 2
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

from $94 / night

(2)

1 / 17

Key Largo Townhouse - 16.2 miles away

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

$200

Excellent (2 reviews)

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from $200 / night

(2)

1 / 20

Key Largo Apartment - 16.4 miles away

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

$135

Very Good (2 reviews)

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from $135 / night

(2)

1 / 18

Key Largo Apartment - 16.5 miles away

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$117

Excellent (2 reviews)

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from $117 / night

1 / 24

Key Largo House - 16.6 miles away

  • 4
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

from $117 / night

1 / 26

Key Largo House - 16.9 miles away

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

from $292 / night

(12)

1 / 14

Key Largo House - 19.5 miles away

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“My wife,daughters and me , stay in these place for a week ,, and really ,, its not enough . Quiet,reserved,peaceful and a lot restaurant for the best breakfast and dinner in the keys .If you enjoy and like scuba diving or snorkeling ..... perfect ....”
- Review left on 07/17/2016

$131

Very Good (12 reviews)

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from $131 / night

1 / 20

Matecumbe Key Townhouse - 20.1 miles away

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

from $100 / night

(17)

1 / 42

Key Largo Cottage - 20.7 miles away

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

$100

Excellent (17 reviews)

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from $100 / night

(2)

1 / 18

Key Largo House - 21.1 miles away

  • 3
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The owners were wonderful to work with; their house was spacious, comfortable, and well-appointed and updated; and the location was a great spot from which to take excursions. Highly recommend...”
- Review left on 01/03/2017

$143

Excellent (2 reviews)

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from $143 / night