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Islamorada Waterfront Vacation Rentals, House Rentals & More - 33 Rentals Available.

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33 Vacation rentals

Filters applied: Waterfront

1 / 17

Islamorada Townhouse

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $200 / night

(1)

1 / 27

Islamorada Townhouse

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$204

Excellent (1 reviews)

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from $204 / night

(7)

1 / 9

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

Excellent (7 reviews)

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from $429 / 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

(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

$714

Very Good (12 reviews)

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from $714 / night

(10)

1 / 29

Islamorada House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Ask about children
“Not more I can say except we all had a great time and thanks to the hosts and location this was an amazing celebration! Definately recommend...”
- Review left on 06/23/2016

$457

Excellent (10 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

(5)

1 / 14

Islamorada House

  • 3
  • 10
  • 30 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“This is a beautiful home exactly as description provides. My family had a great visit...nothing compares to watching the sunset on the beach (a 3 minute walk from house) and seeing all kinds of wildlife including manatees in the canal out back. House...”
- Review left on 04/04/2017

$255

Excellent (5 reviews)

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from $255 / night

1 / 21

Islamorada Apartment

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

from $107 / night

1 / 25

Islamorada Apartment

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

from $147 / night

(1)

1 / 24

Islamorada Apartment

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

$74

Excellent (1 reviews)

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from $74 / night

1 / 25

Islamorada Apartment

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

from $100 / night

(2)

1 / 25

Islamorada House

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

$175

Average (2 reviews)

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from $175 / night

1 / 25

Islamorada Apartment

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

from $67 / night

(2)

1 / 25

Islamorada House

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

$217

Excellent (2 reviews)

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from $217 / night

(1)

1 / 25

Islamorada Apartment

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

$67

Excellent (1 reviews)

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from $67 / night

(6)

1 / 23

Islamorada Villa

  • 1
  • 3
  • 7 nights min
  • Ask about children
  • Pet friendly

$158

Excellent (6 reviews)

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from $158 / night

(1)

1 / 25

Islamorada House

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

$150

Excellent (1 reviews)

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from $150 / night

1 / 24

Islamorada House

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

from $217 / night

(10)

1 / 25

Islamorada Apartment

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

$225

Excellent (10 reviews)

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from $225 / night

1 / 25

Islamorada Apartment

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

from $107 / night

1 / 24

Islamorada Apartment

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

from $74 / night

1 / 23

Islamorada House

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

from $134 / night

1 / 25

Islamorada House

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

from $617 / night

1 / 25

Islamorada House

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

from $199 / 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

(1)

1 / 25

Islamorada House

  • 2
  • 6
  • Min stay varies
  • Ask about children
  • Pet friendly

$117

Excellent (1 reviews)

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from $117 / night

1 / 18

Islamorada House

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

from $82 / night

1 / 25

Islamorada Apartment

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

from $100 / night

(3)

1 / 25

Islamorada Villa

  • 2
  • 6
  • 7 nights min
  • Ask about children
  • Pet friendly

$358

Excellent (3 reviews)

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from $358 / night

(2)

1 / 24

Islamorada Villa

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

$358

Excellent (2 reviews)

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from $358 / night

(4)

1 / 23

Islamorada Villa

  • 2
  • 6
  • 7 nights min
  • Ask about children
  • Pet friendly

$358

Excellent (4 reviews)

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from $358 / night

Your search has been expanded 4.1 miles to include more rentals

1 / 21

Tavernier House - 0.1 miles away

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

from $127 / night

(13)

1 / 17

Tavernier House - 1 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 / 24

Tavernier House - 1 miles away

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

$299

Very Good (1 reviews)

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from $299 / night

(1)

1 / 25

Tavernier House - 2 miles away

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

$217

Excellent (1 reviews)

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from $217 / night

(5)

1 / 6

Tavernier House - 2.3 miles away

  • 2
  • 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“My family and I stayed at the upper apartment March 6-12. It was such a wonderful place to stay! The apartment was perfect for our family of 5. We loved the outdoor screened in porch, the openness of kitchen and the family room were perfect. We...”
- Review left on 03/20/2017

$127

Excellent (5 reviews)

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from $127 / night

1 / 23

Tavernier House - 2.6 miles away

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

from $150 / night

(21)

1 / 24

Tavernier House - 4.1 miles away

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“We were thrilled from the point of arrival till the time we left! The property was immaculate and had kayaks, paddle boats for our use during our stay! Everything was well kept, and we loved the tiki bar on the deck area. Raul was pleasant from the...”
- Review left on 08/16/2016

$450

Excellent (21 reviews)

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from $450 / night