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Islamorada 2-bedroom Vacation Rentals, House Rentals & More - 64 Rentals Available.

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64 Vacation rentals

Filters applied: 2+ Bedrooms

1 / 25

Islamorada House

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

$573.00

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from $573.00 / night

(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

(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

(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

(2)

1 / 25

Islamorada House

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

$157.00

Excellent (2 reviews)

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from $157.00 / night

(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

(3)

1 / 21

Islamorada Apartment

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

$110.00

Excellent (3 reviews)

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from $110.00 / night

(3)

1 / 25

Islamorada Villa

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

$358.00

Excellent (3 reviews)

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from $358.00 / night

(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

(2)

1 / 25

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

(14)

1 / 25

Islamorada Apartment

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

$225.00

Excellent (14 reviews)

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from $225.00 / night

(3)

1 / 24

Islamorada Villa

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

$358.00

Very Good (3 reviews)

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from $358.00 / night

1 / 25

Islamorada Apartment

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

$103.00

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from $103.00 / night

(4)

1 / 23

Islamorada Villa

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

$358.00

Excellent (4 reviews)

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from $358.00 / night

1 / 28

Islamorada House

  • 3
  • 12
  • min stay varies
  • Ask about children
  • Pet friendly

$300.00

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from $300.00 / night

(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

(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

(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

1 / 16

Islamorada Apartment

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

$80.00

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from $80.00 / night

1 / 25

Islamorada House

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

$100.00

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from $100.00 / night

(6)

1 / 25

Islamorada House

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

$261.00

Excellent (6 reviews)

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from $261.00 / night

(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

1 / 25

Islamorada House

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

$173.00

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from $173.00 / night

(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

(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

1 / 23

Islamorada House

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

$133.00

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from $133.00 / night

(1)

1 / 24

Islamorada House

  • 3
  • 10
  • min stay varies
  • Ask about children

$400.00

Excellent (1 reviews)

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from $400.00 / night

(2)

1 / 22

Islamorada House

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

$122.00

Excellent (2 reviews)

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from $122.00 / night

1 / 29

Islamorada Apartment

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

$100.00

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from $100.00 / night

(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

Your search has been expanded 18.6 miles to include more rentals

(18)

Certificate of Excellence

1 / 16

Key Largo Villa - 11.9 miles away

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

Certificate of Excellence

“The Condo was very spacious, clean and very well presented. With a family, we appreciated the room and comfy beds! The washer and dryer were an added bonus. We liked the location and really enjoyed our stay. We wish it was longer and would love...”
- Review left on 12/06/2016

$229.00

Excellent (18 reviews)

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from $229.00 / night

(53)

Certificate of Excellence

1 / 12

Key Largo Cottage - 11.9 miles away

  • 2
  • 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

Certificate of Excellence

“We enjoyed our Key Kargo stay. Our daughter and son in law joined us. Everything on site made for a good vacation. We were lucky to have good weather for snorkeling on the reef. Only request would be to have more plates and cutlery. We like to...”
- Review left on 01/07/2018

$229.00

Very Good (53 reviews)

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from $229.00 / night

(24)

1 / 32

Key Largo Condo - 11.5 miles away

  • 3
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“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

$250.00

Very Good (24 reviews)

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from $250.00 / night

(28)

Certificate of Excellence

1 / 15

Key Largo House - 11.9 miles away

  • 4
  • 10
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

Certificate of Excellence

“We stayed for five days. Two families with five small children. The house was perfect! There are toddler beds tucked into 2 large walk in closets. There were two cribs and a high chair. They even had baby spoons! There is an adorable pirate ship...”
- Review left on 03/03/2016

$516.00

Excellent (28 reviews)

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from $516.00 / night

(1)

1 / 27

Key Largo House - 18.6 miles away

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

$184.00

Excellent (1 reviews)

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from $184.00 / night

(2)

1 / 17

Key Largo Townhouse - 11.4 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“The location is amazing everything is so close, shopping, nightlife! This our second year coming back every one is so friendly. We loved it. You don't need to go nowhere Norman the owner has everything that you need , kayak,snorkeling gear fishing...”
- Review left on 03/23/2017

$250.00

Excellent (2 reviews)

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from $250.00 / night

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

1 / 24

Key Largo Condo - 11.3 miles away

  • 2
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

$201.00

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from $201.00 / night

(5)

1 / 16

Key Largo Apartment - 11.2 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“We were in the Tower unit 212 at the Kawama Yacht Club. Norman Wartman met us and gave a tour of the facilities. Norman was very helpful and kept us in stitches with his barrage of jokes. The condo was in very good condition and the kitchen was...”
- Review left on 11/29/2016

$250.00

Excellent (5 reviews)

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from $250.00 / night

1 / 25

Matecumbe Key House - 0.1 miles away

  • 3
  • 8
  • 28 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$169.00

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from $169.00 / night