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Islamorada Vacation Rentals & House Rentals - 38 Rentals Available

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38 Vacation rentals

(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

(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

1 / 17

Islamorada Townhouse

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

from $200 / night

(19)

1 / 27

Islamorada House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“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

Excellent (19 reviews)

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from $429 / night

(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

(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

(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 / 14

Islamorada House

  • 4
  • 8
  • 30 nights min
  • Ask about children
  • Air conditioning

from $168 / 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

1 / 16

Islamorada House

  • 3
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $572 / night

(10)

1 / 29

Islamorada House

  • 3
  • 6
  • 30 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

$291

Excellent (10 reviews)

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from $291 / night

(7)

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

$256

Very Good (7 reviews)

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from $256 / night

1 / 18

Islamorada House

  • 2
  • 4
  • 7 nights min
  • Child friendly
  • Air conditioning

from $236 / night

1 / 25

Islamorada Apartment

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

from $68 / night

1 / 23

Islamorada House

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

from $83 / night

1 / 24

Islamorada House

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

from $135 / 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 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 / 23

Islamorada Apartment

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

from $80 / night

1 / 17

Islamorada Apartment

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

from $148 / 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)

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 / 24

Islamorada House

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

from $217 / 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 / 23

Islamorada Apartment

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

from $108 / night

(1)

1 / 25

Islamorada House

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

$151

Excellent (1 reviews)

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from $151 / night

1 / 25

Islamorada Apartment

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

from $100 / night

1 / 25

Islamorada Apartment

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

from $100 / night

1 / 25

Islamorada Apartment

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

from $108 / night

(2)

1 / 16

Islamorada Villa

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

$358

Excellent (2 reviews)

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from $358 / night

(6)

1 / 19

Islamorada Villa

  • 1
  • 3
  • Min stay varies
  • Ask about children
  • Pet friendly

$159

Excellent (6 reviews)

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from $159 / night

1 / 16

Islamorada Apartment

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

from $75 / night

(4)

1 / 27

Islamorada Villa

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

$358

Excellent (4 reviews)

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from $358 / night

(2)

1 / 14

Islamorada House

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

$217

Excellent (2 reviews)

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from $217 / 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

(3)

1 / 30

Islamorada Villa

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

$358

Excellent (3 reviews)

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from $358 / night

(1)

1 / 23

Islamorada House

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

$117

Excellent (1 reviews)

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from $117 / night

Your search has been expanded 1.5 miles to include more rentals

(6)

1 / 9

Tavernier Townhouse - 0.3 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“We thoroughly enjoyed our stay at Dave's rental in Futura Yacht Club. The best part was how convenient everything was! The boat slip was right in front of our unit, the tennis courts directly behind it, grills out on the beach which was a short walk...”
- Review left on 08/09/2015

$172

Very Good (6 reviews)

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from $172 / night

1 / 21

Tavernier House - 1.5 miles away

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

from $128 / night

About Islamorada

Islamorada consists of a “Village of Islands” spread out over six islands in the Florida Keys. Surrounded by cerulean ocean waters and soft sands, this destination is a tropical paradise for those looking to get away from it all. Stay in oceanfront Islamorada vacation rentals for the ultimate convenience during your beach getaway.

Climate

With a tropical climate and daytime temperatures that rarely dip below the 70s (F), Islamorada is a fantastic vacation spot any time of the year. During the summer, temperatures typically hover in the upper 80s, and the ocean waters provide a refreshing respite. Pack lots of sunscreen as the sun’s rays are much stronger than they are in northern parts of the U.S. Wintertime brings temperatures in the 70s – cool by Florida standards, but still comfortably warm for vacationers from other parts of the country.

Transit 

Islamorada is best traveled by car or boat. Fly into Miami International Airport or Key West International Airport then rent a car to travel to Islamorada. The island roads are scenic and views from the bridges connecting each island are breathtaking. Just keep in mind that speed limits are strictly enforced in the Florida Keys. Once you’ve arrived, ditch the car and island hop via boat. Rent a boat from Islamorada Watersports Company and spend time cruising the pristine waters.

Things to Do

Islamorada is well-known as the sport fishing capital of the world, and the surrounding ocean and shallow bays teem with a variety of fish, including sailfish, bonefish, swordfish, marlin and tarpon. Embark on a fishing charter led by a knowledgeable captain from Sea Horse Private Charters or Drop Back Fishing Charters for a fun day out on the water. If you’d rather stay on land, explore try fly fishing in the backcountry.

There’s much to see and do in Islamorada besides fishing, though. Soak up sun with the family at Anne’s Beach. Here, there are many coves along the white sands, making it easy to find a quiet, private for the family, and the surrounding mangroves provide an ideal setting to observe Florida marine life. The beach also has shallow waters, and it is a popular destination for kite-boarders. Visit the Theater of the Sea, so everyone can swim with dolphins, interact with sea lions and turtles, and enjoy live snorkeling tours that the park provides.
 
San Pedro Underwater Archaeological Preserve State Park is a historical shipwreck site and a popular diving adventure for visitors. The 18-feet deep waters at this site are best for experienced divers, but divers of all levels will enjoy exploring nearby coral reefs underwater. Another popular attraction is the Windley Key Fossil Reef Geological State Park, which includes nature trails for hiking and features fossilized coral. There are picnic tables and educational tours for kids, and the park is home to a variety of birds and native wildlife.

Events

With ideal weather year-round, the fun never stops and Islamorada hosts events and activities to keep families entertained all year long. Visit in January for the Annual Blessing of the Fleet to kick off another year of fishing. In March, stroll throughout Islamorada during National Wildlife Week or visit the weekly farmer’s market open on Fridays. The summer brings a lively 4th of July celebration, the Spirit of Islamorada as well as numerous weekly events, while winter also brings fun holiday activities and festivals.

This island oasis beckons to vacationers all year long with its divine weather and laidback atmosphere. Islamorada vacation rentals provide easy access to the abundance of water activities without giving up comfort or any of the necessities for the perfect stay. You might even thinking about making Islamorada your permanent home.

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