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Islamorada Vacation Rentals & House Rentals - 68 Rentals Available

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68 Vacation rentals

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

(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

(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

(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

(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

(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

(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

(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

(14)

1 / 23

Islamorada Villa

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

$172.00

Excellent (14 reviews)

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from $172.00 / 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

1 / 28

Islamorada House

  • 3
  • 15
  • 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

(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

(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 / 25

Islamorada Apartment

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

$103.00

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from $103.00 / 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

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 / 23

Islamorada House

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

$133.00

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from $133.00 / 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

(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)

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

(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

(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

(1)

1 / 25

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

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 11.9 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

$287.00

Excellent (18 reviews)

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from $287.00 / 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

(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

(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

1 / 27

Key Largo Cottage - 10.4 miles away

  • 1
  • 4
  • 3 nights min
  • Child friendly
  • Air conditioning

$189.00

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from $189.00 / 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

(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

(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

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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