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Islamorada Cottage & Vacation Rentals

Florida Keys, Florida, US

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About Islamorada

Islamorada is an excellent travel destination when looking to get away from it all and head out to Cottage Country. Islamorada is full of nature to explore. When you visit Islamorada be prepared to take advantage of all the excellent activities Islamorada has to offer.

When planning your trip to Islamorada note that there are many excellent private cottage rentals to choose from. Make sure you browse through the Islamorada listings and pick the one that is right for you and your family.

United States → Florida → Florida Keys → Islamorada
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1 - 18 of 30 Holiday Rentals
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SUNSHINE PLACE - ISH84371OS

Vacation Homes in Islamorada, Florida - #188743
SUNSHINE PLACE - ISH84371OS
From
$950 / week
Bedrooms
1
Bathrooms
1
Sleeps
1-2
Region
Florida Keys
City
Islamorada, Florida
MINIMUM STAY: 7 DAYS You can have it all – privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their ... More →
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THE PALMS 305 - ISCPALM305

Condos in Islamorada, Florida - #188744
THE PALMS 305 - ISCPALM305
From
$2,000 / month
Bedrooms
2
Bathrooms
2
Sleeps
5-6
Region
Florida Keys
City
Islamorada, Florida
MINIMUM STAY: 28 DAYS Relax in this immaculate and spacious two bedroom condo with ocean views. This unit is well appointed with comfortable furnishings, flat screen TV ... More →
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ANGLERS REEF - ISH138ANGL

Vacation Homes in Islamorada, Florida - #184792
ANGLERS REEF - ISH138ANGL
From
$1,800 / week
Bedrooms
2
Bathrooms
2.5
Sleeps
5-6
Region
Florida Keys
City
Islamorada, Florida
MINIMUM STAY: 7 DAYS Extraordinary 2-story single family home in a Key West style neighborhood. This gated ocean front community offers charming narrow winding streets, ... More →
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BEACON REEF 211 - ISCBEAC211

Condos in Islamorada, Florida - #184803
BEACON REEF 211 - ISCBEAC211
From
$3,500 / month
Bedrooms
2
Bathrooms
2
Sleeps
3-4
Region
Florida Keys
City
Islamorada, Florida
MINIMUM RENTAL: 27 NIGHTS (ONE MONTH) This is a very special unit in a premier condominium complex located directly on the Atlantic Ocean and in the heart of Islamorada. ... More →
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BEACON REEF 222 - ISCBEAC222

Condos in Islamorada, Florida - #184809
BEACON REEF 222 - ISCBEAC222
From
$3,500 / month
Bedrooms
2
Bathrooms
2
Sleeps
3-4
Region
Florida Keys
City
Islamorada, Florida
MINIMUM STAY: 30 DAYS Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your private balcony or use the spiral stairs to access the ... More →
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BEACON REEF 302 - ISCBEAC302

Condos in Islamorada, Florida - #184802
BEACON REEF 302 - ISCBEAC302
From
$3,700 / month
Bedrooms
2
Bathrooms
2
Sleeps
3-4
Region
Florida Keys
City
Islamorada, Florida
MINIMUM RENTAL: 27 NIGHTS (ONE MONTH) Beautiful condo - new on the rental market. You'll be so glad the owners have decided to share their piece of paradise! You will ... More →
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BEACON REEF 314 - ISCBEAC314

Condos in Islamorada, Florida - #184808
BEACON REEF 314 - ISCBEAC314
From
$2,200 / month
Bedrooms
2
Bathrooms
2
Sleeps
3-4
Region
Florida Keys
City
Islamorada, Florida
MINIMUM RENTAL: 27 NIGHTS (ONE MONTH) Beacon Reef is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to ... More →
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BLUE WATER RETREAT - ISH137OCEA

Vacation Homes in Islamorada, Florida - #184804
BLUE WATER RETREAT - ISH137OCEA
From
$5,000 / month
Bedrooms
3
Bathrooms
2
Sleeps
7-8
Region
Florida Keys
City
Islamorada, Florida
MINIMUM RENTAL: 28 NIGHTS (ONE MONTH) Relax by the cocktail pool or sunbath in the private roof top sunning area. There are blue water ocean views from almost every room ... More →
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EMERALD COVE - ISH311TOLL

Vacation Homes in Islamorada, Florida - #184798
EMERALD COVE - ISH311TOLL
From
$7,200 / month
Bedrooms
4
Bathrooms
3
Sleeps
9-10
Region
Florida Keys
City
Islamorada, Florida
MINIMUM RENTAL: 28 NIGHTS (ONE MONTH) You'll love watching the fabulous sunsets over the tranquil waters in this semi-private lagoon setting. This is a three story single... More →
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ENCHANTED FISH CAMP - ISH200GALL

Vacation Homes in Islamorada, Florida - #184810
ENCHANTED FISH CAMP - ISH200GALL
From
$4,800 / month
Bedrooms
2
Bathrooms
2
Sleeps
3-4
Region
Florida Keys
City
Islamorada, Florida
MINIMUM RENTAL: 28 NIGHTS (ONE MONTH) Enchanted Fish Camp is a wonderful single family home which exemplifies the charm and character of the Florida Keys. If fishing or ... More →
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LITTLE BAY - Cottage - ISOLBCOTTA

Vacation Homes in Islamorada, Florida - #184790
LITTLE BAY - Cottage - ISOLBCOTTA
From
$2,400 / week
Bedrooms
2
Bathrooms
2
Sleeps
5-6
Region
Florida Keys
City
Islamorada, Florida
MINIMUM RENTAL: 3 NIGHTS This is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique ... More →
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LITTLE BAY - Lower Duplex - ISOLBLO

Vacation Homes in Islamorada, Florida - #184794
LITTLE BAY - Lower Duplex - ISOLBLO
From
$2,400 / week
Bedrooms
2
Bathrooms
2
Sleeps
5-6
Region
Florida Keys
City
Islamorada, Florida
MINIMUM RENTAL: 3 NIGHTS Lower Duplex. This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated... More →
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LITTLE BAY - Upper Duplex - ISOLBUP

Condos in Islamorada, Florida - #184800
LITTLE BAY - Upper Duplex - ISOLBUP
From
$2,400 / week
Bedrooms
2
Bathrooms
2
Sleeps
5-6
Region
Florida Keys
City
Islamorada, Florida
MINIMUM RENTAL: 3 NIGHTS Upper Duplex. This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated... More →
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MATECUMBE JEWEL - ISH119IROQ

Vacation Homes in Islamorada, Florida - #184795
MATECUMBE JEWEL - ISH119IROQ
From
$4,000 / month
Bedrooms
3
Bathrooms
2
Sleeps
5-6
Region
Florida Keys
City
Islamorada, Florida
MINIMUM RENTAL: 28 NIGHTS (ONE MONTH) You will love this home! This is a new listing - make your reservations now before someone else books your dates! This is a jewel of... More →
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MERMAID'S COTTAGE - ISH314PALM

Vacation Homes in Islamorada, Florida - #184807
MERMAID'S COTTAGE - ISH314PALM
From
$3,000 / month
Bedrooms
3
Bathrooms
2
Sleeps
5-6
Region
Florida Keys
City
Islamorada, Florida
MINIMUM RENTAL: 28 NIGHTS (ONE MONTH) Absolutely enchanting! Words are hard to find to accurately describe the charm and tropical personality found in this home. Your ... More →
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MY PARADISE - ISH201SUNS

Vacation Homes in Islamorada, Florida - #184797
MY PARADISE - ISH201SUNS
From
$5,500 / month
Bedrooms
3
Bathrooms
2
Sleeps
5-6
Region
Florida Keys
City
Islamorada, Florida
MINIMUM RENTAL: 28 NIGHTS (ONE MONTH) OCEANFRONT - BEACH -PROTECTED DOCK and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home ... More →
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SUNSET SERENITY - ISH258GULF

Vacation Homes in Islamorada, Florida - #184832
SUNSET SERENITY - ISH258GULF
From
$6,500 / month
Bedrooms
3
Bathrooms
3
Sleeps
7-8
Region
Florida Keys
City
Islamorada, Florida
MINIMUM STAY: 29 DAYS Enjoy the tranquil setting of this single family home located directly on the Florida Bay. This wonderful home has been impeccably maintained and is... More →
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THE PALMS 201 - ISCPALM201

Condos in Islamorada, Florida - #184833
THE PALMS 201 - ISCPALM201
From
$3,000 / month
Bedrooms
2
Bathrooms
2
Sleeps
5-6
Region
Florida Keys
City
Islamorada, Florida
MINIMUM RENTAL: 27 NIGHTS (ONE MONTH) Enjoy the magnificent ocean views of this wonderful condominium complex. You'll love the newly completed renovations. The kitchen ... More →
1 - 18 of 30 Holiday Rentals

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