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Islamorada Vacation Rental Listings

Our Islamorada Vacation Rentals selection includes only the best Islamorada homes, condos, villas, hotels, bed & breakfasts, cabins, and cottages.

Listed below, you will find numerous Islamorada lodging and accommodations to suit your needs. Click on the view details button to explore any of the Islamorada rentals you see listed for more information. Florida Keys, Islamorada Vacation Rentals are continuously added and modified, so if you do not find what you are looking for in our Islamorada Vacation rental inventory, make sure you bookmark us and come back frequently.

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Keys Ocean Front Mansion - Bed and Breakfast in Islamorada

Keys Ocean Front Mansion - Islamorada

10 Bedrooms
Sleeps 2
 

• Pool
• Jacuzzi/Hot Tub
• BBQ
• Utensils
• Refrigerator
• Microwave

Stay in the Florida Keys most prestigious, largest, and luxurious oceanfront mansion located in the heart of the world renown village of Islamorada! Why rent a room when you can roam thousands of luxurious feet of living rooms, dining rooms, decks, ve
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Florida Keys Luxury Condos Rental - Vacation Rental in Islamorada

Florida Keys Luxury Condos Rental - Islamorada

2 Bedrooms
Sleeps 6
From USD900.0 wk

• Sauna
• Pool
• Utensils
• Stove - Electric
• Refrigerator
• Microwave

Totally renovated, this professionally decorated two bedroom, two bath ocean front Islamorada vacation rental condominium is located in Islamorada just south of Key Largo mile marker 90 in Plantation Key. The unit sleeps six comfortably. Our Islamorad
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SUNSETS BAYSIDE - Vacation Rental in Islamorada

SUNSETS BAYSIDE - Islamorada

2 Bedrooms
Sleeps 6
From USD1295.0 wk

• Pool
• Garage
• Covered Parking
• BBQ
• Utensils
• Stove - Electric

Situated in a lush tropical setting, this beautiful, 2 bedroom, 2 bath Islamorada vacation townhouse is located directly on the Gulf of Mexico at MM 75 in Islamorada. Surrounded with bougainvillea, hibiscus, a variety of tropical flowers, coconut tree
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Islamorada Ocean View Home - Vacation Rental in Islamorada

Islamorada Ocean View Home - Islamorada

3 Bedrooms
Sleeps 10
From USD142.0 nt

• Covered Parking
• BBQ
• Stove - Electric
• Refrigerator
• Microwave
• Ice Maker

Wake up to beautiful sunrises over the ocean in this ocean view Islamorada vacation rental in the upper Florida Keys! With an ocean view, refreshing ocean breeze and plenty of relaxing by the water, you’ll forget all about the hustle and bustle you ca
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Sunset Inn 305-664-3454 - Hotel/Motel in Islamorada

Sunset Inn 305-664-3454 - Islamorada

30 Bedrooms
Sleeps 4
From USD55.0 nt

• Pool
• Utensils
• Stove - Electric
• Refrigerator
• Coffee Maker
• Phone

...a little bit of paradise, Islamorada, Florida! In the heart of Islamorada, our landmark motel... The Sunset Inn Mile Marker 82.2 Bayside 82200 Overseas Hwy Islamorada FL 33036 305) 664-3454 Season prices starting at $75 per night for 2 people. Off
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Ragged Edge Resort & Marina - Hotel/Motel in Islamorada

Ragged Edge Resort & Marina - Islamorada

2 Bedrooms
Sleeps 6
 


A small, secluded Paradise right on the Atlantic Ocean. Six beautiful acres filled with palm trees, exotic birds, and tranquility, far away from the main highway. This Islamorada Resort is perfect for boaters, fishing, diving, family vacations, or jus
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Beautiful Oceanfront Islamorada Condominiums - Vacation Rental in Islamorada

Beautiful Oceanfront Islamorada Condominiums - Islamorada

2 Bedrooms
Sleeps 6
 

• Sauna
• Pool
• Covered Parking
• Microwave
• Ice Maker
• Full Kitchen

Terrific oceanfront view in newly remodeled Islamorada condominiums offer all the amenities of home with the bonus of breathtaking oceanfront view, on beautiful Islamorada located in the Florida Keys. Islamorada is known as the Sport Fishing Capital o
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Private secluded Islamorada House - Vacation Rental in Islamorada

Private secluded Islamorada House - Islamorada

2 Bedrooms
Sleeps 4
From USD795.0 wk

• BBQ
• Utensils
• Stove - Electric
• Refrigerator
• Ice Maker
• Full Kitchen

Secluded individual house on the bay, rental Islamorada. View of Everglades National Park from half the house. Free boat basin for boat up to 26 foot. One of the best Florida Keys...Fully equiped house with washer dryer, dishwasher, pots and pans, lin
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Water Front Convertible House in Islamorada FL - Vacation Rental in Islamorada

Water Front Convertible House in Islamorada FL - Islamorada

4 Bedrooms
Sleeps 12
From USD800.0 wk

• BBQ
• Utensils
• Microwave
• Full Kitchen
• Dishwasher
• Coffee Maker

Enjoy yourself in the peaceful surroundings of the Florida Keys. This fine vacation home is a convertible... a duplex with three bedrooms upstairs and one bedroom downstairs... or, rent the whole house! Located on a deep water canal just minutes from
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Lovely condominium in Islamorada - Vacation Rental in Islamorada

Lovely condominium in Islamorada - Islamorada

 
Sleeps 4
 


OUR STUDIO: * Sleeps family of four maximum * Has fully-furnished kitchen with refrigerator, dishwasher, disposal, stove, and microwave * Cable TV and phone * Laundry on every floor * Two elevators * Air conditioning and heat * Lighted parking * Coded
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The Perfect Getaway with HEATED swimming pool - Vacation Rental in Islamorada

The Perfect Getaway with HEATED swimming pool - Islamorada

4 Bedrooms
Sleeps 10
 


This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a beautiful upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of h
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La Jolla Resort - Hotel/Motel in Islamorada

La Jolla Resort - Islamorada

21 Bedrooms
Sleeps 6
From USD89.0 nt

• Pool
• BBQ
• Utensils
• Stove - Electric
• Refrigerator
• Microwave

La Jolla is the perfect place for families & fishermen to kick back and experience the Florida Keys the way they used to be. Our art deco 1950 's style resort has 6 villa's with various rooms and apartments for a total of 21 units. The Blue Heron Cott
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Sunny Condo - Vacation Rental in Islamorada

Sunny Condo - Islamorada

2 Bedrooms
Sleeps 6
 


Escape from the world in this beautiful island paradise in Islamorada Florida. Plenty of room to spread out in a two bedroom condo. Relax by the heated pool overlooking the turqoise bay; fish from the dock, snorkel in the protected cove. Kids can play
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Summer Sea Condo in Islamorada, Florida Keys - Vacation Rental in Islamorada

Summer Sea Condo in Islamorada, Florida Keys - Islamorada

2 Bedrooms
Sleeps 6
From USD875.0 wk

• Sauna
• Pool
• Covered Parking
• BBQ
• Utensils
• Stove - Electric

YES - this IS the view from your livingroom! - AWESOME place - best value in the Florida Keys! NO additional taxes or fees! Book now to researve your space! Apartments #314 and 315, two one-bedroom apartments that have been joined together to form one
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SPECIAL OFFER
5th Floor End Unit, Oceanfront, View, Pool, Tennis - Vacation Rental in Islamorada
10.29% OFF
From: May 23, 2008
To: May 30, 2008

5th Floor End Unit, Oceanfront, View, Pool, Tennis - Islamorada

2 Bedrooms
Sleeps 6
From USD900.0 wk

• Pool
• BBQ
• Utensils
• Stove - Electric
• Refrigerator
• Microwave

This Islamorada accommodation has 2 bedrooms, 2 baths is right on the Ocean and only 75 ft. from the water. It offers spectacular panoramic ocean views. This Upper Florida Keys condo, is newly (2006) redecorated, and is on the ocean end of the 5th flo
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