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Islamorada Villas

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    Travellers to Islamorada are booking December dates now. Secure your holiday rental today, and have the perfect trip.
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully furnished 2 BR 2 BA Condo on second floor.(First is parking only) Spiral Staircase directly down to lushly landscaped grounds. Only this floor has the stairs, others have to go through a lobby with a key. Wander around among our beautiful tropical gardens, bring your drink down to the...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    • Private Outdoor Pool (Heated)
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WE DO NOT ACCEPT WIRE TRANSFERS AS PAYMENT...ALL PAYMENT IS THROUGH FLIPKEY Enjoy the most beautiful sunsets on earth from this gorgeous 4bedroom,5bathroom tropical paradise. Comes complete with Bayfront pool and lounge area that will leave you breathless. Pool table, cabana, outdoor kitchen,...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    Keys Kottage Villa is located in beautiful Islamorada, Florida Keys. We are on mile marker 82. Private Marina access and trailer parking available to guests. Bring your boat and or pet. We can accommodate up to 26 ft. vessels. This is a Fisherman's dream for a week of fishing. Please call for...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Patio
    • Cable/satellite TV
    • Internet Access
    • Parking
    • Balcony
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'The Palms #405' is a diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings are gone. You'll adore the comfortable living room...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    Come to Paradise and Enjoy it with Comfort! Located on Mile Marker 87 in Islamorada ( Fishing Capital of the World ), part of the Wonderful Florida Keys. Executive Bay Club is a Private Gated Community with 24 Hr Security, Heated Pool and Club House, Tennis Courts, Private Beach, Fishing off your...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    CASA DORADO1 / 25
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Patio
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'Casa Dorado' is an exceptional privately owned single family home located directly on Florida Bay on Lower Matecumbe Key in Islamorada. The house is named after the owners' favorite species of fish, the Dolphinfish, also known as Dorado in Spanish speaking coastal...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Southern Diversion Islamorada see our fall special1 / 30
    (7)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Porch
    • Cable/satellite TV
    • Parking
    • Outdoor Dining Area
    • Washer
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, Boat lift, Tiki hut on private beach, Heated pool and Wireless remote Internet. Southern Diversion has just been completely renovated. Brand new...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Balcony
    • Grill
    • Patio
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Irish Ayes' - Elegant tropical waterfront home with pool, Jacuzzi, dock and custom elevator. Plan your Keys getaway to this absolutely beautiful, spacious, tropical waterfront home located in the prestigious Venetian Shores subdivision of Islamorada. Enjoy unforgettable sunsets while relaxing on...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Park Model mobile home located oceanside on beautiful Windley Key in Islamorada, Florida Keys, the 'sport fishing capital of the world.' This is a great spot for relaxing, fishing and/or exploring the Keys, situated 75 miles from Miami and 85 miles from Key West. 1 BR plus upstairs sleeping or...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Beautiful Oceanfront, heated pool, free wifi1 / 54
    (19)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Internet Access
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Oceanfront splendor on the Atlantic ocean has a weekly vacation rental license, which allows for weekly rentals. There is a 350' pier that you can fish off of or simply jump in the ocean. The dock can accommodate most size boats if you wish to bring one. Just relax by the pool on those...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Islamorada 2-bedroom Condo1 / 6
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Grill
    • Waterfront
    • DVD Player
    • Washer
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you’ve been to Islamorada you know it as the sportfishing capital of the world, a place where you’ll find every water-related activity imaginable, with fine restaurants to crab shacks serving local fare, and plenty of nightlife for both the young and young at heart. If you’ve never been here, a...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Sauna
    • Internet Access
    • Balcony
    • Waterfront
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Savor a sun-filled vacation in this charming oceanfront condo, complete with sweeping ocean views and shared amenities such as a gym, saunas, a pool, tennis courts, laundry facilities, barbecues, and a party room. In the Sea Gull Condos complex, this rental is less than one mile off Old Highway 1...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    The PERFECT Escape with pool & jacuzzi1 / 10
    (7)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Waterfront
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful 4 bedroom/ 4 bathroom home has a 60' dock directly behind the home . Canal leads out to Snake Creek and has immediate Ocean and Bay access. The home is located in one of the finest neighborhoods of the Florida Keys- Venetian Shores. Upstairs there are 2 bedrooms/ 2 baths and there...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Florida Keys Bayside Retreat1 / 31
    (23)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Wi-Fi
    • Children's Pool
    • DVD Player
    • Sauna
    • Air Conditioning
    • Cable/satellite TV
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get away from it all in our tranquil waterfront condo at Summer Sea in beautiful Islamorada. Fully equipped, with newly updated kitchen and bathroom, flat screen televisions, and stunning views of Florida Bay from our patio. Located right in the heart of all the Keys has to offer - beautiful...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Seaside Sanctuary 5 bedroom 5 bath pool home1 / 24
    (12)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Waterfront
    • Ocean Views
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This impressive home is located in Islamorada on a private lagoon with quick direct access to the Florida Bay. Featuring 5 bedrooms and 5 bathrooms, this private residence offers plenty of balconies for water viewing, expansive cathedral ceilings, top of the line appliances and ceiling fans...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 15
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    Elegant Bayfront Townhouse with boat slip1 / 27
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Patio
    • Waterfront
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Ocean Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the spectacular view of the Florida Bay from this elegant, tasteful, completely remodelled townhome. 2 bedrooms, 2.5 bathrooms with balconies off the living room and master bedroom. Fully furnished and equipped for vacationers. Wifi and washer dryer in the unit. Very affordable dockage...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    16 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • DVD Player
    • Housekeeping Included
    • Ocean Views
    • Internet Access
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Morada is an upscale sixteen suite privately owned hotel inspired by the informal character of the Caribbean. The atmosphere is private, peaceful, and serene. The staff is renowned for their warmth and attentiveness. We have 11 suites in our Garden House and 5 suites in our Seaview house. The...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 16 Bedrooms, 5 Bathrooms, Sleeps 11
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