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Holiday Rentals with Pools in Islamorada

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    Travellers to Islamorada are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    81 Matching Rentals in IslamoradaView all 160 rentals
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    **Ready After Irma** Family Friendly Executive Bay Townhome with Beach & Pool1 / 25
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    THIS IS IT! Magnificent Oceanfront Paradise!  WE ARE OPEN!!1 / 20
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    **Ready After Irma** Modern Executive Bay Club Condo with Pool & Beach1 / 25
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Air Conditioning
    • DVD Player
    • Grill
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property has been inspected after hurricane Irma, is in good standing and is gladly accepting reservations at this time. We look forward to having you stay with us! *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oceanfront 2 Bedroom/2 Bathroom Well Maintained Condo with Large Balcony1 / 28
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2017
    This was a excellent place for our 30th wedding anniversary week. The owner was exceptional and had everything in the unit we could possibly need. Very helpful on suggestions...
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    About this property
    This condo has been completely restored after Hurricane Irma’s d is now ready for guests to return. There is new drywall, paint, carpets and new furniture and is safe to stay in. Paradise by the Atlantic Ocean and only 50' front the waters edge. Beautiful condominium complex with heated out door...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Luxury condo overlooking harbor with ocean view1 / 20
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Washer
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 January 2017
    This condo is beautiful, clean and has great amenities (swimming pool, hot tub, tennis court and gym). Everything in the condo is first class with excellent quality of...
    Reviewed 2 January 2017
    This condo was gorgeous and well stocked. They kept a collection of brochures for all the activities around the area in the condo. We loved swimming in the pool and fishing in...
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    About this property
    This premier luxury home is situated in a very quiet and peaceful gated community. All the rooms are very spacious with quality furnishings. A large double wide lanai with breathtaking views will make your getaway in the Keys. For your enjoyment it comes with private boat dockage, covered parking,...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Luxury 3 BR condo, boatslip, easy accces to ocean1 / 19
    (5)Excellent
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Air Conditioning
    • Ocean Views
    • Patio
    • Washer
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 June 2017
    We thoroughly enjoyed our stay in this beautiful, luxurious condo. It's roomy and clean and has all the amenities you could possibly want. I only wish we could've stayed longer...
    Reviewed 24 November 2016
    very neat and clean. Great location and views. Easy access to all of the Keys. Spacious nice size kitchen for cooking a meal if you feel like it. Nice location, because it's far...
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    About this property
    Luxurious end unit in Bay Harbour with a boat slip. Upon entering the unit you are greeted with the tranquil views of the harbor and ocean. Enjoy the ocean breeze from the large screen porch. Beautiful Bay Harbour gated condo community on lower Matecumbe, mm 74 1/2. Enjoy the sunrise or sunset...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 6 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 1 BDRM apartment located in Islamorada. Full kitchen and 1 full bath. Home is located on canal within 100 yards of the ocean. You will enjoy access to fully screened and heated pool. WiFi and cable TV included. Close proximity to shopping, restaurants and all the best the Keys have to...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Bay Front Beauty/ Summer Sea Must See!!!!1 / 19
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Ocean Views
    • Children's Pool
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2017
    Everything was perfect. Weather was great, the unit was clean and fully furnished with everything we needed. The other vacationers and full-time residents were friendly and...
    Reviewed 6 May 2016
    This condo was to die for. The decor was fabulous and the location was perfect and close to many restaurants. The sunset from the balcony was breathtaking. The owner was a...
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    About this property
    Beautiful / tropical decorated one bedroom, one bath water front condo in Summer Sea Condominiums located at Mile Marker 88.5 Bayside Islamorada, FL. Bayside means amazing open water views & world famous Florida Keys sunsets from your own private balcony overlooking the Florida Bay. You can also...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.1 / 41
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 February 2016
    We loved our stay at Ocean Harbour Apartments. After viewing photos on your website, we chose this based on the beautiful grounds and lovely accomodations. We could not have...
    Reviewed 6 January 2015
    This spacious condo is beautifully furnished and equipped. The gated community is very quiet and has a heated salt water pool. There is a nice spot to see the moon and...
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    About this property
    Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated security, this premium...
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    Islamorada, Florida Keys FL 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF1 / 25
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Patio
    • Waterfront
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 November 2016
    Everything we expected and more!! Condo very well maintained. Very adequately supplied with everything you need during your stay. Wonderful!! Thank you Susie and Matt for...
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    About this property
    This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Luxurious Anglers Reef with Boat Slip, Pool, Ocean1 / 29
    (26)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Grill
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 August 2017
    We stayed at Angler's Reef and had an amazing time. Jo was very helpful with the booking and very easy to work with. We felt like we were at home in her rental. She has...
    Reviewed 11 July 2017
    The island is beautiful. The condo is so clean and high quality. The area is located on the water. Nice boat docks.
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    About this property
    House, 2 Bedrooms + Convertible Bed(s), 2.5 Baths (Sleeps 5) Islamorada home set in OceanFront gated community with swimming pool and private boat dock This charming home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances. Open porches and balconies, rich...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Oceanfront Anglers Reef Islamorada Florida Keys1 / 14
    (2)Average
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 August 2017
    Very well appointed and comfortable house, conveniently located to local amenities in Islamorada. It was like a home from home with easy to use washing machine, dryer and...
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    About this property
    Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Children's Pool
    • Washer
    • Waterfront
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on...
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    Location Information
    Islamorada, Florida Keys 33023
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Murphy’s Paradise, a one acre private gated beachfront estate in the heart of Islamorada, Florida. This home features a private beach, 4 bedrooms, 3 ½ baths, family room, living room, game rooms, pool/spa and bar. This home can comfortably accommodate 8-12 people with room to spare....
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wonderful two story townhome in a private, gated community with all of the amenities you'd expect while on vacation. Inside: Newly renovated and remodeled unit. Fully equipped kitchen and stainless appliances, large storage cabinets with pull outs. Granite counters etc. Living room area with 60...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oceanfront End Unit, Spectacular Water Views, Pool, WiFi, Tennis1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Air Conditioning
    • Waterfront
    • Sauna
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2016
    Beautiful ocean views! Nicely decorated and well-cared for condo. We hope to return next year. We had everything we needed and felt like we were at home, a lovely relaxing home.
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    About this property
    A Vacation Rental for View Lovers! FREE WIFI Best location in the complex. For two couples or a family with 2 kids. The two new extra long twin beds in 2nd bedroom convert to a comfy King Bed! Master bedroom has new king bed, ocean view and private bath. 2nd bathroom in hallway. This...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    BROCK HAUS ON THE GULF1 / 25
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Balcony
    • Parking
    • Terrace
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2017
    we have been coming to Futura Yacht Club for many years now and I can say unequivocably that Brockhaus is the most desirable unit in the complex. Just a wonderful experience...
    Reviewed 28 May 2017
    Great Condo with excellent views and amenities . You could,t ask for anything better and Keys Holiday Rentals are second to none. great service and great folks
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    About this property
    Minimum Rental: 7 Days (Saturday to Saturday) 'Brock Haus on the Gulf' is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic open...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Islamorada Luxury Home Ocean & Bay Access1 / 14
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Patio
    • Waterfront
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Special vacation rental rates for off-season bookings and also for some last minute dates! Call us now for details. Located in Islamorada the fishing capitol of the world, this is a beautiful home decorated with Island style decor. Over 3,000 square feet of living space. 100' of dock, less than two...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Newly refinished  condo open water views very nice1 / 16
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 April 2017
    Besides the obvious gorgeous outdoor surroundings, this condo was equally as beautiful. It's hard to be inside when you're in the Keys, but Mark's condo makes it easy. The views...
    Reviewed 29 January 2017
    The condo was beautiful and well appointed. The community was beautiful with a great pool, nice beach, and extremely friendly people. Great restaurants and a cozy deli nearby...
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    About this property
    Beautiful professionally decorated condo in Futura Yacht Club. Pool, club house, Tennis, Marina with great fishing. Marker 88 restaurant is a short paddle board away. Private beach with sun set view. Perfect location near everything, restaurants, bars, shopping. Diving centers ,fishing, boat...
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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Balcony
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'The Palms #301' is an exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival. Be sure to look...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    BEACON REEF 2221 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Hot Tub
    • Parking
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2017
    Great location! The pool, tiki bar and dock are all top notch. The ocean views are amazing. All equals the perfect family vacation.
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    About this property
    Minimum Rental: 28 Days 'Beacon Reef 222' is an extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada....
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Patio
    • Washer
    • Internet Access
    • Air Conditioning
    • Grill
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unit is a duplex with 2 full Bedrooms and 2 full Baths - plus a loft in the master bedroom that sleeps an additional 2. There is also an electric EZ Bed for larger groups. Also included is a gas BBQ Grill in the back porch and use of any of the recreational items at the unit. Located in the...
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    Location Information
    Islamorada, Florida Keys 34950
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    PALMS 3141 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Hot Tub
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'The Palms #314' is a sensational oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Watch the fishing charter boats as they come and go from Bud and Mary's Marina. You'll be able to see cruise ships as they...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Islamorada Luxury Waterfront Condo with Boat Slip1 / 21
    (13)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Waterfront
    • Hot Tub
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 May 2017
    Very comfortable condo. Enjoyed a week of R&R. Very quiet place. Great pool. Deanna, the owner, was very helpful giving us help in launching our boat, storing our trailer...
    Reviewed 2 May 2017
    Excellent locationt, accommodations where great, all you need to bring is yourself and clothes. Deanna the owner was prompt in answering any questions regarding the property...
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    About this property
    Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Grill
    • Patio
    • Washer
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ENJOYABLE, CENTRAL LOCATION, PLANTATION KEY, 3 bedroom + loft, 2 bath; 1400 sf 2 story, all bedrooms and 1 full bath are upstairs & downstairs is the living area and 1 additional full bath. The unit is clean, comfortable, quiet and restful. The community is gated with security, no pets are allowed;...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Balcony
    • Cable/satellite TV
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'The Palms #407' is a charming 2 bedroom, 2 bath condo with updated kitchen and baths. Walk out onto your balcony and enjoy the sea breezes and ever changing ocean views. The comfortable furnishings and convenient floor plan provide an inviting place to call home. You...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    BEACON REEF 3101 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Terrace
    • Cable/satellite TV
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 October 2017
    Super clean and very comfortable condo! Property Managers were so easy to work with too! We loved Beacon Reef and had the best vacation!
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    Minimum Rental: 28 Days 'Beacon Reef 310' is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on your own...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    **Ready After Irma** Fully Updated Modern Townhome with Pool, Beach & near1 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
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    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 November 2016
    Fantastic townhouse!! Came here to stay with a couple of friends and went fishing. It is right in the heart of Islamorada. You'll never run out of things to do, or places to eat...
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    About this property
    This property has been inspected after hurricane Irma, is in good standing and is gladly accepting reservations at this time. We look forward to having you stay with us! *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    PALMS 3091 / 27
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Patio
    • Terrace
    • Internet Access
    • Balcony
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2017
    Our three month stay was excellent. We enjoyed the location and close proximity to where we had our boat stored.
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    About this property
    Minimum Rental: 28 Days 'The Palms #309' is an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    FLORIDA KEYS OASIS - The Corona commercial-welcome ****7 DAY MINIMUM RENTAL****1 / 32
    (4)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Ocean Views
    • Patio
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 July 2017
    The property manager was super helpful and walked us through the entire house showing us all the nooks and crannies. I must say I've never had someone take close to 45-an hr to...
    Reviewed 13 February 2017
    On our recent family trip to the keys, we were lucky enough to find this amazing home. We stayed for one week and wish we had stayed a month!The house is 6 stars and the hosts...
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    ***7 day minimum rental - notwithstanding anything in the rates page the MINIMUM rental is 7 days ****This custom built 5 bedroom house has been immaculately taken care of and has a proper size elevator and is fully wheel chair accessible. Enjoy your stay in Sereni-key looking out to an endless...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    PALMS 4171 / 25
    (1)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Grill
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Hot Tub
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'The Palms #417' has great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch the sun rise over the ocean as fishing boats leave on their daily charters...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Cable/satellite TV
    • Terrace
    • Grill
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MINIMUM STAY: 28 DAYS Flamingo Cottage is an adorable 3 bedroom stilt home nestled among tropical foliage. There are two bedrooms and one bath on the main living level of this home plus a private studio type apartment with a private bath on the ground level. This home has a cozy cottage like...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxurious Condo-Exclusive Bay Harbour w/Boat Slip & Marina, Pool, Tennis courts1 / 15
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Grill
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 March 2015
    Great property! Very beautifully decorated. I loved the view, really enjoyed my stay! I look forward to staying there again soon!
    Reviewed 20 January 2015
    This condo is beautifully decorated and chock full of everything you need to make your stay just perfect. The condo and the complex are extremely well maintained and have the...
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    About this property
    Revel in the beauty of the morning sunrise as you relax on your own, private lanai while sipping your morning coffee, or enjoy a meal al fresco to the sound of the waves and gulls. This piece of paradise is sure to become your favorite home away from home. This lovely property is part of a gated,...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    BAYSIDE CONDO MARINA,POOL,TENNIS AND DOCKAGE1 / 78
    (14)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Balcony
    • Terrace
    • Outdoor Dining Area
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2017
    Plantation Key in Islamorada and the Futura Yacht Club is great. Lots do do without having to leave Islamorada. If you love snorkeling, diving, swimming, fishing, kayaking...
    Reviewed 1 May 2017
    Location was perfect for exploring the middle Keys. Pool was awesome. We loved the grill out by the Gulf of Mexico, it made for a memorable dinner/ sunset.
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    About this property
    Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, and dockage for...
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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Terrace
    • Parking
    • Cable/satellite TV
    • Internet Access
    • Patio
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 1 Month Enjoy the magnificent ocean views of this wonderful condominium complex. You'll love the newly completed renovations. The kitchen has been totally remodeled with all new cabinets and appliances. The living room furniture is brand new and there's a big flat screen TV...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    MANATEE MANOR1 / 25
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Terrace
    • Internet Access
    • Patio
    • Parking
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2017
    We enjoyed the month of June at Manatee Manor. You are greeted on the first floor with a comfortable game room area that includes a pool table that converts to ping pong and...
    Reviewed 10 August 2017
    Our family stayed and Manatee Manor for the month of July and had the perfect summer vacation. The layout of the home as well as the quality of the furnishings, location and...
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    About this property
    Minimum Rental: 28 Days 'Manatee Manor' is a 3 Bedrooms and 2 ½ Baths home with POOL, Dock, and all new furnishings make this your opportunity to experience The Florida Keys at its best. Conveniently located on a deep and wide canal with easy access to the Bay or a short ride to Tavernier Creek...
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    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Balcony
    • Patio
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'The Palms #402' is a beautifully remodeled and immaculate condo. You'll love the uncluttered and modern décor along with the recent renovations. Enjoy the picturesque views of Alligator Reef and the Atlantic Ocean from this 4th floor balcony. Watch the fishing boats...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 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)
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2017
    Beautiful home with great access to boat launch and dockage at the house. Very neat and clean and every amenity you could want. Had some AC problems that Keys Holiday Rentals...
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    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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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    LYONS LANDING1 / 24
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
    • Terrace
    • Cable/satellite TV
    • Parking
    • Internet Access
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 June 2017
    Every room is comfortable,charming and the property managed to make you feel comfortable and at home..with every amenity..including an ice maker..so nice to have here in The...
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    Minimum Rental: 28 Days 'Lyons Landing' is an exceptional VENETIAN SHORES single family home with pool, dock, boat lift and outdoor living area! Everything you need for a spectacular holiday awaits you in this extraordinary home. 3 bedrooms and two baths on the upper level plus a bedroom and...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    PALMS 2141 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Hot Tub
    • Internet Access
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 September 2015
    We have always enjoyed the keys and love staying at the Palms of Islamorada. The units are big enough and the amenities are nice. Unit 214 was nice and clean. A big TV for me...
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    About this property
    Minimum Rental: 28 Days 'The Palms #214' is a gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panorama of...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
    • Grill
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in tranquility at 'Windley Cottage', located at 129 Anglers Way in Angler's Reef, Islamorada's premier gated oceanfront community of 52 private homes, built in 2008. With two luxurious bedrooms, each with its own full en-suite bathroom, it's the perfect vacation property for single families...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
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    • Cable/satellite TV
    • Internet Access
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Infinite ocean views from the large balcony at this modern and luxurious oceanfront condo at mile marker 87. BOAT SLIP INCLUDED which can accommodate up to a 30' boat. SLEEPING ARRANGEMENTS (Sleeps 4) Master Bedroom: - King Size...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Hot Tub
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'Beacon Reef 501' is an exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You'll be so glad you have chosen to spend your holiday here. The kitchen was remodeled in 2013 - granite counters, stainless...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alligator Reef is the Perfect getaway for large groups!  You can rent from 1 to 4 homes depending on the size of your group. The Pelican and Egret homes will offer you 2 homes, 5 bedrooms, and one pool.  The Pelican is a 3 bedroom 2 bath ocean front pool home which will sleep up to 8 people.  (Sofa...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Live your tropical dream at this palatial oceanfront estate. Located near mile marker 89, on Islamorada's Millionaires' Row, this 4 bedroom / 6 bath home comes with just about every convenience you can imagine, as well as some you probably haven't even considered. Enjoy a swim in the pool that...
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    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 10
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
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    Pet friendly
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    Smoking allowed
    About this property
    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This beautiful oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Florida Keys Beautiful 2B 2B Townhouse1 / 18
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2016
    This was our first trip to Florida, it was agreed that we would leave Orlando and the parks for a few years as our children are still quite young (4 and 1). We did extensive...
    Reviewed 18 January 2016
    We had very nice time staying in Ana's townhouse in Islamorada. It is nicely decorated, well equipped, comfortable and spotlessly clean. There is more than enough room for a...
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    About this property
    Our unit is a short walk to the beach and dock... No view of the ocean from our unit. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach and a...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Patio
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 bedroom / 2 bath in the heart of Islamorada. With a pool. A short walk to Chica Lodge and Moorings Village and all the best restaurants in the Keys like Morada Bay. Located in the best location of the Florida Keys. The house has many different places to relax, lounge and forget all the...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
    • Balcony
    • Ocean Views
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Watch the sunrise from the spacious balcony overlooking the Atlantic Ocean. This brand new three bedroom, two and-a-half bath condominium sleeps eight people. Master bedroom has a king bed with access to the balcony. Second bedroom has a queen bed and third one has two twin beds. TVs in every...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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