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Holiday Rentals in Islamorada

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    ₹ 19,208 Average
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    All 160 Rentals in Islamorada
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    Oceanfront 2 Bedroom/2 Bathroom Well Maintained Condo with Large Balcony1 / 14
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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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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    Luxury condo overlooking harbor with ocean view1 / 20
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Islamorada Tropical Canalfront Paradise1 / 13
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Patio
    • Parking
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 February 2018
    Wow! This property is just perfect for a quick getaway! The backyard was so fun, for our entire family. My kids loved the hot tub, my wife loved the waterfront view and I loved...
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    About this property
    The moment you step in the back yard, you'll know vacation has begun. . . time stands still as the laid-back island lifestyle takes over...Totally remodeled, canal-front home, quiet and in the nicest of neighborhoods (Plantation Key Colony). The 2 bed/2 bath stilted (upper unit) island retreat is...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    No dockage allowed. Florida Keys. Beautiful condo. Short walk to the beach area.1 / 18
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Washer
    • Parking
    • Air Conditioning
    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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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oceanfront 5th Floor End Unit, Pool, Free WiFi, Million Dollar Ocean Views!1 / 30
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • 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. And new this year, a sandy beach. For two couples or a family with 2 kids. The two new extra long twin Pillow Top beds in 2nd bedroom convert to a comfy King Bed! Master bedroom has new Simmons Beautyrest Pillow Top...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2.5 BR 1.5 Bath Townhouse with Beautiful Beach and Boat Slippage!1 / 13
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    Stunning townhouse that sits on the undisputed best beach in the keys. Boat slippage up to 26 feet. Pictures speak for themselves. The beauty of the Keys surrounds you. Easy access to the ocean side for offshore fishing, or simply fish the canal or the beach. 75 miles to Miami airport, 75 miles to...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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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    THIS IS IT! Magnificent Oceanfront Paradise!  WE ARE OPEN!!1 / 17
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Ocean Views
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2017
    The condo was great! Location was perfect for all the things we wanted to do. Nice quiet atmosphere, the tenants that live there are so nice. It was a perfect Florida Keys...
    Reviewed 9 May 2017
    This condo was perfect for our annual family vacation. The condo was very clean, well-equipped, and the online description was accurate. The owners were excellent to deal with...
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    About this property
    Huge screened in terrace. Spacious and extremely clean.. Peaceful and away from the highway. Sleeps 2-5 people. , large pool on the ocean, . many water-front restaurants and bars nearby. Oceanfront mm 90, Plantation Key. Books up very quickly. Reserve early! Note: We are licensed in Islamorada:...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    THE PERFECT GETAWAY1 / 14
    (6)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 October 2016
    My husband and I searched for six weeks to find the perfect house for our vacation with another couple, and kept coming back to this one. All four of us were looking for a...
    Reviewed 9 April 2016
    We thoroughly enjoyed staying at the Perfect Getaway. My family and I had enough space to sleep, relax and enjoy meals together. The pool was a great addition to the property...
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    About this property
    This four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. It is situated in a clean, upscale neighborhood of all waterfront homes. The house is equipped with all the comforts of home. It is modernly furnished. Upstairs there are...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    This 2 bedroom, 2 bathroom condo located directly on the Florida Bay is the perfect sunny getaway! Situation with perfect views of the community pool, community marina, and open bay, you'll enjoy coffee in the morning while watching the boaters head out for their perfect catch and enjoy a sunset...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE KING MASTER BEDROOM IS DRESSED IN ISLAND FINERY WITH PRIVATE BATHROOM, COMBINATION SHOWER/TUB, AND FLAT SCREEN TV MAKES FOR THE PERFECT RETREAT. THE SECOND BEDROOM OFFERS A QUEEN SIZE BED, A FLAT SCREEN TV, AND AN ATTACHED BATHROOM. YOU CAN “COOK YOUR CATCH” IN THE FULLY EQUIPPED KITCHEN WITH...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Serenity Waterfront-Dock, View, Tiki Hut, spa/hot1 / 22
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2016
    Wonderful vacation nice, relaxing. I would definitely return. Charlie was very informative on where to go to eat. Locals were very nice too.
    Reviewed 16 October 2015
    What a great little spot! Was quiet and very peaceful. Clean and cozy! Had everything we needed. Will be back to Stay again soon! :)
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    About this property
    Located in beautiful Plantation Key, the first Island of Islamorada. An area of all waterfront homes Wifi, boat dock, trailer parking, and all amenities are included also, Lovely Tiki Hut overlooking the water. Plus a huge covered entertainment area complete with dining areas, settee and gas...
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    Islamorada, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This townhome at Executive Bay will sure make your home away from home!  This unit has been completely renovated and decorated beautifully.  This  2 bedrooms and 3 bathrooms has a (1) King Bed, (1) Queen Bed and  there is a bonus room off the Master that has 2 twin beds. Executive Bay Club is a...
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    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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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 on the bay side in Islamorada. The unit comes fully furnished with a full kitchen, dining room, large living room with sleeper sofa, expansive balcony with great views of the Florida Bay and the...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    This unit's kitchen, bathrooms, windows, and doors received a facelift in January 2014! Enjoy the spectacular view of the Florida Bay from either one of the TWO balconies in this 2 story townhome, located off the master bedroom or the living room. Amenities include Wi-Fi, flat panel TV's in...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    3/2 or 6/4 Tropical Parroteyes, Location,Comfort Views!1 / 27
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    We are one of two couples who each have rented a level for the past six winter seasons and we are so looking forward to returning in 2018. The location is perfect-within one...
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    About this property
    Beautifully Decorated, Fully Furnish and Equipped Vacation Pool Home, Located in a Quiet and Safe Residential Area in Islamorada, Florida Keys. Video of house and area available upon request. It consists of Two Levels, Each Separate Level Has 3 Bedrooms/2 Bathrooms. You Can Rent One Level a 3/2...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Islamorada Luxury Waterfront Condo with Boat Slip1 / 21
    (15)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 13 March 2018
    The condo is truly beautiful. We appreciated all the small amenities stocked within it and the furnishings and bed comfort was outstanding. The view was excellent and the staff...
    Reviewed 30 January 2018
    I was looking for place where my family could drink deeply of the “Keys Experience”. A place where we could fish either the ocean or back country, enjoy unbelievable sunsets...
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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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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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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 superior condo in the best location in Islamorada. The unit is superior with the best water views, with everything you need ,full kitchen stocked with cookware, microwave, coffeemaker, large island counter, breakfast nook with ocean view, washer and dryer in...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Islamorada, Florida Keys 33036
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    PALMS 3091 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Patio
    • Parking
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 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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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    BAYSIDE CONDO MARINA,POOL,TENNIS AND DOCKAGE AT FUTURA YACHT CLUB1 / 70
    (16)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Balcony
    • Terrace
    • Outdoor Dining Area
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2018
    Love staying in this condo was our second year hoping to return next winter if available. already made request.. I would never leave if it were up to me but the location and the...
    Reviewed 12 March 2018
    Enjoyed our stay.Everyone very friendly. Grounds well kept.Pool area perfect. Two BBQ grills,great areas to walk. condo very comfy
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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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    Islamorada, Florida Keys 33070
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    132 Columbus Drive1 / 18
    (16)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 January 2014
    Location, location, location; this home was a great getaway, and beautifully landscaped (but not manicured) with older Australian pines, sea grape, palms and silver buttonwood...
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    About this property
    This is a neat house! It sits right on the ocean with a large yard (by keys standards!). Very nicely landscaped (hibiscus, palm trees, tall pine trees, green grass)with statues from all over the world. Very private with a big gate. The house is decorated with pictures taken from all over the world...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    **Spring Discount** Modern Executive Bay Club Condo with Pool & Beach1 / 25
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Terrace
    • Wi-Fi
    • Grill
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 2015
    Our townhouse was clean, spacious, & quiet. Lovely updated kitchen and laundry. The pool was delightful, and the beach & dock were very enjoyable as well. Very peaceful...
    Reviewed 29 March 2015
    I really enjoyed my stay! The place was great. I loved the layout. Very roomy. Enough space for everyone. The pool was great and even played a little tennis.
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** Come and relax at our beautiful town home on...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    FLORIDA KEYS OASIS # The Corona commercial-welcome ****7 DAY MINIMUM RENTAL****1 / 31
    (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 12 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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    About this property
    ***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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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Patio
    • Internet Access
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    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 1 Month Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom overlooking the canal....
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    LITTLE BAY - Cottage1 / 24
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 29 January 2016
    Stayed in the cottage, 5 of us in total. Gorgeous cottage inside and out, set on a fabulous site with beautiful trees, shrubs, birds, green grass, stone paths, lots of parking...
    Reviewed 28 May 2013
    The pictures really don't do this place justice, there are so many comforts that it feels more like a home. It is in a great location and since it is gated, it was safe enough...
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    About this property
    Minimum Rental: 7 Days 'Little Bay's Cottage' 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 floor plan with the main living area in the center of the house with kitchen, dining area, sitting area 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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    BEACON REEF 3101 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Balcony
    • Shared Outdoor Pool (Unheated)
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    • Terrace
    • Cable/satellite TV
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 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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    About this property
    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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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    **Spring Discount** Family Friendly Executive Bay Townhome with Beach & Pool1 / 25
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Patio
    • DVD Player
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    • Balcony
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 September 2015
    We attended with my wife and adult daughters and this apartment had everything we could wish for.The facilities were ideal for our needs and the booking process was simple.Due...
    Reviewed 13 September 2015
    The condo is very nice and spacious for 5 persons. The place is clean and supplies are adequate. Location is good. Swimming pool is big and nice. Able to do a little fishing...
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** *** Owner is highly motivated to rent! Contact...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Islamorada Waterfront Paradise Getaway!1 / 28
    (31)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Ocean Views
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2017
    We spent a wonderful, spirit rejuvenating MONTH with Ewa and Peter at their beautiful home by a lagoon in Lower Matecumbe Key. At first we bustled about, kayaking from the dock...
    Reviewed 1 March 2016
    We had a delightful stay in this lovely property - by the water and with hammocks and a very peaceful setting. The room was well equipped and the owner were very helpful.
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    About this property
    Please contact us for all of our rates for different length of stays! For shorter stays...make sure you have a minimum of 28 days entered in your contact form! DO NOT BOOK THROUGH FLIPKEY! Booking instructions will be provided when you send your inquiry, saving you significant FlipKey booking...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a very spacious and very well-maintained 4 bedroom, 3 bathroom home toward the mouth of the canal on a quiet street in Plantation Key (Tavernier). You and your group will enjoy stunning views from the main level, master suite, & rooftop sundeck. There is approximately 20ft concrete dockage....
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    107 San Remo Drive1 / 36
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 January 2018
    What a fabulous area and home, Nancy and Norm were (the owners) told us places for dining out, Island times grill, Craigs seafood ( Mahi Mahi sandwich is to die for) Mrs Mac...
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    About this property
    Comfortable Venetian Shores canal home that has two bedroom/one bath upstairs and a one bedroom/one bath apartment downstairs.  The downstairs apartment has a complete kitchen and living room and separate bedroom.   There is a screened in porch of the living room upstairs.  The home has awesome...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Come relax in Islamorada, the tropical jewel of the Florida Keys!!1 / 9
    (2)Excellent
    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
    Reviewed 6 March 2018
    Tastefully decorated and very neat and clean. Comfortable throughout, beautiful setting & perfect to relax & get away from it all!!
    Reviewed 3 March 2018
    We arrived at this beautiful rental on January 21, 2018 having escaped the throes of winter in Ohio. The apartment was wonderful for the two of us and had everything we needed...
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    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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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    Incredible Luxury Home with Waterfront!! Paradise1 / 17
    (2)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Grill
    • Washer
    • Hot Tub
    • Balcony
    • Central Heating
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 December 2017
    Cannot even express in words how great of an experience my family had! The house is unbelievable, with two apartments downstairs and three bedrooms upstairs. The yard is amazing...
    Reviewed 5 December 2017
    I loved having everyone at one location and with the 3 separate living areas, there was plenty of space! Easy access to a great bike/walking path. Great restaurants just a...
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    About this property
    Lo-Key Estate is truly a luxury Keys home situated on a private 400’ waterfront peninsula with the use of a tropical swimming pool w/waterfall and hot tub(shared w/guest house) There are Ocean Views from the 2 & 3rd floors. Lo-Key is a custom 5 bedroom/5 bath home that opens onto Florida Bay...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'West Plaza Del Lago' promises to be a favorite. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home as much as the exterior! As you enter...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    MY PARADISE1 / 25
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Balcony
    • Internet Access
    • Parking
    • Patio
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Just returned from our 2nd annual monthly stay at My Paradise. We again had a wonderful stay. The house is right on a beautiful sandy beach and is great for walking and...
    Reviewed 3 October 2016
    The house is a dream! It is located in a quiet dead-end road and right on the sandy beach.Perfect for a family vacation. The house is fully equipped, from the kitchen to...
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    About this property
    Minimum Rental: 28 Days 'My Paradise' is an oceanfront beach house with protected dockage and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SuCasa is located next to Robbie’s Marina where you can hand feed the Tarpon on Lower Matacumbe. The Main House sleeps eight comfortably in four bedrooms with 3 queen-sized beds and two twin beds and comfortably sleeps 8. It has a fully equipped kitchen with a stove, dishwasher, microwave, coffee...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    **Spring Discount** Ocean Front Keys Home with Private Beach - Great for Kite Su1 / 25
    (2)Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Balcony
    • Grill
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2016
    Had a wonderful time beach just out front and did a lot "beaching". Close to a nice supermarket and rental places. Will definitely be back! Thanks for a great get away!
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** Beautiful four bedroom, Ocean Front home with...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Oceanfront Anglers Reef Islamorada Florida Keys1 / 14
    (3)Very good
    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 4 weeks ago
    This home is in a gated community in the heart of Islamorada. The site is beautiful, and seemed to have suffered no damage from Hurricane Irma. There are two artificial...
    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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    Ocean-Front Caribbean Home.1 / 21
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Washer
    • Balcony
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 March 2018
    Very much enjoyed our stay. House was beautiful and clean, staff was friendly and helpful. My mother and I loved relaxing in the hot tub and my father and husband very much...
    Reviewed 24 April 2015
    Rolled out of bed early every day this week with my boys and family friends for my favorite commute: 50 yard walk to a private boat slip at the resort. We rented a boat...
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    About this property
    The Royal Palm, South - Ocean Front Home ( recent fraud. NEVER wire us money. Payment for reservations can only be done via the phone, not online or via wire) Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier. Inspired by owner Phil with nothing compromised this luxurious Caribbean home...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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
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    • 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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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    SUNSHINE PLACE1 / 23
    (9)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
    • Grill
    • Internet Access
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    My husband and I have been visiting Islamorada for the past 5 years. This year we stayed at Sunshine Place for the month of March. Loved it! Great views! Private yet close to...
    Reviewed 10 March 2018
    Sunshine Place has one king bed, kitchen, 1&1/2 bathrooms,. a dining area, living area and a futon. The views from the many windows is spectacular with brilliant sunrises...
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    About this property
    Minimum Rental: 7 Days 'Sunshine Place' is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    82754 Overseas Highway1 / 29
    (4)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2017
    We have been staying in the keys for 5 years in a row & this was the best rental property we found. We are 4 guys (over 50) who want to go fishing and relax and this property...
    Reviewed 9 May 2017
    Our family (three generations) wanted a place in Islamorada with 5 bedrooms. We rented the Osprey Bay Villa for a week and it was a perfect fit. The bay side location provided...
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    About this property
    OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    GULFVIEW GETAWAY1 / 24
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Parking
    • Patio
    • Terrace
    • Grill
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 December 2017
    My family loves this house! It is a home away from home, with all the amenities you could need for an amazing vacation. It's convenient to shopping and restaurants. There is...
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    About this property
    Minimum Rental: 28 Days 'Gulfview Getaway' is a FABULOUS BEACH FRONT HOME! This is what you've been dreaming of - your very own single family home with a private sandy beach in the Keys. This home is new to the rental market. It is located in a highly desirable area of Islamorada on a dead...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** *** Owner is highly motivated to rent! Contact...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    PALMS 3141 / 25
    (2)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
    Reviewed 2 weeks ago
    Key Holiday Rentals are the best, they are there when you need them and are there to answer any questions you have .
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    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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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the spectacular view of the Florida Bay from this beautiful townhome. This townhome is a 2 bedroom and 2-1/2 bath unit.  There are tons of things to keep you and your family busy without having to leave the Futura Condo complex. There are tennis courts and a swimming pool located on the...
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    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Balcony
    • Cable/satellite TV
    • Internet Access
    • Patio
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Grill
    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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