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Islamorada Rentals for Seniors

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    Travelers to Islamorada are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    54 Matching Rentals in IslamoradaView all 212 rentals
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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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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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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
    • Satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 2, 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 January 2, 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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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • 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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    Islamorada, Florida Keys 33023
    Rental Home - 2 Bedrooms, 3 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
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 9, 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
    Rental Home - 2 Bedrooms, 3 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
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 10, 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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    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
    • Satellite TV
    • Patio
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 6, 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 October 16, 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 <BR>Wifi, boat dock, trailer parking, and all amenities are included also, <BR><BR>Lovely Tiki Hut overlooking the water. Plus a huge covered entertainment area complete with dining areas, settee...
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    Islamorada, Florida Keys 33037
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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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
    • Satellite TV
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 8, 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 May 1, 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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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Isla Breeze, Summer Sea1 / 21
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Children's Pool
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Sauna
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 27, 2016
    This vacation was the perfect relaxing trip we have had in a long time. It is less than 2 hours from Miami airport, which is a beautiful drive. The condo was perfect. If I...
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    About this property
    Relax and Unwind in Your Luxuriously Renovated Condo With Oceanfront Views in the Fishing Capital of the World: Islamorada!! Beautiful Open Water Views in a Well-appointed Building That Provides Everything You Need for a Relaxing and Memorable Vacation. the Cozy Patio Invites You to Enjoy Your...
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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Waterfront
    • Ocean Views
    • Washer
    • DVD Player
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your awe moment begins as you drive through the gates of the Moja Draga Estate, located on a beautiful 2 acre parcel of prime ocean front property in the village of Islamorada. Moja Draga is where your vacation dreams begin. Your island vacation home is well appointed with all that you need for a...
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    Location Information
    Islamorada, Florida Keys 33070
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rental amount includes all fees boat dock fee.. This newly renovated modern 4th floor condo in a private gated community has a spectacular Florida Bay sunset view. Futura Yacht Club is just 68 miles south of Miami. Amenities include heated pool, screened in Lanai, 2 lighted tennis courts, and...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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
    • Satellite TV
    • Patio
    • Secure Parking
    • Internet Access
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 4, 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 January 29, 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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    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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    • Satellite TV
    • Washer
    • Air Conditioning
    • Ocean Views
    • Patio
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    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 February 12, 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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    Islamorada, Florida Keys 33036
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
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    Pet friendly
    Kid friendly
    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
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Private Yard
    • Secure Parking
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful home with 3 bedrooms and 2 bathrooms,everything renovated,kitchen remodeled with stainless steels appliances ,the house have comforted beds for 10 people's ,backyard area with BBQ ,private parking inside the house for 6 cars,private ramp for boat and jetski inside the house,beautiful...
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    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Central Heating
    • Terrace
    • DVD Player
    • Grill
    • Sauna
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ****Recently updated paint, furniture and a Beauty Rest Mattress!!**** Looking to escape reality? Look no further! Spacious 1 bedroom/1 bathroom condo located in the newly renovated Summer Seas Condominiums. Sit back and relax at the pool, go swimming at the private beach. Feeling adventurous?...
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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Yard
    • Air Conditioning
    • 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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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • DVD Player
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to paradise! Built in 2012 and designed by well-known Miami architect to mirror the curved shoreline of the beach, this private custom contemporary beach home is a one of a kind, unique design with gated entry, large private beach, and gorgeous ocean views from every room. Built using ICF...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    4 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Private Yard
    • 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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    Islamorada, Florida Keys 33070
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 10
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    Islamorada cottage on deep water canal1 / 13
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Waterfront
    • Wi-Fi
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    • Patio
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our cottage is located in a quaint and quiet neighborhood on a deep water canal, Bayside at Mile Marker 89. A concrete boat dock is available for a 30 foot boat and a fish cleaning station. There is easy ocean access through Snake Creek or Tavernier Creek. The fenced private back garden has a...
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    Location Information
    Islamorada, Florida Keys 33070
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Privately owned condominium unit at the Futura Yacht Club in the Village of Islamorada. Futura is located on the Gulf of Mexico and is a gated complex consisting of 70 units. Enjoy wonderful Bay views and sunsets from our two bedroom / two bath condominium unit that sleeps up to 6 people. Stay in...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • DVD Player
    • Satellite TV
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    • Grill
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    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Satellite TV
    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    There is no other neighborhood like Anglers Reef in Islamorada. It's beautiful Key West style pastel colored homes inside resort community, with garden like flora and fauna such as bougainvillea meticulously maintained, with a fantastic oceanfront swimming pool and boat docks and views over the...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3/2 or 6/4 Tropical Parroteyes, Location,Comfort Views!1 / 27
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • 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 4 weeks ago
    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. It consists of Two Levels, Each Separate Level Has 3 Bedrooms/2 Bathrooms. Offering Modern Granite Counter Tops and Stainless Steel Appliances. Plush...
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    Islamorada, Florida Keys 33070
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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    SANCTUARY IN PARADISE1 / 21
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 23, 2014
    My family/extended family stayed here in June 2012 for two weeks and it was beyond wonderful. The owner ALWAYS was quick to respond to emails even if it was to say "you're...
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    About this property
    WWW.SCHOONERHAMMOCK.COM This unique property offers : -master suite -apartment -cottage -3 full kitchens On Atlantic Ocean. Simple, sweet, and serene sanctuary. Please contact Andy Cancela 828 808 1693 We love The Lord and look forward to sharing our home with you.
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    Location Information
    Islamorada, Florida Keys 33070
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Central Heating
    • Waterfront
    • Balcony
    • Grill
    • Housekeeping Included
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully renovated beach cottage in the heart of Islamorada. Home has a private pool and a 75ft dock for your enjoyment. Guest also have access to private homeowners beach (White Marlin Beach). Main living area, Kitchen and terrace upstairs. Master bedroom with ensuite bathroom and queen sized...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Grill
    • DVD Player
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This impressive home is located in Islamorada on a private lagoon with quick direct access to the Florida Bay. Featuring 5 bedrooms and 5 bathrooms, this private residence offers plenty of balconies for water viewing, expansive cathedral ceilings, top of the line appliances and ceiling fans...
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    Location Information
    Islamorada, Florida Keys 33070
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Wi-Fi
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    • Balcony
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    • Washer
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful and spacious home with three bedrooms, two and half baths, huge new kitchen, new bathrooms, and screened in porches facing East and West. There are great views from every room!!! Tastefully furnished with all linens, comfortable memory foam mattresses, all new appliances, and completely...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Osprey Lagoon Half Duplex House, 28 night minimum1 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Half Duplex Home Are you seeking a beautiful hideaway close to all the amenities? This delightful 1 bedroom half duplex vacation home has deep water dockage for your boat in the back yard with the view of a beautiful lagoon. This lagoon has schools of tarpon to test your angling skills, and...
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    Location Information
    Islamorada, Florida Keys 33070
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Yard
    • Air Conditioning
    • Wi-Fi
    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 BR 2 BA 1 HF BA Sleeps 8 There is no other neighborhood like Anglers Reef in Islamorada. It's beautiful Key West style pastel colored homes inside resort community, with garden like flora and fauna such as bougainvillea meticulously maintained, with a fantastic oceanfront swimming pool and boat...
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    Islamorada, Florida Keys 33036
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Housekeeping Included
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    Pet friendly
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    Smoking allowed
    About this property
    Highend remodeled and luxuriously furnished bay view condo in the gated community of Futura Yacht Club. 2 bedroom 2 full bath Condo with a open den that can be closed off as a third room (queen size murphy bed). Flat screen tv in every room with cable and wifi. Gorgeous modern kitchen with eat in...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Property description Framed by mangroves and the Atlantic Ocean this exquisite Key West style 2 bedroom, 2.5 bathroom home, is located in the quiet oceanfront private community of Anglers Reef -one of the best kept secrets in the Keys. Florida State Licensed Single Family Vacation Rental Dwelling...
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    Islamorada, Florida Keys 33036
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    Pet friendly
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    About this property
    Corner lot, Clear and deep waterways, 3 bedrms, 3 bath, sleeps 8+ Granit Tops This home is located in a prime neighborhood with 150lf of seawall for all your water toys. 3 bedrooms, 3 full bath ,1 king, 2 queens and bunkbeds, Laundry room, Wet bar, Library/Sitting room, Living /Family room and...
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    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Hot Tub
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully furnished 2 BR 2 BA Condo on second floor.(First is parking only) Spiral Staircase directly down to lushly landscaped grounds. Only this floor has the stairs, others have to go through a lobby with a key. Wander around among our beautiful tropical gardens, bring your drink down to the...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Mina Bay - Oceanfront "Million Dollar View"1 / 19
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 12, 2017
    We spent part of the holidays at Mina Bay! The views are stunning! Not to mention you can hear the sound of the waves from the second bedroom - very relaxing! The unit is...
    Reviewed January 24, 2017
    Beautiful spacious oceanfront condo fully detailed and furnished in a gated community in Islamorada. The location is perfect and the beach is on the doorstep. Perfect for two or...
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    Mina Bay - vacation rental with "the million dollar view"! Truly OCEANFRONT on the sandy beach and feet from the pier and dock. Sparkling water's and brilliant sunsets complete this 2 Bd 1.5 Ba plus loft Unit I-1 townhouse. 28 DAY MIMIMUM RENTAL for all guests.  Accommodates a family of 8 perfectly...
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    Islamorada, Florida Keys 33036
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    License #: VR-215, DWE5403682 This resort style community is located at mile marker 85 in Islamorada and is situated directly on the Atlantic Ocean with fantastic views. The community is beautifully landscaped and has a large community pool (heated year-round) that overlooks the ocean! The...
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    Islamorada, Florida Keys 33036
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    • Private Outdoor Pool (Heated)
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WE DO NOT ACCEPT WIRE TRANSFERS AS PAYMENT...ALL PAYMENT IS THROUGH FLIPKEY Enjoy the most beautiful sunsets on earth from this gorgeous 4bedroom,5bathroom tropical paradise. Comes complete with Bayfront pool and lounge area that will leave you breathless. Pool table, cabana, outdoor kitchen,...
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    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    Lower Matecumbe Key condo description Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the water front balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    Premier condo in Islamorada in Upper Florida Keys. Located on 12-acre property with 1,100 feet of oceanfront. Gated complex, large swimming pool, sand beach, and two tennis courts as well as boat ramp and dedicated slip. Spectacular Atlantic Ocean views. This top-floor, freshly-remodeled 2 bed 2...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Ocean-Front Caribbean Home.1 / 21
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 24, 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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    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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    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Oceanfront Luxury Islamorada Estate - 4 bed/pool1 / 45
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Waterfront
    • Internet Access
    • Private Outdoor Pool (Heated)
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * 7 Day Rental minimum - Saturday to Saturday * Please check the calendar prior to inquiry Sleeps 8 adults plus up to 4 children under 6 allowed (fire code regs)...
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    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful four bedroom three bath fully remodeled cottage in Islamorada. 45 ft dock, private pool and extensive wood deck. Short walk to owners private beach park. Two master suites with full ensuite bathrooms. Modern kitchen fully equipped to meet all your needs. One bedroom with a King size...
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    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Islamorada 2-bedroom Condo1 / 6
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Grill
    • Waterfront
    • DVD Player
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    • Satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 18, 2014
    Just wanted to thank Bill for a wonderful four days at his place. Condo has tremendous views -- you are on the top floor -- amenities are great as well as the sleeping...
    Reviewed July 7, 2014
    The pool is sparkling clean. You can enjoy the ocean-view from the pool area. The balcony is a wonderful place to hang out and relax. Close to everything.
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    About this property
    If you’ve been to Islamorada you know it as the sportfishing capital of the world, a place where you’ll find every water-related activity imaginable, with fine restaurants to crab shacks serving local fare, and plenty of nightlife for both the young and young at heart. If you’ve never been here, a...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Terrace
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    Kid friendly
    Smoking allowed
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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Weekend Getaway!!! Enjoy the most beautiful sunsets on earth from this gorgeous 4 bedroom, 5 bathroom plus casita, tropical paradise. There are two master suites, one entry level (no stairs) and one on third floor, both with amazing views. Comes complete with Bayfront pool and lounge area that will...
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    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to paradise! This home is a new listing to Flip Key. If you are looking for a large beautiful home with a pool in a peaceful setting and in an absolutely perfect location for your stay in Islamorada, you have found it! We are located in Venetian shores off Snake Creek with a boat slip for...
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    Islamorada, Florida Keys 33036
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 14, 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 March 1, 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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    Islamorada, Florida Keys 33036
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Smoking allowed
    About this property
    'Irish Ayes' - Elegant tropical waterfront home with pool, Jacuzzi, dock and custom elevator. Plan your Keys getaway to this absolutely beautiful, spacious, tropical waterfront home located in the prestigious Venetian Shores subdivision of Islamorada. Enjoy unforgettable sunsets while relaxing on...
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    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Come to Paradise and Enjoy it with Comfort! Located on Mile Marker 87 in Islamorada ( Fishing Capital of the World ), part of the Wonderful Florida Keys. Executive Bay Club is a Private Gated Community with 24 Hr Security, Heated Pool and Club House, Tennis Courts, Private Beach, Fishing off your...
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    Islamorada, Florida Keys 33036
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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