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Islamorada Vacation Rentals

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    Travellers to Islamorada are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    All 164 Rentals in Islamorada
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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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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    THIS IS IT! Magnificent Oceanfront Paradise!1 / 20
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 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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    • Waterfront
    • Patio
    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Children's Pool
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2017
    Everything was perfect. Weather was great, the unit was clean and fully furnished with everything we needed. The other vacationers and full-time residents were friendly and...
    Reviewed 5 May 2016
    This condo was to die for. The decor was fabulous and the location was perfect and close to many restaurants. The sunset from the balcony was breathtaking. The owner was a...
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    About this property
    Beautiful / tropical decorated one bedroom, one bath water front condo in Summer Sea Condominiums located at Mile Marker 88.5 Bayside Islamorada, FL. Bayside means amazing open water views & world famous Florida Keys sunsets from your own private balcony overlooking the Florida Bay. You can also...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Satellite TV
    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Paradise by the Atlantic Ocean and only 50' front the waters edge. Beautiful condominium complex with heated out door pool, gym, plenty of parking, secured entrances, elevator, and quiet. My condo is kept meticulously with attention to detail. Linens, towels and pool towels are included in the...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    132 Columbus Drive1 / 24
    (16)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Internet Access
    Suitability
    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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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.1 / 41
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 February 2016
    We loved our stay at Ocean Harbour Apartments. After viewing photos on your website, we chose this based on the beautiful grounds and lovely accomodations. We could not have...
    Reviewed 5 January 2015
    This spacious condo is beautifully furnished and equipped. The gated community is very quiet and has a heated salt water pool. There is a nice spot to see the moon and...
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    About this property
    Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated security, this premium...
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    Islamorada, Florida Keys FL 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    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 10 July 2016
    Beautiful ocean views! Nicely decorated and well-cared for condo. We hope to return next year. We had everything we needed and felt like we were at home, a lovely relaxing home.
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    About this property
    A Vacation Rental for View Lovers! FREE WIFI Best location in the complex. For two couples or a family with 2 kids. The two new extra long twin beds in 2nd bedroom convert to a comfy King Bed! Master bedroom has new king bed, ocean view and private bath. 2nd bathroom in hallway. This...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    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 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 <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
    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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    • Satellite TV
    • Children's Pool
    • Washer
    • Waterfront
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on...
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    Location Information
    Islamorada, Florida Keys 33023
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    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 9 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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    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 2 January 2017
    This condo is beautiful, clean and has great amenities (swimming pool, hot tub, tennis court and gym). Everything in the condo is first class with excellent quality of...
    Reviewed 2 January 2017
    This condo was gorgeous and well stocked. They kept a collection of brochures for all the activities around the area in the condo. We loved swimming in the pool and fishing in...
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    About this property
    This premier luxury home is situated in a very quiet and peaceful gated community. All the rooms are very spacious with quality furnishings. A large double wide lanai with breathtaking views will make your getaway in the Keys. For your enjoyment it comes with private boat dockage, covered parking,...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    **Summer Promo** 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
    • Washer
    • Balcony
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 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
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. 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...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    **Summer Promo** 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 28 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
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. 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...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Grill
    • DVD Player
    • Satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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 8 May 2017
    Very comfortable condo. Enjoyed a week of R&R. Very quiet place. Great pool. Deanna, the owner, was very helpful giving us help in launching our boat, storing our trailer...
    Reviewed 1 May 2017
    Excellent locationt, accommodations where great, all you need to bring is yourself and clothes. Deanna the owner was prompt in answering any questions regarding the property...
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    About this property
    Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    **Summer Promo** Gorgeous, Newly Renovated Executive Bay Condo - Families1 / 25
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Patio
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 November 2016
    Loved the home. Everything that was advertised was available and easy to use and find. Nice pool, access to the beach, and close to tons of activities. We were here for a family...
    Reviewed 20 April 2016
    I highly recommend this vacation rental! Very clean the pictures online are exactly what you see when you enter this beautiful home. It’s safe, convenient, well decorated...
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    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. 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...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Florida Keys Beautiful 2B 2B Townhouse1 / 18
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • 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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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Air Conditioning
    • DVD Player
    • Grill
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. 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...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 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
    • Satellite TV
    • Patio
    • Secure Parking
    • Internet Access
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 April 2017
    Besides the obvious gorgeous outdoor surroundings, this condo was equally as beautiful. It's hard to be inside when you're in the Keys, but Mark's condo makes it easy. The views...
    Reviewed 29 January 2017
    The condo was beautiful and well appointed. The community was beautiful with a great pool, nice beach, and extremely friendly people. Great restaurants and a cozy deli nearby...
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    About this property
    Beautiful professionally decorated condo in Futura Yacht Club. Pool, club house, Tennis, Marina with great fishing. Marker 88 restaurant is a short paddle board away. Private beach with sun set view. Perfect location near everything, restaurants, bars, shopping. Diving centers ,fishing, boat...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Islamorada Waterfront Paradise 21 / 29
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Patio
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2016
    House was nice - except we did not feel comfortable - could not feel at ease - felt like we were being watched - paid a lot of money
    Reviewed 22 April 2015
    My husband and I just returned from Casa Rio. The home was clean and comfortable and quaint. The outdoor area was beautiful, charming and relaxing. We had access to bicycles...
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    About this property
    iF YOUR PLANS CALL FOR LESS THAN A MONTH, PLEASE CONTACT ME. i MAY BE ABLE TO HELP. ***PLEASE INQUIRE ABOUT SPECIAL DISCOUNTED RATES AND SEASONAL AVAILABILITY*** Please contact us for all of our rates! For shorter stays...make sure you have a minimum of 28 days entered in your contact form!...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Balcony
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Modern Keys Living with Bay Views! New from top to bottom!!! Newly remodeled and beautifully decorated 1st floor corner unit with a private entrance. Enjoy the mix of vintage and new furniture and the most comfortable sofas, beds, linens and more! This home is equipped with everything...
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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Air Conditioning
    • Grill
    • Satellite TV
    • Washer
    • DVD Player
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Keys home in Anglers Reef with ocean view, dock, community pool & private beach This magnificent home with ocean views from all 4 balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef, a quiet oceanfront community in the Florida Keys. Anglers Reef...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    76300 Overseas Highway1 / 25
    (9)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 April 2016
    Three of us stayed for a week in March 2016. Unfortunately two more friends had to pull out due to illness, so we had a surplus of rooms. The house is not the most modern of...
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    About this property
    Enjoy this Bayfront home with a spectacular sunset view, fenced yard and tile throughout the house. Also has great dockage and clean swimming area. Secured wi-fi, local telephone, & cable television (basic) included. Near the house is the small Anne's Beach. There are nature trails, board walks to...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxurious Anglers Reef with Boat Slip, Pool, Ocean1 / 29
    (25)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Grill
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    The island is beautiful. The condo is so clean and high quality. The area is located on the water. Nice boat docks.
    Reviewed 23 April 2017
    Great place to setup home base in the Keys. The home had everything we needed, including a fully stocked kitchen for cooking our fresh catch. Nice, quiet community with many...
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    About this property
    House, 2 Bedrooms + Convertible Bed(s), 2.5 Baths (Sleeps 5) Islamorada home set in OceanFront gated community with swimming pool and private boat dock This charming home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances. Open porches and balconies, rich...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Fully Updated Townhome with Modern Luxuries with Pool, Beach & near Shopping1 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Satellite TV
    • Washer
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 November 2016
    Fantastic townhouse!! Came here to stay with a couple of friends and went fishing. It is right in the heart of Islamorada. You'll never run out of things to do, or places to eat...
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    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. 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...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Parking
    • Grill
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to your beach-front oasis on the bay side at mile marker 74 in Islamorada, the Sport Fishing Capital of the World. Dig your toes in the sand, bask in the warm, clean waters and soak up the sun at this beautiful retreat. For the fishermen and divers there is a shared dock and boat ramp on...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    "The Beach Fixes Everything". That's the sign that greets visitors as they enter the living room of this newest Freewheeler Vacations home. But while the beach certainly is nice, an awesome vista doesn't hurt either. Located on a narrow residential peninsula in Lower Matecumbe Key, the...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Luxurious Condo-Exclusive Bay Harbour w/Boat Slip & Marina, Pool, Tennis courts1 / 15
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Grill
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 March 2015
    Great property! Very beautifully decorated. I loved the view, really enjoyed my stay! I look forward to staying there again soon!
    Reviewed 19 January 2015
    This condo is beautifully decorated and chock full of everything you need to make your stay just perfect. The condo and the complex are extremely well maintained and have the...
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    Revel in the beauty of the morning sunrise as you relax on your own, private lanai while sipping your morning coffee, or enjoy a meal al fresco to the sound of the waves and gulls. This piece of paradise is sure to become your favorite home away from home. This lovely property is part of a gated,...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    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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    Villa Thenardier1 / 68
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 2016
    What else can be said about this property? It has everything. Pool – check, beach – check, ocean view – check, a gym, and even your own personal luxury outdoor shower. My...
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    ***** Amazing Home For An Amazing Price Through January 31st, 2017 Live your tropical dream at this palatial oceanfront estate that is newly available through Freewheeler Vacations. Located near mile marker 89, on Islamorada's Millionaires' Row, this 4 bedroom / 6 bath home comes with just about...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    **Summer Promo** Ocean Front Keys Home with Private Beach - Great for Kite1 / 25
    (2)Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Balcony
    • Grill
    • Washer
    • 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
    Beautiful four bedroom, Ocean Front home with private beach in sunny Islamorada (near Key Largo, on mile marker 74). Welcome to our little slice of paradise in the Florida Keys! Come and relax at our beautiful ocean front home with breathtaking, panoramic views of the Atlantic ocean. This spit...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Satellite TV
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    Suitability
    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
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
    • Grill
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This relaxing private home, known as "Windley Cottage" is located in Angler's Reef, Islamorada's premier gated oceanfront community with private beaches, boat docks (available for rent), and a resort-style swimming pool overlooking the boat dock lagoon, beaches, and the Atlantic ocean....
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    FLORIDA KEYS 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 2 weeks 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 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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    ***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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    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 27 October 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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Satellite TV
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the "Sport Fishing Capital of the World". Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of...
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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    137 LeSerra Lane1 / 31
    (7)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 March 2015
    We had a terrific time at 137 Lessara this February. The wildlife (birds, fish, manatee) viewing was incredible, the weather great, and the house was fantastic- especially the...
    Reviewed 5 June 2014
    This house had more than enough of everything needed away from home.The decks on both floors were great for relaxing,visiting, grilling and tanning.Plenty of space our three...
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    About this property
    Beautiful designer appointed Oceanside canal home located at the Mile Marker 76.5 in Lower Matecumbe (South part of Islamorada). This home is the second one in on a point and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffee maker, toaster, and blender. There are two...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    76004 Overseas Highway1 / 23
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    Enjoy spectacular sunsets while drinking margaritas on the observation deck of this stunning home nestled back behind swaying palm trees.  This home sits directly on the bay and has 2 bedroom 2 bath upstairs and has a 2 bedroom 1 bathroom apartment.  The home is located at mile marker 76. Near the...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    140 Atlantic Lane1 / 26
    (8)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 January 2015
    We seven people (3 couples and one single) stayed here for one week. This big house is located right on the Atlantic Ocean, but it has no beech. It has a great wraparound porch...
    Reviewed 12 August 2014
    The home that we stayed at was incredible! The accommodations, the view, the boat dock space was all great. It was fast in and out to the Atlantic Ocean to be able to scuba...
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    About this property
    Amazing ocean views can be enjoyed from this beautiful stilt home with separate mother- in-law cottage. You'll fall in love with this little piece of Heaven. Enjoy fishing, diving, and catching lobster with all the comforts of home. Best ocean views in town! Interior photos are available! Mile...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    82754 Overseas Highway1 / 29
    (3)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Hot Tub
    Suitability
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alligator Reef is the Perfect getaway for large groups!  You can rent from 1 to 4 homes depending on the size of your group. The Pelican and Egret homes will offer you 2 homes, 5 bedrooms, and one pool.  The Pelican is a 3 bedroom 2 bath ocean front pool home which will sleep up to 8 people.  (Sofa...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    Islamorada - PARADISE FOUND 3 bedroom/2 bath1 / 20
    (3)Excellent
    3 Bedrooms, Sleeps 6 Quick View
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    • Washer
    • Wi-Fi
    • Ocean Views
    • Balcony
    • Grill
    • Porch
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 April 2015
    We really enjoyed our stay here. We stayed with my husband and I and 3 kids ages 8,6 and 2.It was perfect. We spent a lot of time at the pool which was about 20 steps from the...
    Reviewed 23 February 2015
    The place was beautifully decorated and in excellent condition. From the patio you had an excellent ocean view that was a short walk to a small beach. My teens has a blast and...
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    About this property
    BEAUTIFUL NEWLY REMODELED (Available for 28 day rental) 3 BEDROOM, 2 FULL BATHROOM VACATION RENTAL IS LOCATED IN THE ISLAMORADA BREATHTAKING BAY VIEW FROM YOUR OWN BACK YARD! UNIT HAS BRAND NEW CUTOME KITCHEN CABINETS WITH GRANITE COUNTER TOPS. ALL STAINLESS STEEL APPLIANCES, DOUBLE DOOR...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, and your own private pool (heated in the...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    Beautiful 3 bedroom 2.5 bath luxury condo at MM 74.5 Complex comes complete with two tennis courts, weight room, pool, dockage, fish cleaning station, and free Wi-Fi at community clubhouse (this unit does not have Wi-Fi inside the condo) . The condo boasts some amazing views of the Clear Blue...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak...
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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, 3 Bathrooms, Sleeps 4 Quick View
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    Kid friendly
    Smoking allowed
    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 the...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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