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Rentals for Seniors in Islamorada, FL

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    1 / 41
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 19
    5 of 5 stars (3) Excellent
    3 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    4.5 of 5 stars (13) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    1 / 24
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This is a tropical vacation home away from home and is located in the heart of The Florida Keys. Perfect for families, couples, or a friends getaway. Our beautiful house has 3 bedrooms & 2 baths, and can sleeps 6 to 8 comfortably. It has a full kitchen with a spacious living room, plenty of... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 1 week ago
    We just returned from a week at this house. We had a great time, it is really well equipped, nice to have lots of beach and bath towels, huge fridge and freezer, and the laundry...
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    1 / 21
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This premier luxury home is situated in a very quiet and peaceful gated community. Spacious rooms and large double wide lanai with breathtaking views add to your getaway in the Keys. For your enjoyment it comes with private boat dockage, covered parking, locked storage with bait freezer, bike... View all property information
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    Islamorada, Florida Keys 33036
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 21
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Ocean Views
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    • x
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    About this property
    A Vacation Rental for View Lovers! FREE WIFI Best location in the complex. For a couple with 2 kids or two couples. The two new extra long twin beds in 2nd bedroom convert to a comfy King Bed! This direct oceanfront, well-cared for 5th floor corner unit is right on the ocean in Islamorada at... View all property information
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    Islamorada, Florida Keys 33070
    5 of 5 stars 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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    1 / 16
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Wonderful two story townhome in a private, gated community with all 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 inch... View all property information
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    Islamorada, Florida Keys 33036
    1 / 31
    5 of 5 stars (23) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    About this property
    Get away from it all in our tranquil waterfront condo at Summer Sea in beautiful Islamorada. Fully equipped, with newly updated kitchen and bathroom, flat screen television, and stunning views of Florida Bay from our patio. Located right in the heart of all the Keys has to offer - beautiful... View all property information
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    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed May 1, 2016
    Absolutely fantastic facilities in a wonderful setting. From the time we booked this place until the time we left we had an amazing experience. The flat is really well...
    5 of 5 stars Reviewed April 29, 2016
    Absolutely loved staying here. We enjoyed the home away from home feel, and also a beautiful view of the ocean from the balcony. Very comfortable, and quiet. The owner was so...
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    1 / 9
    5 of 5 stars (1) Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 50 | Quick View
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    About this property
    jaouoroqoaueo9quoruroqwu9euour99n9n9r9wur9ue9adouafiuaeoufasljfaof0askr;oasd-fsd4fas8/da5se/xgv5asqe-0taa8asdg=as9ufaoefauoatwouoasujfgaseuroue9rtasofuoasuaweroasufoauf0aasf5asf6asf6as6f6aseoufawi9rayweriyawiywririyseiyaweiryqwiryiweykcasdyvkshvckcaicaeiycaiyaisyaivyiseyvaifyksdhfikzhfisadkasrhisdhf... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed August 14, 2015
    My husband and I spent a fantastic week at this beautiful condo! The pictures don't do it justice! The view is spectacular. The inside is clean and nicely decorated! The owner is...
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    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 25
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
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    Islamorada, Florida Keys 33023
    1 / 29
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Location: Islamorada, Islamorada Area, Florida Keys, Florida, USA View Map<BR><BR>Accommodations: House, 3 Bedrooms, 2 Baths, sleeps 6<BR><BR>122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West.... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed May 29, 2015
    We thoroughly enjoyed our week here, with our adult children. The home is very clean and well-maintained and beautifully decorated and furnished in a tropical style. The outdoor...
    5 of 5 stars Reviewed May 12, 2014
    We loved staying at Villa Marlin, and the owner was very helpful before and during our stay. The home is prettier than the pictures, and we felt right at home!
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    1 / 33
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    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,... View all property information
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    Islamorada, Florida Keys 33036
    1 / 3
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Keys Kottage Villa is located in beautiful Islamorada, Florida Keys. We are on mile marker 82. Private Marina access and trailer parking available to guests. Bring your boat and or pet. We can accommodate up to 26 ft. vessels. This is a Fisherman's dream for a week of fishing. Please call for... View all property information
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    Islamorada, Florida Keys 33036
    1 / 6
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 45
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    * 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)... View all property information
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    Islamorada, Florida Keys 33036
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 21
    5 of 5 stars (6) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • x
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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... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 3 weeks ago
    Each year we travel to the Keys for lobster season. This year we were very happy with our choice of accomodations. The condo is in a great location with easy access by boat to the...
    5 of 5 stars Reviewed January 5, 2016
    The Lobinskys, the owners, were responsive, informative, and extremely helpful. We traveled as a family with our two teenagers and our boat. Chris and Deanna provided options...
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    1 / 25
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 21
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 21
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The Royal Palm, South - Ocean Front Home ( recent fraud. NEVER wire us money. Payment for reservations can only be done via the phone, not online or via wire) Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier. Inspired by owner Phil with nothing compromised this luxurious Caribbean home... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars 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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    1 / 6
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
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    Islamorada, Florida Keys 33070
    5 of 5 stars 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...
    4 of 5 stars 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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    1 / 21
    5 of 5 stars (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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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. View all property information
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    Islamorada, Florida Keys 33070
    5 of 5 stars 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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    1 / 21
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    About this property
    Wake up every morning and walk right out to your private wrap deck and relax with the sound of the ocean right under your feet. We have a beautifully decorated and updated one bedroom trailer. Kick back in a open concept living room and kitchen with all new appliances. and with stunning views.... View all property information
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    Islamorada, Florida Keys 33036
    1 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 12
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    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... View all property information
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    Islamorada, Florida Keys 33070
    1 / 21
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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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... View all property information
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    Islamorada, Florida Keys 33070
    1 / 16
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
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    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed March 31, 2016
    We were a group of five - four adults and one child (toddler). From the beginning, we knew we wanted a place that could feel like our home away from home. The condo is very...
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    1 / 29
    5 of 5 stars (1) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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 oasis over a full size lap pool. Lay down in the shade on the soft grass bordering the pool and enjoy... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 1 week ago
    This house was a beautiful place to stay with large common areas for gathering our big group, but with private bedrooms and bathrooms. All the ocean toys we needed. We had a...
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    1 / 28
    5 of 5 stars (30) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Amenities & Details
    • Patio
    • Ocean Views
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Satellite TV
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    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! DO NOT BOOK THROUGH FLIPKEY! Booking instructions will be provided when you send your inquiry, saving you significant FlipKey booking fees. Have you considered... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars 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.
    5 of 5 stars Reviewed February 9, 2016
    Great place for vacation, very relaxing. Love chilling in hammocks and tiki hut watching the wildlife and to fish. the restaurants nearby were very good. Take the kayaks to the...
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    1 / 31
    5 of 5 stars (12) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Waterfront
    • Balcony
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Outdoor Dining Area
    • Internet Access
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, basketball and... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 3 weeks ago
    This condo unit worked great for my family. Plenty of room. Pool is nice and the boat basin was great. Very clean and quiet complex. The owner Glenn was very helpful in...
    5 of 5 stars Reviewed July 23, 2015
    Our group consisted of 5 adults and 1 teenager and we had a great time. We had all of the room we needed for sleeping, food prep and eating. Everything else was outside in the...
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    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Internet Access
    • Shared Outdoor Pool...
    • Parking
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Savor a sun-filled vacation in this charming oceanfront condo, complete with sweeping ocean views and shared amenities such as a gym, saunas, a pool, tennis courts, laundry facilities, barbecues, and a party room. In the Sea Gull Condos complex, this rental is less than one mile off Old Highway 1... View all property information
    Location Information
    Islamorada, Florida Keys 33070