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Vacation Rentals near Theater of the Sea

84721 Overseas Hwy, Mile Marker 84.5, Islamorada, Florida 33036-3410
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    Travelers to Islamorada are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 100 Rentals in Islamorada
    Bay Front Beauty/ Summer Sea Must See!!!!1 / 19
    (4)Excellent
    3.5 miles from Theater of the Sea
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    **Fall Promo** Modern Executive Bay Club Condo with Pool & Beach1 / 29
    (3)Very good
    2.7 miles from Theater of the Sea
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3.6 miles from Theater of the Sea
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    107 San Remo Drive1 / 36
    (1)Excellent
    1.5 miles from Theater of the Sea
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    Reviewed January 29, 2018
    What a fabulous area and home, Nancy and Norm were (the owners) told us places for dining out, Island times grill, Craigs seafood ( Mahi Mahi sandwich is to die for) Mrs Mac...
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    About this property
    Comfortable Venetian Shores canal home that has two bedroom/one bath upstairs and a one bedroom/one bath apartment downstairs.  The downstairs apartment has a complete kitchen and living room and separate bedroom.   There is a screened in porch of the living room upstairs.  The home has awesome...
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    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.4 miles from Theater of the Sea
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    Prestigious Venetian Shores subdivision in Islamorada! This vacation home has 5 bedrooms and 3 bathrooms with 100'  concrete dock. The house is situated into two separate living quarters. Upstairs is a large master suite and 2 guest bedrooms, cathedral ceilings & fully stocked, eat-in kitchen,...
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    Islamorada, Florida Keys
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    FALL SPECIAL DISCOUNTED PRICING!!!1 / 35
    (17)Very good
    3.7 miles from Theater of the Sea
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Balcony
    • Terrace
    • Outdoor Dining Area
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 10, 2018
    We recently rented this condo unit for a week for our family of six. It accommodated us great, 3 bedrooms plus a pull out couch. Outside was beautiful, very clean and well...
    Reviewed March 13, 2018
    Love staying in this condo was our second year hoping to return next winter if available. already made request.. I would never leave if it were up to me but the location and the...
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    About this property
    Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, and dockage for...
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    Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    No dockage allowed. Florida Keys. Beautiful condo. Short walk to the beach area.1 / 18
    (7)Excellent
    2.7 miles from Theater of the Sea
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 14, 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 January 18, 2016
    We had very nice time staying in Ana's townhouse in Islamorada. It is nicely decorated, well equipped, comfortable and spotlessly clean. There is more than enough room for a...
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    About this property
    Our unit is a short walk to the beach and dock... No view of the ocean from our unit. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach and a...
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oceanfront Anglers Reef Islamorada Florida Keys1 / 14
    (3)Very good
    0.7 miles from Theater of the Sea
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Grill
    • DVD Player
    • Cable/satellite TV
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 24, 2018
    This home is in a gated community in the heart of Islamorada. The site is beautiful, and seemed to have suffered no damage from Hurricane Irma. There are two artificial...
    Reviewed August 24, 2017
    Very well appointed and comfortable house, conveniently located to local amenities in Islamorada. It was like a home from home with easy to use washing machine, dryer and...
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    About this property
    Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many...
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    THE PERFECT GETAWAY1 / 42
    (6)Very good
    1.6 miles from Theater of the Sea
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
    • Hot Tub
    • Washer
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    • Waterfront
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 2, 2016
    My husband and I searched for six weeks to find the perfect house for our vacation with another couple, and kept coming back to this one. All four of us were looking for a...
    Reviewed April 9, 2016
    We thoroughly enjoyed staying at the Perfect Getaway. My family and I had enough space to sleep, relax and enjoy meals together. The pool was a great addition to the property...
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    About this property
    This four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. It is situated in a clean, upscale neighborhood of all waterfront homes. The house is equipped with all the comforts of home. It is modernly furnished. Upstairs there are...
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    Islamorada, Florida Keys
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.1 / 41
    (4)Very good
    3.3 miles from Theater of the Sea
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 25, 2018
    I was having trouble booking my reservation online (technicality), and had to call in for help. One of the girls there was able to help me quickly, booked me & took my payment...
    Reviewed January 19, 2018
    Yes there was..DO NOT RENT FROM ITRIP/PHOENIX RENTALS.They were totally dishonest with me. They did not tell me that there was major construction going on in the building I...
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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
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.7 miles from Theater of the Sea
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.7 miles from Theater of the Sea
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Patio
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    • Ocean Views
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    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedroom and 2.5 Bath Villa, in Anglers Reef. An upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here,: gorgeous private beach, heated resort style pool, private back yard terrace with barbecue, front porch seating, balcony, and dock....
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1.3 miles from Theater of the Sea
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a beautiful Venetian Shores home... It truly is a must see! The interior is clean and nicely decorated. The large porch on the back allows you to see the famous Florida Keys sunsets from your own home! Located a few houses down from Snake Creek, you'll have quick ocean and bay access. Deep...
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    Islamorada, Florida Keys
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    0.1 miles from Theater of the Sea
    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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    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.7 miles from Theater of the Sea
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    Rental amount includes all fees except boat dock fee. This newly renovated modern 3rd floor condo in Futura Yacht Club unit 302 is in a private gated community and has a spectacular Florida Bay sunset view. Futura Yacht Club is just 68 miles south of Miami. Amenities include heated pool, screened...
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    Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.5 miles from Theater of the Sea
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for an amazing home in Venetian Shores?  This home has everything - 4 bedroom, 4 bath home that has been updated.  The kitchen is amazing, suited for any type of entertaining.  The 3rd floor floor is a lofted master bedroom suite with a walk-in closet.  Two guest bedrooms are located on the...
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    Islamorada, Florida Keys
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3.7 miles from Theater of the Sea
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    About this property
    Enjoy the spectacular view of the Florida Bay from this beautiful townhome. This townhome is a 2 bedroom and 2-1/2 bath unit.  There are tons of things to keep you and your family busy without having to leave the Futura Condo complex. There are tennis courts and a swimming pool located on the...
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Luxurious Anglers Reef with Boat Slip, Pool, Ocean1 / 29
    (26)Excellent
    0.7 miles from Theater of the Sea
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Grill
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    We stayed at Angler's Reef and had an amazing time. Jo was very helpful with the booking and very easy to work with. We felt like we were at home in her rental. She has...
    Reviewed July 10, 2017
    The island is beautiful. The condo is so clean and high quality. The area is located on the water. Nice boat docks.
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    About this property
    House, 2 Bedrooms + Convertible Bed(s), 2.5 Baths (Sleeps 5) Islamorada home set in OceanFront gated community with swimming pool and private boat dock This charming home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances. Open porches and balconies, rich...
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    2.9 miles from Theater of the Sea
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Patio
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** *** Owner is highly motivated to rent! Contact...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    ISLAMORADA Waterfront GREEN IVIS PARADISE Min 28 Ngts. Max 10 ppl. 26% Disc >1mo1 / 17
    (1)Excellent
    1.4 miles from Theater of the Sea
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Balcony
    • Ocean Views
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    • Waterfront
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 6, 2018
    We had. Great time. Can't wait to come back. The house was impeccable and the host gave us great customer service. Amazing time in the water. Great canal!
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    About this property
    Relax in this peaceful keys home with wide canal with easy access to ocean & bay. Located in one of the best neighborhoods in the keys!! You will enjoy a morning stroll, jogging or a bike ride around this picturesque neighborhood. We have plenty of room for your boat and all your toys. Bring or...
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    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Islamorada Luxury Home Ocean & Bay Access1 / 14
    (9)Excellent
    1.4 miles from Theater of the Sea
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Patio
    • Waterfront
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Special vacation rental rates for off-season bookings and also for some last minute dates! Call us now for details. Located in Islamorada the fishing capitol of the world, this is a beautiful home decorated with Island style decor. Over 3,000 square feet of living space. 100' of dock, less than two...
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    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF1 / 25
    (1)Excellent
    0.7 miles from Theater of the Sea
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    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
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1.4 miles from Theater of the Sea
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
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    About this property
    This beautiful 4 bedroom 4.5 bath home has everything you need to make your vacation perfect. This gorgeous Venetian Shores home has the perfect open concept layout, large kitchen and living room, even a game room with a pool table. But there's more! This home comes with a large master bedroom...
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    Location Information
    Islamorada, Florida Keys
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    0.7 miles from Theater of the Sea
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Children's Pool
    • Washer
    • Waterfront
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on...
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    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    **Fall Promo** Family Friendly Executive Bay Townhome with Beach & Pool1 / 29
    (10)Excellent
    2.7 miles from Theater of the Sea
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Balcony
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 17, 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 September 13, 2015
    The condo is very nice and spacious for 5 persons. The place is clean and supplies are adequate. Location is good. Swimming pool is big and nice. Able to do a little fishing...
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** *** Owner is highly motivated to rent! Contact...
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    Location Information
    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Newly refinished  condo open water views very nice1 / 17
    (4)Excellent
    3.7 miles from Theater of the Sea
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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 superior condo in the best location in Islamorada. The unit is superior with the best water views, with everything you need ,full kitchen stocked with cookware, microwave, coffeemaker, large island counter, breakfast nook with ocean view, washer and dryer in...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.3 miles from Theater of the Sea
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3.7 miles from Theater of the Sea
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This tropically decorated 2 bedroom 2 bath unit, has a King bed and (2) Twins beds is approximately 1 hour and 20 minutes from Miami International Airport and 90 Minutes from Ft. Lauderdale airport.  Futura Yacht Club is located in the Village of Islamorada in the Upper Florida Keys. Located...
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    Location Information
    Tavernier, Key Largo
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    PALMS 2141 / 24
    (1)Excellent
    1.3 miles from Theater of the Sea
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Hot Tub
    • Internet Access
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 14, 2015
    We have always enjoyed the keys and love staying at the Palms of Islamorada. The units are big enough and the amenities are nice. Unit 214 was nice and clean. A big TV for me...
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    About this property
    ***FALL SPECIAL*** RECEIVE 10% OFF RENT FOR ALL BOOKINGS IN SEPTEMBER AND OCTOBER. Minimum Rental: 28 Days 'The Palms #214' is a gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.4 miles from Theater of the Sea
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    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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    Islamorada, Florida Keys
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    Alligator Reef Compound1 / 99
    (2)Excellent
    0.3 miles from Theater of the Sea
    10 Bedrooms, 10 Bathrooms, Sleeps 28 Quick View
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    Reviewed July 30, 2018
    We stayed for a week the end of June, we rented all four houses which was perfect for our group of 22. We ranged in age from one to 68 and everyone had a blast!The pools are...
    Reviewed May 30, 2018
    We had a great time at Alligator Reef. The house is so well stocked. The view is breathtaking. And there is so much to do we never left the property. We kayaked, swam in the...
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    About this property
    Got a large group that wants to 'get away from it all'? Or do you need lots of space for a family reunion or wedding? This is the perfect solution! Terrific location, beautiful view, two private pools for you to enjoy... And since it's 4 separate homes, you aren't right on top of each other. Wide...
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    Islamorada, Florida Keys
    Rental Home - 10 Bedrooms, 10 Bathrooms, Sleeps 28
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    Ocean-Front Caribbean Home.1 / 21
    (2)Excellent
    2.5 miles from Theater of the Sea
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 11, 2018
    Very much enjoyed our stay. House was beautiful and clean, staff was friendly and helpful. My mother and I loved relaxing in the hot tub and my father and husband very much...
    Reviewed 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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    About this property
    The Royal Palm, South - Ocean Front Home ( recent fraud. NEVER wire us money. Payment for reservations can only be done via the phone, not online or via wire) Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier. Inspired by owner Phil with nothing compromised this luxurious Caribbean home...
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    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.8 miles from Theater of the Sea
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Ocean Views
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    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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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.7 miles from Theater of the Sea
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedroom and 2.5 Bath Villa, in Anglers Reef. An upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here,: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front porch seating, balcony, and dock. Boat...
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.1 miles from Theater of the Sea
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.7 miles from Theater of the Sea
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ENJOYABLE, CENTRAL LOCATION, PLANTATION KEY, 3 bedroom + loft, 2 bath; 1400 sf 2 story, all bedrooms and 1 full bath are upstairs & downstairs is the living area and 1 additional full bath. The unit is clean, comfortable, quiet and restful. The community is gated with security, no pets are allowed;...
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    Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    82754 Overseas Highway1 / 29
    (4)Excellent
    1.7 miles from Theater of the Sea
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    Reviewed June 7, 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 May 9, 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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    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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    Islamorada, Florida Keys
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    1.9 miles from Theater of the Sea
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units. The Cottage is a bright and airy 1,250 sq ft unit with a huge...
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    Islamorada, Florida Keys
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    0.7 miles from Theater of the Sea
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Waterfront
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Anglers Reef Villa Resort 2 Bedroom and 2.5 Bath Villa, in Anglers Reef. An upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here,: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front porch seating,...
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    BEACON REEF 2221 / 25
    (2)Excellent
    1.3 miles from Theater of the Sea
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Hot Tub
    • Parking
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 22, 2018
    We have so much enjoyed staying in this condo, Beacon Reef 222. The condo is very comfortable with a great kitchen and living area. The master bedroom is amazing with a large...
    Reviewed July 13, 2017
    Great location! The pool, tiki bar and dock are all top notch. The ocean views are amazing. All equals the perfect family vacation.
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    About this property
    ***FALL SPECIAL*** RECEIVE 10% OFF RENT FOR ALL BOOKINGS IN OCTOBER AND NOVEMBER. Minimum Rental: 28 Days 'Beacon Reef 222' is an extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below....
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    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    LITTLE BAY - Lower Duplex1 / 23
    (4)Excellent
    1.3 miles from Theater of the Sea
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Minimum Rental: 7 Days Little Bay's Lower Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit sleeps...
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.3 miles from Theater of the Sea
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Private Outdoor Pool (Heated)
    • Internet Access
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    • Terrace
    • Grill
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***FALL SPECIAL*** RECEIVE 10% OFF RENT FOR ALL BOOKINGS IN SEPTEMBER, OCTOBER AND NOVEMBER. MINIMUM STAY: 28 DAYS 'Flamingo Cottage' is an adorable 3 bedroom stilt home nestled among tropical foliage. There are two bedrooms and one bath on the main living level of this home plus a private...
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Islamorada Yacht Life1 / 23
    (2)Terrible
    2.6 miles from Theater of the Sea
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Best seen by the water Islamorada is yours to explore from this fully appointed yacht. 4 bedrooms one king and 3 with two single beds each make this an ideal spot for a family gathering, romantic getaway or corporate retreat. Luxe island decor abounds and there is ample indoor and outdoor...
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    Matecumbe Key, Florida Keys
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3.6 miles from Theater of the Sea
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Balcony
    • Central Heating
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    Pet friendly
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    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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    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.7 miles from Theater of the Sea
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Ocean Views
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This magnificent home with direct ocean views from the master bedroom, living room and balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef. Lie in bed and view the Ocean! Home also overlooks the community pool. Anglers Reef is a quiet oceanfront...
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3.5 miles from Theater of the Sea
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand NEW tennis court installed 2018! Situated right on the Atlantic Ocean in The Heart of Islamorada! Panoramic views of the water from almost every room, the main house has 3 bed/3baths. Guest cottage has 1bd/1ba. Nestled amongst lush tropical gardens and gated for total privacy. Take a morning...
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    Islamorada, Florida Keys
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    0.3 miles from Theater of the Sea
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    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
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    LITTLE BAY - Upper Duplex1 / 25
    (3)Excellent
    1.3 miles from Theater of the Sea
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 2, 2013
    We have rented the upper duplex of Little Bay in April for the last few years. it is a beautiful property in a perfect setting. The grounds are kept immaculately and the area...
    Reviewed November 5, 2012
    We found Little Bay after our previously planned accomodation had been damaged in a fire so Andi & Katy at Keys Holiday Rentals literally saved us from camping on the beach...
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    About this property
    Minimum Rental: 7 Days Little Bay's Upper Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each unit...
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    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.4 miles from Theater of the Sea
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Cable/satellite TV
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    • Ocean Views
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a great canal with easy access to the open ocean and the bay. We have plenty of room for your boat and all your toys. Bring or rent your boat, bike, paddleboards, jetskis or kayak. You have a world of fun in the sun awaiting. Located in one of the best neighborhoods in the keys!! Modern...
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    Location Information
    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    3.1 miles from Theater of the Sea
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Wi-Fi
    • Waterfront
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Gated Oceanfront 1.8 Acre Estate located in Islamorada featuring amazing ocean views. 5 Bedrooms, 4 Baths, Winding Staircase, Expansive Ocean Views, Over 4000 Sq. Ft. of Living Space. Heated Pool, Sandy Back Yard, Gated Entrance Lined With Palm Trees. Enjoy the Ocean Views and...
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    Islamorada, Florida Keys
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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