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Villas in Long Key

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    Travellers to Long Key are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 28 Rentals in Long Key
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury will be at your fingertips when you book your next family getaway to this Long Key retreat with amenities like a pool, hot tub, kayaks, a swim-up bar, and access to a beach. Set right on the beach, you'll be just two miles from Long Key State Park and two-and-a-half miles from Layton. This...
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    Long Key, Florida Keys 33001
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Balcony
    • Waterfront
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    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Everyone wants to leave their worries behind and escape on a soothing beachfront vacation - why not make your next one something special? This top-floor Long Key condo has it all: a gorgeous white sand beach, a shared swimming pool with a swim-up bar, and an amazing selection of games and...
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    Long Key, Florida Keys 33001
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Bay Harbour A-304- 7 night minimum1 / 23
    (12)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Reviewed 30 April 2016
    There is no beach but the pool is not crowded. A hot tub is near-by. This unit,304A was very nicely decorated. Loounge chairs make watching TV comfortable. Kitchen pans...
    Reviewed 4 January 2015
    This condo was great for us...3 couples(family) each having their own bedroom..2 1/2 bathrooms ...we used the kitchen and 5 people could work together in it! The kitchen was...
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    About this property
    Beautiful 3 bedroom and 2.5 luxury condo located at mile marker 74.5 bayside.  This condo is nicely decorated and very spacious for you and your family. The unit has a great screened in porch off the living room.  The complex has 2 tennis courts, weight room, dockage, pool, fish cleaning station,...
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    Long Key, 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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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'Gulfview Getaway' is a FABULOUS BEACH FRONT HOME! This is what you've been dreaming of - your very own single family home with a private sandy beach in the Keys. This home is new to the rental market. It is located in a highly desirable area of Islamorada on a dead...
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    Long Key, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    SEA GRAPE1 / 25
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Patio
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2016
    What a wonderful place! So comfortable and the views!!!! We were 6 people and had the best time. There is ample room, the views are unbelievable, the porch is out of this...
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    About this property
    Minimum Rental: 28 Days 'Sea Grape' is a serene, quaint part of paradise that the entire family will enjoy at this ultra-charming BEACH HOUSE just footsteps from the SEA. Come and stay in this adorable home located on the crystal clear Atlantic Ocean! The home has plenty of room for your whole...
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    Long Key, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Paradise On The Water-58 Ft Dock Space On Premises1 / 18
    (1)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 Quick View
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    • Children's Pool
    • Secure Parking
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    If you want a comfortable home away from home this is the place for you. Ana is very friendly and always kept in touch via email whenever I had any questions. Would definitely...
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    About this property
    Gated community spacious double wide mobile home, 1 bedroom - with 32' Flat Screen TV, Queen size bed, 2 full baths, Living room with 55 ' Flat Screen . 2 sleeper sofas 1-Double, 1-Queen), well equipped Kitchen, clothes washer & dryer, sleeps 5. 24 hour security, beautiful views from inside of the...
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    Long Key, Florida Keys 33001
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 5
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    Oceanfront duplex with beautiful beach and dock for boat access!1 / 42
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Satellite TV
    • Washer
    • Internet Access
    • Waterfront
    • Grill
    • Parking
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 November 2016
    We had our 2 children with us on this trip. (5years, and 3 years.) The beach was beautiful and the kids had a great time swimming and fishing. The house was perfect. We can not...
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    About this property
    Discover the very best of the Florida Keys in this charming pet-friendly rental with a dock and beach! The unique home offers the makings of a romantic getaway or intimate retreat with friends. The rental is three miles from town and a few hundred feet from the Long Key Viaduct. Located in Henry...
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    Long Key, Florida Keys 33001
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, 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 Pelican House, is a 3 bedroom, 2.5 bathroom ocean front home featuring beautiful views, ocean breezes, and your own private pool (heated in the cooler seasons),...
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    Long Key, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Pack your bags!  We've got the perfect vacation home for you and your family!  This adorable 3 bedroom/2 bath home is located on a deep water canal at the 74 mile marker Bayside.  Great yard with room for your boat trailer!  All 3 bedrooms are on one floor.  House is stilted.  Screened porch on...
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    Long Key, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Awesome renovated home in Port Antigua.  The upstairs has 3 bedrooms and 2 baths.  The kitchen has granite counter tops, stainless steel appliances, along with a serving window if you are out on the balcony.  The downstairs has a great tv room with a sectional and a kitchenette a full bath. You can...
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    Long Key, 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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    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    Located at MM 73 in Lower Matecumbe, Islamorada - this 3 bedroom and 2.5 bath will sure to be your home away from home.  Nicely decorated and very comfortable.  You can sit outside in the hot tub and enjoy the peaceful canal.  Great home for your next vacation. Near the house is the small Anne's...
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    Long Key, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy, canalfront, pool home at MM 74 in Islamorada's desirable Port Antigua (Lower Matecumbe Key) with quick Florida Bay access and a short ride to the Atlantic Ocean. The downstairs only of this house is rented.  Super cute 2 bedroom.  No one would be in the upstairs while house is rented.  Great...
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    Long Key, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 4
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    Fisherman's Paradise with a 30 Ft Boat Slip1 / 22
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • DVD Player
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    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 December 2014
    my family stayed here the week of december the 5 2014 from the first contact with bob till the day we left can say nothing but great things bob got right back with me asap he...
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    About this property
    Fishermans Paradise at Oceanside Isle Condominiums with 1,800 Square Feet of Living Space, on Long Key, which is a Secluded Island with direct access to both Atlantic Ocean and the Bay of Florida through Channel #5. Expansive Master Suite and with Large Tub & walk-in shower. Relax on your one of...
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    Long Key, Florida Keys 33001
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a getaway in one of Islamorada's most prestigious neighborhoods when you rent this three-bedroom, three-bathroom home. Located at the end of a cul-de-sac within the Port Antigua neighborhood on Lower Matecumbe Key, the home quickly enchants arriving guests with its peach-colored exterior set...
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    Location Information
    Long Key, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Wi-Fi
    • Satellite TV
    • Grill
    • Balcony
    • Patio
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Straight from the pages of a travel magazine, this 2BR/2BA Islamorada house commands a prime location overlooking the jewel-toned waters and white sands. Inside, bright sunshine comes in through multiple sliding glass doors, bathing the open spaces in natural light. Start and end your day out on...
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    Long Key, 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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    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful modern luxury unit with 3 bedrooms and 2 full bathrooms, along with a half guest-bath! Plasma TV, VCR and DVD player in the living room. This unit does have Wi-Fi.  The Bay Harbour Complex comes complete with two tennis courts, weight room, pool, your own dedicated boat slip, a fish...
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    Long Key, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This delightful 2 bedroom, 2 bathroom home is located in Port Antigua (south Islamorada) at the 74 mile marker. While not located directly on the bay, you'll still be able enjoy the homeowners park that has a beach and beautiful sunsets. The home comes equipped with Wi-Fi internet. Near the house...
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    Long Key, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
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    • Waterfront
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    • Sauna
    • Ocean Views
    • DVD Player
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean view 2 bedrooms 3 baths right across from heated community pool, convenience store and club house. Location Location Location. 50' TV, golf cart available, all high end appliances, furniture, houseware and kitchenware . All you need to bring is your clothes, bathing suit, fishing gear and...
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    Long Key, Florida Keys 33001
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Internet Access
    • Waterfront
    • Satellite TV
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    • Washer
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let this picturesque 3-bedroom, 2-bathroom Islamorada vacation rental house serve as the perfect setting for your next trip to Florida! Featuring comfortable sleeping space for 8, top-notch amenities and an unrivaled location near beaches and main attractions - this alluring abode will not...
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    Long Key, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Waterfront
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From the minute you step foot in this luxurious condo, the water dominates your view and your activities. Oceanfront views from living room and master bedroom, 3 balconies... lush gardens, pool, palm trees, the finest sandy beach in the keys and the magnificent Atlantic Ocean are your constant...
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    Long Key, Florida Keys 33001
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Parking
    • Balcony
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take a stroll out to the beach just across the road or cast a line into the canal out back from this charming Islamorada vacation rental. This home offers a covered, furnished patio, a well-equipped modern kitchen, and space for up to six guests, making it ideal for a family vacation in the Florida...
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    Long Key, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Give yourself over to the island lifestyle when you book an escape to this oceanfront Islamorada home with a shared dock. A shared pool and hot tub are coming soon! With a canal at the back of the house and the ocean just across the highway, you're surrounded by water. Start your day with a...
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    Long Key, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Waterfront
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    When it's time for a break from the daily grind, come soak up the warm Florida sun and relax with your favorite traveling companion at this stylish Islamorada oceanfront condo. Not only will you be treated to lovely ocean views, you'll have an outdoor firepit and a shared dock. A pool and a hot tub...
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    Long Key, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
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    • Waterfront
    • Patio
    • Air Conditioning
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    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to Islamorada and settle in at this conveniently located oceanfront condo, where you'll have lovely ocean views, a shared dock, and an outdoor firepit. This rental is perfect for a couple wanting to get away from it all and enjoy each other's company. A pool and a hot tub are coming soon!...
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    Long Key, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Washer
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    • Waterfront
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Surprise your special someone with a seaside getaway at this oceanfront Islamorada condo. Up to two guests can enjoy ocean views and a shared dock. A shared pool and hot tub are coming soon! With a canal behind the house and ocean views from the front, you'll enjoy water on all sides. Fishermen...
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    Long Key, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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