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Smoking Allowed Holiday Rentals in Florida Keys

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    Travellers to Florida Keys are booking December dates now. Secure your holiday home today, and have the perfect trip.
    17 Matching Rentals in Florida KeysView all 1,498 rentals
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    Sunrise Suite Key West 2 Bed Rooms 2 Full Baths1 / 25
    (69)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Tropical Cottage with Sandy Beach1 / 12
    (51)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Family vacation rental, kayak, pool, 50” dock1 / 36
    (2)Average
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Duval Balcony - Suite Mischief1 / 13
    (11)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Balcony
    • Cable/satellite TV
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 February 2018
    Perfect location in the 800 block of Duval Street. Paid parking lot across the street if needed for car or golf cart! Rented bicycle and golf cart right across the street. The...
    Reviewed 15 August 2017
    Great place to stay. In the middle of things to do. Place was clean and Tom kept checking to make sure that everything was satisfactory. WILL definitely stay there again.
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    About this property
    Located in the heart of Duval St, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a private balcony overlooking Duval St. This property features a 1 bedroom with a king size bed, full bath and...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Tee by the Sea - NO DAMAGE FROM HURRICANE IRMA , Plus 7 Bikes FREE1 / 30
    (67)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • DVD Player
    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2017
    This lovely condo was great for our stay in Key West. Located on Stock Island just at the entry of Key West, it was perfect for staying "out of the frenzy" of town, but...
    Reviewed 13 May 2017
    We had a great three days on the island. Condo was well equipped although we ate out or got pizza - pizza place across the road served delicious pizzas. Ther were 5 of us so my...
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    About this property
    Very nice luxury 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in very well maintained gated community, including huge heated pool, clubhouse with fitness center. Sleeps up to 6 with a queen bed in each room and a queen sleeper/sofa with a 5' thick memory...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Cable/satellite TV
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the 'Sport Fishing Capital of the World'. Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Conch Key Villas Unit 1, Quiet, Clean with Awesome VIews in Paradise1 / 19
    (13)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2018
    I could write a novel about this place and most importantly the amazing couple that run it. They make me feel at home everytime I am there. Hurricane Irma brought me to the keys...
    Reviewed 4 March 2018
    I was so lucky to stay two nights at the Conch Key Villas during my bicycle touring trip from Virginia to Florida. I can’t think of a more perfect place to end my trip! The view...
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    About this property
    If Comfort, Fun, Fishing and Views Are on Your List, Stay Here! We have ground level or second floor units. We provide outside table and chairs, and just around the corner the barbecue grill is located to grill up those freshly caught Florida Keys' lobster or our wonderful assortment of Keys'...
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    Conch Key, Florida Keys 33050
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    A quiet spot in paradise close to fishing with dockage included (#4)1 / 13
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 May 2018
    Best view in the Keys! Extremely clean and spacious! Owners very attentive and friendly! Had the most relaxing holiday weekend! Recommend without a doubt and will be back!
    Reviewed 17 May 2018
    Awesome spot, Owners gracious and very helpful with local attractions.Would love to book for next year.
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    About this property
    This second floor Studio has a King-size bed as well as a pull out futon in the living room. We can accommodate 2 adults and 1 child under12. This Villa is situated facing due West right on the water and has a combined living and dining area. The Villa has a kitchen equipped with microwave, coffee...
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    Conch Key, Florida Keys 33050
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Royal Palm House1 / 20
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Grill
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 December 2016
    Brian should have mentioned that the whole back of the house opened up (sliding doors that folded together) to the screened in up stairs patio. We could have spent the whole 20...
    Reviewed 11 January 2016
    The house was perfect and very clean. We felt right at home for our month stay. Brian and Janice were very accommodating. Not only will we rent again but our friends are also...
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    About this property
    Welcome to Royal Palm House. Home is located at Mile Marker 54.5 in Coco Plum Beach Subdivision in the heart of the Florida Keys. This custom built contemporary home features 1,515 square foot of central air condition and heated living space. Massive Great Room has vaulted ceilings, clay tile...
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    Marathon, Florida Keys FL
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Comfortable Clean HouseBoat in an amazing location1 / 25
    (4)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Grill
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 October 2016
    What's not to love? Heidi greeted us with warmth and a smile. She showed us around and provided recommendations for great dinner and SCUBA spots. The house boat was spotless, it...
    Reviewed 3 August 2016
    This is a great little houseboat, clean and comfortable. The owner is kind and responsive. I would highly recommend. There is a little bar and grill at the marina, it closes at...
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    About this property
    Very spacious Houseboat. One bedroom with queen size bed. Very comfortable queen size pull out sleeper sofa, and extendable single sleeper Large closet and lots of storage space. Full bathroom, shower and bath towels, hand towels and washcloths. A fully equipped galley with all the comforts of...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 5
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    Paradise By The Bay1 / 27
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Hot Tub
    • Ocean Views
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 May 2017
    Place was great. Pool, jacuzzi, outdoor bar/kitchen. Was very relaxing. Being on the water was convenient for your boat. Really no complaints. Everything u want if your a...
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    About this property
    Come bring your boat and leave your worries at home. And enjoy our little Paradise By The Bay. This is a beautiful mobile home,3 bedrooms 2.5 bath with spacious living room and a flat smart screen TV and comfortable furniture. The master bedroom has a Quinn size bed with half a bathroom a flat...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Private Island Rental with 19' Boat, Seabird Key1 / 62
    (11)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Ocean Views
    • Grill
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 January 2016
    Seabird Key was absolutely perfect for our family. We were were a party 4 adults, a 2 year old and an infant. The island was well-suited for all. We enjoyed going to the beach...
    Reviewed 19 March 2015
    Wow. Seabird Key is one of a kind. We felt like we were in the swiss family robinson movie. The house's main floor is perched at the same level as the tree canopy. If you...
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    About this property
    Seabird Key is a ten acre private island available for rental by the week featuring an architecturally stunning home with gracious porches and multi level decks; a private, sandy beach and beautiful, tropical gardens throughout. Only 5 minutes offshore by boat, this is the Island that has it...
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    Location Information
    Marathon, Florida Keys 33156
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Conch Key Villas Unit 2 Spectacular open water views!1 / 16
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 April 2018
    We had a wonderful week stay at the Conch Key Villas. I would highly recommend Conch Key Villas to anyone and everyone. The owners Stewart and Katie are absolutely fantastic...
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    About this property
    We live onsite and do our best to make sure you enjoy your a relaxing vacation. Welcome to Conch Key Villas! We are located in the heart of the Florida Keys. Conch Key is a quiet island where relaxing is a way of life. When you first walk through our entrance gate you know you made a great...
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    Location Information
    Conch Key, Florida Keys 33050
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    P27 Sunsplash Paradise - Pool home with private beach access!1 / 25
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • Grill
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 December 2017
    This home was EXACTLY as described and pictured. Extremely clean and nicely furnished. It was very quiet and we were able to take a much needed RELAXING vacation! Nice pool...
    Reviewed 5 July 2017
    This home was exceptional and extraordinarily clean, clean, clean! The home was well equipped and I loved the furnishings, decor, beds, quiet atmosphere and I could go on! We...
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    About this property
    Now offering Private Beach Access! 'Sunsplash Paradise' is a dreamy three bedroom, two bath home located in a prestigious neighborhood on Key Colony Beach. But it’s more than that – it’s a place in paradise to create many happy, fun and sun-filled memories with family and friends. We wanted to...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Truman Treasure1 / 19
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Patio
    • Internet Access
    • Washer
    • Grill
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 October 2017
    Lovely property. I have stayed in the shipyard condo's, that have small rooms and only room for 1 person in the kitchen - this home gave all of my guests plenty of space with...
    Reviewed 28 February 2014
    This three bedroom condo (two upstairs bedrooms with king and twin beds and ensuite baths and a downstairs bedroom with full-sized bed and right-next-door half-bath) exceeded...
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    About this property
    Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition plasma TV found in every bedroom in addition to the living room and high speed internet available throughout. There is access to a large private association pool. This beautiful home is close to ocean and the...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 5
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    the private & secluded Peninsular house off Grassy Key harbor.1 / 20
    (39)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Waterfront
    • Ocean Views
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 July 2018
    So glad we stumbled upon this listing! Dave and his son were so welcoming when we arrived, and everything one could need for fishing, kayaking, and paddleboarding, was all...
    Reviewed 7 January 2018
    Just got home to freezing northern Wisconsin from a week at this wonderful home with my husband and 5 adult or adult-size children. Convenient and private location between Key...
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    About this property
    An attractive house with heated pool/spa plus new Hot Tub for 6/7 persons, boat dock & beach, in a unique tucked away, completely private location. The Peninsularhouse only rents Sat to Sat. check-in at 3pm, check-out at 10am the following Sat. 8 Kayaks on site,doubles & singles inc.catamaran...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Air Conditioning
    • Balcony
    • DVD Player
    • Patio
    • Washer
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the heart of it all, Plantation Key is the most convenient of all the Keys. We are near a supermarkets, a pharmacy, and a hospital. There are also plenty of restaurants and a movie theater. The neighborhood offers a boat ramp directly on the bay. Ocean access is a short ride through Snake or...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 8
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