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Holiday Rentals with Pools in Duck Key

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    Travellers to Duck Key are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    15 Matching Rentals in Duck KeyView all 24 rentals
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    Duck Key Paradise1 / 34
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Gorgeous, recently-updated, waterfront home w/ beach, pool, dock, & kayaks1 / 42
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Children's Pool
    • Washer
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The unit is located in the beautiful Duck Key, right in the middle between Miami and Key West, framed by the ocean and with spectacular sunsets. This 60-acre retreat is fantastic and you won’t even need to go anywhere else - everything you need for a great vacation is inside! Spend a day by the...
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    Duck Key, Florida Keys 33050
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Hot Tub
    • Housekeeping Included
    • Air Conditioning
    • Cable/satellite TV
    • Children's Pool
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The unit is located in the beautiful Duck Key, right in the middle between Miami and Key West, framed by the ocean and with spectacular sunsets. This 60-acre retreat is fantastic and you won’t even need to go anywhere else - everything you need for a great vacation is inside! Spend a day by the...
    View all property information
    Location Information
    Duck Key, Florida Keys 33050
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • Wi-Fi
    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully appointed home with Open Floor plan, tropically decorated living spaces, plantation shutters and nice screened in porch off living areas. 2 bedrooms and 2 bath in the main house. One bedroom with a king and the second with a queen. This home then has a screened breezeway that...
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    Duck Key, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Housekeeping Included
    • Cable/satellite TV
    • Children's Pool
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Close your eyes and drift away. You're now far removed from life's demands. The seas are calm and the faces friendly. Enjoy your stay in this villa with stylish Caribbean Island decor furnishings accented with warm jewel-toned fabrics. Start your day with a breakfast in one of several dining...
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    Duck Key, Florida Keys 33050
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Hot Tub
    • Washer
    • Housekeeping Included
    • Wi-Fi
    • Cable/satellite TV
    • Children's Pool
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Close your eyes and drift away. You're now far removed from life's demands. The seas are calm and the faces friendly. Enjoy your stay in this villa with stylish Caribbean Island decor furnishings accented with warm jewel-toned fabrics. Start your day with a breakfast in one of several dining...
    View all property information
    Location Information
    Duck Key, Florida Keys 33050
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check-in Check-out
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    Payment Protection
    Amenities & Details
    • Housekeeping Included
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Children's Pool
    • Air Conditioning
    • Waterfront
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Close your eyes and drift away. You're now far removed from life's demands. The seas are calm and the faces friendly. Enjoy your stay in this villa with stylish Caribbean Island decor furnishings accented with warm jewel-toned fabrics. Start your day with a breakfast in one of several dining...
    View all property information
    Location Information
    Duck Key, Florida Keys 33050
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Grill
    • Patio
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 bedroom 2.5 bath canalfront home with private pool.  Seaside decor and casual elegance defines this comfortable home on Duck Key.  Open floor plan and spacious well-equipped kitchen.  The master suite is on the main floor, with king size bed and onsuite private bath.  The foyer area has...
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    Location Information
    Duck Key, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    • Grill
    • Waterfront
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looks like South Beach Living but in The Florida Keys, this home is completely renovated and ready for your fishing and diving adventures.  Fantastic large kitchen and Open Floor plan. Large open deck overlooking the pool and the beautiful canals of Duck Key.  45 feet of dockage, Large pool....
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    Location Information
    Duck Key, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Grill
    • Washer
    • Parking
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Three to Four night minimum depending on the time of year.  Max Occupancy is 6 (Does not matter age). This is a rule of 2 per bedroom plus 2. NO EXCEPTIONS. Duck Key Darling is a 2 bed 2 bath Townhouse Villa in Hawks Cay that over looks beautiful Tom's Harbor! This unit has gorgeous...
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    Location Information
    Duck Key, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Hot Tub
    • Cable/satellite TV
    • Ocean Views
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tropical Paradise Book this lovely waterfront home and start your vacations off on the right foot! Gather with your friends and relax in the screened-in porch while admiring the water views or read a good book and enjoy some time on your own. Take advantage of the private swimming pool and hot tub...
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    Location Information
    Duck Key, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Ocean Views
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dolphin View is located next to the World Famous Dolphin Research Center in Grassy Key Marathon Florida. From our dock you able to watch their Dolphin shows. You will have a very private property with a long driveway set back from the main road on the Gulf of Mexico. House is about 3000 sq ft. It...
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    Location Information
    Duck Key, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check-in Check-out
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    Amenities & Details
    • Washer
    • DVD Player
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make vacation wishes come true at this 2BR/2.5BA Duck Key waterfront villa. Set right on a canal in the heart of the Florida Keys, this lovely retreat features shimmering water views. Take in the beautiful vistas from the private pool, or head directly to the water and launch the provided kayak...
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    Location Information
    Duck Key, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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