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    Travellers to Florida Keys are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1,952 Matching Rentals in Florida KeysView all 3,564 rentals
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    The Fabulous Florida Keys! Come Enjoy 28 Days Or More!!! Please Call .1 / 48
    (36)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Direct Oceanfront Views In Anglers Reef, Islamorada.  Resort Pool, Dock, Beach1 / 22
    (14)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    The Conch House: Pool, Dock with Quick Ocean Access: May Special $1700.00/week1 / 49
    (15)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Eyebrow Suite at the Eyebrow House1 / 20
    (17)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Bay Front Home With Magnificent Views1 / 39
    (34)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Tavernier, Key Largo 33070
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    New kitchen upgrade is a must see!  Blue Moon is open and ready for bookings!1 / 44
    (36)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    WATERFRONT 46' DOCK, POOL, WALK 2 CABANA BEACH CLUB *ON SALE  9/28-10/11 $1099WK1 / 34
    (35)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Rent Your Own Private Island with boat...Seabird Key, Marathon, Florida USA1 / 50
    (43)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    THANKSGIVING OPEN-WEEKLY STAYS ALLOWED-WATERFRONT HOME-WIFI-PRIVATE DOCKAGE1 / 24
    (24)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Layton, Long Key 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Blue Coral:  A Private Oasis In The Heart Of Old Town Key West1 / 24
    (45)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    The Perfect Getaway with Heated Swimming Pool, Jacuzzi and Boat Slip1 / 24
    (21)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Matecumbe Key, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Water Front, Private Boat Dockage, Heated Private Pool.1 / 44
    (108)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Tropical Tranquility ~ 5 Star Caribbean Resort-Style Villa1 / 32
    (15)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Waterfront! Why rent on a canal when you can be on Bonefish Bay?1 / 30
    (59)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Sanctuary in Paradise Featured on H G T V1 / 24
    (35)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Tavernier, Key Largo 33070
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Waterfront Sgl Family Pool Home:60' Dock: Direct Ocean Access:Kayaks:Ocean1 / 50
    (55)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    E1LUXURY 4 bed 3 bath home with pool and dockage, central & close to everything!1 / 36
    (33)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Upscale Beautiful Duplex W/Pvt.Pool/Cabana Club & Inch Beach !1 / 23
    (54)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Key Colony Beach, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Sombrero Beach Home w/ Pool - Hot Tub - & deep dock! Walk to the beach !!!1 / 35
    (31)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Scenic Solitude Private,  Luxurious and tropical Pool Home1 / 29
    (12)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    RATES REDUCED!! White Marlin Beach House, Islamorada1 / 24
    (33)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Long Key, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Custom Built Luxury Home on Canal; Walk to Beach; Close to Everything!1 / 24
    (28)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    Paradise Place with Boats, Kayaks, Canoes, and Bicycles1 / 50
    (60)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Villa Casa Cayo.....Ocean Side Canal Sombrero Beach Area1 / 37
    (28)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful New Island Home for 2 Small Families1 / 25
    (83)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Tavernier, Key Largo 33070
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    'SUNKISSED'~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!1 / 22
    (40)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Key Lime Kottage, Waterfront, Secluded and Very Private House1 / 45
    (24)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Craig & Cindy's Key West 2 Bdrm Poolside Coral Hammock Royal Palm House1 / 23
    (22)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Southern Comfort! Canal front on 10th w/screened room,2 Kayaks& CABANA CLUB Incl1 / 38
    (23)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Islamorada Escape - Bungalow #3 - Cozy, clean, tropical oasis!1 / 49
    (20)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Layton, Long Key 33036
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Fran's Place on the Water1 / 24
    (33)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Tavernier, Key Largo 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Outstanding Oceanfront 4 bedroom House with Pool and Deep Water Pier!!1 / 25
    (38)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    3BD, 2BA, Pool, Waterfront Canal.WIFI +Cabana Club Pool/Beach! FISHING!1 / 28
    (76)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Parking
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    • Patio
    • Hot Tub
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    Pet friendly
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    Smoking allowed
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Breathtaking Waterfront Home! Open Jul 14-21st! Ready to Rent!1 / 36
    (31)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Pet friendly
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Key Colony Pool Home-Not too Soon to Book Christmas!  Small Dog Friendly!1 / 44
    (24)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Keys Sanctuary In A  Gated Community With Dock And Pool  On Atlantic Ocean1 / 49
    (25)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Luxurious Oceanfront Home on Beach w/Heated Pool, Dock, Kayaks, Bikes, Fire Pit1 / 50
    (69)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Location Information
    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Spacious 3 bdrm 2 1/2 bath House on Gulf w/ Cabana Club1 / 48
    (58)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Grill
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    Pet friendly
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Elegant 4 Bedroooms-Oceanside - PRIVATE DOCK Behind House1 / 40
    (28)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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