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Smoking Allowed Holiday Rentals in Key West

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    $845 Average
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    Travellers to Key West are booking February dates now. Secure your holiday rental today, and have the perfect trip.
    8 Matching Rentals in Key WestView all 408 rentals
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    Duval Balcony - Suite Mischief1 / 13
    (10)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Catamaran CALYPSO with Summerallthetime Sailing Co1 / 62
    (12)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Secure Parking
    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 April 2017
    We had the pleasure to sail around the Florida Keys on the Calypso last month. The boat was great and very well kept. Beds were comfortable and cabins felt clean and polished...
    Reviewed 28 March 2017
    Capt John took our family of 4 on an ultimate Spring Break Keys journey!The sailboat is well equipped and very clean and modern. We had plenty of room to rest and play on...
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    About this property
    The Beautiful 42' Catamaran Calypso is a spacious Luxury Boat with all the latest Amenities. With 3 Cabins available... it sleeps 6 people comfortably. Each cabin has its own bathroom with all new faucets and electric flush toilets. Aboard Calypso you will find several places to lounge, sit back,...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Secure Parking
    • Air Conditioning
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful home in the desirable canal front community of Key Haven. At the end of a quiet street this 3/2 home features a 2010 renovated kitchen, gorgeous enclosed back porch for relaxing, 2 boat lifts on the canal. The home is set deeply off the street for privacy, and has a long driveway for 2+...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    KEY WEST MANSION - Incredible 3-Story Mansion W/ Private Beach, Pool, & Spa This KEY WEST MANSION is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. This Chateau is designed in true keys...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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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 1 March 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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    Sailboat Camping 4 The Adventurous!1 / 15
    (1)Terrible
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rosie is at anchor in harbor just off the bustling downtown life of Key West. She has a very comfortable queen size V berth bed, a cozy saloon (living room) great for curling up, amazing sunset views, and in a very friendly neighborhood of boats! Rosie is a 33ft Pearson Sloop anchored only a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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