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Holiday Rentals in Key West

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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 199 Rentals in Key West
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    Azure Morning- Oceanfront, near Marina, Pool & Jacuzzi1 / 24
    (43)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Key West Gem - Large, Bright 2 BR Condo on Ocean w/ Olympic-size Pool1 / 29
    (90)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Enjoy More Privacy in a Truman Annex End Unit Townhome1 / 24
    (42)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Spectacular Atlantic Ocean View Condo At Oceanside Marina (MONTHLY RENTAL)1 / 24
    (67)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    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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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    ~$~1,500/wk - Best Deal in Key West - Plus 7 Bikes Included!1 / 50
    (88)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Skiing: Property Is In A Ski Resort
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    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    My Condo by the Beach with Ocean View1 / 50
    (73)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    82’ THE BEST KEPT SECRET IN KEY WEST “Catchin Moments”1 / 25
    (8)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
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    33040, Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Sea Breeze Cottage- in Beautiful Truman Annex1 / 44
    (68)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West1 / 38
    (20)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Rent a Piece of Paradise!1 / 36
    (48)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!1 / 24
    (55)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Boli Townhouse - Luxury Rental in Key West - Truman Annex1 / 50
    (69)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.1 / 41
    (84)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Attitude Key West at the Beach, 2 Bikes and Internet, Pool, Whirl Pool, Sauna1 / 50
    (112)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Craig & Cindy Key West Truman Annex 212 Fleming House1 / 47
    (16)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Oceanfront Condominium - Key West's Crown Jewel1 / 47
    (173)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    33050, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Majestic Escape near Duval!  Pool, wifi, renovated 2/2 1/2, private courtyard.1 / 50
    (38)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Spacious Truman Annex End Unit Townhouse /Side Courtyard1 / 24
    (58)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Nautical Keys Suite at Top Of Duval1 / 24
    (13)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Decorators own Coastal Chic home1 / 22
    (63)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    08736, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Duval Square Retreat: A beautiful condo steps from the action1 / 38
    (48)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Attitude Key West (2 Bikes and Wireless Internet)1 / 49
    (78)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Beach House with Ocean View1 / 24
    (56)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Simonton Studio, an Old Town get-away for 21 / 50
    (162)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Reviewed 15 December 2017
    My friend & I stayed Dec 3-8, 2017 and everything was perfect! You can't beat the location in Old Town and having two bikes makes it easy to get around and work off all that...
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    33040, Key West, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    'A Touch of Paradise' Great Pool, by the Beach, Duval, Music, Bars. 2 FULL baths1 / 50
    (78)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Mojitoville: 3 bedroom pet-friendly, Old Town, Private Pool, Historic Seaport1 / 26
    (36)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 3 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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    33040, Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Superb Location, Affordably Priced1 / 50
    (96)Excellent
    Studio, 1 Bathroom, Sleeps 1 Quick View
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    33040, Key West, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 1
    Sunshine Daydream: Private Home 1/2 Block Off Duval in Gallery District -1 / 20
    (56)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Bonus!!!  Two bicycles provided! Beautifully appointed first floor condo.1 / 20
    (25)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Apple of Your Eye in Paradise (Truman Annex)!1 / 19
    (51)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Key Lime Pie Suite at Top Of Duval1 / 24
    (9)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    'VILLA AZUL' ~ Beautiful Unit Located in Truman Annex - Walk to all the Fun!1 / 18
    (35)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Newly Renovated 4 bedroom/3 full bath home w/private pool in Old Town Truman Ann1 / 45
    (88)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    William Skelton House - Available Easter Weekend!1 / 50
    (66)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
    'DANCING PALMS' ~ Truman Annex, Covered Parking Spot, Gas Grill,  & Hot Tub!1 / 26
    (36)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Peaceful Setting Amongst The Active Island Life Style1 / 28
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Tiki BeachToo! Pre holiday special.  just 2 blocks to Duval, bikes, pool, grill1 / 16
    (36)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Club Cuba Suite at Top of Duval1 / 26
    (12)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Truman Annex: The Plantation SELF CATERING  beautifully landscaped rear patio1 / 17
    (61)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    New Luxury townhouse in the Gallery District of Old Town, Key West.1 / 22
    (2)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Key West Golf Club - Completely Renovated - Tree House Too.1 / 21
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Luxury 1 Bedroom with Full Kitchen - Sleeps 3 - Walk to the Beach & Nightlife1 / 27
    (53)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Casa Cay West ~ Beautiful Tropical House - 2 King Beds! Sleeps 81 / 42
    (232)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Catherine House: A charming Old Town Key West cottage1 / 29
    (95)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi1 / 49
    (159)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    33040, Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Villa Paradiso: A unique mid-town paradise1 / 39
    (84)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Chavez House! C 1870: New for Winter 2016! Spacious and Luxurious!1 / 37
    (34)Excellent
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    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Chick-a-Pea's Cottage: Pet-Friendly with Fenced Yard! Parking & Private Pool1 / 28
    (69)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    33040, Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    1
    Holiday Rental Accommodation on Key West

    The diversity of the holiday rental accommodation available on Key West means that there is something available to suit every budget and surely all tastes. From cottages and modest condos, to villas and townhouses, to penthouses and country estates, Key West has it all, meaning that your holiday in Key West can be as free of restriction as possible, at a price you can afford. If you want the freedom to explore Key West at a time and in a manner of your choosing, selecting the holiday rental best suited to your individual requirements is the way to achieve your goal.

    Water sports in Key West

    The weather and geography of Key West make it an ideal location for a great many different types of water sports. Fishermen of all disciplines can choose from the art of fly fishing for tarpon, to deep sea fishing expeditions from a boat and most options in between. Those simply interested in being out on the water can go pleasure cruising on a charter boat, perhaps to view the dolphins and other marine life, hire a kayak and meander through the waterways at their own pace, or even jump on a jet ski and enjoy some high speed thrills. Scuba divers can admire the natural coral reefs or explore the wrecks in the area, some of which were deliberately sunk to form artificial reefs.

    Popular attractions in Key West

    The beaches of Key West are both numerous and beautiful but a visit to the Fort Zachary Taylor State Park allows you to combine your beach relaxation and activities with an inexpensive tour of the fort, or perhaps a casual stroll along one of the nature trails. Art lovers will find a great many galleries of interest in Key West, with the majority local to the popular Duval Street part of town. Key West Golf Club is not only about allowing golf lovers to practise their swing, it also has a popular restaurant and bar, which could perhaps serve as a point at which non-golfers can arrange to meet players after their round. One monument not to miss in Key West is the small round landmark which denotes the most southerly part of the continental United States.

    Restaurants and bars in Key West

    Duval Street is the popular centre of Key West in so many ways, not least when it comes to restaurants. When you are eating out from your Key West holiday rental of an evening, you may wish to sample popular outlets such as Nine One Five or Mangoes, or try the Banana Café for breakfast or lunch. Blue Heaven in the Bahama Village is the place to sample outdoor dining of the highest quality, with an indoor option available if preferred. The bars and clubs of Key West are plentiful in the extreme, with options to suit all tastes and requirements and allow you to party the night away in style.

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