- Key West Golf Club
- Key West Harbour Yacht Club
- La Brisa
- Meadows
- Oceanside Marina (formerly Kings Pointe)
- Private Homes, DownTown
- Private Homes, Historic Seaport
- Private Homes, Mid Town
This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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Key West Vacation Rentals Show this location only Back to top
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Bahama Dreaming
3BR/2BA
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Sleeps 8
– Other Key West Properties #3245873ha
$418 - $906 per night
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Shipyard Treasure
2BR/1BA
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Sleeps 4
– Other Key West Properties #3245856ha
$186 - $399 per night
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Duval Breeze
2BR/2.5BA
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Sleeps 6
– Other Key West Properties #3245844ha
$186 - $435 per night
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Linger Longer
2BR/1.5BA
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Sleeps 5
– Other Key West Properties #3245864ha
$186 - $409 per night
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Key West Crown Jewel
2BR/2BA
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Sleeps 6
– Other Key West Properties #3245869ha
$306 - $531 per night
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Caribbean Duval
2BR/2.5BA
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Sleeps 6
– Other Key West Properties #3245845ha
$186 - $435 per night
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Key West Ginger House
2BR/2BA
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Sleeps 6
– Other Key West Properties #3245872ha
$171 - $413 per night
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Amelia Home
2BR/2.5BA
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Sleeps 6
– Other Key West Properties #3245880ha
$300 - $681 per night
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Papaya Place
2BR/2BA
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Sleeps 6
– Other Key West Properties #3245848ha
$179 - $381 per night
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Egret Cottage
1BR/1BA
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Sleeps 4
– Other Key West Properties #3245885ha
$150 - $384 per night
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Surf Side
3BR/2BA
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Sleeps 6
– Other Key West Properties #3245868ha
$336 - $662 per night
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Duval Street Hideaway
2BR/2.5BA
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Sleeps 6
– Other Key West Properties #3245846ha
$200 - $456 per night
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Duval Courtyard
3BR/2BA
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Sleeps 6
– Other Key West Properties #3468746ha
$290 - $822 per night
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Alluring Porches
3BR/3BA
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Sleeps 6
– Truman Annex #3468749ha
$243 - $446 per night
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Tropical Dreaming
2BR/2.5BA
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Sleeps 6
– Other Key West Properties #3245884ha
$300 - $681 per night
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Bahamian Reed
2BR/1.5BA
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Sleeps 5
– Other Key West Properties #3245871ha
$186 - $409 per night
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Key West Found
2BR/2.5BA
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Sleeps 6
– Other Key West Properties #3245851ha
$229 - $487 per night
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Crowner's Jewel
2BR/2.5BA
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Sleeps 6
– Other Key West Properties #3245874ha
$214 - $450 per night
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Coral Villa
3BR/3BA
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Sleeps 8
– Other Key West Properties #3491240ha
$186 - $413 per night
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Truman's Hideaway
2BR/2BA
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Sleeps 5
– Other Key West Properties #3468747ha
$257 - $518 per night
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Osprey
1BR/1BA
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Sleeps 2
– Other Key West Properties #3245887ha
$93 - $321 per night
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Easy Livin'
3BR/4BA
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Sleeps 8
– Other Key West Properties #3245867ha
$571 - $1314 per night
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Sundown Refuge
2BR/2BA
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Sleeps 5
– Other Key West Properties #3468745ha
$257 - $518 per night
- Truman Annex, Old Town, Key West, Private Setting with Luxury Features 2BR/2.5BA – Sleeps 5 – Other Key West Properties #123714ha
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'Windows on the Gulf @ the Annex': Lavish Oceanfront 2BR/2.5BA Penthouse Condo..
2BR+/2.5BA
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Sleeps 4-6
– Other Key West Properties #390177ha
$3300 - $5500 per week 7 night min stay
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Simonton Studio, an Old Town Get-Away for 2. New Pricing
Studio/1BA
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Sleeps 2
– Other Key West Properties #332511ha
$107 - $230 per night
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Historic Restored 'Eyebrow' Home. Reduced Prices!!!
3BR/3BA
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Sleeps 6
– Other Key West Properties #169698ha
$5600 - $7560 per month 28 night min stay
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Walk to the Beach!
1BR/1BA
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Sleeps 2
– Other Key West Properties #392129ha
$2884 per month 28 night min stay
- Direct Oceanfront Free Wifi & Hbo 3BR/2.5BA – Sleeps 6 – Other Key West Properties #149233ha
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William Skelton -- Location, Location, Location -- in Old Town Key West!
6BR/3BA
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Sleeps 16
– Other Key West Properties #172563ha
$650 - $1200 per night
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Namaste Key West - Tropical Retreat in a Key West Conch Cottage 2BR/1BA – Sleeps 4 – Other Key West Properties #373062ha
Special offer June 2013 - Month at 20% SAVINGS
Jun 3, 2013 to Aug 29, 2013
$100 - $167 per night -
2 Bed / 2 Bath Luxury Condo on the Ocean - Sleeps 6 (Next to Smather's Beach)
2BR/2BA
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Sleeps 6
– Other Key West Properties #266703ha
$212 - $390 per night 3 night min stay
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Private Key West Weekly Vacation Rental in the Heart of Old Town
2BR/2BA
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Sleeps 4
– Other Key West Properties #187859ha
$420 - $490 per night 3-7 night min stay
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Charming Cottage Located on Quiet Walking Lane
2BR+/1BA
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Sleeps 5
– Other Key West Properties #389177ha
$1400 per week 7 night min stay
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Quiet, Elegant, Key West Condo Close to the Ocean
2BR/2BA
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Sleeps 4-6
– Other Key West Properties #342925ha
$210 - $225 per night 2 night min stay
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Four Bedroom Private Home
4BR/2BA
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Sleeps 8
– Other Key West Properties #258917ha
$5000 - $7550 per month 28 night min stay
- Tropical Retreat Near Duval Street! 3BR+/3BA – Sleeps 6 – Other Key West Properties #273425ha
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Pink Iguana - Beautiful Fairway View...Location...Location
2BR+/1.5BA
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Sleeps 6
– Other Key West Properties #328375ha
$1200 - $1900 per week 7 night min stay
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Villa Nomade, Elegant Truman Annex Condo in Old Town
2BR/1BA
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Sleeps 4
– Other Key West Properties #158403ha
$171 - $257 per night
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Tom's Parrot Perch: Gut Renovation Completed 9/16/11!!
2BR/2BA
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Sleeps 6
– Other Key West Properties #375693ha
$350 per night
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Walking to Everything, Close to Beach, Old Town
3BR/3.5BA
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Sleeps 6
– Truman Annex #299550ha
$460 - $540 per night 3-7 night min stay
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Real World Mtv House---Not Just a House Your Own Private Resort
10BR+/5.5BA
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Sleeps 20-24
– Other Key West Properties #326563ha
$1333 - $2000 per night
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'Sea Captain'S Haven @ the Annex': Immaculate Villa Near Duval & Sunset Pier...
2BR+/2.5BA
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Sleeps 4-6
– Other Key West Properties #996654ha
$2100 - $3600 per week 7 night min stay
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'Mango Gardens' Charming, Walking Distance to Duval, and Historic Seaport Area
4BR/0BA
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Sleeps 8
– Other Key West Properties #369876ha
$4000 - $6825 per month 28 night min stay
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Large Private Home Just 2 Blocks to Duval St
4BR/4BA
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Sleeps 10
– Other Key West Properties #272959ha
$629 - $929 per night
- Fully Equipped Condo in the Heart of Beautiful Key West 2BR/1BA – Sleeps 4 – Truman Annex #162533ha
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Villa Soleil, Elegant Truman Annex Condo in Old Town Key West
2BR/1BA
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Sleeps 4
– Other Key West Properties #188516ha
$171 - $214 per night
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'Coral Isle' Beautiful 3bed/3bath Two Story Townhome at Coral Hammock
3BR/3BA
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Sleeps 6
– Key West Harbour Yacht Club #236965ha
$300 per night 3 night min stay
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'the Lilac Cottage @ Solares Hill': 2.5BR/2BA Old Town Cottage, Quiet Street...
2BR+/2BA
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Sleeps 7
– Other Key West Properties #390179ha
$5000 - $11000 per month 28 night min stay
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Old Town Location Close to Beach, Shops & More
2BR/1BA
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Sleeps 5
– Other Key West Properties #234468ha
$161 - $286 per night
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'Villa Paradiso @ Casa Marina': Airy & Spacious Villa + Large Pool..
2BR/2BA
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Sleeps 4-6
– Other Key West Properties #915976ha
$4000 - $7700 per month 28 night min stay
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'Fat Nancy'S Villa @ the Club': Airy 2BR/2BA Townhome Near Community Pool...
2BR+/2BA
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Sleeps 4-6
– Other Key West Properties #390186ha
$2350 - $4900 per month 28 night min stay
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My Condo by the Beach with Ocean View
1BR/1BA
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Sleeps 4
– Other Key West Properties #379068ha
$139 - $221 per night
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Brass Palm Villa, Private Luxury Home - Escape to Paradise!!
3BR/2.5BA
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Sleeps 6
– Other Key West Properties #296145ha
$183 - $273 per night
- Affordable, Charming, Quiet, Walking Distance to Town, Shopping, Dining, Beach 1BR/1BA – Sleeps 3 – Other Key West Properties #299544ha
- Charming Yacht Located in Exclusive, Beautiful Key West Harbour Yacht Club 2BR/1BA – Sleeps 4 – Truman Annex #968728ha
- Hemingway Hideaway in the Heart of Key West--Tasteful, Charming 3BR+/2BA – Sleeps 4 – Other Key West Properties #127835ha
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3 BR Condo at 1800 Atlantic
3BR/2BA
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Sleeps 6
– Other Key West Properties #294543ha
$4900 per month 28 night min stay
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Modern Luxury and Privacy Just Steps from Duval
2BR+/2BA
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Sleeps 4-6
– Other Key West Properties #326701ha
$425 - $2800 per night
- Monthly Rates-Kw Living at its Finest-Quiet Neighborhood, Near Duval and Beach 3BR+/3BA – Sleeps 10 – Other Key West Properties #180167ha
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'Toba'S Tree House @ Casa East': Breezy 2BR/2BA Cottage & Pool Near Beach...
2BR/2BA
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Sleeps 6
– Other Key West Properties #3015070ha
$4000 - $7700 per month 28 night min stay
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'Tropical Splendor' 3 Bd Luxury Condo&Ocean View at Oceanside Marina.
3BR/2BA
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Sleeps 7
– Other Key West Properties #238646ha
$400 per night 3 night min stay
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A Little Piece of Paradise in the Truman Annex
2BR/1BA
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Sleeps 4-6
– Other Key West Properties #3497683ha
$980 - $2520 per week 7 night min stay
- Key West - Poolside Conch Paradise at Key West Golf Club 2BR/1.5BA – Sleeps 4 – Other Key West Properties #164920ha
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Private House: a Peaceful Oasis, Monthly Rental Only
4BR/3BA
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Sleeps 8
– Other Key West Properties #173113ha
$15000 per month 30 night min stay
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Rose Lane Villa - Aqua, 1/2 Block Off Duval
2BR/1BA
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Sleeps 4
– Other Key West Properties #243693ha
$249 - $519 per night
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Quiet Waterfront Condo with Boat Slip, Beach and Pool! One of a Kind!
2BR/2BA
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Sleeps 4
– Other Key West Properties #335989ha
$117 - $150 per night
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Treehouse Island: Private Home with Pool & Internet, Walk to Key West Hot Spots!
3BR+/4BA
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Sleeps 8
– Other Key West Properties #3013423ha
$643 - $929 per night
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Top-Floor Smathers Beach Condo with Gorgeous Pool, Tennis and Steps from Beach.
2BR/2BA
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Sleeps 4
– Other Key West Properties #254856ha
$150 - $350 per night
- Located on Key West Golf Course, Newly Decorated & Modern 3BR+/2BA – Sleeps 8 – Other Key West Properties #331171ha
- Key West Oceanfront Condo - 'the Sea Jay' 2BR/2BA – Sleeps 6 – Other Key West Properties #134883ha
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Attitude Key West at the Beach
1BR/1BA
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Sleeps 4
– Other Key West Properties #994355ha
$275 per night 3 night min stay
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Rose Lane Villa's Villa Alta 1 BR -- Quiet and Just Steps to Duval!
1BR/1BA
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Sleeps 4
– Other Key West Properties #243695ha
$169 - $379 per night
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Modern Home with Great Location - Room for Whole Family - Including Pets
3BR/1.5BA
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Sleeps 6
– Other Key West Properties #938871ha
$83 - $133 per night
- Ocean Front Condo at 1800 Atlantic - Next to Smathers Beach 2BR/2BA – Sleeps 6 – Other Key West Properties #174733ha
- Still a Few Feb Weeks,,,Ck Today !!!! 2BR/1.5BA – Sleeps 6 – Other Key West Properties #212518ha
- Petronia Palms for Budget Minded by Duval St Has a Large Pool! Studio/1BA – Sleeps 2 – Other Key West Properties #258192ha
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'Maison Tropicale @ Solares Hill': Lush 3BR/3BA Old Town Home, Pool & Spa...
3BR+/3BA
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Sleeps 8
– Other Key West Properties #390192ha
$220 - $500 per night
- Luxurious Ocean Front Oasis in Key West 3BR/2BA – Sleeps 6 – Other Key West Properties #257495ha
- Oceanfront 2BR/2BA – Sleeps 6 – Other Key West Properties #162417ha
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Rose Lane Villa - Grande, 1/2 Block Off Duval; Perfect Location!
3BR/2BA
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Sleeps 6
– Other Key West Properties #243689ha
$349 - $759 per night
- Key West Luxury Art Deco Style Oceanside Condo with Pool and Beach 2BR/2BA – Sleeps 6 – Other Key West Properties #255720ha
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Old Town Key West 2 Bedroom Cottage with Private Pool
2BR/0BA
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Sleeps 6
– Truman Annex #390412ha
$4500 - $7500 per month 30 night min stay
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The Tree House - an Authentic Key West Experience.
2BR/2BA
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Sleeps 4
– Other Key West Properties #282583ha
$117 - $183 per night
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Key West - Truman Annex Cottage-Best Location on the Island-Newly Renovated!
2BR/2BA
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Sleeps 5
– Other Key West Properties #273217ha
$393 per night
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Sunkissed Vision: Key West Condo Near Beach & Old Town-Fabulous Dining!
3BR/2.5BA
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Sleeps 7
– Other Key West Properties #3012153ha
$707 per night
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Casa Colonial Island Luxury in Key West
4BR/3BA
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Sleeps 7
– Other Key West Properties #329361ha
$743 - $829 per night
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Nassau Suite - Old Town Key West Villa
1BR/1BA
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Sleeps 4
– Other Key West Properties #390414ha
$185 - $285 per night 3-7 night min stay
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Canal-Front Home with Ocean Access in Beautiful Key West, Florida
4BR/0BA
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Sleeps 10
– Other Key West Properties #3005929ha
$333 - $500 per night
- Key West Rental (Casa De Suenos) House of Dreams! 1BR+/1BA – Sleeps 4 – Other Key West Properties #182589ha
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Charming Queen Conch Cottage - 2 Blocks to Duval Street!
2BR/1.5BA
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Sleeps 6
– Other Key West Properties #3013405ha
$571 per night
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Duval Street Luxury Home with Private Pool-Perfect for Family Reunions
5BR/4BA
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Sleeps 10
– Other Key West Properties #3013408ha
$1500 per night
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Key Haven Elegance
4BR/4.5BA
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Sleeps 10
– Other Key West Properties #3013415ha
$1000 per night
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Southernmost Oasis: Bbq Grill, Jacuzzi, Heated Pool with Waterfall
3BR/2BA
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Sleeps 6
– Truman Annex #3012231ha
$383 per night
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Rose Lane Villa's 'Villa Rosa' 1 Bedroom, 1/2 Block Off Duval
1BR/1BA
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Sleeps 4
– Other Key West Properties #299233ha
$159 - $369 per night
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Rose Lane Villa's Villa Porta 1 Bedroom, 1/2 Block Off Duval
1BR+/1BA
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Sleeps 4
– Other Key West Properties #299236ha
$159 - $369 per night
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'Waterfront Retreat @ the Florida Bay': 3BR/3BA Canal Front Home...
3BR+/3BA
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Sleeps 8
– Key West #3469621ha
$4000 - $8000 per month 28 night min stay
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Old Town Beauty - Charming Home 2 Blocks from Beach!
3BR/2BA
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Sleeps 6
– Other Key West Properties #3012142ha
$643 per night
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Old Town Oasis
4BR/3BA
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Sleeps 8
– Other Key West Properties #3013409ha
$1143 per night
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Pet Friendly Cottage
Studio/0BA
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Sleeps 4
– Other Key West Properties #391123ha
$148 - $168 per night 2-3 night min stay
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Bahama Dreaming
3BR/2BA
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Sleeps 8
– Other Key West Properties #3245873ha