- Harbour Place
- Key Haven
- Key West Beach Club
- Key West Cuban Club
- 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
- Private Homes, New Town
- Private Homes, Old Town
- Private Homes, Unspecified
- Private Homes, UpTown
- Seaside Resort
- Sunrise Suites
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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Beautiful Newly-Renovated Historic House
3BR+/3BA
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Sleeps 6-8
– Casa Marina #430840
$4,500 - $7,500
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The Orchid Cottage Nestled in the Peaceful Meadows
1BR/0BA
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Sleeps 1-2
– Meadows #451542
$2400 - $3750 per month 30 night min stay
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Spacious One Bedroom Condo in the Casa Marina District
1BR/1BA
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Sleeps 4
– Key West Cuban Club #475046
$2400 - $4480 per month
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Historic Seaport District
3BR/2BA
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Sleeps 6
– Private Homes, Historic Seaport #3483367ha
$4500 - $9500 per month
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Ellen's Retreat - Tropical Living, 28 Days Minimum Stay.
3BR/2BA
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Sleeps 2-6
– Private Homes, Old Town #422831
$5488 - $9520 per month 28 night min stay
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Private Waterfront Key West Home with Pool
3BR/3BA
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Sleeps 6
– Other Key West Properties #3002764ha
$3999 per month
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Charming Old Town Cottage for Single or Couple
1BR/1BA
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Sleeps 2
– Private Homes, Historic Seaport #384413
$3500 high season Feb., March, April
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Relaxing, Quiet, Get-Away Close to Duval Street and the Beach
3BR+/2.5BA
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Sleeps 6-8
– Private Homes, Old Town #294667
From $2700/wk - $4000/mo
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Great Taste - Great Location - Newly Restored 2 Bedroom - Pool
2BR/2BA
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Sleeps 4
– Private Homes, Old Town #252753
$4000- $6000/mo
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Garden Studio in Historic Old Town
Studio/1BA
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Sleeps 2
– Private Homes, Old Town #330201
$2500- $4000/mo
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Villa Al Mar
6BR/6BA
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Sleeps 13
– Key Haven #295078
$7000-$8000/wk, $2800-$32000/mo
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Luxury Tropical Villa with Private Pool 4BR/3BA – Sleeps 8 – Casa Marina #465555
Special offer Summer discounts available
Jun 1, 2013 to Sep 30, 2013
$6990 - $9900 per month 30 night min stay -
Adorable Cottage Steps from Duval
3BR/2BA
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Sleeps 6
– Private Homes, Old Town #990915ha
$7700 per month 28 night min stay
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Southernmost City Historic Vacation Home II
2BR/2BA
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Sleeps 4-6
– Private Homes, Old Town #449895
from $3000/month
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Galleon Ocean Splendor
2BR+/2BA
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Sleeps 6
– Galleon #466459
$485 - $565 per night 5 night min stay
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Scullys Key West Condo : Truman Annex: Best Spot in Key West
2BR+/2BA
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Sleeps 2-4
– Truman Annex #309732
$1400-$2000/wk - $4200-$6000/mo
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Studio Apartment in Downtown Key West
Studio/1BA
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Sleeps 2
– White St. Gallery #450018
$219 - $249 per night 3-4 night min stay
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Last Minute April Special $2200 Beach Condo 2 Pools One Month Min.
1BR+/1BA
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Sleeps 2
– Seaside Resort #358407
From $1400/mo
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Ocean View Key West Condo
2BR/2BA
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Sleeps 4-6
– 1800 Atlantic #377163
2500- 4500/mo
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Tropical Paradise Surrounds 2BR 2BA Old Town Cottage
2BR/2BA
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Sleeps 4
– Private Homes, Old Town #308865
$2200- $5000/mo
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Studio & Private Bath, Old Town
Studio/1BA
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Sleeps 2
– Bahama Village #459387
$85 - $100 per night 3 night min stay
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Oceanfront 2bd/2bath Condo on One of Keywest's Natural Beaches!
2BR+/2BA
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Sleeps 6
– Casa Marina #431375
$2500 per week
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Writer's Personal Residence in Old Town
2BR/1BA
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Sleeps 4
– Private Homes, Historic Seaport #381042
$7000.00/mo
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Conch Wind Windward Park
2BR/2BA
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Sleeps 4
– Truman Annex #3246322ha
$186 - $471 per night
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Tranquility
1BR/1BA
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Sleeps 3-4
– Other Key West Properties #3245886ha
$161 - $413 per night
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Amelia Home
2BR/2BA
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Sleeps 6
– Other Key West Properties #3245880ha
$300 - $681 per night
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Duval Breeze
2BR/2BA
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Sleeps 6
– Other Key West Properties #3245844ha
$186 - $435 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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Shipyard Treasure
2BR/1BA
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Sleeps 4
– Truman Annex #3245856ha
$186 - $399 per night
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Crowner's Jewel
2BR/2BA
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Sleeps 6
– Truman Annex #3245874ha
$214 - $450 per night
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Villa Soleil
2BR/2BA
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Sleeps 6
– Truman Annex #3245863ha
$229 - $487 per night
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Caribbean Duval
2BR/2BA
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Sleeps 6
– Other Key West Properties #3245845ha
$186 - $435 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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Key West Found
2BR/2BA
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Sleeps 6
– Truman Annex #3245851ha
$229 - $487 per night
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Sundown Refuge
2BR/2BA
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Sleeps 5
– Truman Annex #3468745ha
$257 - $518 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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Linger Longer
2BR/1BA
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Sleeps 5
– Truman Annex #3245864ha
$186 - $409 per night
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Duval Street Hideaway
2BR/2BA
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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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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
– Truman Annex #3468747ha
$257 - $518 per night
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Bahamian Reed
2BR/1BA
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Sleeps 5
– Truman Annex #3245871ha
$186 - $409 per night
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Lavender Jungle
2BR/1BA
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Sleeps 4
– Truman Annex #3245841ha
$157 - $362 per night
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Paradise Place
1BR/1BA
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Sleeps 4
– Other Key West Properties #3245889ha
$129 - $333 per night
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Southern Wind
2BR/2BA
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Sleeps 4
– Other Key West Properties #3245883ha
$225 - $471 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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Papaya Place
2BR/2BA
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Sleeps 6
– Other Key West Properties #3245848ha
$179 - $381 per night
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Tropical Dreaming
2BR/2BA
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Sleeps 6
– Other Key West Properties #3245884ha
$300 - $681 per night
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Brisa Del Mar
2BR/2BA
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Sleeps 6
– Other Key West Properties #3245855ha
$186 - $387 per night
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Easy Livin'
3BR/4BA
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Sleeps 8
– Truman Annex #3245867ha
$571 - $1314 per night
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Island Pearl
1BR/1BA
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Sleeps 2
– Other Key West Properties #3245879ha
$171 - $391 per night
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Duval Sea Turtle
2BR/2BA
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Sleeps 6
– Other Key West Properties #3245843ha
$186 - $435 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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Alluring Porches
3BR/3BA
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Sleeps 6
– Other Key West Properties #3468749ha
$243 - $446 per night
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Bahama Dreaming
3BR/2BA
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Sleeps 8
– Other Key West Properties #3245873ha
$418 - $906 per night
- Truman Annex, Old Town, Key West, Private Setting with Luxury Features 2BR/2BA – Sleeps 5 – Truman Annex #123714ha
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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
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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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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
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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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Perfect Location -- in Old Town Key West, Sleeps 16!
6BR/4BA
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Sleeps 16
– Other Key West Properties #172563ha
$650 - $1200 per night
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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
- Steps from Duval $79-$129 Night - Free Bikes Included!!! Studio/1BA – Sleeps 2 – Other Key West Properties #233787ha
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Real World Mtv House---Not Just a House Your Own Private Resort
10BR+/5BA
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Sleeps 20-24
– Other Key West Properties #326563ha
$1333 - $2000 per night
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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
$975 - $1550 per week
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Villa Soleil, Elegant Truman Annex Condo in Old Town Key West
2BR/1BA
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Sleeps 4
– Truman Annex #188516ha
$1200 - $1500 per week
- Tropical Retreat Near Duval Street! 3BR+/3BA – Sleeps 6 – Other Key West Properties #273425ha
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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
- Key West - Poolside Conch Paradise at Key West Golf Club 2BR/1BA – Sleeps 4 – Other Key West Properties #164920ha
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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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Old Town Location Close to Beach, Shops & More
2BR/1BA
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Sleeps 5
– Truman Annex #234468ha
$1125 - $2000 per week
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Namaste Key West - Tropical Retreat in a Key West Conch Cottage
2BR/1BA
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Sleeps 4
– Other Key West Properties #373062ha
$3500 - $5000 per month
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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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'Avalynn House @ the Annex': Incredibly Spacious 5BR Home, Large Pool..
5BR/3BA
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Sleeps 12
– Truman Annex #996261ha
$8000 - $11900 per week 7 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
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Pink Iguana - Beautiful Fairway View...Location...Location
2BR+/1BA
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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
– Truman Annex #158403ha
$1200 - $1800 per week
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Walking to Everything, Close to Beach, Old Town
3BR/3BA
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Sleeps 6
– Other Key West Properties #299550ha
$460 - $540 per night 3-7 night min stay
- Ocean Front Condo at 1800 Atlantic - Next to Smathers Beach 2BR/2BA – Sleeps 6 – Other Key West Properties #174733ha
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Brass Palm Villa, Private Luxury Home - Escape to Paradise!!
3BR/2BA
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Sleeps 6
– Other Key West Properties #296145ha
$5500 - $21429 per month
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'Sea Captain'S Haven @ the Annex': Immaculate Villa Near Duval & Sunset Pier...
2BR+/2BA
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Sleeps 4-6
– Truman Annex #996654ha
$2100 - $3700 per week 7 night min stay
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Rose Lane Villa - Grande, 3bedroom 1/2 Block Off Duval; Perfect Location!
3BR/2BA
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Sleeps 6
– Other Key West Properties #243689ha
$349 - $759 per night
- Hemingway Hideaway in the Heart of Key West--Tasteful, Charming 3BR+/2BA – Sleeps 4 – Other Key West Properties #127835ha
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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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Tom's Parrot Perch: Gut Renovation Completed 9/16/11!!
2BR/2BA
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Sleeps 2-6
– Other Key West Properties #375693ha
$270 per night
- Fully Equipped Condo in the Heart of Beautiful Key West 2BR/1BA – Sleeps 4 – Other Key West Properties #162533ha
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Waterfront Luxury in Old Town Key West
1BR+/1BA
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Sleeps 2-5
– Galleon #232060
$286 - $460 per night
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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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'the Artist'S Hideaway @ Old Town': 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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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
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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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'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
$6600 - $15000 per month 28 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
– Truman Annex #3497683ha
$980 - $2520 per week 7 night min stay
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Rose Lane Villa - Aqua, 2 Bedroom, 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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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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'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
- Located on Key West Golf Course, Newly Decorated & Modern 3BR+/2BA – Sleeps 8 – Other Key West Properties #331171ha
- 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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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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Beautiful Newly-Renovated Historic House
3BR+/3BA
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Sleeps 6-8
– Casa Marina #430840