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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Truman Annex Vacation Rentals Show this location only Back to top
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Truman Annex Best Location in Town
2BR+/2BA
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Sleeps 4-6
– Truman Annex #67476
$1400 - $2200 per week 7 night min stay
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Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access
2BR+/1BA
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Sleeps 4
– Truman Annex #236217
$1300 - $1950 per week 7 night min stay
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'Old Town Oasis @ Truman Annex': Luxurious 2BR/2BA Condo + Oceanside Pool...
2BR+/2BA
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Sleeps 4-6
– Truman Annex #71538
$2100 - $3800 per week 7 night min stay
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Truman Annex House, 2b/2.5b, Add 1b/1b Cottage=3BR/3.5BA, Pool
3BR/3.5BA
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Sleeps 6
– Truman Annex #1614
$2150 - $5500 per wk
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Key West Condo in Truman Annex with Whirlpool Tub, 2 Bikes, & Access to Pool!
2BR/1BA
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Sleeps 4
– Truman Annex #385544
$1300 - $1950 per week 7 night min stay
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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
– Truman Annex #390177ha
$3300 - $5500 per week 7 night min stay
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Full Month Discounts Now Available in Truman Annex, Key West
2BR/2.5BA
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Sleeps 4-5
– Truman Annex #406936
$1750 - $2751 per week 7 night min stay
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Ocean Paradise
3BR+/4BA
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Sleeps 8
– Truman Annex #216159
$4900 - $6900 per week 7 night min stay
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'Conch Casa Grande @ the Annex': Enormous 7BR/7BA in Truman Annex...
7BR/7BA
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Sleeps 12
– Truman Annex #390171ha
$1000 - $1843 per night
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Craig & Cindy's Truman Annex Key West Property
2BR+/2.5BA
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Sleeps 4-6
– Truman Annex #108809
$1400- $2400/wk
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'Cool Breeze @ the Annex': Meticulously Furnished 2BR/2.5BA Old Town Villa...
2BR+/2.5BA
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Sleeps 6
– Truman Annex #390190ha
$1950 - $3200 per week 7 night min stay
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'Eden @ the Annex': 2BR/1.5BA Old Town Villa Near Beach & Sunset Pier...
2BR+/1.5BA
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Sleeps 4-6
– Truman Annex #390205ha
$1650 - $2500 per week 7 night min stay
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Ocean Retreat
3BR/2.5BA
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Sleeps 5
– Truman Annex #280619
$2900 - $4900 per week 7 night min stay
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Tiki Beach Too, Charming Townhome, Old Town, Pool Access, Great Porch!
2BR/1BA
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Sleeps 4-6
– Truman Annex #3539485ha
$1195 - $1895 per week 7 night min stay
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A Truman Annex Condo
2BR+/1BA
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Sleeps 4-6
– Truman Annex #296278
$1100- $1800/wk
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Luxury Townhouse Key West Gated Community. Easy Walk to Downtown
2BR/2.5BA
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Sleeps 6
– Truman Annex #453182
$1750/wk - $8250/mo
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Southern Palm 2BR/2.5BA Townhome in Historic Truman Annex
2BR+/2.5BA
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Sleeps 4-6
– Truman Annex #215928
$1750- $2750 Special events may be more
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Truman Annex - Shipyard Condominium
2BR/1BA
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Sleeps 4
– Truman Annex #9633
$1200-$1800/wk - $3000/mo
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Beautiful Truman Annex End Unit Townhouse with Side Courtyard
2BR+/2.5BA
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Sleeps 4-6
– Truman Annex #140996
$1800- $2100/wk
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Bargain Rates in Truman Annex - Heart of Old Town, Key West
2BR/1BA
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Sleeps 4-6
– Truman Annex #68720
$185 - $350 per night
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Tropical Island Get-Away, Garden Level Condo in Truman Annex
2BR+/1BA
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Sleeps 4
– Truman Annex #55381
$1050-$1900/wk - $2800/mo
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Luxurious Truman Annex 4 BR/3 Full BA (Private Pool)
4BR/3BA
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Sleeps 8
– Truman Annex #219779
$2900- $4900/wk
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Truman Annex Flamingo Beach Garden Level
2BR/1BA
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Sleeps 4
– Truman Annex #215927
$1300- $1950/wk some special Event rates
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Annex, Harbor Place Best Location Key West
2BR+/2.5BA
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Sleeps 4-6
– Truman Annex #230431
$2600.00 3500/wk
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Beautiful Key West Condo, Great Location in Truman, Near All
2BR/1BA
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Sleeps 4
– Truman Annex #138096
$1200- $2100/wk
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Truman Annex Key West D & D's Paradise
2BR/1BA
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Sleeps 4
– Truman Annex #291222
$1225- $1925/wk
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Always Your Paradise - Old Town Truman Annex Condo
2BR+/1BA
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Sleeps 4
– Truman Annex #283300
$900- $1800/wk
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Truman Annex Town Home
2BR/2.5BA
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Sleeps 4-6
– Truman Annex #465198
$1645 - $2100 per week 7 night min stay
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A Touch of Bermuda at Truman Annex
2BR+/2BA
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Sleeps 6
– Truman Annex #361238
$2100 per week 7 night min stay
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Truman Annex - Foundry Townhouse - One of a Kind!
2BR/2.5BA
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Sleeps 4
– Truman Annex #159305
From $2350 per week
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Gated Private Luxurious Getaway-Truman Annex (Private Pool)
4BR/4BA
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Sleeps 8
– Truman Annex #99721
$5500- $7500/wk
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Charming Home in Old Town Key West
3BR+/3BA
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Sleeps 6-8
– Truman Annex #310066
$3500- $5500/wk
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House by the Beautiful Sea- Stunning Key West Sunsets
3BR+/3BA
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Sleeps 6-8
– Truman Annex #240137
$4800/wk
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Tropical Hideaway for Laid Back Living
2BR+/1BA
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Sleeps 4-6
– Truman Annex #263478
$1250- $1600
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Waterfront Views from Dolphin Watch
4BR/3BA
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Sleeps 8
– Truman Annex #297639
$4500- $6500/wk
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Sea Breeze Cottage-Gulf View in Truman Annex
3BR/2BA
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Sleeps 3-6
– Truman Annex #987489ha
$357 per night
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Elegantly Furnished Key West Condo in the Truman Annex.
2BR+/1BA
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Sleeps 3-6
– Truman Annex #347511
$165 per night 3 night min stay
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Blue Lagoon
3BR/2BA
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Sleeps 6
– Truman Annex #264827
$2500- $3500/wk
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Stay in the Nicest Part of Key West
2BR+/1.5BA
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Sleeps 4-6
– Truman Annex #279984
$1400- $2800/wk
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'Amberjack' a Little Slice of Key West Heaven
2BR/1BA
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Sleeps 4-6
– Truman Annex #3486581ha
$175 - $393 per night
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One of a Kind Luxury Home - Admirals Treasure
4BR/4BA
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Sleeps 8
– Truman Annex #290548
$5900- $8900/wk
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Key West on the Water with a Spectacular Sunset View Sleeps 6
2BR+/2.5BA
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Sleeps 4-6
– Truman Annex #362398
From $2,400 to $3,500 US
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Quaint Townhouse in the Heart of Old Town Key West
2BR/1.5BA
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Sleeps 4-5
– Truman Annex #446454
$1505 - $2380 per week 7 night min stay
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Oceanfront View Large Expansive Deck Great Sunsets 2wk-Monthly
2BR/2BA
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Sleeps 4
– Truman Annex #337229
$6,500 - $8,000 mo. US
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Shipyard 253
2BR/1BA
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Sleeps 6
– Truman Annex #3174183ha
$117 - $300 per night
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Luxury Truman Annex Condo - Walk to Beach/Duval St.
2BR/1BA
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Sleeps 4-5
– Truman Annex #200351
$1300- $1925/wk, discounted monthly rates
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Gated Private Luxurious Getaway-Truman Annex (Private Pool)
3BR/3.5BA
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Sleeps 7
– Truman Annex #99722
$4500- $6500/wk
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Quiet and Beautiful Truman Annex 2 BR End-Unit Old Town
2BR+/1BA
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Sleeps 4
– Truman Annex #420646
From $1100 - $1875 / week
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Key West Truman Annex 2bed/3bath Sleeps 6 Min to Duval/Water
2BR/2.5BA
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Sleeps 3-6
– Truman Annex #373185
From $1600/wk
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Hemingway's Hideaway
2BR+/2.5BA
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Sleeps 4
– Truman Annex #175251
$1855 per week 7 night min stay
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Truman Annex - 1BR/1BA - Renovated Corner Unit with Great Reviews!!!
1BR+/1BA
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Sleeps 2-4
– Truman Annex #50666
$1050- $5400/mo
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Céad Míle Fáilte - a Thousand Welcomes to Our Innisfree
2BR/1BA
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Sleeps 4
– Truman Annex #78945
$1400- $1900/wk
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Conch Retreat in Key West Truman Annex with 2 Bikes
2BR/1BA
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Sleeps 4
– Truman Annex #226298
$171 per night
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Chilmark South Tropical Key West Waterfront Condo
2BR+/2BA
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Sleeps 6
– Truman Annex #165220
$2400- $3800/wk
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Waterfront Luxury Condo in Old Town Key West
2BR/2BA
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Sleeps 4
– Truman Annex #110202
From $2500/wk + housekeeping +bed taxes
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Shipyard/Truman Annex - Private Tropical Retreat in Key West
1BR/1BA
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Sleeps 2
– Truman Annex #84372
From $1100/wk - $3000/mo
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Key West Charming - Two Bedroom Condo in Truman Annex
2BR+/1BA
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Sleeps 4
– Truman Annex #93294
$1100- $1750/wk
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Three Bedroom Shipyard Townhome
3BR/2BA
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Sleeps 6
– Truman Annex #236720
$2000 per week 7 night min stay
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Key West, Gated Truman Annex Condo, Partial Ocean View, Beach
2BR/1BA
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Sleeps 4
– Truman Annex #328241
from $1100- 1800
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Rent a Piece of Paradise!
2BR/1BA
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Sleeps 4
– Truman Annex #201892
From $1000/wk
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Unique Cottage in Truman Annex Shipyard Free Wifi
2BR/2BA
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Sleeps 4
– Truman Annex #246337
$1700 - $2400/wk
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Key West Casa
3BR/2BA
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Sleeps 6
– Truman Annex #3245858ha
$286 - $725 per night
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A Place in Paradise
2BR/2.5BA
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Sleeps 6
– Truman Annex #3245878ha
$214 - $414 per night
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The Hemingway
2BR/2BA
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Sleeps 6
– Truman Annex #3245860ha
$186 - $409 per night
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Paradise Found
2BR/1BA
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Sleeps 4
– Truman Annex #3170337ha
$117 - $300 per night
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Shipyard 106-2
1BR/1BA
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Sleeps 4
– Truman Annex #3174185ha
$100 - $250 per night
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Key West Charming
2BR/1BA
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Sleeps 4
– Truman Annex #3245859ha
$157 - $362 per night
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Parrot Perch
2BR/2BA
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Sleeps 5
– Truman Annex #3245862ha
$157 - $362 per night
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Island Spice
2BR/2.5BA
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Sleeps 6
– Truman Annex #3245852ha
$229 - $487 per night
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Artist Garden
2BR/2.5BA
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Sleeps 6
– Truman Annex #3245849ha
$243 - $489 per night
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Rare 2BR/2BA Shipyard Condo Truman Annex Key West!
2BR+/2BA
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Sleeps 4-6
– Truman Annex #57100
From $900/wk to $2500/wk
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Truman Annex: the Plantation, Beautifully Landscaped
3BR/3BA
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Sleeps 6
– Truman Annex #194366
$2500- $3500/wk Some Special Event prici
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Truman Annex: Paradise Lost Garden Level Condominium
2BR+/2BA
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Sleeps 4-6
– Truman Annex #198738
$1500- $2200/wk Special event Pricing
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Ann's Tropical Paradise in Key West
2BR/1BA
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Sleeps 3-4
– Truman Annex #73629
$225 per night 3 night min stay
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Truman Annex, Foundry Townhouse, Free Wifi Internet
2BR/2.5BA
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Sleeps 4
– Truman Annex #148626
From $1350/wk
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Key West Ocean View 3 Bedroom Truman Annex Vacation Condo
3BR/3BA
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Sleeps 6
– Truman Annex #223802
$3300 - $5000 per week 7 night min stay
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Anderson's Key West Home
4BR/3.5BA
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Sleeps 10
– Truman Annex #30934
$900 per night 2 night min stay
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Villa Fleur, Elegant Truman Annex Condo in Old Town
2BR/1BA
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Sleeps 4
– Truman Annex #207098ha
$214 - $257 per night
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Key West Vacation Townhouse Rental in the Truman Annex
2BR/2.5BA
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Sleeps 6
– Truman Annex #226962
$183 - $393 per night
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Truman Annex - Beautiful Townhome - President's Lane
2BR+/1.5BA
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Sleeps 4-6
– Truman Annex #55160
$1300/wk - $4300/mo
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Island Escape Condo in Beautiful Truman Annex
1BR/1BA
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Sleeps 3
– Truman Annex #383457
$171 per night
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Shipyard at Truman Annex "Where the Sun Sets in Old Key West"
2BR/1BA
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Sleeps 4
– Truman Annex #103761
$975- $1200/wk
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Relax in Paradise
1BR+/1BA
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Sleeps 2-4
– Truman Annex #151616
$175 - $215 per night 2-7 night min stay
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Garden Oasis Has a Large Tranquil Garden for Outside Enjoyment.
2BR/1BA
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Sleeps 4
– Truman Annex #3510442ha
$200 - $225 per night 3 night min stay
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Key West Truman Annex Town Home
2BR/1.5BA
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Sleeps 4
– Truman Annex #216176
$1500-$2400/wk - $4500-$7200/mo
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Enjoy More Privacy in a Truman Annex End Unit Townhome
2BR/1.5BA
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Sleeps 4-5
– Truman Annex #3552474ha
$250 - $500 per night 3 night min stay
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Foundry on the Waterfront - Island Brownstone Residence
2BR/2.5BA
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Sleeps 4
– Truman Annex #139485
$300-$425/nt - $1500-$2500/nt
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Awesome Truman Annex Shipyard with Tropical Garden
2BR+/1BA
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Sleeps 4
– Truman Annex #20158
From $850/wk - $2800/mo
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Our Place in Key West
1BR+/1BA
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Sleeps 2-4
– Truman Annex #31180
$1300- $1900/Wk
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Truman Annex Getaway...August & September Special! Only $1300/Week
2BR/2BA
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Sleeps 4-6
– Truman Annex #472075
$1300 - $2450 per week 7 night min stay
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Classic Key West Charm and Location Too!
3BR/3BA
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Sleeps 6
– Truman Annex #309835
$1,989 to $3,849/wk!
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Attitude Key West - Get that Chillin' Feeling
2BR+/1BA
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Sleeps 4
– Truman Annex #287741
$1200- $1850
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Shipyard Tropical Retreat
2BR/1BA
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Sleeps 4-5
– Truman Annex #465554
$3480 - $5673 per month 30-31 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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Steps to Famous Dvual Street
2BR/1BA
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Sleeps 4-6
– Truman Annex #466455
$1099 - $1575 per week 7 night min stay
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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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Linger Longer
2BR/1.5BA
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Sleeps 5
– Truman Annex #3245864ha
$186 - $409 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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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/1.5BA
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Sleeps 5
– Truman Annex #3245871ha
$186 - $409 per night
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Truman Annex Best Location in Town
2BR+/2BA
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Sleeps 4-6
– Truman Annex #67476
Overview of Truman Annex Vacation Rentals
Live Like a Key West Local at Truman Annex Vacation Rentals
With Truman Annex resort rentals, you can stay in the heart of Old Town Key West but feel miles away from the bustle of this exciting city. The gated community of Truman Annex is just minutes away from the sights of Old Town Key West, so you can walk or ride a bike to all the activities Key West has to offer and feel like a resident. Remember not to be surprised by the freely roaming chickens on the streets during your Key West travel, or you'll give away your tourist status.
Famous Restaurants and Bars Are Close to Truman Annex Vacation Rentals
Just a few blocks from Truman Annex vacation rentals, the famed Duval Street area features a variety of hip bars, nightclubs for dancing, and great restaurants. Visit the oldest blues bar in the country, The Green Parrot, and Sloppy Joe's Bar for sandwiches and wraps. Seafood is as fresh as you can get, and some restaurants will even cook the fish you caught yourself!
Key West Travel Features History and Recreation
Fort Zachary Taylor Park, better known to locals as Fort Zach, was deemed a National Historic Landmark in the '70s. Once an active military fort that was important in the Civil and Spanish-American War, the structure was built in the 1800s as a defense for the nation's most southern coastline. You can soak up this history with a tour of the fort just steps from Truman Annex vacation rentals, and then spend the rest of the day at the park's gorgeous white sand beach snorkeling, swimming, fishing, or sunbathing with a book while the kids play. Bring a picnic from your Truman Annex resort rental or buy snacks from the refreshment and souvenir stand on the beach.