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Vacation Rentals in Truman Annex, Key West

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

DEAL!! Emma House & Cottage Plus Pvt. Pool
Key West House Rental Picture
  • House Rental Deals and Discounts $500 off = $2,750 per week
  • House Rental Deals and Specials Housekeeping ($150)
  • bedrooms 3
  • community Truman Annex
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $2,250 - $5,500 /wk
    $9,000 - $17,500 /mth
 
 
 
 
 

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DEAL!! Old Town Condo near Beach
Key West Condo Rental Picture
  • Condo Rental Deals and Discounts $200 off = $1,150 per week
  • bedrooms 2
  • community Truman Annex
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,125 - $2,100 /wk
 
 
 
 
 

9 reviews write a review

Key West's Truman Annex Sunset & Ocean View, Two Bicycles
Key West Condo Rental Picture
  • bedrooms 2
  • community Truman Annex
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,400 - $2,050 /wk
    $6,600 - $7,000 /mth
 
 
 
 
 

62 reviews write a review

Key West's Truman Annex Poolside & Ocean Peek with 2 Bikes
Key West Condo Rental Picture
  • bedrooms 1
  • community Truman Annex
  • rental type Condo
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $1,300 - $2,700 /wk
    $4,400 - $6,600 /mth
 
 
 
 
 

42 reviews write a review

Attitude Key West
Key West Condo Rental Picture
  • bedrooms 2
  • community Truman Annex
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,150 - $2,500 /wk
    $4,500 - $6,660 /mth
 
 
 
 
 

18 reviews write a review

A Touch of Bermuda in Key West
Key West Cottage Rental Picture
  • bedrooms 2
  • community Truman Annex
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,750 - $2,200 /wk
    $5,250 - $6,900 /mth
 
 
 
 
 

7 reviews write a review

Classic Key West Charm
Key West House Rental Picture
  • bedrooms 3
  • community Truman Annex
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $549 - $859 /nt
    $2,789 - $4,289 /wk
    $8,995 - $16,495 /mth
 
 
 
 
 

37 reviews write a review

Ocean Paradise
Key West House Rental Picture
  • bedrooms 3
  • community Truman Annex
  • rental type House
  • sleeps 8
  • baths 4
  • rates (USD) $5,200 - $12,500 /wk
 
 
 
 
 

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Ocean Retreat
Key West Townhome Rental Picture
  • bedrooms 3
  • community Truman Annex
  • rental type Townhome
  • sleeps 5
  • baths
  • rates (USD) $3,200 - $7,500 /wk
 
 
 
 
 

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Truman Annex 2bed/1bath condo in premier downtown location
Key West Condo Rental Picture
  • bedrooms 2
  • community Truman Annex
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,050 - $1,900 /wk
 
 
 
 
 

10 reviews write a review

Prime location! Rare 2BR, 2B in Truman Annex
Key West Condo Rental Picture
  • bedrooms 2
  • community Truman Annex
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $1,400 - $2,400 /wk
    $3,629 - $8,571 /mth
 
 
 
 
 

28 reviews write a review

Mermaid's Dream
Key West Townhome Rental Picture
  • bedrooms 2
  • community Truman Annex
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $1,800 - $2,300 /wk
    $6,700 - $8,500 /mth
 
 
 
 
 

5 reviews write a review

Blue Lagoon
Key West Townhome Rental Picture
  • bedrooms 3
  • community Truman Annex
  • rental type Townhome
  • sleeps 6
  • baths 2
  • rates (USD) $2,500 - $3,500 /wk
 
 
 
 
 

1 reviews write a review

Truman Annex Shipyard with Tropical Garden
Key West Villa Rental Picture
  • bedrooms 2
  • community Truman Annex
  • rental type Villa
  • sleeps 4
  • baths 1
  • rates (USD) $850 - $1,800 /wk
 
 
 
 
 

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Ivory Coast
Key West Townhome Rental Picture
  • bedrooms 2
  • community Truman Annex
  • rental type Townhome
  • sleeps 6
  • baths
  • rates (USD) $1,600 - $2,800 /wk
 
 
 
 
 

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A Paradise Vacation
Key West Condo Rental Picture
  • bedrooms 2
  • community Truman Annex
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $900 - $1,800 /wk
    $3,600 - $5,400 /mth
 
 
 
 
 

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