Truman Annex Rentals - Key West

Truman Annex is an exclusive gated community on the ocean and in the heart of Old Town. President Harry Truman spent his winters here at his home, famously known as "The Little White House". The grounds within the Truman Annex are meticulously maintained to a very high standard. This quiet community is a unique combination of large private homes, townhomes and condos. Truman Annex is perfect for guests that want a vacation home that is close to Duval Street, yet “away from it all”.

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Conch Casa Grande $726.00 - $3,190.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 5Bedrooms:
    • 7Baths:
    • 8Sleeps:
    24 people are interested in this property!
  • Description:
    3-Story Large Private 5BR/7BA Home in Truman Annex w/ Private Pool. Sleeps 8. Available Weekly & Monthly....Read More

Plantation Tropicale $1,222.10 - $4,400.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 5Bedrooms:
    • 4Baths:
    • 8Sleeps:
    23 people are interested in this property!
  • Description:
    Two Story Private Home + Two Guest Houses & Large Private Pool, 5 Bedrooms, 4 Bathrooms, Available Weekly & Monthly....Read More

2 Cool Fish $220.00 - $1,061.50 Nightly

  • Property Highlights
    Type: Townhouse
    Pets Allowed: No
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 2Bedrooms:
    • 1.5Baths:
    • 4Sleeps:
    19 people are interested in this property!
  • Description:
    2-Story 2BR/1.5BA Townhome in Truman Annex w/ Community Pool Access. Sleeps 4. Available Weekly & Monthly....Read More

Brisa Fresca $495.00 - $2,200.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: No
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 3Bedrooms:
    • 3Baths:
    • 8Sleeps:
    18 people are interested in this property!
  • Description:
    2-Story 3BR/3BA Private Home w/ Private Pool in the Truman Annex, Sleeps 6-8. Available Weekly & Monthly....Read More

Southernmost Palms $220.00 - $1,245.20 Nightly

  • Property Highlights
    Type: Townhouse
    Pets Allowed: No
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 2Bedrooms:
    • 2.5Baths:
    • 6Sleeps:
    18 people are interested in this property!
  • Description:
    3-Story 2BR/2.5BA Townhome in Truman Annex w/ Pool Access. Sleeps 4-6. Available Weekly & Monthly....Read More

Eden @ The Annex $198.00 - $1,225.40 Nightly

  • Property Highlights
    Type: Townhouse
    Pets Allowed: No
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 2Bedrooms:
    • 1.5Baths:
    • 5Sleeps:
    14 people are interested in this property!
  • Description:
    2-Story 2BR/1.5BA Townhome in Truman Annex w/ Community Pool Access. Sleeps 4-5. Available Weekly & Monthly....Read More

Gulfside Vistas $330.00 - $1,650.00 Nightly

  • Property Highlights
    Type: Condominium
    Pets Allowed: No
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 2Bedrooms:
    • 2.5Baths:
    • 6Sleeps:
    21 people are interested in this property!
  • Description:
    3rd Floor 2BR/2.5BA Waterfront Condominium in Truman Annex w/ Waterfront Community Pool Access. Sleeps 4-6. Available W...Read More

The Admiral's Estate $535.70 - $1,375.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: No
    Neighborhood: Truman Annex
    Stay Type: Monthly
    • 5Bedrooms:
    • 5.5Baths:
    • 8Sleeps:
    12 people are interested in this property!
  • Description:
    Historic Truman Annex Home + Guest House & Private Pool, 5 Bedrooms, 5.5 Bathrooms. Available Monthly....Read More

Southernmost Comfort $770.00 - $3,850.00 Nightly

  • Property Highlights
    Type: House
    Pets Allowed: Yes
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 4Bedrooms:
    • 4Baths:
    • 8Sleeps:
    26 people are interested in this property!
  • Description:
    3-Story 4BR/4BA Private Home w/ Private Pool & Fully Fenced Yard in Truman Annex. Sleeps 10. Available Weekly & Monthl...Read More

Windows on the Gulf $588.50 - $1,155.00 Nightly

  • Property Highlights
    Type: Condominium
    Pets Allowed: No
    Neighborhood: Truman Annex
    Stay Type: Weekly, Monthly
    • 2Bedrooms:
    • 2.5Baths:
    • 6Sleeps:
    16 people are interested in this property!
  • Description:
    3rd Floor 2BR/2.5BA Waterfront Condominium in Truman Annex Harbour Place Complex w/ Pool Access. Sleeps 4-6. Available W...Read More