Historic Hideaways

Historic Hideaways Through Historic Hideaways, you can rent and enjoy a Key West Vacation Rental for the same amount of

Through Historic Hideaways, you can rent and enjoy a Key West Vacation Rental for the same amount of money…or less…than it costs to rent a hotel room! Choose from private and historic Key West Vacation Rental homes with private pools, or a cozy cottage, or condominiums or townhomes with a shared pool. Each of the unique and charming Key West Vacation Rentals on our website has a detailed descripti

on, along with great interior and exterior photos, a list of amenities, and a map location. In addition to the convenience of our Online Booking and Real Time availability check, our website can answer your most Frequently Asked Questions. You can also get information on our Rental Rules and Procedures, see copies of our Rental Contracts, and even get some information on Travel Insurance. We think you’ll enjoy looking through some of the beautiful properties that Historic Hideaways is proud to offer!

🌴 JANUARY SPECIAL at The Cat’s Meow! 🐾🌴Escape to paradise at The Cat’s Meow, where your Key West getaway is always worth...
09/05/2026

🌴 JANUARY SPECIAL at The Cat’s Meow! 🐾🌴

Escape to paradise at The Cat’s Meow, where your Key West getaway is always worth purring about! 🐱🌴A beautifully refreshed vacation rental in the highly sought-after Truman Annex in Key West! ☀️🌊

✨ 2 Bedrooms | 3 Bathrooms
✨ Office that can convert to a 3rd bedroom
✨ All-new artwork & furniture
✨ Heated pool & spa
✨ Private parking spot
✨ Located in the heart of the Truman Annex

Whether you’re planning a relaxing winter getaway, a family vacation, or an extended stay in Key West, The Cat’s Meow has everything you need to settle in and enjoy island life. 🏝️

🐾 JANUARY SPECIAL: $18,000 rental fee

🌴 January in Paradise – Monthly Rental Available! 🌴Escape to beautiful Key West this January and enjoy a month in the so...
08/25/2026

🌴 January in Paradise – Monthly Rental Available! 🌴

Escape to beautiful Key West this January and enjoy a month in the sought-after Shipyard community, located within the quiet and exclusive Truman Annex.

🏡 Property Features:
• 2 Bedrooms
• 1 Bathroom
• Shared heated swimming pool
• Private reserved parking space
• Peaceful, gated community just steps from Duval Street, Fort Zachary Taylor Beach, and Key West's best restaurants, shops, and attractions

📅 Available: January
💲 Monthly Rent: $6,000

Whether you're looking to trade winter for sunshine or enjoy an extended stay in one of Key West's most desirable neighborhoods, this condo offers the perfect combination of comfort, convenience, and location.

☀️ January 2027 Available at Noah's Retreat! ☀️Escape to paradise and spend the entire month of January 2027 at Noah's R...
08/06/2026

☀️ January 2027 Available at Noah's Retreat! ☀️

Escape to paradise and spend the entire month of January 2027 at Noah's Retreat, located in the sought-after Truman Annex in Key West, Florida.

🏡 Property Features:
✨ 3 Bedrooms
✨ 2½ Bathrooms
✨ Private Heated Pool
✨ Outdoor Grill
✨ Off-Street Parking

Whether you're escaping the winter or looking for an extended island getaway, Noah's Retreat offers the perfect combination of comfort, privacy, and an unbeatable location just moments from Key West's beaches, dining, shopping, and historic attractions.

📅 Available: January 2027 (Full Month)
💲 Monthly Rental Rate: $16,000

Don't miss your chance to enjoy a month in paradise! 🌴

✨ January Special in Key West! 🌴☀️Escape to paradise this January and enjoy the charm of this beautiful 3-bedroom, 3-bat...
07/15/2026

✨ January Special in Key West! 🌴☀️

Escape to paradise this January and enjoy the charm of this beautiful 3-bedroom, 3-bathroom cottage nestled in the peaceful Meadows neighborhood of Key West.

🏡 Property Features:
✔️ 3 spacious bedrooms & 3 full bathrooms
✔️ Large heated swimming pool
✔️ Quiet, relaxing location just minutes from Key West's attractions
✔️ Perfect for an extended winter getaway with family or friends

🌺 January Special: $10,000 for the month!

Whether you're looking to unwind by the pool, explore Old Town, or soak up the island lifestyle, this cottage offers the perfect home away from home.

🌴 Now Available: Annie's Hideaway! 🌴Looking for the perfect seasonal escape? Annie's Hideaway is now available for month...
06/16/2026

🌴 Now Available: Annie's Hideaway! 🌴

Looking for the perfect seasonal escape? Annie's Hideaway is now available for monthly rentals, including in-season availability!

Nestled in the quiet and desirable Shipyard Condos, this charming retreat offers everything you need for a relaxing stay:

✨ Beautiful shared swimming pool
🚗 Private reserved parking spot
🌿 Peaceful surroundings in a well-maintained community
☀️ Ideal location for enjoying the best of the season

Whether you're planning an extended getaway or a seasonal stay, Annie's Hideaway provides comfort, convenience, and a relaxing atmosphere you'll love.

easonalRental

🌴 Escape to paradise at Pineapple Conch House 🌴Tucked away on a quiet lane in the heart of Old Town Key West, this charm...
05/12/2026

🌴 Escape to paradise at Pineapple Conch House 🌴

Tucked away on a quiet lane in the heart of Old Town Key West, this charming 2 bedroom, 2 bathroom monthly vacation rental getaway is the perfect island retreat. Featuring a recently renovated kitchen, beautifully updated interiors, and your own heated pool, Pineapple Conch House offers the ideal blend of comfort, privacy, and tropical charm. ☀️🏝️

Spend your days exploring Key West, then come home to relax poolside in your private oasis.

✨ 2 Bedrooms
✨ 2 Bathrooms
✨ Recently Renovated Kitchen
✨ Heated Private Pool
✨ Quiet Old Town Location

Your Key West escape is waiting! 🌺

🌴 New Unit: Back to the Island 🌴Escape to your own slice of paradise with Back to the Island, a charming 1 bedroom, 1 ba...
03/24/2026

🌴 New Unit: Back to the Island 🌴

Escape to your own slice of paradise with Back to the Island, a charming 1 bedroom, 1 bath unit now available in our monthly rental program!

✨ Features include:
✔️ Private parking spot
✔️ Access to a shared heated pool
✔️ Comfortable, island-inspired living

🌊 Whether you're looking for a relaxing getaway or a longer stay, this cozy retreat has everything you need.

📅 Open availability — secure your spot today!

🌴 Island Living in Paradise – Book Your Last Minute Key West Getaway! 🌴Escape to the beautiful Truman Annex in sunny Key...
02/13/2026

🌴 Island Living in Paradise – Book Your Last Minute Key West Getaway! 🌴

Escape to the beautiful Truman Annex in sunny Key West, Florida!

This stunning 2-bedroom, 2.5-bath rental offers the perfect blend of comfort and location. Whether you're planning a relaxing retreat or a fun-filled island adventure, this property has everything you need:

✨ 2 Spacious Bedrooms
✨ 2.5 Bathrooms
✨ Shared Heated Pool
✨ Private Parking Spot
✨ Prime Location in Truman Annex

Rental Fee: $6,510 / month + taxes & fees (March or April)

Enjoy tropical breezes, walkable access to beaches, dining, and attractions, and the charm of Old Town living.

📅 Book now while it’s still available! Paradise is calling — don’t miss your chance to stay in one of Key West’s most desirable communities.

Address

1109 Duval Street
Key West, FL
33040

Opening Hours

Monday 9am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 5pm
Thursday 9am - 5pm
Friday 9am - 5pm
Saturday 12pm - 5pm

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