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Historic Hideaways

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Key West, FL
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!

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! 🌺

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!

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.

01/24/2026

🌴 March Rental in Key West – Harbor Place, Truman Annex! 🌴

Escape to paradise this March! Our beautiful 2 bedroom, 2 bathroom condo in the highly sought-after Harbor Place at The Truman Annex is available for the entire month.

✨ Property Highlights:
🏡 Sleeps 4 guests comfortably
🛗 Convenient elevator access
💦 Shared heated pool
📍 Prime location in the exclusive Truman Annex community

💰 Cost for March (excluding taxes & fees): $13,673

This is the perfect spot for a month-long getaway—close to beaches, dining, and all the charm of Old Town Key West.

01/08/2026

✨ Campbell Cottage is BACK — Newly Renovated & Better Than Ever! ✨

Welcome to Campbell Cottage, a beautifully updated 1 bedroom / 1 bathroom condo in one of the best locations in Old Town! 🏝️

🏡 Highlights:
• Entire unit on the first floor
• Freshly renovated with modern updates
• Shared heated pool to enjoy year-round
• Located on charming Fleming Street
• Perfect blend of comfort, convenience, and classic Old Town charm

Whether you’re planning a relaxing getaway or an extended stay, Campbell Cottage puts you right in the heart of it all — walkable, welcoming, and wonderfully refreshed.

12/29/2025

🌴 Escape to Conch Republic Retreat – Your Key West Getaway! 🌴

Relax and unwind at Conch Republic Retreat, a beautiful 2-bedroom, 2-bath vacation rental located in the quiet Meadows of Key West, Florida. Perfect for couples, friends, or a small family looking for comfort and island charm.

✨ What you’ll love:
🏡 Spacious 2BR / 2BA layout
🏊‍♂️ Heated pool for year-round enjoyment
🌺 Peaceful Meadows location, close to everything Key West has to offer

💰 AVAILABLE JAN or MARCH
Total cost: $6,990 + taxes and fees

Sun, palm trees, and island vibes are waiting for you 🌞🌊

12/08/2025

🌴 Key West March Rental — Old Town Oasis! 🌴

Looking for the perfect Key West getaway this March?
Ameila by the Sea is a 3-bedroom, 2-bathroom home in Old Town is available for the full month — and it has everything you need for a relaxing island stay.

✨ Highlights:
• Private heated pool
• Dedicated private parking spot (a rare find in Old Town!)
• Spacious 3BR/2BA layout
• Prime Old Town location — walkable, charming, and close to everything

📅 Available: March
💲 Monthly Rate: $13,732

11/04/2025

🏝 Available MARCH – Luxury 3BR/3BA Home in Truman Annex!

Escape to paradise this March in this beautiful 3-bedroom, 3-bathroom home located in the exclusive Truman Annex community! ☀️

✨ Features include:

Private heated pool 💦

Spacious, beautifully furnished interior

Prime location just steps from Duval Street, dining, and beaches

📅 Available for the month of March
💰 Monthly rental: $18,000

Don’t miss your chance to enjoy Key West living at its finest!

10/13/2025

Did you forget to book your monthly stay this winter? We have a great selection of properties still available for January, February, and March.

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

Website

http://www.HistoricHideaways.com/

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