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Key West Vacation Rental Deals

Traveling to Key West soon? We are happy to offer some last-minute vacation Specials on our Weekly and Monthly Key West Vacation Rentals!

Restrictions and limitations on the discounts apply such as, but not limited to: Discounts are only available for new reservations and may not be used retroactively. Holidays and Island Events are generally excluded from discounts. Only Reservations made by Guests through Historic Hideaways directly (via phone or online) are eligible for possible discounts. (Discounts are not available on Reservations made through outside Reservation Agents, Travel Agents or Services.) Discounts may not be available for the period you requested. Any discounts given will be taken off the published normal rates for the property, and may not be combined with other discounts.

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The Mermaid's Garden

Nightly and Weekly Rentals
4 Bedrooms
3 Full - 2 Half Bathrooms
Comfortably Sleeps 8
Max Occupancy 8

DISCOUNTED Monthly stays this summer! See Rate Tab!

(For new 2021 arrival date bookings, only monthly stays are being accepted, except for Fantasy Fest, Christmas, and New Years weeks. 2022 is available for short- and long-term stays, please see minimum night stay information on rate tab.)...

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Admiral's Lane

Nightly and Weekly Rentals
4 Bedrooms
3 Bathrooms
Comfortably Sleeps 8
Max Occupancy 8

DISCOUNTED Monthly stays this summer! See Rate Tab!

(For new 2021 arrival date bookings only monthly stays are being accepted, except for Christmas and New Years weeks. 2022 is available for short- and long-term stays, please see minimum night stay information on rate tab.)

As part...

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Noah's Retreat

Nightly and Weekly Rentals
3 Bedrooms
3 Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

NEW UNIT! START UP SPECIALS!

If you are in a Key West state of mind, you are going to find "Noah's Retreat," a custom-built home, ideal for your vacation rental: 3 bedrooms, 3 baths, dedicated parking, and professional landscaping around a climate-controlled private pool. All this...

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Banana Key

Nightly and Weekly Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 5

DISCOUNTED Monthly stays this summer! See Rate Tab!

Impressive. Distinctive. Comfortable. The perfect spot for your tropical get away. This second floor, two bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one...

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Havana Hideaway

Nightly and Weekly Rentals
2 Bedrooms
2 Full - 1 Half Bathrooms
Comfortably Sleeps 4
Max Occupancy 5

DISCOUNTED Monthly stays this summer! See Rate Tab!

Call it casual luxury. Call it tropical chic. This two bedroom/two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area below, you can enjoy breathtaking views just...

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La Buena Vida

Monthly and Seasonal Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

SEPTEMBER STILL AVAILABLE!

Quintessentially Key West in terms of location and architecture, La Buena Vida won't disappoint as your next vacation rental. In fact, you'll be delighted. The location is Old Town's Bahama Village, an artsy and cultural quarter offering some of the best attractions and...

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La Isla Vita

Monthly and Seasonal Rentals
2 Bedrooms
2 Full - 1 Half Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

DISCOUNTED Monthly stays this summer! See Rate Tab!

Here's how to craft a perfect vacation. First, buy tickets to fabulous Key West. Second, shop for flipflops and shorts. Third, reserve La Isla Vita for your stay! This two-story, two-bedroom, three-bath home offers what you'd expect and...

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Amelia by the Sea

Monthly and Seasonal Rentals
3 Bedrooms
2 Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

SEPTEMBER/OCTOBER STILL AVAILABLE!

This superbly designed three-bedroom, two-bath conch house named "Amelia By the Sea" is located, as the name suggests, near sandy beaches and the wildly beautiful Atlantic Ocean. It's part of Bahama Village, a 16-block historic subsection of Old Town Key West that hosts...

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Anchor's Away

Monthly and Seasonal Rentals
3 Bedrooms
2 Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

NEW UNIT! SUMMER SPECIALS!

Need a refresher course in relaxation? Find it behind the brass seahorse knocker on the front door of this three-bedroom, two-full-bath conch cottage in Old Town Key West. Recently restored and updated to include amenities such as a heated pool with rainforest...

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