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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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Kemp House

Nightly and Weekly Rentals
3 Bedrooms
3 Full - 1 Half Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only...

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Noah's Retreat

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

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 in the most desirable gated...

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The Meadows House

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

If you choose this two-bedroom, two plus bath home for your Key West vacation, you won't be sorry. While Key West has some fourteen neighborhoods, locals identify The Meadows area, your vacation neighborhood, as the most neighborly. Here you'll find houses with a statistically high year-around...

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Banana Key

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

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 floor below, you can enjoy breathtaking views just...

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The Courtyard

Nightly and Weekly Rentals
1 Bedroom
1 Bathroom
Comfortably Sleeps 2
Max Occupancy 2

Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyard unit at Campbell Court. You can step off your front porch and up to the deck of the enticing, heated, residents-only Monaco pool. Steps to the right, you'll find a raised deck with table, chairs,...

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Rose Haven

Nightly and Weekly Rentals
1 Bedroom
1 Bathroom
Comfortably Sleeps 2
Max Occupancy 2

NEW UNIT!

If you want to engage with Key West's past and be perfectly positioned to take advantage of its present, Rose Haven is the ideal vacation residence. The charming, open floor plan studio with queen bed, full bath, private garden with pool, and off-street parking...

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Campbell Eyebrow House

Monthly and Seasonal Rentals
1 Bedroom
2 Bathrooms
Comfortably Sleeps 2
Max Occupancy 2

NEW UNIT!

The uniqueness of Campbell Eyebrow House starts with its Classical Revival "eyebrow" styling, an iconic gable roof creating an awning over top floor windows. The pleasure of Campbell Eyebrow House comes from its ideal location on the island, its verdant garden setting, its lux...

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Conch Republic Retreat

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

This historic conch home, circa 1890, is your dream vacation spot. The welcoming property has been completely renovated and refurbished to contemporary standards and expectations: two bedrooms, two baths, an impressive great room, outstanding pool area, and one of the best geographic locations on the island....

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Ultimate Pool Cottage

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

This three-bedroom, three-full-bath cottage exudes the kind of at-ease ambiance that tells you you're right where you need to be to have the best vacation ever. The cottage is in the Meadows neighborhood on the grounds of an impressive Key West estate. Like something out of...

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Dugan's Den

Monthly and Seasonal Rentals
3 Bedrooms
2 Full - 1 Half Bathrooms
Comfortably Sleeps 6
Max Occupancy 6

NEW UNIT!! Start Up Discounts!!

A tree-lined residential street just blocks from Higgs Beach on the Atlantic. A three bedroom, two and a half bath home with a private dipping pool. And just blocks from three of the island's best restaurants. The whole scene celebrates a...

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Azure Daydream

Monthly and Seasonal Rentals
4 Bedrooms
3 Bathrooms
Comfortably Sleeps 8
Max Occupancy 8

Great bones. Fascinating history. Outstanding location. With four bedrooms, three baths, and a private pool oasis, the home named Azure Daydream is the first-class ticket for your next vacation. More than a century ago, the residence was cut in half and moved by mules to its...

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