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The Mermaid's Garden

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

DISCOUNTED RATES for Open Dates this SUMMER!

Even if you're an experienced vacationer, The Mermaid's Garden will hold you in its thrall. As the name promises, the chaperone of this four bedroom, 3 full, 2 half bath Truman Annex estate is a life-sized brass mermaid sculpture...

Admiral's Lane

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

DISCOUNTED RATES for Open Dates this SUMMER!

As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little...

Banana Key

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

DISCOUNTED RATES for Open Dates this SUMMER!

Impressive. Distinctive. Comfortable. The perfect spot for your tropical getaway. This second-story, 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...

La Prive

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

DISCOUNTED RATES for Open Dates this SUMMER!

This is the real deal-a light, airy, well-appointed Key West townhome with two stories, two bedrooms, two full baths, and all the amenities needed to enhance your vacation lifestyle. Not to mention a large private deck and an inviting...

The Courtyard

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

DISCOUNTED RATES for Open Dates this SUMMER!

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...

Ann Street Gardens

Nightly and Weekly Rentals
1 Bedroom
1 Bathroom
Comfortably Sleeps 2
Max Occupancy 3

DISCOUNTED RATES for Open Dates this SUMMER!

The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens offers...

Royal Palm

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

DISCOUNTED RATES for Open Dates this SUMMER!

There's no better way to experience "Island Time"-that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this...

Rose Treehouse

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

DISCOUNTED RATES for Open Dates this SUMMER!

Classic Key West style defines this two-story Bahamian Colonial tucked away on Rose Lane, which runs only one block in its entirety, from Simonton to Duval. Rose Treehouse is a charming King bed, one-full-bath studio that occupies the whole...

Amelia Lane

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

DISCOUNTED SUMMER RATES!

Sun, fun, and relaxation are the mainstays of life on the little island of Key West. To enjoy this tropical haven for yourself, the first step is securing the right accommodations. If a single-family home with three bedrooms, two full baths, a sparkling...

Blackbeard's Treasure

Monthly and Seasonal Rentals
3 Bedrooms
3.5 Bathrooms
Comfortably Sleeps 6
Max Occupancy 8

DISCOUNTED SUMMER RATES!

In addition, save 3% off final negotiated rates if you pay by check.

To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era...

Ultimate Pool Cottage

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

DISCOUNTED SUMMER RATES!

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...