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  • (305) 294-7358
Key West Time
June 16th
6:04am · 85°F

Tropical Chill ~ Weekly Rental

2BR 2BA ~ Weekly Rental
Sleeps 4

If you’re looking for a place to chill-out in the tropical warmth of Key West, this cottage-style flat is a wonderful place to relax and take a breather from everyday life. Situated in the elegant gated condominium community of Truman Annex, the location sets the stage for down-time and fun! Here you’re nicely nestled in secure luxurious surroundings of the ‘Shipyard’ complex, yet just outside the gates are all the home town conveniences plus all the Old Town fun.

Gates on one side of the complex lead to Downtown Old Town Key West, with its international restaurants, famous bars, restaurants, theaters, and Mallory Square. Gates on the other side lead to Fort Zachary State Park with Caribbean Beaches, and the new Truman Waterfront recreational complex. Truman waterfront is an expansive new waterfront 'green space,' with a wonderful waterpark playground and impressive concert amphitheater. All the best features of Old Town Key West are just out your door from this cottage style flat we call Tropical Chill.

Recently purchased, the new owners completely renovated and re-decorated this flat to give it a fresh look!


This flat is easily accessed via an interior switch-back stairway leading from the front of the building. Situated near the 2nd floor, a fabulous feature is the spacious covered balcony with a birds-eye view of the swimming pool gardens and pool cabana below. Both the living room and the master bedroom have doors connecting to the balcony, where a café dining table and chairs provide a place to sit outside and take-in the scene below.

The Key West classic 2-bedroom layout, with living/dining/kitchen on one side, and the bedrooms and bathrooms on the other makes for a comfortable and convenient living space. Situated on the balcony side of the flat, the master bedroom provides a king size bed, and an en-suite bathroom with a double sink vanity and a shower.

The guest bedroom is on the opposite side off the kitchen. This bedroom provides a king-size bed. A second bathroom is steps from the bedroom, with the bedroom and bathroom doors next to each other. The second bathroom provides a single vanity sink, and a bathtub with in-tub shower.

Furnishings are traditional tropical with light wood, wicker and bentwood cane. Walls painted Caribbean teal, coral, sunny yellow, and key-lime green, keep the interior light and happy. The fully equipped U-shape kitchen provides plenty of counter space for the cook to whip up a meal. 

Grounds: The picture-perfect pool gardens with cabana is just downstairs and is reserved for the Shipyard complex. The pool garden and surrounding lush landscaping is kept immaculate. Chaise lounge chairs, sun umbrellas, and awnings are staged for sunning or resting in the shade.

Bedding Summary:

  • Master Suite - 1 King size bed
  • Guest Suite - 1 King size bed
  • Living room - Queen sleeper sofa

Amenities: Fully equipped kitchen. Central A/C, washer / dryer, flat screen TV's in the great room and each bedroom, Wi-Fi, stereo. Heated resort-style swimming pool, perfectly manicured tropical landscaping, private porch, fully fenced, Linens and towels are provided. 

Activities: Fort Zachary Taylor State Park Beach and the Truman Waterfront with children’s water-park and the Key West amphitheater are a short walk away. Downtown Old Town Key West, and Duval Street are a five-minute walk away. Walk to restaurants, night life, shopping, museums, sailing, boating, snorkeling, diving, beach, theater, and family activities. Famous Sunset Celebration at Mallory Square is a fifteen-minute walk away.

Area: Down Town Key West. Located in Truman Annex Just steps away from all Key West Old Town features. A unique feature of the Shipyard complex, is that it is complete fenced and gated for added security. Grounds throughout the Truman Annex neighborhood are exquisitely landscaped and manicured to picturesque perfection, providing a story-book neighborhood to walk and bicycle. White picket fences, freshly clipped hedges, green grounds and fountains create an impressive back drop for your stroll around this unique neighborhood.

Parking:  A convenient feature of this residence is a free private designated parking space which is located about 200 feet from the front door. If you do bring a car, plan to park and forget about it. Parking is limited and expensive throughout Old Town. Enjoy walking or biking everywhere you'll see more that way.  

Restrictions: Smoke Free House. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian. The property is in a private gated residential complex in a secured neighborhood, and is not suitable for staging loud parties. 

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special rates available


June 14 - June 30
Weekly $2100

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Dates Weekly Nightly Terms
Jun 10, 2024 - Aug 11, 2024 $2600$500.007 night minimum
Aug 12, 2024 - Oct 2, 2024 $2230$430.007 night minimum
Oct 3, 2024 - Oct 17, 2024 $2600$500.007 night minimum
Oct 18, 2024 - Oct 27, 2024 $3925$755.007 night minimum
Oct 28, 2024 - Nov 3, 2024 $2330$450.007 night minimum
Nov 4, 2024 - Nov 11, 2024 $2600$500.007 night minimum
Nov 12, 2024 - Nov 21, 2024 $2330$450.007 night minimum
Nov 22, 2024 - Nov 30, 2024 $2600$500.007 night minimum
Dec 1, 2024 - Dec 18, 2024 $2230$430.007 night minimum
Dec 19, 2024 - Dec 27, 2024 $3440$660.007 night minimum
Dec 28, 2024 - Jan 3, 2025 $4140$800.007 night minimum
Jan 4, 2025 - Jan 10, 2025 $2985$570.007 night minimum
Jan 11, 2025 - Jan 17, 2025 $2985$570.007 night minimum - Sat/Sat Only
Jan 18, 2025 - Jan 31, 2025 $2985$570.007 night minimum
Feb 1, 2025 - Feb 14, 2025 $3560$680.007 night minimum
Feb 15, 2025 - Feb 21, 2025 $3560$680.007 night minimum
Feb 22, 2025 - Apr 11, 2025 $3560$680.007 night minimum
Apr 12, 2025 - May 28, 2025 $2600$500.007 night minimum
May 29, 2025 - Jun 8, 2025 $2330$450.007 night minimum
Jun 9, 2025 - Aug 10, 2025 $2330$450.007 night minimum
Aug 11, 2025 - Oct 1, 2025 $2230$430.007 night minimum
Oct 2, 2025 - Oct 16, 2025 $2330$450.007 night minimum
Oct 17, 2025 - Oct 25, 2025 $3925$755.007 night minimum
Oct 26, 2025 - Nov 2, 2025 $2330$450.007 night minimum
Nov 3, 2025 - Nov 10, 2025 $2600$500.007 night minimum
Nov 11, 2025 - Nov 20, 2025 $2330$450.007 night minimum
Nov 21, 2025 - Nov 29, 2025 $2330$450.007 night minimum
Nov 30, 2025 - Dec 19, 2025 $2230$430.007 night minimum
Dec 20, 2025 - Dec 27, 2025 $3560$685.007 night minimum
Dec 28, 2025 - Jan 5, 2026 $4260$825.007 night minimum

Additional Notes:

  • High Season generally requires a 7 night minimum stay. Shorter stays of 3 - 5 nights may be available within 60 days of your arrival date or in special situations. Certain dates may not be available if they minimize optimal booking for the property's reservation calendar. Please contact us to inquire about stays less than 7 nights.
  • Shoulder and Low Season is a 3 - 5 night minimum available on reservations made within 60 days of arrival May through mid-August. From mid-August through mid-December, 3 - 5 night minimum stays are available any time.
  • Short Stays are available if there are open nights that are less than the minimum stay, shorter stays may be possible depending on the property. Please contact us to inquire.
  • Holiday, Festival, and Event Rates are 20% to 25% higher. These include, but are not limited to: Fantasy Fest, Thanksgiving, Christmas, New Years, Power Boat Races, Mini-Lobster Season, Labor Day, Parrot Heads Meeting of the Mind, 4th of July, Easter. A 7 night minimum stay is required for most major holidays, festivals, and events.

Rates and Terms are subject to change without notice. Above rates do not include taxes and fees. Click here for more details on additional fees. Please contact us for specific pricing and to confirm rates. Rates in US Funds. (305) 294-7358 Ext 1 -

Apply here for Travel Guard Trip Cancellation and Interruption Insurance.

VHKW offers promotional specials for purchasing trip insurance for stays between Aug 10 and Oct 20. Please call for more details.

  • Master Suite - 1 King size bed
  • Guest Suite - 2 Twins (Can be converted to a King)
  • Living room - Queen sleeper sofa
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