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  • (305) 294-7358
Key West Time
October 3rd
7:45am · 81°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. 

Book Direct For The Best Price Guaranteed

special rates available


Sept 29- Oct 10
Oct 31 - Nov 16

Weekly $2100

view all specials

Dates Weekly Nightly Terms
Oct 1, 2023 - Oct 20, 2023 $2600$501.507 night minimum
Oct 21, 2023 - Oct 30, 2023 $3925$673.007 night minimum
Oct 31, 2023 - Nov 5, 2023 $2330$449.507 night minimum
Nov 6, 2023 - Nov 13, 2023 $2600$464.507 night minimum
Nov 14, 2023 - Nov 18, 2023 $2330$449.507 night minimum
Nov 19, 2023 - Nov 27, 2023 $2600$464.507 night minimum
Nov 28, 2023 - Dec 16, 2023 $2230$494.007 night minimum
Dec 17, 2023 - Dec 25, 2023 $3260$582.257 night minimum
Dec 26, 2023 - Jan 2, 2024 $3925$673.007 night minimum
Jan 3, 2024 - Jan 12, 2024 $2875$550.007 night minimum
Jan 13, 2024 - Jan 19, 2024 $2875$550.007 night minimum
Jan 20, 2024 - Feb 2, 2024 $2875$550.007 night minimum
Feb 3, 2024 - Feb 16, 2024 $3440$660.007 night minimum
Feb 17, 2024 - Feb 23, 2024 $3440$660.007 night minimum
Feb 24, 2024 - Apr 12, 2024 $3440$660.007 night minimum
Apr 13, 2024 - May 29, 2024 $2600$500.007 night minimum
May 30, 2024 - Jun 9, 2024 $2330$450.007 night minimum
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 8, 2024 $2330$450.007 night minimum
Nov 9, 2024 - Nov 16, 2024 $2600$500.007 night minimum
Nov 17, 2024 - Nov 21, 2024 $2330$450.007 night minimum
Nov 22, 2024 - Nov 30, 2024 $2600$500.007 night minimum
Dec 1, 2024 - Dec 16, 2024 $2230$430.007 night minimum
Dec 17, 2024 - Dec 25, 2024 $3440$660.007 night minimum
Dec 26, 2024 - Jan 2, 2025 $4140$800.007 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 - 1 King size bed
  • Living room - Queen sleeper sofa
Apr 17, 2023,
We had a great time. Our condo was clean and perfectly located . We loved the pool.

Mar 08, 2023,
It was great as usual! It was a little frustrating that I could not use my master bed room shower for the first 2 weeks of my stay!!

Jan 04, 2023,
Super responsive and friendly

Dec 21, 2022,
Easy to book, easy to pay. Nice condo with all of the essentials we needed. Great location and quiet. 😊 I thought your fees were a little high but not ridiculous and better than most vacation booking companies. 😊

Nov 30, 2022,
Great condo complex! Nice pool area, really close to everything!

Oct 28, 2022,
Great unit! Many small touches that make very convenient. You can tell it is loved by the family that owns it. Love the shipyard. Not our first stay. Hope to visit again !

May 06, 2022,
We had a great time staying in Key West at Tropical Chill!! The place was really clean, the location was perfect, and it had everything we needed!! Thank you for ease and comfort of knowing we had a great place with no issues with booking, checking in and out, and with our place itself! We'll definitely be a repeat costumer! Thank you again!!!

Feb 11, 2022,
Great place!

Jan 05, 2022,
Entire process was smooth! We were very happy with our condo, location and pool.

Oct 27, 2021,
Excellent experience, the place was perfect for our vacation. Hope to stay with you again someday.

Jun 21, 2021,
We had a great time at Tropical Chill Condo. The location was perfect, I would have wished for a few more basic cooking items in the pantry. Overall, we would definitely recommend staying here.

Jun 10, 2021,
Thanks for rental info on Tropical chill. As advertised and better . Loved the condo. All questions were answered and all worked out as planned. Called concierge and booked a tiki bar raft too. Thanks for that service too. Towels provided and all kitchen /bedding items we needed. Thanks.

May 13, 2021,
We had an amazing stay with VHKW in Tropical Chill. Our condo was 2BR/2BA. It was so spacious and close to all the shopping and great restaurants, most in walking distance. The patio outside which overlooked the pool was so relaxing. There were no noisy neighbors & I felt very safe. If you go, don’t forget to visit Ft. Zachary, right behind the complex. Enjoy!

May 10, 2021,
Great vacation. Tropical Chill was a great condo with a nice pool and super location. We wee able to walk and bike everywhere we wanted to go.

Jan 23, 2021,
Excellent experience. We hope to return once the virus situation is more clarified.

Nov 10, 2020,
You all were nice to talk with while finding and subsequently canceling the rental in Key West. Only wish times weren't so crazy where I could of enjoyed Key West.

Oct 23, 2020,
We stayed at Tropical Chill, the condo was beautiful, just as pictures on web site. Pool and grounds also were very nice and peaceful. VHKW staff always available and helpful. We would definitely use their services again.

Apr 07, 2020,
I recently stayed at VHKW's Tropical Chill property on my annual girlfriend getaway. It was perfect in every way, and the whole experience from reservation to checkout was very easy. The unit was lovely and very well appointed. We enjoyed the view of the pool and grounds from the balcony and hearing the many birds singing (and crowing!) nearby. This is the second property I've rented through VHKW (the other was Tropical Tranquility- HIGHLY recommend!) and I would absolutely rent from them again.

Mar 25, 2020,
People very nice to work with, and made planning upcoming trip very easy.

Dec 24, 2019,
Paige and Teo were wonderful to work with. The property was lovely.

Nov 22, 2019,
This condo had everything you could possibly need! It was very clean and well stocked. I would definitely recommend it ❀️

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