Craig & Cindy Key West Rentals

Craig & Cindy Key West Rentals

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Hi! We are Craig & Cindy and we have been offering vacation rentals in Key West since 1995! www.rentmyparadise.com

Photos from Craig & Cindy Key West Rentals's post 10/03/2026

Truman Annex Shipyard Condo Unit 185 is finishing its first year as one of our weekly vacation rental and it was time for some refreshing to keep it worthy of a Craig & Cindy Key West Rentals property. At the direction and work of Randy & Cindy, we just replaced the TV's with larger and smarter ones, changed out blinds where needed, repainted the entire condo interior (including in the closets) in a lighter color, replaced some interior baseboards and exterior decking, repainted the outside deck and updated the landscaping. She is looking great! Who is ready for a Key West vacation with Craig & Cindy Key West Rentals! Next opening for our 2 bedroom 1 bath Truman Annex Shipyard Condo Unit 185 is 6/05/27-6/12/27 at $2500/wk plus 12.5% sales tax and NO other fees.

www.rentmyparadise.com/SY185.htm

Photos from Craig & Cindy Key West Rentals's post 10/03/2026

Making sure your vacation is the best it can be. Upkeep is important. This morning we put a new writing desk and chair in the master bedroom of the Truman Annex Porter House and replaced blinds in the bedrooms. Who is ready for a Key West vacation with Craig & Cindy Key West Rentals!

www.rentmyparadise.com

Key West news-4 weeks this summer at a great rate! 10/02/2026

Craig & Cindy Key West Rentals: Click on the Logo for more information!

Truman Annex Shipyard Condo Unit 174 (2 bedroom 1 bath) is an extremely popular first floor condo with a great back deck (and outdoor gas grill) and now being offered 08/07/27-09/04/27

The regular weekly rate during summer is $2,500/wk plus 12.5% sales tax. HOWEVER if you book by Monday you can claim a special rate of only $4,000 plus 12.5% sales tax for all 4 weeks and we will WAIVE the $300 clean fee!!

Yes, that's $4,000 plus 12.5% sales tax NO clean fee for all 4 weeks. Also no other fees such as booking fees!

All 4 weeks are available for your use and you are more than welcomed to invite family and friends to enjoy the condo. It is your 4 weeks to use as you want...just don't exceed the occupancy limit of 4 guests at any one time.

See www.rentmyparadise.com/SY174.htm

https://conta.cc/4y2pgZs

Key West news-4 weeks this summer at a great rate! Email from Craig & Cindy Key West Rentals 08/07/27-09/04/27 at our lowest rate offered!     Offering Key West Rentals Since 1995! Special Rate Alert!! This Special ends at any time! Offering 28 nights

Craig & Cindy Truman Annex Porter House 10/01/2026

"Hi! We are heading home today. We’re moving into our new home in Fort Lauderdale, so left a bit early. Thought the girls might want (extra time) to clean. I cannot tell you how much we loved our stay. I’ve already told you that the house is perfect. If you have any cancellations for the Porter House we’d love to fill the spot. Thank you again!!!! Pam"

(Pam stayed at our 4 bedroom 3 bath Truman Annex Porter House with private pool, next open 07/10/27-08/07/27 which includes mini lobster season)

Craig & Cindy Truman Annex Porter House

Craig & Cindy Truman Annex Shipyard Unit 265 09/26/2026

"Craig and Cindy,
We checked out of Shipyard 265 this morning. This unit is our favorite so far!! Everything was fantastic and we had the BEST week! Thank you as always for sharing your piece of paradise with us! We will be returning. Hopefully sooner than later!! Happy Fall!"
Jen

(Jen stayed at our 2 bedroom 1 bath Truman Annex Shipyard Condo Unit 265, which is a popular second floor end unit with two balconies and next open 06/05/27-06/12/27 at $2500/wk plus 12.5% sales tax and NO other fees, including no cleaning fee).

Craig & Cindy Truman Annex Shipyard Unit 265

Photos from Craig & Cindy Key West Rentals's post 09/24/2026

"Thanks, Cindy. We loved your place and the location. We will be back!" Laura

(Laura stayed at our 2 bedroom 2 full bathroom Truman Annex Shipyard Condo Unit 202-3, which is next open 6/05/26-6/12/26 at $3300/wk plus 12.5% sales tax and NO other fees).

www.rentmyparadise.com/SY2023.htm

Photos from Craig & Cindy Key West Rentals's post 09/23/2026

UPDATE: THIS HAS BEEN BOOKED BUT THANKS FOR YOUR INTEREST IN OUR Craig & Cindy Key West Rentals!

Cancellation Alert for Fantasy Fest week!

The guests that booked Truman Annex Shipyard Unit 261 (2 bedrooms 2 baths) for 10/17/26-10/26/26 has had to cancel. The regular rate for Fantasy Fest week is $4800/week plus 12.5% sales tax but we will consider any last minute offers for a minimum of 7 nights up to a maximum of 9 nights.

See www.rentmyparadise.com/SY261.htm

Email [email protected] with any interest or questions.

09/21/2026

Yes, we still have 4 Truman Annex Shipyard Condos that can be rented weekly and below are the next openings for each of them. For each rate quote just add 12.5% sales tax. NO other fees such as cleaning fees or booking fees. As only 12 of the 183 Shipyard condos can continue to be rented weekly, we will sell out quickly.

Truman Annex Shipyard Condo Unit 185 (2 bedroom 1 bath first floor condo): 06/05/27-06/12/27 at $2500/wk plus tax. See www.rentmyparadise.com/SY185.htm

Truman Annex Shipyard Condo Unit 265 (2 bedroom 1 bath second floor end unit with more widows and privacy and 2 balconies): 06/05/27-06/12/27 at $2500/wk plus tax. See www.rentmyparadise.com/SY265.htm

Truman Annex Shipyard Condo Unit 261 (2 bedroom 2 full bathroom second floor condo just remodeled): 06/05/27-06/12/27 at $2900/wk plus tax. See www.rentmyparadise.com/SY261.htm

Truman Annex Shipyard Condo Unit 202-3 (2 bedroom 2 full bathroom, second floor with two balconies and approx 25% larger than a normal Shipyard condo): 06/05/27-06/12/27 at $3300/wk plus tax. See www.rentmyparadise.com/SY2023.htm

Email [email protected] with any interest or questions.

09/21/2026

Sitting at our favorite bar in New Orleans on a Sunday night!

Key West-July/Aug 4 weeks including Mini Lobster at Truman Annex Foundry Townhouse! 09/19/2026

Craig & Cindy Key West Rentals: Click on the logo for more information!!

Truman Annex Foundry Townhouse (2 bedroom 2.5 bath, sleeps up to six guests when using the sleeper sofa) is an extremely popular three story townhouse with a great front deck and also a front balcony off one of the bedrooms. The first floor is the living room, dining room, kitchen and 1/2 bath. The second and third floors each contain a private bedroom and attached en-suite full bathroom. There is also a washer & dryer, outdoor gas grill, and all the amenities of home!

The regular rate for a 28 night stay from 07/17/27-08/14/27 is $5,950 plus 12.5% sales tax and a one-time $300 clean fee. HOWEVER if you book before next Friday we are offering an extremely special discounted total rate of $5,750 plus 12.5% sales tax and NO clean fee and no other fees including no booking fees! This $500 off special rate can end at any time.

These 4 weeks include the super popular Mini Lobster week at no additional charge!

Email [email protected] with any interest or questions.

www.rentmyparadise.com/F14.htm

https://conta.cc/4rnWWPy

Key West-July/Aug 4 weeks including Mini Lobster at Truman Annex Foundry Townhouse! Email from Craig & Cindy Key West Rentals Enjoy 4 weeks for less than the weekly rate for 2 weeks!     Offering Key West Rentals Since 1995! Rare opening for a Truman Annex Foundry Townhouse with 2 be

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