Craig & Cindy Key West Rentals

09/01/2026

CANCELLATION ALERT FOR THE NOVEMBER POWERBOAT RACES!! This never happens....the powerboat races typically rent one year out. You can now book our Truman Annex Shipyard Condo Unit 202-3 for Monday-Monday 11/02/26-11/09/26. This Shipyard condo is approximately 25% larger than a normal Shipyard condo and has 2 bedrooms and 2 full bathrooms plus a back balcony and front balcony. It is by far our most popular Shipyard Condo. Sleeps up to 5 guests.

The rate of the Powerboat Races is $4400/wk plus 12.5% sales tax and NO other fees. Plus by booking this condo for this year's Powerboats, you get the first right to rebook it for the 2027 Powerboat races as long as you commit by current departure.

Email [email protected] with any questions or interest.

www.rentmyparadise.com/SY2023.htm

08/30/2026

Wanna join our email mailing lists?

Some of our Craig & Cindy Key West Truman Annex vacation rental properties are monthly and we have two email mailing lists.

The first list if for December-April winter monthly rentals and when we have a cancellation we email it out to everyone on this list and it tends to rebook instantly. This is known as LIST WINTER.

The second list is mainly for non-winter monthly rentals (May-November) and we have periodic special deals to fill these months as they are not as popular as the winter months. Some of the specials are crazy good and tend to be less than what a normal 2 week rental rate goes for. If you are on this list you get an email for any monthly open, including winter monthly. This is know as LIST BOTH.

Email [email protected] if you would like to join either list. Just let us know if you want LIST WINTER or LIST BOTH. We can't add you with a FB post or message so please email.

www.rentmyparadise.com

08/30/2026

Craig & Cindy Key West Rentals May 2027 Special: Click on our logo below for more information

Truman Annex Shipyard Condo Unit 102-9 (2 bedroom 1 bath) is an extremely popular second floor condo with a great back and front balcony and now being offered for a 28 night stay from 05/05/27-06/02/27 at an extremely special discounted rate of $5,300 plus 12.5% sales tax and a NO clean fee and no other fees including no booking fees!

The normal rent for these open dates for Shipyard 102-9 is $5,800/wk plus tax and a one-time $300 clean fee but, for a limited time, you can get all four weeks for $5,300 plus tax and NO clean fee for all 4 weeks!

You can come and go during those 4 weeks or have family/friends join you or split the weeks with family or friends as it is YOUR vacation rental for the entire 4 weeks to do with what you want...just no subleasing or exceeding the occupancy limit of four guests at any one time.

This $800 off special rate ends on Friday!

Email from Craig & Cindy Key West Rentals Enjoy 05/05/27-06/02/27 at a super special rate!     Offering Key West Rentals Since 1995! Now Booking 2027!! Offering 28 night May 2027 stay as follows: 05/

08/29/2026

For those staying at our Truman Annex Shipyard Condo Unit 265, we have a couple improvements just delivered and installed today!

First, the dining room table at our recently renovated Shipyard Unit 261 has been such a hit that we bought one for Shipyard 265. The condo can sleep 4 and the table has two seats and a bench...the best part is when the table is not being used, the bench can be pushed under the table so that the table is flush against the wall. This creates a lot of additional space for walking around the condo.

The second improvement is that we eliminated the outdoor mesh/metal bar height dining table and replaced it with strong poly resin so that it lasts longer and looks nicer longer...that salt air reeks havoc on outdoor furniture!

Always looking for ways to improve our Key West vacation rental properties!

The week of 9/19/26-9/26/26 is our last opening in Shipyard 265 until next May. Email [email protected] if interested in a last minute special.

www.rentmyparadise.com/SY265.htm

08/29/2026

We have only a few weeks still open until next May 2027. Who would like a great deal on these weeks: 09/12-09/19, 09/19-09/26, & 09/26-10/03????

We only have one or maybe two Truman Annex Shipyard condos open for those dates and will privately quote a deal to you (or make us an offer) when you email [email protected].

Let's sell out the 2026 season!!! Yes, the newly remodeled Shipyard pool will be open (see pic of the renovated pool below)

Email [email protected] with any interest.

www.rentmyparadise.com/SY.htm

08/28/2026

The newly renovated Truman Annex Shipyard Pool will open next week! Updated photos below.

www.rentmyparadise.com/SY.htm

Email [email protected] for last minute special rates for the weeks of 9/12-19 or 9/19-26 or 9/26-10/03

08/28/2026

"Hello! My friends LOVED the trip, you have new followers! 🎉 Jen"

(Jen stayed at one of our 2 bedroom Truman Annex Shipyard Condos and we have these weeks available at at last minute pricing: 09/12-09/19, 09/19-09/26 & 09/26-10/03)

Email us at [email protected]

www.rentmyparadise.com/SY.htm

08/28/2026

The countdown for the grand opening of the renovated Truman Annex Shipyard Condo pool is on!! Some pressure washing and pool water and then its pool time!

We still have a couple openings for 9/12-9/19, 9/19-9/26, & 9/26-10/03 so email us for last minute special rates at [email protected].

www.rentmyparadise.com/SY.htm

08/27/2026

We have only a few weeks still open until next May 2027. Who would like a great deal on these weeks: 09/12-09/19, 09/19-09/26, 09/26-10/03 & 10/10-10/17????

We only have one or maybe two Truman Annex Shipyard condos open for those dates and will privately quote a deal to you (or make us an offer) when you email [email protected].

Let's sell out the 2026 season!!! Yes, the newly remodeled Shipyard pool will be open.

Email [email protected] with any interest.

www.rentmyparadise.com/SY.htm

08/18/2026

We have 2 openings in Truman Annex Shipyard for the week of 09/12/26-09/19/26 so offering at 50% or more off the regular rate!!

Regular rate of our 2 bedroom 2 full bathroom Truman Annex Shipyard Condo Unit 261 is $2900/wk plus tax so you can book it for $1450/wk plus tax!! See www.rentmyparadise.com/SY261.htm

Our larger than normal 2 bedroom 2 full bathroom Truman Annex Shipyard 202-3 is $3300/wk plus tax BUT how about MORE THAN 50% off or only $1450/wk plus tax!! See www.rentmyparadise.com/SY2023.htm

There are no hidden fees such as cleaning fees or booking fees!

Email [email protected] with any interest or questions!!