Craig & Cindy Key West Rentals

09/10/2026

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

Truman Annex Shipyard Condo Unit 160 (2 bedrooms 2 full bathrooms) is one of our most popular condos....this first floor condo with 2 bedrooms & 2 full bathrooms is now being offered for a 28 night stay from 06/19/27-07/17/27. The posted rate is $5600 plus 12.5% sales tax and a one time $400 clean fee....BUT how about a special rate down to $5,400 plus tax for all 4 weeks and NO OTHER FEES including no cleaning or booking fees! This special rate will end Monday so take advantage of it now. This special includes 4th of July week at no additional charge!

You get all 4 weeks at a first floor 2 bedroom 2 full bathroom for $600 off the regular rate or just $5400 plus 12.5% sales tax and NO other fees! These are your 4 weeks to do with as you want so you can share with family and friends or just come and go over the 4 weeks...even if you cannot use all 4 weeks the rate is too good to pass up!! This special is for a limited time only.

For more information email [email protected]

Email from Craig & Cindy Key West Rentals This rate is one of the lowest we have ever offered!!     Offering Key West Rentals Since 1995! Offering 28 nights at a special rate as follows: 06/19/27-07/

09/09/2026

Hi Cindy and Craig, Thank you all so much for the amazing property at 30 coral hammock. When you all say the only thing you need to bring is your clothes and toothbrush you truly mean that. You all truly think of every single detail and it’s very much appreciated. We have found our new little hideaway from the busy downtown area. Thanks, Mike

(Mike stayed in our 2 bedroom 2.5 bath poolside Coral Hammock Royal Palm House at Mile Marker 5, currently available for nightly rentals)

www.rentmyparadise.com/coralhammock.htm

09/09/2026

Hi Cindy, We had a wonderful time; we really enjoyed the condo and the large deck.
Iveta was a pleasure to work with as always and everything was perfect! I have to admit it's been difficult adjusting to being back home after spending a month in Key West, LOL! Until next time, Robert and Michelle

(Robert & Michelle stayed at our Truman Annex Shipyard Unit 199, 2 bedrooms 1 bath and next open the month of July 2027)

www.rentmyparadise.com/SY199.htm

09/09/2026

"Hi there. We had a wonderful visit at your property Shipyard #261. We were so impressed with how clean the unit was. Your staff did a fantastic job. We have stayed many places over the 35+ years and by far this is the cleanest. We look forward to more times at your units. Bill and Michele"

(Bill & Michele stayed at our Truman Annex Shipyard 261, 2 bedrooms 2 full bathrooms, and next open the week of 05/29/27-06/05/27 at $2900/wk plus 12.5% sales tax and NO other fees)

www.rentmyparadise.com/SY261.htm

09/07/2026

Hi - this is our fifth different rental location we’ve stayed in of yours . We love them all, but this morning my husband said, “This one is perfect. Why can’t we just live in this one. Bedroom and bath on first floor. Or it can be your office Parking right in front. Plenty of room and privacy for guests upstairs. Just right pool that wouldn’t require a lot of maintenance. Perfect location. Great location. Can’t find anything more we’d need.” I agree with him. Thank you. We’re completely spoiled.
Pam

(Pam is staying at our 4 bedroom 3 bath Truman Annex Porter House with private pool, next open 07/10/27-08/07/27)

www.rentmyparadise.com/502.htm

09/06/2026

Craig & Cindy Key West Rentals: Click on the logo for more information! Save $300 by booking now!

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 06/02/27-06/30/27 at an extremely special discounted rate of $5,000 plus 12.5% sales tax and a NO clean fee and no other fees including no booking fees!

The already super low 4 week rent for these open dates for Shipyard 102-9 is $5,000/wk plus tax and a one-time $300 clean fee but, for a limited time, you can get all four weeks for $5,000 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.

Email from Craig & Cindy Key West Rentals Enjoy 06/02/27-06/30/27 at a super special rate!     Offering Key West Rentals Since 1995! Now Booking 2027!! Offering 28 night June 2027 stay as follows: 06

09/05/2026

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

Truman Annex Shipyard Condo Unit 160 (2 bedrooms 2 full bathrooms) is one of our most popular condos....this first floor condo with 2 bedrooms & 2 full bathrooms is now being offered for a 28 night stay from 05/22/27-06/19/27. The posted rate is $5800 plus 12.5% sales tax and a one time $400 clean fee....BUT how about a special rate down to $5,600 plus tax for all 4 weeks and NO OTHER FEES including no cleaning or booking fees! This special rate will end Friday so take advantage of it now.

You get all 4 weeks at a first floor 2 bedroom 2 full bathroom for $600 off the regular rate or just $5600 plus 12.5% sales tax and NO other fees! These are your 4 weeks to do with as you want so you can share with family and friends or just come and go over the 4 weeks...even if you cannot use all 4 weeks the rate is too good to pass up!! This special is for a limited time only.

Email [email protected] with any interest or questions.

Email from Craig & Cindy Key West Rentals This rate is one of the lowest we have ever offered!!     Offering Key West Rentals Since 1995! Offering 28 nights at a special rate as follows: 05/22/27-06/

09/01/2026

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

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/