Craig & Cindy Key West Rentals

06/01/2026

"Hi Cindy, Just wanted to write to let you know we enjoyed our time at the house. It was a great location, and had everything we needed. We had family and friends come to visit during the month that worked out great. Our granddaughter asked every morning to go to splash pad at Truman Park. Also Iveta was wonderful. We hope to be able to return in the future. Thank you, Donna"

(Donna stayed at our 4 bedroom 3 bath Truman Annex Porter House with private pool)

05/31/2026

Craig & Cindy Key West Truman Annex Shipyard Condo w/ balcony at Mile Marker 0!
Reservation ID -9Z552R (5 stars out of 5 stars)
Had an awesome time, condo was perfect for 2 couples. Clean and beautifully appointed. Loved the surroundings and the pool. It’s close to all the hubbub, but quiet at the condo. Very central to all that KW has to offer. Would certainly stay here again, indeed our cousins can’t wait to come back. They have been converted to KW now. Margo
Date of arrival - May 9, 2026

(Margo stayed at our Craig & Cindy Key West Truman Annex Shipyard 261, which is a 2 bedroom 2 full bath and can be rented weekly).

www.rentmyparadise.com/SY261.htm

05/26/2026

The 3 bedroom 3 full bath Shipyard Penthouse was booked at $7,700 plus tax last year just for the week of Fantasy Fest...how about paying $6,000 plus tax for 4 weeks 09/27/26-10/25/26 that includes the week of Fantasy Fest!

Click on the picture below for more information!!

Email [email protected] with any interest or questions.

Email from Craig & Cindy Key West Rentals Cancellation Alert!!     Offering Key West Rentals Since 1995! The 3 bedroom 3 full bath Shipyard Penthouse was booked at $7,700 plus tax last year just for t

05/20/2026

Always trying to keep our Key West vacation rentals looking the best they can be...new sleeper sofa and chair were delivered to Truman Annex Shipyard Unit 174 this week.
www.rentmyparadise.com/SY174.htm

05/18/2026

Yes, we can offer weekly rentals in Truman Annex Shipyard...how about spending the week of 4th of July 06/27/26-07/04/26 at one of our 2 bedroom 1 bath Truman Annex Shipyard condos at low season rates!! The Shipyard pool is calling your name!

Normally holidays are a higher rate but we have 2 Shipyard condos left and you can rent either one for the low season rate of $2500/wk plus 12.5% sales tax and NO other fees! Friday 7/03/26 is the day off for this holiday so you can stay the week and only use 4 vacation days from work!

www.rentmyparadise.com/SY265.htm
www.rentmyparadise.com/SY185.htm

Email [email protected] with any interest or questions.

05/12/2026

Craig & Cindy Key West Poolside Coral Hammock Royal Palm House 2 bdrm 2.5 bath
Reservation ID -D6W69B (5 stars out of 5 stars)
"We had a great stay at this house and really enjoyed our time here. The home was clean, comfortable, and very pleasant overall. Since we had a car, the location worked very well for us, and the gated community felt friendly, safe, and convenient. Having parking right by the house was also a big plus. The kids spent hours in the pool, and it was easy to drive into town whenever we wanted to go for a walk or dinner. The furniture was comfortable, the kitchen was very well equipped with dishes and everything we needed, and it was also great to have plenty of towels available, including extras. We also appreciated having a gas grill, which was a nice bonus during our stay. The only suggestion would be to give some attention to the kitchen knives, as some of them were not very convenient to use and could use sharpening. Thank you for your hospitality - we would definitely recommend this home." Andrei
Date of arrival - April 24, 2026

Andrei stayed at our 2 bedroom 2.5 bath poolside Key West Coral Hammock Royal Palm House at Mile Marker 5 across from the Key West Golf Club. This property can be rented nightly (4 night min) or longer and sleeps up to six guests when using the sleeper sofa.
www.rentmyparadise.com/coralhammock.htm

05/10/2026

The Truman Annex Shipyard Pool is scheduled to be renovated during the first 2 weeks of August but the entire month of August is being blocked in case of rain or set backs during the renovation....if using the Shipyard pool is not a requirement for your Key West vacation email [email protected] for a quote on a August weekly rental and we will sharpen that pencil for you! Enjoy Ft. Zachary Beach or South Beach or even Dante's Pool Bar & Restaurant.

Email [email protected] for more information and to get a personal quote.

www.rentmyparadise.com/SY.htm

04/22/2026

CLICK ON THE PICTURE FOR MORE INFO!
Truman Annex Shipyard Condo Unit 106-4 (2 bedroom 1 bath) is an extremely popular first floor condo with a great back patio and just steps to the Shipyard Pool and now being offered for a 28 night stay from 07/11/26-08/08/26 at $4,000 plus 12.5% sales tax and a one-time $300 clean fee. No other fees.

An additional up to two weeks can be added past 08/08/26 at an even more reduced rate of $500/wk plus tax and no other fees (note the Shipyard pool will be closed for the month of August for renovation).

Our two bedroom one bath Shipyard Condos currently rent for $2,500 PER WEEK plus tax so this special 28 night rate reduces that rate down to $1,000/week plus tax or even lower if you add additional weeks at $500/wk plus tax!!

Even if you can't use all 4 weeks this is a great deal!! You are also free to share the weeks with family and friends as they are your 4 weeks to do with what you want. You can even come and go during your 4 week period so that you can make sure all is good at home or attend that one meeting or family event before heading back to paradise! This special is for new bookings only.

Email from Craig & Cindy Key West Rentals Rent 2 weeks and get 2 more weeks free!!     Offering Key West Rentals Since 1995! Offering 28 night July/August 2026 stay as follows: 07/11/26-08/08/26 at o

04/15/2026

How about some good news bad news??

Bad news: The Truman Annex Shipyard Pool will be closed during the month of August as it undergoes a renovation.

Good news: If the pool being closed is not a deal killer (we do have beaches and an ocean an easy walk away), we have some special weekly and monthly rates for August.

Email us at [email protected]

www.rentmyparadise.com