Southernmost Sanctuary

Southernmost Sanctuary is a beautiful two bedroom, one bath condominium has recently been updated located in the Shipyard Condominiums in the award winning Truman Annex. The charming master bedroom has a queen bed, flat screen tv and plenty of storage.

Price: Starting at $2,345.00 weekly.

Sweet’s Spot at the Harbour Place

This breathtaking penthouse enjoys open water views from all rooms. Sweeping and luxurious with three bedrooms, four and one half baths and plenty of room to spread out and relax. The master suite has stunning views of the Key West sunsets, features a large walk in closet and a charming bathroom. The handsome office/study enjoys a front row seat of the community pool complex below and the inner mole pier! Each bedroom includes a bathroom.

Price: Starting at $4,998.00 weekly.

A Palm Oasis

This very quiet private location, in the historic Mills Place complex, enjoys a very large refreshing pool with both sunny and shady areas. Also included here is an assigned off-street parking space and several bike racks. This charming two bedroom, two and one half bath townhome has recently been updated and added to our rental program!

Price: Starting at $3,899.00 weekly.

Our Banana Republic

This historic gem in Old Town Key West has recently been completely renovated TOP to BOTTOM! As you enter the front gate walking over brick pathways, you are immediately drawn in by the charm of this beauty which features a lovely porch swing and sitting area. You will not find a better place to live while enjoying everything that Key West has to offer!!! See you soon!

Price: Starting at $3,255.00 weekly.

Sea-shells at Harbour Place

A luxury, ocean front, 3 bedroom, (king in master, twins or twins as king in guest bedroom, sleeper sofa in office) 2.5 bath condo at Harbour Place in the award winning Truman Annex in Old Town Key West. This first-floor condominium features spectacular Key West sunsets, a large deck just above the pool with plenty of lounge area.

Price Starting at $5747.00 weekly

Latitude Adjustment

This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been recently renovated to accommodate an individual couple, family, or vacationing couples that each desires the privacy of their own bedroom suite with full, private baths. This two bedroom, two and one half unit will comfortably sleep up to six is located in the beautiful community of Truman Annex.

Price Starting at $3,000.00 weekly


‘Manatee’ is a beautiful two bedroom, one bath, 1st floor condominium located within the prestigious gated community of ‘Truman Annex’ in Key West’s ‘Old Town’ area. This home has the advantage of a beautiful outside deck overlooking foliage and the pool area. The deck is accessed by a set of French Doors and comes complete with a table & chairs for comfortable outside living that makes Key West so desirable.

Price: Starting at $2,450.00 weekly.

It’s A Salt Life After All

This 2 bedroom 2 bath town-home is just what you are looking for. *****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONLY.***** | The amenities include two community pools, a gym, and a butterfly garden.  This community is located on Stock Island which is five miles from Duval Street and all of the Historic Old Town Key West attractions.

Price: Starting at $816.69 weekly.

Isle Be Back

Thank you for considering Isle Be Back for your escape to the tropical paradise of Key West. Here you will enjoy the lap of luxury with this two-bed & two-bath upstairs unit located in the highly desirable Shipyard section of the Truman Annex. Paradise awaits you just two blocks from the sights and sounds of Duval Street.

Price Starting at $2,350.00 weekly

Dancing Palms

Walk into the bright and airy first floor living area with an open floor plan, well-appointed kitchen, one full bathroom, huge dining table and lovely sitting area which opens to the partially covered back patio for the Florida outdoor living experience.

Price: Starting at $2,550.00 weekly.


The ‘Coconut’ as it’s so lovingly referred to is the perfect Pied A Terre for your vacation in the Florida Keys. Open living area with great front and back porches. There is a loft bedroom has a queen bed and the living-room has a queen Murphy bed. Built in late 1800’s it’s steeping with history and charm.

Price Starting at $723.31 weekly


Stepping through the white picket gate into this town home located in the gated Truman Annex community, in the heart of Old Town, you will find old-world charm along with high-end amenities. The open main floor has a fully equipped kitchen, a large sectional-sleeper and a 65 inch television. Upstairs are 2 en suites each with well appointed recently updated full bathroom.

Price: Starting at $2,550.00 weekly.

Afternoon Delight

This amazing 2 bedroom/2 bath condo has one of the best views in Key West. Located in the historic Mills Place in Truman Annex. You have the views of the Gulf and ships that pass by the windows as they arrive and leave port. The apartment has two balconies. You can see the sunset over the ocean every evening.
Condo association requires 7 night minimum and no pets.

Price: Starting at $5,750.00 weekly.

Adrift in Key West

Stunning, Modern Nautical-themed 2 bedroom, 1 bathroom ground floor condo in the Truman Annex Shipyard Complex completely transformed. Fully appointed, sleek kitchen with all new appliances (oven/microwave combo unit), lighted kitchen drawers, washer/dryer in unit, comfortable private back patio oasis with comfortable furniture for lounging and entertaining. and outdoor Shower. End unit, bike rack right outside, gated community.

Price Starting at $2,250.00 weekly

Low Tide

A Low Tide is a charming first floor end unit in the Shipyard Condominiums in the award wining gated community of the Truman Annex. | This property has recently been refreshed featuring new appliances, tvs, bedding, etc.! | It is is located 2 blocks from Duval Street and all of the Old Town Key West attractions and includes off street parking for one vehicle. | Enjoy both the front and back rear deck has outdoor dining and lounging all year long. | The refreshing community pool is just steps from the back deck! *Pets may be considered with 28+day stays

Price: Starting at $2,250.00 weekly.

Sun, Sea, And Sky

Sun Sea and Sky is only two blocks from bustling Duval Street, the heart of Old Town Key West, with an easy walk to restaurants, shops and many other Key West attractions. Sun, Sea & Sky, decorated with private art and lots of mirrored walls, boasts a large rear deck with a 50% overhang to protect you from the elements while enjoying the shade of lush palm trees and other vegetation. You’ll stroll through floral-lined lanes to Shipyard’s around-the-corner private pool.

Price Starting at $1,850.00 weekly

Marlin Blue

Make your special trip to paradise most memorable with a stay in your bright and airy Shipyard Unit. Located within Truman Annex, Key West’s most premier address, you are only a minute from the fine restaurants, shops, and galleries of Duval Street. Sit on your 40 foot veranda and cool off in the gentle trade winds as you watch the world go by.

Price: Starting at $2,050.00 weekly.

A Peace of Paradise

Swanky condo in The Shipyard of Truman Annex! Luxury touches everywhere. This end unit was completely remodeled with flair and detail. Open design with new flooring, coastal hues and furnishings -feels spacious and decadent. The kitchen sparkles with quartz countertops, mermaid backsplash, new stainless appliances, and a show-stopping chandelier. Relax on the Italian leather couch and enjoy the custom artwork designed for this property.

Price Starting at $1,995.00 weekly

Best Time

This Shipyard unit is a one level condominium on the second floor which has 2 decks to enjoy the beautiful weather and evening cocktails. This is a nicely appointed unit with 2 full bedrooms and 1 bathroom. This unit has 2 flat screen TV’s and wireless internet access. Perfect location and just 2 blocks from Duval. This condo is just minutes from all the sun-kissed festivities, yet perfectly situated a block off Duval in a gated community giving you the best of both worlds. *Pets may be considered with a 28+ day stay

Price Starting at $2,150.00 weekly