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SMOOTH SAILING ~ 2 Bedroom, 1 Bath Renovated Condo w/ Community Pool!

Photo gallery for SMOOTH SAILING ~ 2 Bedroom, 1 Bath Renovated Condo w/ Community Pool!

Fridge, microwave, oven, stovetop
TV
Pool
Outdoor dining
Exterior

Reviews

10 out of 10

Exceptional

Entire condo

2 bedrooms1 bathroomSleeps 460 sq m

Popular amenities

  • Parking available
    Parking available
  • Washer
    Washer
  • Kitchen
    Kitchen
  • Air conditioning
    Air conditioning
  • Dryer
    Dryer
  • Free WiFi
    Free WiFi

About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

SMOOTH SAILING ~ 2 Bedroom, 1 Bath Renovated Condo w/ Community Pool!

A TRUMAN ANNEX DREAM...
Come discover this beautifully renovated condo within the desirable Shipyard neighborhood in the Truman Annex area pairing comfort and modern luxuries at your fingertips. A cozy home base with just steps to the lively Key West action, this home is sure to make you never want to leave. 
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE

DETAILS AND AMENITIES…
Slip inside from an inviting front porch up to the 2nd level to a cheery and open Great Room bringing your loved ones together. Brand new furnishings surround the living area with a cozy place to hang for card night or your favorite movies on the flat screen TV. Craft up your meals and cocktails in the beautifully designed kitchen with stainless steel appliances and sprawl out at the dining table. Balconies lie off both the front and back of the unit with lush, sunny views and a table for 4. 

SLEEPING ARRANGEMENTS…
Sleep tight in the twin guest room that can be converted to a king upon request. The primary guest room comes with a king bed and access to the outdoor balcony to enjoy views of the vibrant neighborhood over a morning cup of coffee. Both rooms come with closet storage, a flat screen TV and share a hallway bathroom with a shower. A sofa sleeper occupies the living area.

OUTDOOR LIVING…
This home offers an incredibly peaceful escape allowing for the best kind of R & R on your island retreat. Although just walking distance to Mallory Square, Ft. Zachary Taylor and all the lively action, a parking spot is available for seamless coming and going should you head out for a scenic drive. The unit also offers a refreshing community pool lined with lounge chairs and is just steps away from the Truman Waterfront Park. 

PARKING!
This home does offer parking for one vehicle, but oversized trucks and extra large SUV's are not permitted and will have to park outside of this community.

CONCIERGE SERVICES...
Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!

TIME TO UNWIND...

Property manager

Wendy Zintsmaster & Team

Languages

English

Property amenities

Pool/Spa

  • Shared/communal pool

Internet

  • Free WiFi

Parking and transportation

  • Onsite parking

Kitchen

  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Toaster
  • Cookware/dishes/utensils
  • Coffee/tea maker

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bed sheets provided
  • Sofa bed

Bathrooms

  • 1 bathroom
  • Hair dryer
  • Towels provided

Living spaces

  • Living room

Entertainment

  • TV with cable/satellite service

Outdoor areas

  • Balcony

Laundry

  • Washing machine and dryer

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Concierge services
  • Iron/ironing board

Location highlights

  • Near the sea
  • In the city center
  • Near a hospital

Things to do

  • Fitness facilities nearby
  • Birdwatching nearby
  • Swimming nearby
  • Golf nearby
  • Cycling nearby
  • Snorkeling nearby
  • Windsurfing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Marina nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Unit size: 646 sq ft (60 sq m)

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets not allowed

Children and extra beds

Children are welcome

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

2450-222260

About the neighborhood

Map
Key West, Florida

What's nearby

  • Duval Street - 6 min walk
  • Ernest Hemingway Home and Museum - 9 min walk
  • Mallory Square - 11 min walk
  • Fort Zachary Taylor Historic State Park - 11 min walk
  • Southernmost Point - 16 min walk

Getting around

  • Key West Intl. Airport (EYW) - 15 min drive

Restaurants

  • ‪Margaritaville - ‬7 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Green Parrot Bar - ‬6 min walk
  • ‪Bourbon Street Pub - ‬8 min walk
  • ‪Mangoes Restaurant & Island Cuisine - ‬7 min walk

Frequently asked questions

Is SMOOTH SAILING ~ 2 Bedroom, 1 Bath Renovated Condo w/ Community Pool! pet-friendly?

No, pets are not allowed at this property.

What time is check-in at SMOOTH SAILING ~ 2 Bedroom, 1 Bath Renovated Condo w/ Community Pool!?

Check-in begins at 4:00 PM.

What time is check-out at SMOOTH SAILING ~ 2 Bedroom, 1 Bath Renovated Condo w/ Community Pool!?

Check-out is at 10:00 AM.

Where is SMOOTH SAILING ~ 2 Bedroom, 1 Bath Renovated Condo w/ Community Pool! located?

Located in Key West Historic District, this condo building is within a 10-minute walk of We Cycle Key West, Duval Street, and Ernest Hemingway Home and Museum. Mallory Square and Fort Zachary Taylor Historic State Park are also within 15 minutes.

SMOOTH SAILING ~ 2 Bedroom, 1 Bath Renovated Condo w/ Community Pool! Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 36 out of 38 reviews" "
Rating 8 - Good. 2 out of 38 reviews" "
Rating 6 - Okay. 0 out of 38 reviews" "
Rating 4 - Poor. 0 out of 38 reviews" "
Rating 2 - Terrible. 0 out of 38 reviews" "

10/10

Cleanliness

Reviews

8/10 Good

Dean S.

Liked: Cleanliness
Stayed 7 nights in May 2024

10/10 Excellent

Victoria R.

Liked: Cleanliness
Great place
Our stay was great. The grounds were very well kept. Location was close to all the bars and restaurants. Great place to stay!
Stayed 7 nights in Jun 2024

8/10 Good

Jeffery K.

Liked: Cleanliness
Check-In, Gate Keys & check-out
We enjoyed the property. We stay in the Shipyard Condos every year for the past twenty years so we were very familiar with the specific condo location. So much so that I asked if our parking spot was indeed in the small parking lot just off the entrance to Truman Waterfront Park rather than the Shipyard main lot lot accessed off of Thomas Street. It was. Upon arrival, someone is in the parking spot. Understand that parking in the wrong spot within this tow zone can get you towed and likely causes a cascade affect when the client of the spot I had to take can't park. It turns out it was Melanie, our Property Manager. In response to my comment that one of the worst things you can do to a Shipyard client is take their parking spot, she apologized with the caveat that,"... but that's the only spot I have to park in because it is also bad form to use another tenant's spot." Think about that for a second. I did not reply, "Oh, better to piss off the client you know?" or "So, you're to lazy to park on the street and walk in?" Now, in Melanie's favor is her rapid obtainment of two Annex Gate keys that did not come with the original pool and condo keys, but are provided with our usual Realty Company. If you don't know, pedestrian gates to the Annex are locked after 6pm. The gates we often use are located down by Mel Fisher's Treasures and at the end of Caroline Street. Last annoyance, cleaning crew rep looking for keys prior to 10am.
Stayed 14 nights in Apr 2024

10/10 Excellent

Barbara C.

Liked: Cleanliness
Our vacation
Everything was perfect. the house & location. Exactly where we wanted to be. Anything you are looking for is just a walk away.
Stayed 9 nights in Oct 2023

10/10 Excellent

Verified traveler

Liked: Cleanliness
Perfect Place
The property was clean, comfortable, quiet, and exactly as advertised. Property manager was very communicative, concierge service was super helpful. Great location, we rented bikes but barely needed them — so much is within walking distance! First vacation where I absolutely didn’t want to go home. Would definitely stay again.
Stayed 7 nights in Aug 2023

10/10 Excellent

Sheryl F., Louisville, Kentucky

Liked: Cleanliness
Beautiful Condo
We enjoyed the condo and the location near Zachary Taylorstate park. Easy walking to restaurants and shops.Had all the supplies needed. Air conditioning was mice and cold as it was extremelyhotthat week! Would definitely stay here again!
Stayed 7 nights in Jun 2023

10/10 Excellent

Amy R.

Liked: Cleanliness
Great stay!
Property manager is excellent with communication and the location is perfect. No noise at night. Don’t plan on sleeping on the pull-out couch. We ended up putting the mattress on the floor which made it hard to hang out in the living room at night. It really is impossible on the pull-out. Bumps where the bars are and completely slanted from top to bottom. All mattresses are pretty bad but we dealt with it. Other than that, highly recommend!
Stayed 7 nights in Jun 2023

10/10 Excellent

Kelly Z.

Liked: Cleanliness
Great little spot in Truman annex
Great little unit, spacious and comfortable. Lovely ac, fans and tvs. Great property manager. Nice location in the shipyard
Stayed 7 nights in Jun 2023

10/10 Excellent

Eric M.

Liked: Cleanliness
Key West Fishing and Dry Tortugas
Property was immaculate. Check in process was flawless. Did not have any issues with this property at all. We have used this property management team before and they did not disappoint. Thank you for making our vacation one to remember!
Stayed 7 nights in Feb 2023

10/10 Excellent

Pat W.

Liked: Cleanliness
Perfect spot
We had a great stay in Key West. We enjoy the Shipyard Condominium location because it is a quiet and easy place to relax. There is easy access to the state park, walks along the Truman Annex Park, and it is definitely easy to walk to all the shops and restaurants. Smooth Sailing is a very nice condo, well maintained, comfortable and quiet. It is easy to settle into a daily routine of exploring the city, reading a book on the deck, or walking to one of the many restaurants for dinner out. Thanks for a great visit!
Stayed 14 nights in Jan 2023

10/10 Excellent

Kari H.

Liked: Cleanliness
Perfect Location!
Property was clean and located close to the pool, Duval St, Ft Zachary park, Mallory Square, and Southernmost Point. We never rented a cart or bike, was able to walk everywhere. Nice quiet neighborhood.
Stayed 7 nights in Jan 2023

10/10 Excellent

Heike S., Highlands Ranch

Liked: Cleanliness
perfect location
Property was as expected. clean and cute. Close proximity to all attractions. Having parking was great, though walked most everywhere. Duvall Street, about a 5 minute walk, with nearby restaurants. The place was really cute and we enjoyed the 2 balconies. Great location.
Stayed 7 nights in Dec 2022

10/10 Excellent

Sara-Marni H.

Liked: Cleanliness
Gorgeous condo near the water
I visited Key West for a week in November with my Mom and this was the perfect place to stay. Walking distance to a great beach, and all the restaurants and shopping. The unit itself is very nice with comfortable beds, nice shower, two balconies, and a well equipped kitchen. 10/10.
Stayed 7 nights in Nov 2022

10/10 Excellent

Betty M.

Liked: Cleanliness
Fantastic Property
Fantastic condo that was beautifully decorated, comfortable, and immaculate. Beautiful upgraded kitchen with quartz countertops and a bathroom with walk-in shower (plenty of hot water, great water pressure, 2 shower heads). Best of all was a very comfortable KING SIZE BED and well designed closets with tons of storage space. We loved the flooring, TVs, lighting features, etc. The location was very quiet and private and the property manager was really nice. We highly recommend this property and would definitely stay again. It would be absolutely perfect if black out shades were on the bedroom windows/doors (the sun shines in very bright and early for vacationers, however they’ve never been present at any of the other properties where we’ve stayed) and if there were a few more items in the kitchen; some non breakable dishes for use on the deck and a couple more large skillets (we like to cook breakfast sometimes when we stay a couple of weeks).
Stayed 14 nights in Oct 2022

10/10 Excellent

Darlene V., Gainesville

Liked: Cleanliness
Location Location Location
Beautifully appointed second-story condo. The location of this condo is truly what we liked most. Close to so many places. But far away enough to feel quiet, privacy, peaceful area in the Truman annex community (despite the crowing roosters. Lol). Only a 7 to 10 minute walk to DuVall Street, Mallory Square, Zachary Taylor Fort, various shops, and restaurants and museums and the waterfront area. Definitely recommend renting a bike for the entire week because the entire city of Key West is completely naviggable by bicycle, so if you want to get to the other side of the island on the southern most area a bike would be beneficial. Lots of sidewalks and the scenery is astounding. The condo itself is very well appointed, with fully equipped kitchen, porch, and patios., modern, colorful and CLEAN!!! this is a second floor condominium just to be aware in case someone has mobility issues or difficulty walking up and down a full flight of steep steps. Lastly, the management company was extremely attentive and communicated with us readily and easily and timely and friendly!!
Stayed 7 nights in Oct 2022

10/10 Excellent

Victor H.

Liked: Cleanliness
Perfect get away spot
My husband and I enjoyed our stay and the unit was tastefully decorated. Staff was super helpful. Location is perfect for enjoying everything to see in Key West. We will be back!
Stayed 7 nights in Oct 2022

10/10 Excellent

Ariel K., Minnesota

Liked: Cleanliness
Great location, very comfortable stay
This spot is nice and quiet, yet close to everything. The rooms are comfortable and the apartment has everything you need for a week away. We spent lots of time at the pool, and enjoyed local restaurants like Blue Heaven and the Eaton Street Fish Market. Walk to everything, including the beach at the state park. Great host - lots of communication and everything was very smooth. Thanks!
Stayed 7 nights in Oct 2022

10/10 Excellent

Kevin S.

Liked: Cleanliness
Great quiet location
Easy rental
Stayed 7 nights in Sep 2022

10/10 Excellent

Debbie B.

Liked: Cleanliness
Key West adventure
This place is a great place to stay since it is within easy walking distance to Duvall St. and all the fun things to do. It is also in a very quiet part of town and we felt very safe here. A few things I'd change would be to have a 12 cup coffee maker instead of the 4 cup one which is really only 2 cups! Also to have more mirrors around, the only one is in the bathroom so it would be great to have some in the bedrooms so us girls can get ready when the bathroom is occupied. Hooks on the back of the bedroom doors would be great too for hanging towels, the bathroom is too small to hang 4 towels...these are just a few observances that I think would improve the place with little effort...otherwise everything was great and we would definitely stay here again!
Stayed 7 nights in Sep 2022

10/10 Excellent

Claire G.

Liked: Cleanliness
Great location
Awesome experience! Check-in was super easy, and the property manager made us feel welcome before we even arrived. Pictures are an accurate depiction of the space. Four adults sharing one bathroom took a little maneuvering, but we managed. Great to have a washer and dryer in the villa. The pool is close by. Keep the blinds and curtains drawn as the afternoon sun heated the interior to 80 despite the AC set to 75; it just couldn't keep up. Finally, the baby coffee pot caused us to make several pots of coffee each morning. Consider adding a full-size coffee pot. Highly recommended.
Stayed 7 nights in Aug 2022

10/10 Excellent

Imran L.

Liked: Cleanliness
Fantastic all round
My family and I really enjoyed staying at Truman Annex. The apartment was fantastic inside and out - clean, well located, parking (which cannot be underestimated)… a lot of fun for my family with two young children. Great communication with the property manager via text too. We hope to stay again, in future!
Stayed 7 nights in Jul 2022

10/10 Excellent

Marc D.

Liked: Cleanliness
Great times in Key West
Had a great one week stay. Location provided easy walking access to restaurants and activities. Chose this property due to its location and not needing a car to take advantage of key west fun. Avoided the energy of Duval street. Many great restaurants on Petonia street made awesome food and drink. Property was easy and fit perfectly for two adults. Pool is small for the number of properties being served. Property management people checked in and were helpful throughout. Would return
Stayed 7 nights in May 2022

10/10 Excellent

stephanie w.

Liked: Cleanliness
Quiet and Fun location!
I have been coming to Key West since 1985 and our first time in the Truman Annex … fantastic!!! First place I look next time !!!
Stayed 8 nights in Mar 2022

10/10 Excellent

Nancy C.

Liked: Cleanliness
Life just got better: Truman Annex through Best
Through Best of Key West Rentals, Smooth Sailing in Truman Annex…. Newly updated with lovely decor, situated a hop from the Waterfront Park. A couple blocks from the Little White House, Green Parrot, Blue Heaven, Rams Head, Moondog Cafe, and Duvall Street if that’s part of your plans. Very helpful and responsive property staff. Front and back porches - this unit is on the second floor - were pleasant and quiet places for a relaxing morning coffee. Lots of good things to say about this rental.
Stayed 7 nights in Feb 2022

10/10 Excellent

Verified traveler

Liked: Cleanliness
Spring break
Great place close to all the action
Stayed 7 nights in Feb 2022