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

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Welcome to Smooth Sailing!
Welcome to the Shipyard
Your peaceful sanctuary
Bright surroundings with new furnishings
Step up to your island sanctuary

Reviews

10 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 460.0 sq m

Popular amenities

  • Dryer
  • Parking available
  • Washer
  • Pool
  • Kitchen
  • Air conditioning

Explore the area

Map
Key West, Florida
  • Duval Street
    ‪6 min walk‬
  • Ernest Hemingway Home and Museum
    ‪9 min walk‬
  • Mallory Square
    ‪11 min walk‬
  • Key West, FL (EYW-Key West Intl.)
    ‪19 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 King Bed

Bedroom 2

2 Single Beds

Other Space 1

1 Double Sofa Bed

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Kitchen
Balcony
Dining area

About this property

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!

CANCELLATION...
Bookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.

TIME TO UNWIND...

Property manager

Wendy Zintsmaster & Team
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning

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  • Kitchen
  • Washer
  • Dryer
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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

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
On-site 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 that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
Property Registration Number 25230-131479

About the area

Key West

Located by the sea, this condo is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. USCGC Ingham Maritime Museum and Florida Keys Eco - Discovery Center are also worth visiting. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with cycling and ecotours.
Map
Key West, Florida

What's nearby

  • Duval Street - 6 min walk - 0.5 km
  • Ernest Hemingway Home and Museum - 9 min walk - 0.8 km
  • Mallory Square - 11 min walk - 1.0 km
  • Fort Zachary Taylor Historic State Park - 11 min walk - 1.0 km
  • Southernmost Point - 16 min walk - 1.4 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 19 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

Does SMOOTH SAILING ~ 2 Bedroom, 1 Bath Renovated Condo w/ Community Pool! have a pool?

Yes, this property has a pool.

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!?

Checkout is at 10:00 AM.

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

Located in Old Town Key West, 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.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 40 out of 42 reviews
Rating 8 - Good. 2 out of 42 reviews
Rating 6 - Okay. 0 out of 42 reviews
Rating 4 - Poor. 0 out of 42 reviews
Rating 2 - Terrible. 0 out of 42 reviews

10/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Raymond D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Pleasant Surprise

This was our first Key West experience. Upon walking in to the condo we were thrilled with the place. It was clean, very modern, comfortable. It was truly a home away from home and the location was ideal for the area. We would readily rent again.
Stayed 7 nights in Jan 2025

10/10 Excellent

Stacy H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Condo!

The condo was very clean, beautifully decorated and updated. The host was very accommodating in our early arrival. Loved the two decks.
Stayed 10 nights in Dec 2024

10/10 Excellent

Patti c.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Sep 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Peggy R.

Everything We Hoped For

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Smooth Sailing is a beautiful unit in a quiet and safe community, within walking distance of Old Town. The ease of checkin and checkout was greatly appreciated and communication from the agency was timely, consistent and extremely helpful for all our needs. Highly recommend and we will be back!
Stayed 7 nights in Sep 2024

8/10 Good

Dean S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in May 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Lori L.

Charming Condo in great location

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Thoroughly enjoyed our stay at the Smooth Sailing - Steps to Everything condo! It looked exactly like the photos, was clean and comfortable. Very walkable to most locations - except for the high humidity in July. Close enough to the action, but still quiet. The pool is close by and feels great after a hot day out. Management responded quickly to a couple of requests we texted about. Would definitely recommend this charming place.
Stayed 7 nights in Jul 2024

10/10 Excellent

Victoria R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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, location, listing accuracy
Disliked: Check-in, communication

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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kristen R.

Lovely unit in Shipyard

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The location and the furnishings in this Shipyard unit make for a relaxing stay in Key West.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Robert S.

Nice Condo near the water

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We rented in Truman Annex many times but this is our first time here. It is clean, ,well maintained and updated nicely. The bathroom and kitchen are renovated and look great. The location in the Shipyard is perfect. A quiet spot, not far from the pool, and overlooking Truman Park and the waterfront. We would stay again but i would recommend the owner install a full size mirror somewhere in the condo. Perhaps on the thermostat wall to enlarge the space. There is only one mirror in the unit and that is in the bath. It was just my wife and I staying, but it would have been difficult if we stayed with another couple. There are 2 bedrooms and we used the bedroom with the king size bed. It needs to be replaced and in our opinion is too big for the room. The TV on the wall and the king bed makes it tight in that room. There are 3 large TVs in the unit and we did not use any. For us, no time for TV as there is so much to do in Key West. For downtime, you can relax on the 2 balconies and even the front porch. Overall, one of the nicest condos we rented in over 15 years going to Key West.

10/10 Excellent

Barbara C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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 traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Theresa R., Chagrin Falls, Ohio USA

Loved this place!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The layout of this place was great! I had three women staying in this place and it was great! Everything was well thought out.
Stayed 2 nights in May 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Thomas S.

Funtastic!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Super clean and comfortable! Loved the balconies and the parking was convenient. Close to everything! Manager Brian, was in contact and made the arrival and departure seamless.
Stayed 7 nights in Apr 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

A guest from Lewes, DE

Smooth Sailing

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Excellent property in the perfect location

10/10 Excellent

Eric M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Neil G.

My Own Private Margaritaville

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Really enjoyed the condo - close to EVERYTHING - Walkable EVERYWHERE. I will book again in the future.
Stayed 7 nights in Dec 2022
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Lee H.

Updated townhouse in great location!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Excellent communication from Brian at Best Rentals in Key West. Updated townhouse was beautiful, clean and well stocked. Beds were comfortable. Neighborhood was quiet every night. Great overall experience! AC problem on day 1 but property manager arranged for tech service and full repair within an hour of my text message. Bravo!!

10/10 Excellent

Pat W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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

About the host

Hosted by Wendy Zintsmaster & Team

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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