See all properties
Condo

**SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..

Seafront with hot tub, near Duval Street

Photo gallery for **SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..

Smooth Sailing has a stunning view of the Atlantic Ocean...
The living room has been renovated in a modern coastal feel...
The dining table seats six comfortably...
No need to go anywhere to watch the sunset...
Smooth Sailing is located on the 3rd floor...

Reviews

10 out of 10
Exceptional

Popular amenities

  • Dryer
  • Washer

Explore the area

View map
  • Place, Smathers Beach
  • Place, Duval Street
  • Place, Southernmost Point
  • Airport, Key West, FL (EYW-Key West Intl.)

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Cozy furnishings
ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!
  • Ocean view
  • Pool
  • Hot tub
  • Kitchen
9.8 out of 10, (216 reviews)
ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!

Frequently asked questions

Does **SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES.. have a pool?

Yes, this property has a pool.

Is **SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES.. pet-friendly?

No, pets are not allowed at this property.

How much is parking at **SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..?

On-site parking is available at the property.

What time is check-in at **SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..?

Check-in begins at 4:00 PM.

What time is check-out at **SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..?

Checkout is at 10:00 AM.

Where is **SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES.. located?

Nestled on the beach, this Beachside condo building is within 2 mi (3 km) of Florida Keys Beaches, Duval Street and Southernmost Point. Mallory Square is 2.7 mi (4.3 km) away.

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. 144 out of 158 reviews
Rating 8 - Good. 13 out of 158 reviews
Rating 6 - Okay. 1 out of 158 reviews
Rating 4 - Poor. 0 out of 158 reviews
Rating 2 - Terrible. 0 out of 158 reviews

10/10

Cleanliness

9.4/10

Amenities

8.8/10

Property conditions & facilities

10/10

Eco-friendliness

9.8/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Holly A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Rosa was wonderful! Enjoyed our stay very much
Stayed 3 nights in Nov 2025

10/10 Excellent

Jim P.

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

Vacation

Very spacious and well appointed unit.
Stayed 6 nights in Jan 2025

10/10 Excellent

Sara M.

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

Great time!!

The condo was perfect for our family of 4 and our first trip to Key West!
Stayed 4 nights in Mar 2023

10/10 Excellent

Jeni G.

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

great accommodations

Very comfortable apartment with everything you could need - beautifully decorated, loved the access to the pool & gym and couldn't beat the view of the ocean from the balcony. Would definitely come back!
Stayed 4 nights in Apr 2024

10/10 Excellent

Sara F.

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

Excellent Stay!!!

We absolutely loved staying here. Perfect for two couples! We loved the ocean views, the pool and being able to easily get to downtown! Christian was terrific and took care of anything we needed. We would most definitely stay here on our next trip!!
Stayed 4 nights in Mar 2024

10/10 Excellent

Cristy R.

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

Great Stay!

Everything was clean and check-in was very easy. We ubered everywhere -much easier than finding parking.
Stayed 7 nights in Jul 2023

10/10 Excellent

Randall C.

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

Honeymoon dream stay

This place was simply amazing. Service was top notch!!!! I am already looking at planning another trip back in February.
Stayed 3 nights in Jun 2023

10/10 Excellent

David I., Statesville, NC

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

Great condo!!

We loved our stay at Smooth Sailing! The condo and area were amazing. Well stocked kitchen and our property manager was great! Highly recommend!
Stayed 7 nights in Jun 2021

10/10 Excellent

Verified traveller

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

Highly Recommend

Beautiful condo, great location, great service from The Last Key
Stayed 3 nights in Apr 2024

10/10 Excellent

Steven M.

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

What a gorgeous condo

Close to perfect ... only thing that could be better was the distance to all the action (and the price 😉)
Stayed 4 nights in Jan 2020

10/10 Excellent

John M.

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

Smooth Sailing

Very Well Managed
Stayed 3 nights in Dec 2023

10/10 Excellent

Matthew H.

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

Just perfect!

Property manager was very thorough and accommodating. The unit had everything you could possibly need, was clean and the amenities were awesome. We’ll be back!
Stayed 3 nights in Sep 2023

10/10 Excellent

Asa H.

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

A+++ Everything except party scene

Above expectations in every way. Clean, high quality, great pool, excellent communication and service.
Stayed 3 nights in Sep 2023

10/10 Excellent

Vickie G.

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

Beyond Amazing

I’ve never been this happy in my life. I wanted for nothing. We could see both the luxurious pool, or the beautiful Atlantic Ocean from this condo. I forgot nice jewelry when we left. Cleaning crew found them and gave them to the manager. He contacted me and mailed my jewelry to me. They have more rentals in the area too. Already planning our next trip!
Stayed 4 nights in Aug 2024

8/10 Good

catherine c., Where do you live?

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

Beautiful View Great location

The unit is lovely - well equipped and inviting. The view is beautiful, pool large and residents friendly. We had an issue with one of the bedrooms that Last Key responded to quickly and I expect is now resolved. The only reason for a 4/5 review. Otherwise would surely recommend for a visit. Easy to get to town and a lovely walk just outside down Smathers beach.
Stayed 5 nights in Jan 2023

10/10 Excellent

Karen L.

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

Great place for family

Very nice condo unit with beautiful ocean views from family room and both bedrooms. Well stocked kitchen and nearby grocery store. Nice large pool and hot tub right near the beach. Communication with the realty company was fantastic. Monique stayed in regular touch in the couple of days before our stay as we watched the forecast for Tropical Storm Elsa. She also gave us great recommendations for places to stop along the way, and restaurants when we got there. A nice welcome package was much appreciated upon our arrival. The only downside was that the smell of the beach, which we were not prepared for, but that is apparently everywhere in Key West. We did spend a day at the beach in Fort Zachary Taylor State Park, which I highly recommend. Lovely spot with shaded picnic table, and the sargassum odor was far less pungent there. Would definitely stay there again. Highly recommend.
Stayed 4 nights in Jul 2021

8/10 Good

Jim R.

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

Wonderful Condo. Last Key Reality kind of dropped the ball.

We loved the Condo. Very comfortable and well furnished. We had mentioned when we booked it that we were beginning our retirement and there were cupcakes waiting for us with a congratulatory note. We also needed to have something shipped to us in Key West and Last Key Reality was very good about receiving it and delivering it to our condo. So the accommodations were very nice. Our only issues were with Last Key Reality's services. Their web site makes a big point about personally greeting you and making you feel like you're special, 'like a celebrity' in their words. Well, that is not how things went. We were not greeted upon arrival and were actually given the wrong information via a text message for check-in. As a result, we had unloaded our luggage and gone to the wrong condo and could not get in. When we contacted Monique, our Guest Service Coordinator, she said she realized she had sent us the wrong information and meant to send us a correction. So we had to go back down to the lobby to get the correct keys and code. Not exactly Celebrity service. In fact many times she apologized with the excuse that she had a lot of people coming in that day. Again, not making us feel real special. We also called their Concierge to book a cruise for us the on Friday morning. We gave them all the information needed for the booking include our credit card and assumed it would be handled. We became concerned when we hadn't received any information confirming our booking. When we checked back with the concierge service, we were told the cruise was full and they couldn't get a booking for us. We received no call from anyone that they were not able to complete the booking or to offer an alternative. Again, not Celebrity service. While we enjoyed the condo, and would consider rebooking it again, I guess we would be arriving with a much lowered set of expectations about the service we could receive.
Stayed 3 nights in Jan 2022

10/10 Excellent

David C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice, upgraded condo. Clean pool and grounds outside. Very relaxing. Great view of the ocean from the spacious balcony. Easy walk to the beach.
Stayed 4 nights in Sep 2025

10/10 Excellent

Gary P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location was great. We had an unobstructed view of the ocean and the pool was fantastic. We will visit again.
Stayed 4 nights in Oct 2025

10/10 Excellent

Kaitlyn C.

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

10/10 Highly Recommend, Best Place to Stay in Key West!

This was the CLEANEST rental unit we've ever stayed at. The unit is even nicer in person - so spacious! Our host, Brian met us upon arrival and walked us through the unit. He even offered great local recommendations. We absolutely loved the location that came with parking, and the balcony overlooking the ocean is to die for. While you cannot swim in the ocean at this property, Smathers Beach is very close. The pool facilities are great. Highly highly recommend this unit!!
Stayed 3 nights in Apr 2025

10/10 Excellent

Julie D.

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

First time

First time in the keys.Was a fantastic trip.We enjoyed everything about this vacation.
Stayed 3 nights in Mar 2025

10/10 Excellent

Lynn F.

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

Beautiful villa

Spacious modern villa with great gulf views. Well stocked and maintained.
Stayed 5 nights in Mar 2025

10/10 Excellent

Stanley L.

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

1st Visit toKey West

Ease of getting to downtown areas was good. The unit was clean and everything needed was provided. Host was always accessible.
Stayed 4 nights in Feb 2025

10/10 Excellent

Patricia S.

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

Heaven on Earth—Key West

Property was amazing!!! The pool was clean and relaxing, with Smathers Beach only a 5 minute walk from the unit. Brian, the property manager, met us on arrival and checked us into our unit. Everything was just as described on the website. The property is a ten minute Uber ride to all of the fun on Duval Street/Wharf, etc…If you are coming to Key West, I’d definitely recommend that you stay here. We can hardly wait to come back.
Stayed 3 nights in Feb 2025

10/10 Excellent

Laura S.

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

Smooth Sailing Stay

This place is gorgeous! We could not have had a more comfortable and relaxing stay. The condo was superb. Well worth every penny spent. You will not be disappointed. We came down to Key West to meet friends for my husband's 60th. Brian, with Key West Realty, was great, very accommodating. He coordinated meeting our friends, who flew in early, to retrieve their luggage and store it at their location; allowing our friends to enjoy walking around Key West until the condo was ready. We all had a great time and many, wonderful memories made. If you have a chance, take the Catamaran Sunset cruise with Sebago. They crew was very entertaining/nice, had a live band and wrapping it up with a beautiful, Key West sunset.
Stayed 3 nights in Feb 2025
Tell us how we can improve our siteShare feedback