RATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be at Sailor's Son. This home is located in the private community of Key Cove Landings, on an exclusive lane of waterfront residential homes. The perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. This home includes plenty of off-street parking in the private garages, as well as on private driveways leading to the house.
UNIQUE FEATURES: 2 EnSuite bedrooms, both facing the water with porch access. 4 Full Baths.
This home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with a couch around a large HD flat screen Smart TV. There is a dining table with seating for up to 8 diners, with additional seating for 6 at the kitchen bar. The master bedroom has a King sized bed, a large flat-screen HD TV, and an en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony. The second bedroom has a King sized bed, a flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The third bedroom is also on the 2nd floor with twin beds, flat screen TV, and also with balcony access. On the main floor there is a fourth bedroom with twins bed. There is a full bath down the hall for convenience. Out back is one of the highlights of this home: the covered lanai and pool area. The covered outdoor dining area comfortably seats six for a poolside meal. The pool is heavenly, with views of the open water and visiting heron on the tropical greenery that surrounds the back yard. There is also a pool lounge area with comfortable chaises in a piece of deck that gets equal sunshine and shade. AMENITIES: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. This property will accommodate 8 adults.
Dockage is not available at this home's development.
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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 not indicated whether there is a smoke detector on the property
About the area
Key West
Located on the waterfront, this holiday home is in Northside Resort, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. With jet skiing, snorkelling and fishing nearby, you'll find plenty of adventures in the water.
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Sailor's Son- ALL FEES INCLUDED?
As of 11 October 2026, prices found for a 1-night stay for 2 adults at Sailor's Son- ALL FEES INCLUDED on 13 November 2026 start from NZ$8,787, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Sailor's Son- ALL FEES INCLUDED pet-friendly?
No, pets are not allowed at this property.
How much is parking at Sailor's Son- ALL FEES INCLUDED?
On-site parking is available at the property.
What time is check-in at Sailor's Son- ALL FEES INCLUDED?
Check-in begins at 4:00 PM.
What time is check-out at Sailor's Son- ALL FEES INCLUDED?
Checkout is at 10:00 AM.
Where is Sailor's Son- ALL FEES INCLUDED located?
Located in Northside Resort, this holiday home is 0.6 mi (1 km) from Regal Key West and within 3 miles (5 km) of Florida Keys Beaches and Duval Street. Southernmost Point and Mallory Square are also within 3 miles (5 km).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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:
All enjoyed the home and accommodations. Great customer service and I hope we followed instructions properly.
This was one of the prettiest houses at which we have ever stayed. The location was wonderful, the view from the porch, the pool, and the perfect open kitchen and living area. We absolutely loved it.
Stayed 6 nights in Apr 2026
From a partner site
10/10 Excellent
Teresa T.
1 September 2026
Great Experience
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 had 4 couples stay in this location. The location was great! Plenty of room and very clean! A short drive to Duval St but far enough away to enjoy the peace and quiet. It was great to have our own pool, grill, etc. Manager of the property was very helpful!
The management was very accommodating to our needs. Very responsive! And the house was amazing. Clean and well appointed. Beautiful location. Hope to return.
Stayed 7 nights in Feb 2026
From a partner site
10/10 Excellent
Pamela V.
23 March 2026
Key west home
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:
Great place and clean
Sailor’s Son was an awesome house. Our family throughly enjoyed our stay. The house was spacious, extremely clean and the kitchen was well equipped. It was also close to restaurants and everything else we wanted to do. We enjoyed the pool and the view was beautiful. Also, we had an unexpected family death and the owners showed us unbelievable kindness by allowing us to change our dates. We are grateful and appreciative of the support and understanding that they extended to us. We will definitely stay at this house again on our next visit to Key West. Highly recommend!!
Stayed 5 nights in May 2026
From a partner site
8/10 Good
Dwight P.
3 April 2026
Family in KW
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:
Great location. Easy access to old town KW, charter docks, and shopping for basics. Got to have good knees, lots of stairs.
From a partner site
10/10 Excellent
Harry & Sue K.
18 January 2026
Sailors Son, Key West
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 house was great, location was great.
Fantastic stay. Everything was great! Couldn’t have asked for a better host. Will definitely be staying with them again, and recommending to all our friends.Thank you!!!
Very easy check in and out with easy communication! The house was just as listed, great space, beautiful views and refreshing pool. Very easy 10 min drive into downtown Key West and lots of shopping within talking distance.
This beautiful property was the perfect place for a family respite. The views are outstanding and the home was spotless. Thank you for a great vacation home.
This was a great place to stay in the Keys. Off the busy Duval St but only a quick ride on the golf cart. Beautiful home with a great view of the water. We'll be looking to rebook in April for another visist.
Stayed 3 nights in Aug 2024
From a partner site
10/10 Excellent
Kristopher K.
13 October 2025
Great place. Beautiful and spacious
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was more than happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
This is a spacious and well appointed space. Great common area, nice view.
From a partner site
10/10 Excellent
20 April 2026
2nd time we've stayed here!
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:
This is our favorite mansion to stay in! We've stayed in this home twice now and rented with this same company 5 years in a row. They take wonderful care of us, the home's are always clean and the communication is wonderful! Very easy to work with, the bedrooms are spacious, pool is lovely. We always do a home cooked grilled meal as well on the bbq. There's laundry in the home also so its easy to pack less. We'll be back next year!
We had a large group of 8 people. House was perfect to meet our needs. My daughter loved the pool- weather was cold in December, but she went in anyway. Beautiful house and we had a blast in key west.
Stayed 5 nights in Dec 2023
About the host
Hosted by Javier Garrido
Languages:
English, Spanish
Premier Host
They consistently provide great experiences for their guests