
Cutthroat Harbor Estates Vacations from ¥260,146
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The Latest Cutthroat Harbor Estates Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Cavalier Hotel South Beach
South Beach
Price was ¥313,648, price is now ¥260,146 per person
¥260,146
per person
May 24 - May 28
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.6/10 Excellent! (1,000 reviews)
Great location but the hotel is very loud. It’s old so all wood floors make it loud when cleaners are cleaning anywhere near your room or people just walking around in general.
Reviewed on Apr 3, 2026

Bentley Hotel South Beach
South Beach
Price was ¥414,208, price is now ¥330,463 per person
¥330,463
per person
May 24 - May 28
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
9.2/10 Wonderful! (703 reviews)
The hotel was a great location in old South beach well maintained and updated. The staff was very friendly. We weren’t able to get any of our rooms early even though we had 3 rooms including a penthouse suite and called two days ahead asking for early check in. The manager told me that check in was 4pm, which I already understood. I just couldn’t understand how they couldn’t prioritize even one of the three rooms for us. They also wouldn’t allow us a late checkout. Aside from that, everything else was fantastic. Clean, nicely appointed. I would come back, just don’t plan on any flexibility to your stay.
Reviewed on Apr 3, 2026

The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was ¥405,080, price is now ¥325,504 per person
¥325,504
per person
May 24 - May 28
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
9.4/10 Exceptional! (151 reviews)
While the hotel was great in all the different categories the staff going out of their way to help stood out the most. I had some issues with parking and really appreciated the efforts they went to resolve them!
Reviewed on Mar 25, 2026

The Local House
South Beach
Price was ¥356,208, price is now ¥292,432 per person
¥292,432
per person
May 24 - May 28
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
9.2/10 Wonderful! (1,004 reviews)
We liked the hotel vibe and location. Close to the beach and many different restaurants. Carpet was a bit dirty when walked on barefoot.
Also no phone or way to reach reception unless you call from your phone.
Reviewed on Mar 31, 2026

President Hotel
South Beach
Price was ¥317,164, price is now ¥263,670 per person
¥263,670
per person
May 24 - May 28
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.4/10 Very Good! (2,145 reviews)
Flooring was peeling up all over the room. Sink didn’t drain. AC broken. Not impressed. It’s Miami though. Nearly every hotel is garbage until you spend some $$$, so expect it, which is really sad.
Reviewed on Apr 4, 2026
Where to stay in Cutthroat Harbor Estates
Find the best Cutthroat Harbor Estates areas and neighborhoods for the activities you enjoy most. Learn more about Cutthroat Harbor Estates

Sugarloaf Shores
While Sugarloaf Shores isn't home to many top sights, Florida Keys Beaches and Sugarloaf Beach are some notable places to visit nearby.
Cutthroat Harbor Estates Hotel Deals

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Cudjoe Key FL
8.4/10 Very Good! (125 reviews)
Great location for all we wanted to do. The house is an older property and could use a bit more maintenance but it worked well for us, not fancy but very clean!
Reviewed on Mar 20, 2026

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is ¥40,093 per night from Apr 19 to Apr 20
¥40,093
¥54,086 total
Apr 19 - Apr 20
includes taxes & fees
8.2/10 Very Good! (2,038 reviews)
Breakfast was cooked and delicious
Reviewed on Apr 5, 2026

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is ¥27,679 per night from Apr 7 to Apr 8
¥27,679
¥46,408 total
Apr 7 - Apr 8
includes taxes & fees
8.6/10 Excellent! (2,111 reviews)
When I arrived, they issued, the wrong rooms, then I informed them these aren't the display on Expedia site, they informed me, the mistake was false advertisement on you guys site, but as personal favor to me, they would the one seen on Expedia, but would've wait several hours, before they were cleaned, ...
Reviewed on Apr 4, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

