Cutthroat Harbor Estates Holidays

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Price found within the past 48 hours. Click for updated prices.
The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Save 100% on your flight
Price was €1,836, price is now €1,095 per person
€1,095
per person
24 Mar - 29 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
Yes the WiFi wasn’t working though !

Reviewed on 5 Feb 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was €19,800, price is now €9,758 per person
€9,758
per person
24 Mar - 29 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Miami (MIA)
8/10 Very Good! (1 review)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
Price was €2,117, price is now €1,181 per person
€1,181
per person
24 Mar - 29 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Prime location within walking distance to all the hot spots. Included are 2 beach chairs with towels per day. Philip at the concierge received us warmly…checking us in early and giving us great recommendations. Room was a great size, A/C, with bathroom amenities. Overall, totally recommend.

Reviewed on 31 Jan 2026

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
Price was €5,328, price is now €3,107 per person
€3,107
per person
24 Mar - 29 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Miami (MIA)
9.4/10 Exceptional! (1,365 reviews)
Amazing hotel. Beyond our expectations. Rooms are huge. Modern and stylish Lobby is fabulous as is the bars and restaurants You must stay here !!! Total wow

Reviewed on 21 Jan 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 featuring a bay or harbor

Sugarloaf Shores

Though Sugarloaf Shores may not have many top sights, you can venture to the surrounding area to see attractions like Florida Keys Beaches and Sugarloaf Beach.

Find hotels in Sugarloaf Shores

Top hotels in Cutthroat Harbor Estates

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Cudjoe Key FL
The price is €597 per night from 22 Feb to 23 Feb
€597
22 Feb - 23 Feb
includes taxes & fees
8.2/10 Very Good! (118 reviews)
Great location. Quiet.

Reviewed on 3 Jan 2026

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
The price is €399 per night from 9 Feb to 10 Feb
€399
9 Feb - 10 Feb
includes taxes & fees
8.8/10 Excellent! (1,801 reviews)
Good location and service

Reviewed on 1 Feb 2026

Oceans Edge Key West Resort, Hotel & Marina
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is €416 per night from 8 Feb to 9 Feb
€416
8 Feb - 9 Feb
includes taxes & fees
8/10 Very Good! (1,915 reviews)
Great property! We had a junior suite and it was extremely spacious. The staff was very nice and the free shuttle to Duval St was a great perk. My only complaint was that nobody, but nobody told you to make a reservation for the free shuttle. I talked to multiple people at the front desk, concierge ...

Reviewed on 1 Feb 2026

Blue Flamingo Resort Key West
See all 1,399 properties in Cutthroat Harbor Estates
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

How much does a Cutthroat Harbour Estates holiday package cost?
From as low as €1,095. Yes, you read that right. Our Cutthroat Harbour Estates packages are an easy way to make your budget go further. Bundle your hotels, flights and car rentals and get to know this wonderful destination.
How do I get a cheap travel package to Cutthroat Harbour Estates?
Lock in flights that fit in with your schedule, add a hotel to your booking and watch the savings pile up with a Cutthroat Harbour Estates holiday package. It's as easy as that! From hotels and flights to tours and rental cars, Expedia makes travelling cheaply a cinch. And with over 550 airlines and 1,000,000 hotels throughout the world to select from, you won't be short of choice.
What are the top hotels in Cutthroat Harbour Estates?
Get your holiday off to a fantastic start by booking a stay at Oceanfront Home With Large Private Deck With Boat Dockage. It's one of most popular properties in Cutthroat Harbour Estates. Another option is Dazzling Bayfront Home With 2 Boat Docks.
How far in advance should I book my Cutthroat Harbour Estates holiday?
Browse Expedia to compare international flights as soon as you know your travel dates. You can usually purchase a seat up to 12 months before departure. If you don't see your preferred carrier, or you've left things to the last moment, don't despair. Cheap tickets to Cutthroat Harbour Estates sometimes emerge just weeks before the date of departure.
What does an Expedia Cutthroat Harbour Estates travel package include?
Expedia has all you need to organise your Cutthroat Harbour Estates trip, but how you structure your package is your choice. Pick from a combination of rental cars, flights and hotels. Searching for some tours or activities to keep you busy? Once you've made your booking, you can add them on too. Whatever your budget or style, there's a package deal to meet your needs.
What should I know before booking a Cutthroat Harbour Estates travel package?
Find deals that fit your budget with an Expedia package. Flights, hotels, rental cars — we have them all. You'll save big dollars just for combining your bookings. Whether you're taking off on a ski adventure or sipping cocktails on a beach, your dream holiday is only a few clicks away.
Can I choose my airline with a Cutthroat Harbour Estates Expedia holiday package?
Yes, the choice is yours. Expedia has access to more than 550 partner airlines around the world, so you can tailor your Cutthroat Harbour Estates adventure according to your needs and budget.
If I'm not able to travel, can I cancel my Cutthroat Harbour Estates holiday package?
Your situation can change in a flash, so yes, you can. You may be able to cancel or alter your Cutthroat Harbour Estates holiday package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, hotel or airline may charge additional fees. Want more information? Take a look at our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.