Cutthroat Harbor Estates Holidays

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

President Hotel

3.5 out of 5
South Beach
Price was €2,111, price is now €1,523 per person
€1,523
per person
13 Jan - 19 Jan
found 6 hours ago
Return flight included
Johannesburg (JNB) to Miami (MIA)
8.4/10 Very Good! (1,905 reviews)
It was great! Breakfast & a welcome drink. Bartender and front desk person were very friendly and professional! I will stay here again!

Reviewed on 7 Nov 2025

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was €3,030, price is now €2,038 per person
€2,038
per person
13 Jan - 19 Jan
found 6 hours ago
Return flight included
Johannesburg (JNB) to Miami (MIA)
8.2/10 Very Good! (1,118 reviews)
Staff was great and friendly. Breakfast was excellent!

Reviewed on 5 Nov 2025

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was €2,273, price is now €1,573 per person
€1,573
per person
13 Jan - 19 Jan
found 6 hours ago
Return flight included
Johannesburg (JNB) to Miami (MIA)
8.4/10 Very Good! (1,004 reviews)
Room was clean. Staff was friendly beach, restaurants and shops nearby. Also a convenient parking garage within walking distance.

Reviewed on 4 Nov 2025

EAST Miami

EAST Miami

5 out of 5
Downtown Miami
Price was €3,267, price is now €2,352 per person
€2,352
per person
13 Jan - 19 Jan
found 6 hours ago
Return flight included
Johannesburg (JNB) to Miami (MIA)
9.2/10 Wonderful! (3,480 reviews)
One of my best staycations spots. The staff is very top tier. The room service is amazing and fast. 10/10

Reviewed on 5 Nov 2025

President Villa

President Villa

3.5 out of 5
South Beach
Price was €2,111, price is now €1,523 per person
€1,523
per person
13 Jan - 19 Jan
found 6 hours ago
Return flight included
Johannesburg (JNB) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
Very nice staff. Very accommodating.

Reviewed on 28 Oct 2025

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
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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
The price is €479 per night from 21 Nov to 22 Nov
€479
21 Nov - 22 Nov
includes taxes & fees
8.4/10 Very Good! (117 reviews)
Property was clean and comfortable. Location was ideal for our visit and the host gave hreat instructions on locating our unit. Its not a 5 star hotel- if thats what you want, this isnt the place. But if you want a clean, comfortable, affordavlble and convenient location. This is it. Cant wait to ...

Reviewed on 19 Aug 2025

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 €245 per night from 12 Nov to 13 Nov
€245
12 Nov - 13 Nov
includes taxes & fees
8.8/10 Excellent! (1,734 reviews)
We’ve stayed here twice now. Staff is great, the shuttle into town is super convenient (hi Jeffrey!). We love that you can use the kayaks or paddleboards every day. The tiki hut crew is the best! The place is clean and I feel safe walking around there. It’s well lit and easy to navigate.

Reviewed on 2 Nov 2025

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 €147 per night from 17 Nov to 18 Nov
€147
17 Nov - 18 Nov
includes taxes & fees
7.8/10 Good! (1,649 reviews)
Staff were friendly and responsive. Be prepared for free roaming chickens and roosters. Food was good. Concierge hours were not always convenient and this is clearly a later morning town, which is reflective in the timing of the shuttle, concierge availability, etc.

Reviewed on 3 Nov 2025

Blue Flamingo Resort Key West
See all 1,413 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 €1,523. 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.