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
per person
5 Sept - 9 Sept
found 10 hours ago
Return flight included
Chicago (CHI) to Miami (MIA)
8.2/10 Very Good! (1,329 reviews)
Exactly what I was looking for. Small Art Deco hotel with a beach front view and right on the edge of everything Southbeach has to offer

Reviewed on 22 Jul, 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
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per person
5 Sept - 9 Sept
found 10 hours ago
Return flight included
Chicago (CHI) to Miami (MIA)
9.4/10 Exceptional! (1,212 reviews)
Good stay, hotel was accommodating whenever I needed something. Great location in south beach. Will be back

Reviewed on 20 Jul, 2025

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
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per person
5 Sept - 9 Sept
found 10 hours ago
Return flight included
Chicago (CHI) to Miami (MIA)
8/10 Very Good! (6,535 reviews)
Overall it is nice and huge property. The pool area is great with easy access to the beach. The property, carpets and rooms are dated. Unfortunately, we had a horrible check in process. It took close to an hour with multiple times going up and down the elevator. The hotel lobby, elevators, coffee shop, and bar was packed with convention attendees. Way too many people in the lobby everyday. I am not sure why they all hangout in the lobby and not in the convention area.

Reviewed on 22 Jul, 2025

Kimpton EPIC Hotel by IHG

Kimpton EPIC Hotel by IHG

5 out of 5
Downtown Miami
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per person
5 Sept - 9 Sept
found 10 hours ago
Return flight included
Chicago (CHI) to Miami (MIA)
8.8/10 Excellent! (1,881 reviews)
Easily one of the best properties in miami the view and rooms take your breathe away.

Reviewed on 22 Jul, 2025

EAST Miami

EAST Miami

5 out of 5
Downtown Miami
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per person
5 Sept - 9 Sept
found 10 hours ago
Return flight included
Chicago (CHI) to Miami (MIA)
9.2/10 Wonderful! (3,202 reviews)
Loud construction noise is all you hear till 5:00

Reviewed on 22 Jul, 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

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is S$258 per night from 5 Aug to 6 Aug
S$258
5 Aug - 6 Aug
includes taxes & fees
8.4/10 Very Good! (1,353 reviews)
"It was anice property. Bed was super hard and uncomfortable. Booked this particular hotel for the private beach, its man made and no access to the water. Wouldn't want to swim there anyway. Nice but not worth the price."

Reviewed on 19 Jul, 2025

Beachside Resort & Residences
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 S$247 per night from 21 Aug to 22 Aug
S$247
21 Aug - 22 Aug
includes taxes & fees
7.6/10 Good! (1,474 reviews)
"amazing"

Reviewed on 19 Jul, 2025

Blue Flamingo Resort Key West
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 S$380 per night from 28 Jul to 29 Jul
S$380
28 Jul - 29 Jul
includes taxes & fees
8.8/10 Excellent! (1,691 reviews)
"The only negative thing I can say; is that the A/C in our room didn’t work to well or it was just that hot!"

Reviewed on 20 Jul, 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 1,376 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 S$496. 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.