Cutthroat Harbor Estates Holidays from AU$4,544

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Top Holiday Package Deals in Cutthroat Harbor Estates

Price found within the past 48 hours. Click for updated prices.
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was AU$6,208, price is now AU$4,544 per person
AU$4,544
per person
9 Jan - 14 Jan
found 9 hours ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
8/10 Very Good! (1,003 reviews)
Amazing for young families! Heading back again!

Reviewed on 29 Nov 2025

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was AU$8,257, price is now AU$5,969 per person
AU$5,969
per person
9 Jan - 14 Jan
found 9 hours ago
Return direct flight included
Sydney (SYD) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Beautiful private oasis

Reviewed on 25 Nov 2025

Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

5 out of 5
Price was AU$7,475, price is now AU$5,590 per person
AU$5,590
per person
9 Jan - 14 Jan
found 9 hours ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
9.2/10 Wonderful! (1,055 reviews)
Beautiful property, stunning vistas, clean, spacious rooms, friendly staff.

Reviewed on 23 Nov 2025

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Key West Historic District
Price was AU$6,564, price is now AU$5,116 per person
AU$5,116
per person
9 Jan - 14 Jan
found 9 hours ago
Return direct flight included
Sydney (SYD) to Key West (EYW)
9.2/10 Wonderful! (845 reviews)
Location was great and convenient to Shopping/Entertainment/Food. Staff was pleasant and helpful. Drawback was bathroom not fully updated w/walk in shower and lack of chairs in room. Room was on 2Fl, not sure was prepared for the stairs but managed ok. Info at check in was not fully delivered. These comments would not deter us from returning but would be more mindful of the room location and inside of room accommodations.

Reviewed on 2 Dec 2025

Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

4 out of 5
Price was AU$6,383, price is now AU$5,000 per person
AU$5,000
per person
9 Jan - 14 Jan
found 9 hours ago
Return direct flight included
Sydney (SYD) to Miami (MIA)
8.8/10 Excellent! (1,003 reviews)
The place was great and appropriately named because it was very tranquil and relaxing. The only disappointment was that there is no spa facility and breakfast available only in your room.

Reviewed on 27 Nov 2025

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Our guide on 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

Our pick of the best Cutthroat Harbor Estates Hotel Deals

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 AU$341 per night from 16 Dec to 17 Dec
AU$341
16 Dec - 17 Dec
includes taxes & fees
8.6/10 Excellent! (1,721 reviews)
Great place. Excellent food. We had a suite big rooms. Love t pool & t bar-restaurant by t pool. Employees very accommodating

Reviewed on 27 Nov 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 AU$291 per night from 4 Dec to 5 Dec
AU$291
4 Dec - 5 Dec
includes taxes & fees
8/10 Very Good! (1,735 reviews)
Excellent resort, just gorgeous, wonderful staff, very clean, not noisy, clean and refreshing pools with lots of shade.

Reviewed on 26 Nov 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 AU$362 per night from 4 Dec to 5 Dec
AU$362
4 Dec - 5 Dec
includes taxes & fees
8.8/10 Excellent! (1,748 reviews)
The property was beautiful. The staff was welcoming and helpful. The room and accommodations were wonderful. Enjoyed the convenience of the concierge services as well as the shuttle. Everyone from the bellmen Sam to the shuttle drivers were friendly and made the time spent on property a joy.

Reviewed on 25 Nov 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 1,402 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.
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Frequently asked questions

How much does a Cutthroat Harbour Estates holiday package cost?
From as low as AU$4,544. 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.