Cutthroat Harbor Estates Holidays from NZ$3,411

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Top Holiday Package Deals in Cutthroat Harbor Estates

Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
Price was NZ$5,476, price is now NZ$3,411 per person
NZ$3,411
per person
12 Feb - 19 Feb
found 9 hours ago
Return direct flight included
Weyers Cave (SHD) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Room was good .. except for a dusty smell

Reviewed on 24 Dec 2025

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was NZ$9,055, price is now NZ$5,125 per person
NZ$5,125
per person
12 Feb - 19 Feb
found 9 hours ago
Return direct flight included
Weyers Cave (SHD) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Being right on Duval Street if city noise bothers you you might want to stay a block or two off Duval. But if you want all the action then this place is fantastic. Staff is great and the room was nicely appointed and very comfortable.

Reviewed on 12 Dec 2025

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
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Price was NZ$9,076, price is now NZ$5,830 per person
NZ$5,830
per person
12 Feb - 19 Feb
found 9 hours ago
Return direct flight included
Weyers Cave (SHD) to Key West (EYW)
9.4/10 Exceptional! (390 reviews)
The check in staff was not hospitable. The pool was not heated, and the couch in our suite was very dirty/dinghy. Location is great and property is beautiful. We had amazing staff at check out. I recommend staying at Winslows Bungalows their sister property. More pool options, bar, and impeccable customer service.

Reviewed on 20 Dec 2025

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Key West Historic District
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Price was NZ$6,963, price is now NZ$4,548 per person
NZ$4,548
per person
12 Feb - 19 Feb
found 9 hours ago
Return direct flight included
Weyers Cave (SHD) to Key West (EYW)
9.2/10 Wonderful! (845 reviews)
Excellent location with access to all areas of the island either on foot or bus. Breakfast was staffed by Sonia who went out of her way to meet any requests. The staff were very friendly and helpful.

Reviewed on 21 Dec 2025

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
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Price was NZ$5,867, price is now NZ$3,884 per person
NZ$3,884
per person
12 Feb - 19 Feb
found 9 hours ago
Return direct flight included
Weyers Cave (SHD) to Key West (EYW)
9/10 Wonderful! (831 reviews)
Property location was excellent walkable. Staff was awesome. Breakfast was good. Air conditioner kept up! Loved our room and front porch!

Reviewed on 24 Dec 2025

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 Upper Sugarloaf Sound and Florida Keys Beaches.

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 NZ$523 per night from 4 Jan to 5 Jan
NZ$523
4 Jan - 5 Jan 2026
includes taxes & fees
8.6/10 Excellent! (1,804 reviews)
Excellent & Beautiful hotel The staff at the front desk is very kind & professional Thank you.

Reviewed on 20 Dec 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 NZ$546 per night from 8 Jan to 9 Jan
NZ$546
8 Jan - 9 Jan 2026
includes taxes & fees
8/10 Very Good! (1,785 reviews)
Clean room and amenities

Reviewed on 21 Dec 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 NZ$562 per night from 26 Jan to 27 Jan
NZ$562
26 Jan - 27 Jan 2026
includes taxes & fees
8.8/10 Excellent! (1,755 reviews)
Not convenient to resturants unless you have a car

Reviewed on 20 Dec 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 1,415 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 NZ$3,411. 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.