Cutthroat Harbor Estates Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Cutthroat Harbor Estates

Price found within the past 48 hours. Click for updated prices.
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $1,606, price is now CA $826 per person
CA $826
per person
Apr 10 - Apr 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
5.8/10 (311 reviews)
I stood in the multiple bed 1 bedroom everything was good beach right there pool and security where very friendly

Reviewed on Nov 12, 2025

Creekside Inn

Creekside Inn

2.5 out of 5
Price was CA $2,125, price is now CA $904 per person
CA $904
per person
Apr 10 - Apr 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1,004 reviews)
Room was clean, spacious with a wonderful canal view.

Reviewed on Jan 27, 2026

W South Beach

W South Beach

5 out of 5
South Beach
Price was CA $15,159, price is now CA $7,698 per person
CA $7,698
per person
Apr 29 - May 6
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
9.2/10 Wonderful! (1,002 reviews)
Clean rooms great service

Reviewed on Jan 29, 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 CA $26,470, price is now CA $14,654 per person
CA $14,654
per person
Apr 26 - May 1
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very Good! (1 review)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Price was CA $19,925, price is now CA $11,095 per person
CA $11,095
per person
Apr 29 - May 6
found 1 day ago
Roundtrip flight included
Montreal (YMQ) 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 Jan 21, 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

While Sugarloaf Shores isn't home to many top sights, Upper Sugarloaf Sound and Florida Keys Beaches are some notable places to visit nearby.

Find hotels in Sugarloaf Shores

Cutthroat Harbor Estates Hotel Deals

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 CA $480 per night from Feb 22 to Feb 23
CA $480
CA $957 total
Feb 22 - Feb 23
includes taxes & fees
8.2/10 Very Good! (118 reviews)
Great location. Quiet.

Reviewed on Jan 3, 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 CA $437 per night from Feb 9 to Feb 10
CA $437
CA $576 total
Feb 9 - Feb 10
includes taxes & fees
8.8/10 Excellent! (1,801 reviews)
The room was very nice and homey feeling. The staff was very nice. We enjoyed breakfast lunch and diner at the restaurant the Waite staff was very friendly and food was good. We enjoyed the shuttle that is offered the drivers were knowledgeable about the island and history. Jeffery was the best. ...

Reviewed on Feb 3, 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 CA $466 per night from Feb 8 to Feb 9
CA $466
CA $602 total
Feb 8 - Feb 9
includes taxes & fees
8/10 Very Good! (1,917 reviews)
Very nice stay, staff was wonderful, rooms very nice and it was easy to get another room when our plane experience a weather delay.

Reviewed on Feb 5, 2026

Blue Flamingo Resort Key West
See all 1,398 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 Harbor Estates vacation package cost?
From as low as CA $826. Yes, you read that right. Our Cutthroat Harbor 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 Harbor 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 Harbor Estates vacation package. It's as easy as that! From hotels and flights to tours and rental cars, Expedia makes traveling 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 Harbor Estates?
Get your vacation 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 Harbor Estates. Another option is Dazzling Bayfront Home With 2 Boat Docks.
How far in advance should I book my Cutthroat Harbor Estates vacation?
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 Harbor Estates sometimes emerge just weeks before the date of departure.
What does an Expedia Cutthroat Harbor Estates travel package include?
Expedia has all you need to organize your Cutthroat Harbor 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 Harbor 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 vacation is only a few clicks away.
Can I choose my airline with a Cutthroat Harbor Estates Expedia vacation package?
Yes, the choice is yours. Expedia has access to more than 550 partner airlines around the world, so you can tailor your Cutthroat Harbor Estates adventure according to your needs and budget.
If I'm not able to travel, can I cancel my Cutthroat Harbor Estates vacation package?
Your situation can change in a flash, so yes, you can. You may be able to cancel or alter your Cutthroat Harbor Estates vacation 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.