Cutthroat Harbor Estates Holidays

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Price found within the past 48 hours. Click for updated prices.
  • View from property
    Aug 8 - Aug 16

    Creekside Inn + Flight

    Tavernier
    8 nights
    2.5 star property
    7.8/10 - Good (1,003 reviews)
    "Clean room, friendly staff, cold ac and plenty of parking. Really like that this place is on the water."
    Reviewed June 2, 2026
    Return • London (LCY) - Miami (MIA)
    LCY - MIA • 1 stop MIA - LHR • 1 stop
    £1,536
    £977
    per traveller
    found 1 day ago
    Creekside Inn
  • 3 outdoor pools
    Aug 17 - Aug 20

    The Retreat Collection at 1 Hotel & Homes South Beach + Flight

    South Beach
    3 nights
    5.0 star property
    8.0/10 - Very good (1 review)
    "Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay...."
    Reviewed June 22, 2016
    Return • London (LHR) - Miami (MIA)
    LHR - MIA • 2 stops MIA - LHR • 2 stops
    £7,259
    £3,653
    per traveller
    found 1 day ago
    The Retreat Collection at 1 Hotel & Homes South Beach
  • City view
    Aug 14 - Aug 28

    The Crosby Miami Worldcenter + Flight

    Downtown Miami
    13 nights
    4.0 star property
    8.2/10 - Very good (195 reviews)
    "While this LOOKS like a great place to stay, there were several issues we ran into 1) ZERO parking. 2) the pool closes crazy early our kids could not utilize. 3) not even an option to buy bottled waters. 4) ONLY a flat sheet for the sofa bed. My children were uncomfortable due to this issue. No blankets. We went to the front desk to ask for blankets, the “security” tells us he has no access to anything and is unable to get ahold of any manager. 5) 150.00 security charge plus an additional..."
    Reviewed May 30, 2026
    Return • London (LGW) - Miami (MIA)
    LGW - MIA • 2 stops MIA - LGW • 2 stops
    Save 100% on your flight
    £2,040
    £1,236
    per traveller
    found 1 day ago
    The Crosby Miami Worldcenter
  • Deluxe Suite, 1 Bedroom, Balcony, Ocean View | Balcony view
    Jul 13 - Jul 27

    Fort Lauderdale Beach Resort by Vacatia + Flight

    East Fort Lauderdale
    14 nights
    4.0 star property
    8.4/10 - Very good (697 reviews)
    "My family and I was given an amazing experience. Parking was different but everything was outstanding it for 9 of us perfectly. A full kitchen with EVERYTHING pots,pans,casseroles dish dinnerware dish soap dishwasher with dishwasher liquid mop, enough towels clean room comfortable bed… the AC was kicking lol. The view was great and less than 2 minutes walk to the beach and Bonnet museum. I know this pulse seems like I’m rambling, but it really was a great experience. We drove from Georgia and..."
    Reviewed June 5, 2026
    Return • Manchester (MAN) - Miami (MIA)
    MAN - MIA • 2 stops MIA - MAN • 2 stops
    Save 100% on your flight
    £1,894
    £1,201
    per traveller
    found 1 day ago
    Fort Lauderdale Beach Resort by Vacatia
  • Lobby
    Jul 23 - Aug 1

    Cavalier Hotel South Beach + Flight

    South Beach
    9 nights
    3.5 star property
    8.6/10 - Excellent (1,005 reviews)
    "Super cute and great location. Waiting staff was great and front was nice but a little lack of communication. Our room air wasn’t working really well so they switched our room and comp our breakfast the rest of the stay."
    Reviewed June 3, 2026
    Return • London (LHR) - Miami (MIA)
    LHR - MIA • 2 stops MIA - LHR • 2 stops
    Save 100% on your flight
    £1,593
    £1,012
    per traveller
    found 0 hours ago
    Cavalier Hotel South Beach

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

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

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 £155 per night from 8 Jun to 9 Jun
£155
8 Jun - 9 Jun
includes taxes & fees
8.4/10 Very Good! (2,337 reviews)
"We asked for towels never recieved. Property confusing with extra charges"

Reviewed on 6 Jun 2026

Blue Flamingo Resort Key West
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is £166 per night from 1 Jul to 2 Jul
£166
1 Jul - 2 Jul
includes taxes & fees
9/10 Wonderful! (1,798 reviews)
"Dirty room, loud guests, and my pregnant wife almost fell down in the hotel room due to a leaky A/C"

Reviewed on 5 Jun 2026

Havana Cabana at Key West
The Laureate Key West

The Laureate Key West

3.5 out of 5
3444 N Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is £155 per night from 14 Jun to 15 Jun
£155
14 Jun - 15 Jun
includes taxes & fees
9.2/10 Wonderful! (1,019 reviews)
"Vg"

Reviewed on 5 Jun 2026

The Laureate Key West
See all 1,385 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
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Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Cutthroat Harbour Estates travel package cost?
From as little as , you can tailor make your Cutthroat Harbour Estates travel package. Simply combine hotels, flights and rental cars and we'll reward you with discounts.
If I'm not able to travel, can I cancel my Cutthroat Harbour Estates travel package?
Yes you can, and we're here to help. You may be able to change or cancel your Cutthroat Harbour Estates travel package at no cost if you booked in the last 24 hours. However, you may incur a fee from your airline, hotel or car rental company if you booked more than 24 hours ago. If your travel plans unexpectedly change, take a look at our Customer Service Portal for more information.
How do I get a cheap travel package to Cutthroat Harbour Estates?
Book everything in the one place with our Cutthroat Harbour Estates travel packages. You'll find bargains on hotels, flights, tours and more that'll keep your budget happy and your adventurous side busy. And, with more than 550 partner airlines and 1,000,000 hotel options across the globe to pick from, there are endless opportunities to mix and match as you like.
Does Expedia offer Book Now, Pay Later Cutthroat Harbour Estates holidays?
Expedia has joined forces with online lender Klarna to make your next trip a bit easier on the wallet. Paying by instalment means you can spread the costs of your next big holiday, leaving you with more money to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find one that falls within your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month sounds right for you, Klarna offers just that! Paying in convenient monthly instalments will make that dream holiday possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay for your holiday in multiple transactions.
  • Low deposit holidays: Clicking the "book now" button is easier with this option. Just put down a small deposit on your holiday and then start packing your bags.

What are the top hotels in Cutthroat Harbour Estates?
Get your holiday off to a great start by booking a room at Waterfront Fresh And Cosy 2 Bedroom 35 Sea Wallnew Uv Light Air Purification Safe. It's one of most popular properties in Cutthroat Harbour Estates. Another welcoming option is Oceanside Paradise In The Fl Keys Free Kayaks Bikes Wifi Outdoor Bbq Grill.
How far in advance should I book my Cutthroat Harbour Estates holiday?
It all depends on the airline, but you can normally compare international flights on Expedia up to 12 months in advance. While it's advisable to book ahead of time, lucky customers will occasionally nab a cheaper ticket just weeks before the date of departure.
What does an Expedia Cutthroat Harbour Estates travel package include?
That depends entirely on you. You can pick from a range of Cutthroat Harbour Estates bundles, such as a rental car, flight and hotel. You can also book a flight with a hotel, or a rental car and a flight. Once you've made your booking, you can add on the fun stuff like activities and experiences. Whatever your Cutthroat Harbour Estates trip looks like, you'll save!
What should I know before booking a Cutthroat Harbour Estates travel package?
When you book your hotels, flights and car rentals together, you'll enjoy amazing discounts. Whether you're planning a beach break in a villa or want to stay in a fancy hotel in the city, Expedia will help make it happen.
Can I choose my airline with a Cutthroat Harbour Estates Expedia travel package?
You certainly can. We offer more than 550 airline partners all over the world, so fly with the carrier that matches your budget and travel needs.

Things to do

12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

£20
per adult
88% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Key West Parasailing Downtown

Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides

£53
per traveller
92% of travellers recommend
Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides
Kayak the mangrove tidal creeks

Key West Mangrove Kayak Eco Tour

£59
per adult
100% of travellers recommend
Key West Mangrove Kayak Eco Tour
See all activities in Summerland Key

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.