Cudjoe Key Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

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Top hotels in Cudjoe Key

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$276 per night from 21 Jul to 22 Jul
S$276
21 Jul - 22 Jul
includes taxes & fees
8.4/10 Very Good! (1,302 reviews)
"Expensive compared to a “real resort”"

Reviewed on 6 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 11 Aug to 12 Aug
S$247
11 Aug - 12 Aug
includes taxes & fees
7.6/10 Good! (1,451 reviews)
"Been a couple times. Never disappoints"

Reviewed on 9 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$405 per night from 14 Jul to 15 Jul
S$405
14 Jul - 15 Jul
includes taxes & fees
8.8/10 Excellent! (1,670 reviews)
"Large rooms, beautiful views, quiet area, the free shuttle to otherside a bonus, so many things to do or just relax by one of six pools. We would definitely stay again."

Reviewed on 9 Jul, 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 1,739 properties in Cudjoe Key
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 Cudjoe Key holiday package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Cudjoe Key from just . And the more you bundle, the more dollars you save. Your dream escape has never been so affordable.
How do I get a cheap travel package to Cudjoe Key?
Booking a Cudjoe Key holiday package with Expedia is an easy way to save. We have more than 550 air carriers and 1,000,000 hotel options around the globe. With such a fabulous range to select from, you'll have no issues putting together your ideal adventure.
Where should I stay in Cudjoe Key?
There's so much to see in Cudjoe Key, so spend your evenings near its attractions and spend more time sightseeing. Upper Sugarloaf Key is one spot to add to your must-see list.
What are the top hotels in Cudjoe Key?
If you're thinking of staying in the Cutthroat Harbour Estates neighbourhood, some of your best options are Judy's Place At Venture Out and Dog - Friendly Resort Community Home With Pool. Cudjoe Gardens is also a popular Cudjoe Key area. We recommend Comfortable Waterfront Holiday Rental or Cosy, Perfect Conch Cottage if you prefer this part of town.
How far in advance should I book my Cudjoe Key holiday?
Smart travellers will likely want to book as early as possible. You can normally look up international airfares on Expedia up to a year before your flight. If you're booking at the last minute, fear not. Discounted prices occasionally appear in the last weeks prior to departure.
What does an Expedia Cudjoe Key travel package include?
Expedia has all you need to arrange your Cudjoe Key trip, but how your package is structured is your choice. Choose from any combination of hotels, flights and rental cars. Chasing some tours or experiences to keep you on the move? Once you've made your booking, you can add them on too. Whatever your style, there's a deal to match your needs.
What should I know before booking a Cudjoe Key travel package?
So many places to visit, so many things to see and do. With a package, you'll be able to tick more of them off your list. Bundle your flights, rental cars and hotels and make big savings.
Can I choose my airline with a Cudjoe Key Expedia holiday package?
You can, and with over 550 airlines to choose from all over the world, you have plenty of choice. Take a look at the available options and see which airline fits your budget and needs.
If I'm not able to travel, can I cancel my Cudjoe Key holiday package?
Yes you can, and we're here to help. You may be able to cancel or change your Cudjoe Key holiday package for free within 24 hours of booking. But you may be charged a fee by your airline, hotel or car rental company for older bookings. If life gets in the way of your holiday, browse our Customer Service Portal for more information.

* 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.