Cudjoe Key Holidays

Book a Hotel + Flight or Car together to unlock savings

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 2.803.264 ₫ per night from 17 Aug to 18 Aug
2.803.264 ₫
5.666.507 ₫ total
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (2,403 reviews)
"The pool was close to the room, the food at the restaurant was good (albeit a little on the expensive side) and the rooms were clean. The clogged toilet and labyrinth and confusing apartment halls were the worse part. There were some unattended children slapping pool noddles at midnight right outside ..."

Reviewed on 5 Aug 2026

Beachside Resort & Residences
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is 2.979.925 ₫ per night from 11 Aug to 12 Aug
2.979.925 ₫
4.200.143 ₫ total
11 Aug - 12 Aug
includes taxes & fees
8.2/10 Very good! (2,331 reviews)
"Beware there is a “resort fee” that I was not aware of. Maybe missed during check and “fine print”, but had paid in full through Expedia when I booked. Looking for just an overnight stay (last minute) for short visit to Key West. So for two rooms I booked there was a total $66 additional charge that ..."

Reviewed on 5 Aug 2026

Ibis Bay Beach Resort
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 3.049.831 ₫ per night from 20 Aug to 21 Aug
3.049.831 ₫
4.908.691 ₫ total
20 Aug - 21 Aug
includes taxes & fees
Blue Flamingo Resort Key West
See all 1,780 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 1null000null000 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.