Cudjoe Key Holidays

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Cudjoe Key Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
5 Sept - 9 Sept
found 7 hours ago
Return flight included
Chicago (CHI) to Miami (MIA)
8.2/10 Very Good! (1,329 reviews)
Pour mon séjour je donnerai une note de 3 sur 5, en raison du système de climatisation très brouillant. Le personnel m'a paru aussi un peu distant, aimable à la limite.

Reviewed on 22 Jul, 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
5 Sept - 9 Sept
found 7 hours ago
Return flight included
Chicago (CHI) to Miami (MIA)
9.4/10 Exceptional! (1,212 reviews)
Good stay, hotel was accommodating whenever I needed something. Great location in south beach. Will be back

Reviewed on 20 Jul, 2025

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
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per person
5 Sept - 9 Sept
found 7 hours ago
Return flight included
Chicago (CHI) to Miami (MIA)
8/10 Very Good! (6,535 reviews)
Overall it is nice and huge property. The pool area is great with easy access to the beach. The property, carpets and rooms are dated. Unfortunately, we had a horrible check in process. It took close to an hour with multiple times going up and down the elevator. The hotel lobby, elevators, coffee shop, and bar was packed with convention attendees. Way too many people in the lobby everyday. I am not sure why they all hangout in the lobby and not in the convention area.

Reviewed on 22 Jul, 2025

Kimpton EPIC Hotel by IHG

Kimpton EPIC Hotel by IHG

5 out of 5
Downtown Miami
Save 100% on your flight
per person
5 Sept - 9 Sept
found 7 hours ago
Return flight included
Chicago (CHI) to Miami (MIA)
8.8/10 Excellent! (1,881 reviews)
I love everything about the hotel I will definitely come back The only issue I had the pool could have stayed open at least until 9:00pm unfortunately it closes at 7:00 pm

Reviewed on 22 Jul, 2025

EAST Miami

EAST Miami

5 out of 5
Downtown Miami
Save 100% on your flight
per person
5 Sept - 9 Sept
found 7 hours ago
Return flight included
Chicago (CHI) to Miami (MIA)
9.2/10 Wonderful! (3,202 reviews)
Loud construction noise is all you hear till 5:00

Reviewed on 22 Jul, 2025

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$258 per night from 3 Aug to 4 Aug
S$258
3 Aug - 4 Aug
includes taxes & fees
8.4/10 Very Good! (1,353 reviews)
"It was anice property. Bed was super hard and uncomfortable. Booked this particular hotel for the private beach, its man made and no access to the water. Wouldn't want to swim there anyway. Nice but not worth the price."

Reviewed on 19 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 20 Aug to 21 Aug
S$247
20 Aug - 21 Aug
includes taxes & fees
7.6/10 Good! (1,474 reviews)
"amazing"

Reviewed on 19 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$380 per night from 28 Jul to 29 Jul
S$380
28 Jul - 29 Jul
includes taxes & fees
8.8/10 Excellent! (1,691 reviews)
"The only negative thing I can say; is that the A/C in our room didn’t work to well or it was just that hot!"

Reviewed on 20 Jul, 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 1,738 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 S$496. 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.