Cudjoe Key Holidays

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Top Flight + Hotel Deals in Cudjoe Key

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
per person
2 Sept - 9 Sept
found 8 hours ago
Return flight included
St. Louis (STL) to Miami (MIA)
8.4/10 Very Good! (1,003 reviews)
Beautiful property!!! We really enjoyed it and the staff was so friendly. Walking distance or the beach and beach chairs available as well

Reviewed on 11 Jun 2025

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
per person
2 Sept - 9 Sept
found 8 hours ago
Return flight included
St. Louis (STL) to Miami (MIA)
8.2/10 Very Good! (1,284 reviews)
Staff wasn’t properly instructed guess regarding about their stay

Reviewed on 22 Jun 2025

President Hotel

President Hotel

3.5 out of 5
South Beach
per person
2 Sept - 9 Sept
found 8 hours ago
Return flight included
St. Louis (STL) to Miami (MIA)
8.4/10 Very Good! (1,579 reviews)
Very nice place to stay, close to beach and Ocean dr, restaurants.

Reviewed on 22 Jun 2025

President Villa

President Villa

3.5 out of 5
South Beach
per person
2 Sept - 9 Sept
found 8 hours ago
Return flight included
St. Louis (STL) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
AC did not work, windows cant be opened either. We had No AC for 2 nights before we were finally placed in a smaller room with AC for our last night.

Reviewed on 18 Jun 2025

Kimpton EPIC Hotel by IHG

Kimpton EPIC Hotel by IHG

5 out of 5
Downtown Miami
per person
2 Sept - 9 Sept
found 8 hours ago
Return flight included
St. Louis (STL) to Miami (MIA)
8.8/10 Excellent! (1,848 reviews)
The property and staff are great. Rooms are beautiful. Pool is great.

Reviewed on 19 Jun 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 €175 per night from 23 Jun to 24 Jun
€175
23 Jun - 24 Jun
includes taxes & fees
8.4/10 Very Good! (1,214 reviews)
"Very nice one bedroom suite by the pool. If you have more than two I would get the two bedroom or you have to share the master bath. It was a little noisy at the pool at night but didn't really bother us much but some may not. We would stay again!"

Reviewed on 20 Jun 2025

Beachside Resort & Residences
Margaritaville Beach House Key West
Margaritaville Beach House Key West
4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is €289 per night from 6 Jul to 7 Jul
€289
6 Jul - 7 Jul
includes taxes & fees
8.6/10 Excellent! (1,726 reviews)
"Great staff"

Reviewed on 19 Jun 2025

Margaritaville Beach House 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 €191 per night from 29 Jun to 30 Jun
€191
29 Jun - 30 Jun
includes taxes & fees
8.8/10 Excellent! (1,667 reviews)
"We loved our 4 nights here, quiet and relaxed with no over crowding. Beautiful place, would defo stay again."

Reviewed on 20 Jun 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 1,742 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 €426. 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.