Cudjoe Key Holidays from £831

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Your Cudjoe Key Holiday

Say bye-bye to the hassle of planning and hello to a Cudjoe Key holiday package. With everything organised before you go, you can focus on discovering this city, starting with Sugarloaf Shores, which is great for families, fishing and views. Make your trip to Cudjoe Key even more fulfilling by including some sightseeing. Florida Keys Beaches, Sugarloaf Beach and Upper Sugarloaf Sound are among the most popular attractions worth exploring. Whoever you're going away with and whether your budget is big or small, your ultimate Cudjoe Key holiday is just a few clicks away with Expedia.

The Latest Cudjoe Key Holiday Deals

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
22 Jul - 29 Jul
found 4 hours ago
Return direct flight included
Edinburgh (EDI) to Miami (MIA)
8.4/10 Very Good! (1,000 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

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
22 Aug - 29 Aug
found 1 day ago
Return direct flight included
London (LHR) to Miami (MIA)
9.2/10 Wonderful! (1,175 reviews)
The vibe is natural and luxury

Reviewed on 13 Jun 2025

The Shelborne By Proper

The Shelborne By Proper

4 out of 5
South Beach
Save 100% on your flight
per person
22 Jul - 29 Jul
found 4 hours ago
Return direct flight included
Edinburgh (EDI) to Miami (MIA)
10/10 Exceptional! (3 reviews)
Everything was amazing- The accommodations, the property decor, the staff like Adrian and Chef Luis were very personable and welcoming. Our room was upgraded from partial ocean view to full as we were celebrating our 23rd wedding anniversary, so that was a nice touch. We would definitely book again.

Reviewed on 31 May 2025

Pelican Hotel

Pelican Hotel

4 out of 5
South Beach
per person
22 Jul - 29 Jul
found 4 hours ago
Return direct flight included
Edinburgh (EDI) to Miami (MIA)
9.2/10 Wonderful! (340 reviews)
The hotel was very clean and the service was wonderful; however, the mattress caused

Reviewed on 12 May 2025

Miami accommodations BeachFront

Miami accommodations BeachFront

2 out of 5
South Beach
per person
22 Aug - 29 Aug
found 1 day ago
Return direct flight included
London (LHR) to Miami (MIA)
10/10 Exceptional! (1 review)
Great landlord Good hospitality Spacious unit All in all good environment for family to stay

Reviewed on 31 May 2025

Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
South Beach
Save 100% on your flight
per person
22 Jul - 29 Jul
found 4 hours ago
Return direct flight included
Edinburgh (EDI) to Miami (MIA)
9.2/10 Wonderful! (157 reviews)
The staff were great and the property is nice.

Reviewed on 12 Jun 2025

Cudjoe Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)
Population
1,750
Max Temp Winter
24ºC
Max Temp Summer
29ºC
Top Sights
Florida Keys Beaches, Sugarloaf Beach and Big Pine Key Flea Market

Our pick of the best Cudjoe Key Hotel Deals

Beachside Resort & Residences
Beachside Resort & Residences
3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Stay at this 3.5-star beach hotel in Key West. Enjoy free Wi-Fi, 2 restaurants and a private beach. Our guests praise the pool and the helpful staff in their ...
8.4/10 Very Good! (1,175 reviews)
"Very nice hotel."

Reviewed on 14 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
Stay at this 4-star beach hotel in Key West. Enjoy breakfast (surcharge), room service and a 24-hour fitness centre. Our guests praise the pool and the restaurant ...
8.6/10 Excellent! (1,712 reviews)
"Loved the place!"

Reviewed on 12 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
Stay at this 4-star luxury hotel in Key West. Enjoy free Wi-Fi, 6 outdoor pools and a marina. Our guests praise the pool and the restaurant in their reviews. ...
8.8/10 Excellent! (1,666 reviews)
"The property is beautiful, quiet and shuttle was a plus. The staff are very friendly. Loved our visit and plan to return! Thank you for the experience."

Reviewed on 12 Jun 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 1,745 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Cudjoe Key travel package cost?
Starting from an incredible £831, you can tailor your Cudjoe Key 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 Cudjoe Key travel package?
Don’t worry if you’re rethinking your Cudjoe Key travel package — you can cancel or change your booking. And if you’ve booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We get that your circumstances can change suddenly, so make your way to our Customer Service Portal if that happens. When you’re ready to make changes, we’re ready to help.
How do I get a cheap travel package to Cudjoe Key?
Booking a Cudjoe Key travel package with Expedia is such a simple way to save. We have over 550 partner airlines and 1,000,000 hotel options worldwide. With such a fabulous range to select from, you’ll have no issues putting together your ideal trip.
Does Expedia offer Book Now, Pay Later Cudjoe Key holidays?
Yes. Expedia has teamed up with online lender Klarna to help you easily pay for your trip in instalments. Simply click on the payment plan that works for you during the checkout process and take the stress out of budgeting for your trip. Be sure to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your buck. Check out our flexible payment options below:

  • Pay monthly holidays: Klarna offers convenient monthly payment plans that suit all budgets, so you can take that well-deserved holiday now.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay off your trip in multiple transactions.
  • Low deposit holidays: When you spot an unbeatable deal but your budget doesn’t quite cover it yet, Klarna’s low deposit holiday plan will help you get what you want.

Where should I stay in Cudjoe Key?
A getaway in Cudjoe Key wouldn’t be complete without seeing Upper Sugarloaf Key. Why not choose a hotel near this popular attraction?
What are the top hotels in Cudjoe Key?
Waterfront Fresh And Cosy 2 Bedroom 35 Sea Wallnew Uv Light Air Purification Safe and Oceanside Paradise In The Fl Keys Free Kayaks Bikes Wifi Outdoor Bbq Grill are both well-liked options in the Cutthroat Harbour Estates neighbourhood. If you prefer to spend time in the Cudjoe Gardens area, consider booking a room at Waterfront Fresh And Cosy 2 Bedroom 35 Sea Wallnew Uv Light Air Purification Safe or It’s The Caribbean Of The Usa Illness Prompts Winter Opening. Prefer Monthly.
How far in advance should I book my Cudjoe Key holiday?
To land discount prices, book early. Airlines typically release tickets, along with some of the lowest fares, around a year in advance. Hotels, experiences and car rental should also be booked early so you can have the pick of the bunch. If you’ve decided on a last-minute getaway in Cudjoe Key, there are always plenty of great deals to be had on Expedia. Book something in today!
What does an Expedia Cudjoe Key travel package include?
With Expedia, you can choose a combination of car rentals, hotels and flights to create your ideal Cudjoe Key travel package. Once you’ve made your booking, you can add on the fun things like sightseeing tours and activities. Remember, the more you bundle, the more you’ll save!
What should I know before booking a Cudjoe Key travel package?
Our prices are always low. However, you’ll score an even better deal when you book your flights, hotels and car rentals together. With an Expedia travel package, you’ll get transparent pricing and lots of choice.
Can I choose my airline with a Cudjoe Key Expedia travel package?
Yes — that’s one of the best things about an Expedia package. You can mix and match your flights, hotels and more. We have access to more than 550 partner airlines throughout the world, so you have options galore when arranging your Cudjoe Key trip.

* 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.