Explore top 2026 4 Star Hotels in Cudjoe Key

Name: WINTER WEEK - KEY WEST - 2 Bedroom 2 Bathrooms Sleeps 6
Rating: 10

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Top Cudjoe Key 4 Star hotels

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$382 nightly

$430 total

Mar 10 - Mar 11

Total with taxes and fees

This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and an arcade/game room, and families will appreciate ...

8.2/10 Very Good! (1,953 reviews)

Bathroom was not cleaned properly. Elevator was out of service. This place was overrated and super expensive in addition to the $66 resort fee. I would not recommend it.

Reviewed on Feb 25, 2026

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue Key West FL

Fully refundableReserve now, pay when you stay

$373 nightly

$420 total

Mar 4 - Mar 5

Total with taxes and fees

A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. ...

9/10 Wonderful! (1,807 reviews)

check in was not the greatest from previous stays

Reviewed on Feb 26, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$427 nightly

$480 total

Mar 25 - Mar 26

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll ...

8.8/10 Excellent! (1,779 reviews)

Staff very friendly and helpful, received daily texts for anything we needed, room accommodations excellent, hotel restaurant food very good and really no complaints. Will definitely stay there again!

Reviewed on Feb 24, 2026

The Perry Hotel & Marina Key West

7001 Shrimp Road Key West FL

Fully refundableReserve now, pay when you stay

$428 nightly

$481 total

Mar 2 - Mar 3

Total with taxes and fees

A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling for business? Take advantage of the free WiFi in public areas, ...

9.4/10 Exceptional! (1,212 reviews)

Staff was very responsive. Great hotel! Only complaint was the bar got my food order wrong.

Reviewed on Feb 25, 2026

DoubleTree Resort by Hilton Grand Key - Key West

3990 S Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$411 nightly

$462 total

Mar 22 - Mar 23

Total with taxes and fees

This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...

8.2/10 Very Good! (1,000 reviews)

Nice clean hotel. Smathers beach right down the road. Shuttle to Duval and the airport were very nice.

Reviewed on Feb 24, 2026

Parrot Key Hotel & Villas

2801 N Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$433 nightly

$487 total

Mar 4 - Mar 5

Total with taxes and fees

This smoke-free hotel features 4 outdoor pools, a gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, ...

9/10 Wonderful! (1,305 reviews)

Everything was exceptional

Reviewed on Feb 25, 2026

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$359 nightly

$404 total

Mar 23 - Mar 24

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub ...

8.8/10 Excellent! (1,691 reviews)

This is an excellent place. Clean, adorable, extremely comfortable. We loved it.

Reviewed on Feb 25, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. Families will appreciate the onsite laundry facilities and babysitting. Enjoy ...

8.4/10 Very Good! (999 reviews)

Room was clean and comfortable but after first day towels were shorted. Had to ask for more twice Desk staff were very nice and helpful. Concierge was helpful with rentals Restaurant was not as good as past stays when Sheraton. Food even pancakes were tough and overcooked. Shuttle drivers were very ...

Reviewed on Dec 4, 2025

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Key West - Stock Island

Key West FL

This vacation home features laundry facilities.

9.6/10 Exceptional! (37 reviews)

Wonderful host and very nice/clean place with just about everything you need! Very efficient and communicative host!

Reviewed on Jan 3, 2026

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WINTER WEEK - KEY WEST - 2 Bedroom 2 Bathrooms Sleeps 6

Key West FL

An outdoor pool is featured at this condo, along with laundry facilities and barbecue grills.

10/10 Exceptional! (1 review)

Cozy Key West

Great stay over Christmas, very cozy, clean, comfortable and safe. Just minutes from everything. Loved the Boat House Bar, the Front Desk Gal was awesome, informative and friendly, Plenty of parking, bike and motorcycle storage. Plan to stay again in the next few months.

Reviewed on Jan 9, 2019

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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.

4 Star Hotels Cudjoe Key

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Cudjoe Key 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Cudjoe Key will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Cudjoe Key, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.