Explore top 2026 4 Star Hotels in Dredgers Key

Name: Winslow's Bungalows - Key West Historic Inns
Price range: $309 total
Rating: 9.2

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Top Dredgers Key 4 Star hotels

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$166 nightly

$187 total

Oct 28 - Oct 29

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 a playground, and families will appreciate ...

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

$255 nightly

$287 total

Oct 28 - Oct 29

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like a free airport shuttle. You'll appreciate the hot tub, ...

8.8/10 Excellent! (1,808 reviews)

"Great property."

Reviewed on Oct 24, 2026

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$209 nightly

$235 total

Nov 16 - Nov 17

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 ...

9/10 Wonderful! (1,897 reviews)

"Great hotel, not crowded, great staff. Enjoyed the breakfast and drinks that came with the package. Would recommend."

Reviewed on Oct 27, 2026

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

$221 nightly

$249 total

Oct 28 - Oct 29

Total with taxes and fees

A full-service spa, 3 outdoor pools, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 2 conference rooms, free WiFi ...

8.6/10 Excellent! (3,655 reviews)

"Clean room, clean pools, great bars, great staff, so great"

Reviewed on Oct 27, 2026

Parrot Key Hotel & Villas

2801 N Roosevelt Blvd Key West FL

$194 nightly

$218 total

Oct 28 - Oct 29

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! (1,487 reviews)

"We love the sunset pier and the beach chairs a lot"

Reviewed on Oct 27, 2026

Hilton Key West Resort & Marina

5950 Peninsular Avenue Key West FL

$166 nightly

$187 total

Oct 29 - Oct 30

Total with taxes and fees

A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas ...

9/10 Wonderful! (1,805 reviews)

"Cleanest resort in the keys!"

Reviewed on Oct 27, 2026

Pier House Resort & Spa

1 Duval St Key West FL

$257 nightly

$289 total

Nov 2 - Nov 3

Total with taxes and fees

This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...

Opal Key Resort & Marina, Key West

245 Front Street Key West FL

$294 nightly

$331 total

Oct 28 - Oct 29

Total with taxes and fees

A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Enjoy the outdoor pool and visit the 3 bars/lounges and poolside bar for ...

9.2/10 Wonderful! (1,221 reviews)

"Great location, friendly staff, awesome Mexican restaurant. Cold pool!"

Reviewed on Oct 27, 2026

DoubleTree Resort by Hilton Grand Key - Key West

3990 S Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$149 nightly

$167 total

Oct 29 - Oct 30

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 ...

Winslow's Bungalows - Key West Historic Inns

725 Truman Avenue Key West FL

$275 nightly

$309 total

Oct 28 - Oct 29

Total with taxes and fees

This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. WiFi in public areas is free. Self parking, a garden, and luggage storage are ...

9.2/10 Wonderful! (1,475 reviews)

"We had a small cottage and the humidity was so high that everything was damp all the time . When you get in bed with very damp sheets and pillows too . There was a small dehumidifier in the room and did take 2 cups of water out of the air . Place was very well kept, grounds was amazing, we were in ..."

Reviewed on Oct 27, 2026

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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 Dredgers 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 Dredgers 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 Dredgers 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 Dredgers 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.