Dredgers Key Vacation Packages 2026 from $1,005

Dredgers Key flight + hotel vacation packages

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

Southernmost Beach Resort and Guesthouses

Old Town Key West

$1,005

per person

Apr 17 - Apr 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,454

per person

Apr 17 - Apr 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. Luggage storage and concierge services are also provided.

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$1,296

per person

Feb 22 - Feb 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

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. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

Old Town Key West

Save 100% on your flight

$1,796

per person

Apr 2 - Apr 7

just found

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and concierge services are also provided.

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$1,283

per person

Mar 1 - Mar 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, concierge services, and barbecue grills are also on offer.

Top Dredgers Key hotels deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

$585 total

per night

Jan 26 - Jan 27

Pool

Spa

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue Key West FL

Free Cancellation

Reserve now, pay when you stay

$547 total

per night

Jan 28 - Jan 29

Pool

Pet friendly

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$470 total

per night

Jan 25 - Jan 26

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 the picnic area. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.

Pool

Hot Tub

Parrot Key Hotel & Villas

2801 N Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$484 total

per night

Feb 2 - Feb 3

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, and valet parking. Unwind with a drink at the bar/lounge and enjoy perks like a free beach shuttle.

Pool

Pet friendly

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$441 total

per night

Jan 25 - Jan 26

This smoke-free hotel features a private beach, a marina, and 2 restaurants. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and an area shuttle.

On private beach

Pool

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$424 total

per night

Jan 26 - Jan 27

This Art Deco hotel features a private beach, a marina, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the outdoor pool and free perks like continental breakfast and WiFi in public areas.

On private beach

Pool

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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.

Frequently asked questions

How much are vacation packages to Dredgers Key?

Starting at just $1,005, hotel and flight packages are the perfect way to make your travel budget stretch further. Get ready Dredgers Key — here you come!

Where can I get the best vacation package deals for Dredgers Key?

No matter your adventure, Travelocity can help you lock in an unbeatable Dredgers Key package deal. All you need to do is pick and choose between our 400 partner airlines and 1,000,000 properties across the globe.

Why should I purchase my Dredgers Key vacation package with Travelocity?

Travel is all about making cherished memories and leaving all your stresses behind — which is why we have a team of customer service experts on hand around-the-clock should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our superb range of getaway packages. So what are you waiting for? There's no time like the present to secure that vacation you've always dreamed of.

Can I save on my Dredgers Key car rental if I combine it with my hotel or flight?

With a Dredgers Key vacation package, you can combine your car, flight and hotel bookings and save a whole lot. When you're ready to explore the best of this fabulous part of the world, why not start with Zoo Miami? This well-known sight is 110 mi from Dredgers Key. With your own set of wheels, you'll be there in no time.

What is the best time of year to go to Dredgers Key?

You'll land the lowest hotel prices in and pay the highest prices during . You can usually expect it to be more relaxed in August, September and October, while you'll find a lot more like-minded travelers to meet in January, February and July. It all depends on what you're willing to pay, the climate and how well you deal with crowds.

Which airport is best for Dredgers Key?

Key West Intl. Airport (EYW), the major terminal in Dredgers Key, is where you'll get off the plane. It's located 2 mi southeast of the center of town.