Dredgers Key Vacation Packages 2026 from $2,172

Dredgers Key flight + hotel vacation packages

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

Southernmost House - Adult Exclusive

Old Town Key West

Save 100% on your flight

$2,172

per person

Dec 30 - Jan 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. WiFi in public areas is free. Self parking, a terrace, and a picnic area are also offered.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,864

per person

Dec 30 - Jan 5

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.

The Marker Key West Harbor Resort

Key West Historic District

Save 100% on your flight

$2,630

per person

Dec 30 - Jan 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This smoke-free hotel features 3 outdoor pools, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

Southernmost Beach Resort and Guesthouses

Old Town Key West

Save 100% on your flight

$2,229

per person

Dec 30 - Jan 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

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 in public areas, and laundry service. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a gym.

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Old Town Key West

$5,470

per person

Dec 29 - Jan 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

An outdoor pool is featured at this cottage, along with free WiFi in public areas.

Top Dredgers Key hotels deals

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

$265 nightly

$298 total

Oct 13 - Oct 14

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, poolside bar, and concierge services.

Pool

Hot Tub

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$175 nightly

$197 total

Oct 13 - Oct 14

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 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

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$187 nightly

$210 total

Oct 14 - Oct 15

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 and perks like free self parking.

Pool

Hot Tub

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$192 nightly

$216 total

Oct 13 - Oct 14

Total with taxes and fees

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

$172 nightly

$193 total

Oct 13 - Oct 14

Total with taxes and fees

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

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$276 nightly

$310 total

Oct 25 - Oct 26

Total with taxes and fees

A private beach, a full-service spa, and 2 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the gym and perks like free WiFi.

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 $2,172, 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.