Dredgers Key Vacation Packages 2026 from $1,182

Dredgers Key flight + hotel vacation packages

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

The Southernmost Inn - Adults Only

Old Town Key West

Save 100% on your flight

$1,182

per person

Nov 2 - Nov 7

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel's 2 outdoor pools and hot tub are among the featured amenities. Enjoy the free continental breakfast each morning. Self parking, a coffee shop, and a terrace are also offered.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,524

per person

Nov 2 - Nov 7

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 Gardens Hotel

Old Town Key West

Save 100% on your flight

$2,210

per person

Nov 24 - Nov 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

2 outdoor pools, 2 bars/lounges, and a restaurant are among this bed & breakfast's featured amenities. Business travelers can take advantage of the free WiFi in public areas. Relax with a drink at the poolside bar and enjoy the free cooked-to-order breakfast each morning.

The Marker Key West Harbor Resort

Key West Historic District

Save 100% on your flight

$2,268

per person

Nov 2 - Nov 7

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 House - Adult Exclusive

Old Town Key West

Save 100% on your flight

$1,739

per person

Nov 2 - Nov 7

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.

Top Dredgers Key hotels deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$210 nightly

$237 total

Sep 16 - Sep 17

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, along with dry cleaning/laundry services. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a gym.

Pool

Spa

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$188 nightly

$212 total

Sep 13 - Sep 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

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$160 nightly

$180 total

Sep 13 - Sep 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

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$234 nightly

$263 total

Sep 23 - Sep 24

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

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$166 nightly

$187 total

Sep 27 - Sep 28

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

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$306 nightly

$344 total

Sep 20 - Sep 21

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 $1,182, 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.