Dredgers Key Vacation Packages 2026 from $841

Dredgers Key flight + hotel vacation packages

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

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$841

per person

Oct 16 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

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 also offered.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,215

per person

Oct 10 - Oct 17

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.

Ella's Cottages - Key West Historic Inns

Old Town Key West

$1,726

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

An outdoor pool, self parking, and concierge services are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.

Ibis Bay Beach Resort

Northside Resort

Save 100% on your flight

$1,035

per person

Nov 14 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

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.

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

Old Town Key West

Save 100% on your flight

$1,972

per person

Nov 21 - Nov 26

found 1 hour ago

Roundtrip 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 is also provided.

Top Dredgers Key hotels deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$203 nightly

$228 total

Sep 2 - Sep 3

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

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$136 nightly

$153 total

Aug 30 - Aug 31

Total with taxes and fees

On private beach

Pool

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$200 nightly

$225 total

Sep 13 - Sep 14

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

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$166 nightly

$187 total

Aug 30 - Aug 31

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

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$182 nightly

$204 total

Aug 30 - Aug 31

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

Hyatt Centric Key West Resort and Spa

601 Front St Key West FL

Free Cancellation

Reserve now, pay when you stay

$270 nightly

$304 total

Sep 28 - Sep 29

Total with taxes and fees

This smoke-free resort features a full-service spa, a marina, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.

Pool

Spa

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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 $841, 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.