Dredgers Key Vacation Packages 2026 from $1,431

Dredgers Key flight + hotel vacation packages

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

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$1,431

per person

Jul 2 - Jul 6

found 1 day ago

Roundtrip non-stop 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.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,499

per person

Jul 2 - Jul 6

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.

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

Old Town Key West

Save 100% on your flight

$2,540

per person

Jun 7 - Jun 12

found 16 hours 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.

The Reach Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

$1,573

per person

Jul 12 - Jul 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This resort features a private beach, a full-service spa, and a restaurant. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. Enjoy the outdoor pool and unwind at the bar/lounge and poolside bar.

Sky Suites Retreat by Brightwild 2 Stunning Condos

Old Town Key West

Save 100% on your flight

$6,212

per person

Jul 1 - Jul 6

just found

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

Free WiFi in public areas is available at this apartment. Take advantage of the free self parking.

Top Dredgers Key hotels deals

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$211 nightly

$238 total

May 25 - May 26

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

$256 nightly

$288 total

May 11 - May 12

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

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$250 nightly

$281 total

May 26 - May 27

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a 24-hour gym on site, and a 24-hour front desk and dry cleaning are also provided.

Pool

Pet friendly

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$377 nightly

$425 total

May 3 - May 4

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

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

Reserve now, pay when you stay

$330 nightly

$372 total

May 19 - May 20

Total with taxes and fees

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.

Pool

Spa

Hilton Garden Inn Key West / The Keys Collection

3850 N Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$177 nightly

$199 total

May 25 - May 26

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an outdoor pool, and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like a free area shuttle.

Pool

Hot Tub

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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 $1,431, 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.