Dredgers Key Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Dredgers Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
Old Town Key West
Price was CA $2,672, price is now CA $1,994 per person
CA $1,994
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.6/10 Excellent! (376 reviews)
Great location, wonderful room, great pool, and great views. Lacking services: no shuttle, no restaurant, you pay resort fees per night but no amenities? We feel like they used the bait and switch on us, great reservation price on room but hit you with nightly fees once you get there. That was our only real negative

Reviewed on Jun 16, 2026

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was CA $4,199, price is now CA $2,985 per person
CA $2,985
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (558 reviews)
We loved staying here and highly recommended it. Only thing that people might not like is the solo musicians play till 11pm every night. We didn’t mind it since we are not early birds.

Reviewed on Jun 7, 2026

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was CA $3,184, price is now CA $2,291 per person
CA $2,291
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,121 reviews)
Loved the layout of the suites - perfect for traveling with family and/or kids. Property was very clean with pool, sand volleyball, multiple yard games, outdoor bar, hammocks, etc. Parking was easy and convenient.

Reviewed on Jun 15, 2026

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Price was CA $3,048, price is now CA $2,227 per person
CA $2,227
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,094 reviews)
Clean room and quiet property. Short distance by car to Duval Street. Nice amenities on property. Enjoyed the pool. Would stay here again.

Reviewed on Jun 14, 2026

Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
Price was CA $2,798, price is now CA $2,164 per person
CA $2,164
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (1,171 reviews)
Great location for Duval Street. Rooms were dated. Service at restaurants was slow. I expected more for what we paid. Very average.

Reviewed on Jun 16, 2026

Ready to book your vacation to Dredgers Key?

 

Choose your dates

Dredgers Key Hotel Deals

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Jun 21 to Jun 22
CA $175
CA $276 total
Jun 21 - Jun 22
includes taxes & fees
8.4/10 Very Good! (2,402 reviews)
"It was amazing! Staff is friendly and helpful. We can’t wait to return"

Reviewed on Jun 17, 2026

Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $285 per night from Jun 29 to Jun 30
CA $285
CA $423 total
Jun 29 - Jun 30
includes taxes & fees
8.8/10 Excellent! (3,406 reviews)
"Easy to get around, excellent pools, clean rooms. Just a very relaxing place to stay."

Reviewed on Jun 17, 2026

Southernmost Beach Resort and Guesthouses
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from Jun 22 to Jun 23
CA $183
CA $245 total
Jun 22 - Jun 23
includes taxes & fees
8/10 Very Good! (1,239 reviews)
"We had a great time. No complimentary breakfast as advertised but the shuttle to downtown was great"

Reviewed on Jun 17, 2026

Hilton Garden Inn Key West / The Keys Collection
See all 2,783 properties in Dredgers Key
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

Can I cancel my flight booking to Dredgers Key due to COVID-19?
Visit our Customer Service Portal for important information about changing or canceling flights because of COVID-19. Also, check the terms and conditions of the airline you're considering before booking your journey to Dredgers Key.
What's the best way to find cheap flights to Dredgers Key that have flexible change policies?
We know that plans can change in the blink of an eye, so choosing a flexible fare with Expedia is always a smart move. Just check the "No change fee" box underneath the "Flexible change policies" filter. Your low-cost, flexible flight to Dredgers Key is only a few clicks away.
What are some of the general tips for travelers to Dredgers Key during the COVID-19 outbreak?
COVID-19 has triggered dramatic changes to how we travel. If you're flying to Dredgers Key, the following tips will help you navigate travel's newest challenges:
  • Investigate the restrictions and rules in both your origin and destination. You may not be able to travel depending on local circumstances, so check before you book your flight.
  • You must wear a face mask at the airport, including at screening checkpoints. Be ready to lower your mask for ID purposes when asked.
  • Do not hand your boarding pass directly to a TSA employee. Instead, place your pass on the reader and then hold it up for the agent to visually inspect it.
  • One container of liquid hand sanitizer is now allowed in your carry-on bag. It must not be larger than 12 oz (350 ml), and you'll need to remove it from your bag at the X-ray machine for scanning.
  • Put any personal items (phone, wallet and keys) in your carry-on instead of a bin to reduce handling during screening.
  • Transport any food items in a clear plastic bag and also put them in a screening bin. Keeping food separate from your carry-on makes it less likely that a TSA officer will need to touch and open your bag for inspection.

Which airlines fly to Dredgers Key?
Let Delta take you there. This top carrier provides 191 services every month to Key West Intl. Airport (EYW), a Dredgers Key gateway.
How can I find cheap tickets to Dredgers Key?
You'll always pick up an awesome deal with Expedia, but our "flexible dates" feature makes it that much easier. Enter your preferred flight date, then check the flexible dates box above to compare prices for nearby days. was the cheapest price for a flight to Dredgers Key in the last seven days.
How much is a flight to Dredgers Key?
In the last seven days, return airfares to Dredgers Key sold from just and reached a maximum cost of . For one-way trips departing from (), the lowest amount paid during this same period was just .
What are the most popular airports to fly into in Dredgers Key?
The principal gateway to Dredgers Key, about 1119 flights touch down at Key West Intl. Airport (EYW) each month. Find a great deal, reserve your fare and get ready to discover this popular region.
When is the cheapest time to fly to Dredgers Key?
Take off for Dredgers Key early in the week and you'll usually be rewarded with lower-priced fares. Tuesday is typically the cheapest day to get on a plane, with Monday a close second. If you want to avoid the most expensive flights, keep clear of Saturdays.
How much is a plane ticket to Dredgers Key?
Plane fares varied from to over the last seven days. When you're ready to book, we'll help you grab the best price to Dredgers Key.
Which airlines with flights to Dredgers Key employ COVID-19 cleanliness policies?
In response to the ongoing COVID-19 pandemic, the majority of airlines have adopted extra steps and measures to help their passengers fly with extra peace of mind. Check out what these carriers are doing:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.