Dredgers Key Vacation Packages

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Top Dredgers Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was CA $1,581, price is now CA $1,173 per person
CA $1,173
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,234 reviews)
A nice property. Kim, the shuttle driver is terrific. Diana at the front desk is very kind. Spacious rooms. You should get a marina facing room.

Reviewed on Apr 11, 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was CA $4,530, price is now CA $2,862 per person
CA $2,862
per person
May 15 - May 18
found 17 hours ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.2/10 Wonderful! (542 reviews)
Great location! We were very impressed with Chris! He told us where to park and was very welcoming when we arrived. The loft room setup was perfect for us and the Bali Bar did not disappoint! We will be back!!

Reviewed on Apr 5, 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 $2,254, price is now CA $1,565 per person
CA $1,565
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,004 reviews)
This place was beautiful and immaculate. Wonderful views of the water. Very nice pool, sandy beach area, tiki bar and hot tub. The rooms could not be nicer. Parking was ample. No restaurant but plenty nearby. Will definitely want to come back here

Reviewed on Apr 12, 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 $2,050, price is now CA $1,471 per person
CA $1,471
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,011 reviews)
Stayed for 5 nights and it could not have been better. Amazing views of the ocean and beautiful room. We were out on the balcony more than inside. Incredibly spacious and more than enough room for our family. Very quiet and away from the craziness of duval

Reviewed on Apr 11, 2026

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
Old Town Key West
Price was CA $3,057, price is now CA $2,217 per person
CA $2,217
per person
Jun 12 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
8.4/10 Very Good! (595 reviews)
We had a great time. The hotel is beautiful and in a great location. The beach and two pools are perfectly located. A easy walk to Duval st. The rooms are nice but not much storage or closet space for clothing. The showers could use some shelving for personal shower products. The food and drinks are outrageously expensive, so you may wa t to think about dinner and drinks elsewhere. Overall we really loved the place. The staff was amazing. We will come back next year.

Reviewed on Apr 11, 2026

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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 $248 per night from May 10 to May 11
CA $248
CA $357 total
May 10 - May 11
includes taxes & fees
8.2/10 Very Good! (2,087 reviews)
Clean room, 2 nice pools, everything has been remodeled. Definitely would stay there again.

Reviewed on Apr 12, 2026

Blue Flamingo Resort Key West
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $349 per night from May 12 to May 13
CA $349
CA $480 total
May 12 - May 13
includes taxes & fees
8.8/10 Excellent! (1,813 reviews)
Hotel pictures online have not been updated to current condition. All room doors are located outside. Gaps under the door which can let bugs in. After checking into our room, my family brought dinner to the room. After about 15 mins our counter and food was covered in ants. Ants were also in the ...

Reviewed on Apr 8, 2026

Margaritaville Beach House Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
The price is CA $444 per night from May 12 to May 13
CA $444
CA $600 total
May 12 - May 13
includes taxes & fees
8.8/10 Excellent! (3,211 reviews)
Clean, great location

Reviewed on Apr 12, 2026

Southernmost Beach Resort and Guesthouses
See all 2,804 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.
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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.

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