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 $1,431, price is now CA $1,018 per person
CA $1,018
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,277 reviews)
Loved my stay. Will come again!

Reviewed on May 26, 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 $2,346, price is now CA $1,416 per person
CA $1,416
per person
Aug 20 - Aug 25
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,098 reviews)
The room and balcony were fantastic. The pool, grounds, and view of the ocean were lovely. The staff was super welcoming and friendly when we arrived. We enjoyed the close restaurant and walking path right across the street.

Reviewed on May 28, 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 $2,547, price is now CA $1,682 per person
CA $1,682
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,060 reviews)
Everything was great during our stay - the villa, the property and friendly, helpful staff. Very convenient, easy access to all Key West activities, great amenities on the property, lovely beach area, pool and tiki-hut, good restaurants around. Will definitely book there again.

Reviewed on May 26, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Price was CA $2,985, price is now CA $2,008 per person
CA $2,008
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,000 reviews)
Beautiful property. Excellent service.

Reviewed on May 15, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Price was CA $1,514, price is now CA $1,097 per person
CA $1,097
per person
Aug 20 - Aug 25
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.8/10 Excellent! (3,329 reviews)
I liked the room and the resort , the pool was great , I think for me a few times it was just other guests that was a turn off in one way or another. P.S. add a smoking section somewhere , would t be a bad idea . Over all was great stay !!

Reviewed on May 27, 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 $186 per night from May 31 to Jun 1
CA $186
CA $287 total
May 31 - Jun 1
includes taxes & fees
8.4/10 Very Good! (2,291 reviews)
"Excelente lugar a la entrada de Key West, muy cómo, excelente atención del personal que domina varios idiomas, la habitación super limpia y ordenada."

Reviewed on May 28, 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 $317 per night from Jun 7 to Jun 8
CA $317
CA $444 total
Jun 7 - Jun 8
includes taxes & fees
8.8/10 Excellent! (1,802 reviews)
"The hotel/resort was large yet the pool had 11 umbrella and many thirty loungers to use. It was almost impossible to get a seat in shade. The rooms had one chair in it that was extremely low to the floor and difficult to get in and out of. We did love the access to downtown shuttles. Next time I ..."

Reviewed on May 27, 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 $282 per night from Jun 11 to Jun 12
CA $282
CA $418 total
Jun 11 - Jun 12
includes taxes & fees
8.8/10 Excellent! (3,341 reviews)
"I liked the room and the resort , the pool was great , I think for me a few times it was just other guests that was a turn off in one way or another. P.S. add a smoking section somewhere , would t be a bad idea . Over all was great stay !!"

Reviewed on May 27, 2026

Southernmost Beach Resort and Guesthouses
See all 2,813 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.