Dredgers Key Vacations from $379
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The Latest Dredgers Key vacation packages
Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $550, price is now $379 per person
$379
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,068 reviews)
easy access to fishing, shuttle to key west, great rooms
Reviewed on Aug 20, 2025
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,869, price is now $996 per person
$996
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (775 reviews)
The property is cute with its own unique vibe. Our room did smell a bit musty, but it’s damp south Florida…so I took that with a grain of salt. There was some mold in our bathroom grout also, but I wasn’t in the mood to complain about something so petty. One thing I will rave about was Jefferson, he was working at the pool bar and not only was he a joy to talk to, he made a great drink!
Reviewed on Aug 19, 2025
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $963, price is now $571 per person
$571
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,008 reviews)
Hotel was very spacious. Enjoyed the view of the beach. The concierge was very friendly and helpful.
Reviewed on Aug 18, 2025
Bishop Hotel Key West
Old Town Key West
Save 100% on your flight
Price was $725, price is now $504 per person
$504
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (220 reviews)
Great stay all the way around.
Reviewed on Aug 19, 2025
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Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $207 total per night from Aug 25 to Aug 26
$207 total
Aug 25 - Aug 26
Total with taxes and fees
8.4/10 Very Good! (1,471 reviews)
"I decided to go with this property despite some negative reviews and I am so glad i did. The entire stay was perfect. Staff was so nice and helpful. Special shout out to Ro for making sure we were taken care of. Definitely book again!"
Reviewed on Aug 20, 2025
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $247 total per night from Sep 2 to Sep 3
$247 total
Sep 2 - Sep 3
Total with taxes and fees
8.8/10 Excellent! (1,716 reviews)
"I loved everything about this resort. So clean and easy to navigate our way around. Transportation offered worked well for us."
Reviewed on Aug 18, 2025
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $142 total per night from Sep 1 to Sep 2
$142 total
Sep 1 - Sep 2
Total with taxes and fees
7.8/10 Good! (1,069 reviews)
"Most excellent facility with very accommodating staff."
Reviewed on Aug 18, 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.