Dredgers Key Vacations from $621
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The Latest Dredgers Key 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
Price was $1,050, price is now $621 per person
$621
per person
Jan 20 - Jan 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,016 reviews)
This was our third time staying there, and we are booked for next June
Super clean, all amenities you need for a couple of days or a couple of weeks.
Reviewed on Nov 6, 2025
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,783, price is now $1,462 per person
$1,462
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,021 reviews)
Good breakfast. Nice pools.
Reviewed on Nov 6, 2025
The Key West Hotel
Key West Historic District
Price was $4,515, price is now $2,471 per person
$2,471
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (498 reviews)
Great location and friendly staff. They have remodeled a lot and are doing a super job. Nice decorations and LOVE the tiki bar and pool area. Key West Aloe products were a nice touch as well as the key lime cookies. The porch deck and handrail outside the Envy/Lust room needs a little attention. Overall, very comfortable and accommodating. I would definitely stay here again.
Reviewed on Oct 17, 2025
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $2,827, price is now $1,593 per person
$1,593
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (1,732 reviews)
Room was typical Florida room. Clean, but musty. Staff was very nice. Location not good. Nothing around the hotel. Can’t stand the $50 resort fee add on - just include it in the advertised room rate
Reviewed on Nov 4, 2025
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Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
$206 nightly
The price is $232 total per night from Nov 16 to Nov 17
$232 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (1,733 reviews)
We’ve stayed here twice now. Staff is great, the shuttle into town is super convenient (hi Jeffrey!). We love that you can use the kayaks or paddleboards every day. The tiki hut crew is the best! The place is clean and I feel safe walking around there. It’s well lit and easy to navigate.
Reviewed on Nov 2, 2025
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $177 total per night from Nov 30 to Dec 1
$177 total
Nov 30 - Dec 1
Total with taxes and fees
7.8/10 Good! (1,648 reviews)
Beautiful room, great view, love the pools, bars and lawn games
Reviewed on Nov 3, 2025
Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $209 total per night from Nov 30 to Dec 1
$209 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (1,655 reviews)
Staff good but never clean our room
Reviewed on Nov 3, 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.
Find the Best Dredgers Key Vacation Packages
Dredgers Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Key West Intl. Airport (EYW) |
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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.
