
Dredgers Key Vacations from $592
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to $1,045 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
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 $896, price is now $592 per person
$592
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,016 reviews)
Room was wonderful, just a few signs of wear and tear in the bathrooms.
Didnt realize how close it was to the airport but was not a problem.
Enjoyed the balcony and the swimming pool
Reviewed on Sep 20, 2025

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,440, price is now $899 per person
$899
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (791 reviews)
The Light House Hotel in Key West has always been an enjoyable stay. Right from Checking in at the desk. The staff if so welcoming also the staff that prepares and sets up the complimentary breakfast service and my most
Recent visit during the bars remodeling the” Grab and Go Breakfast Service was so nicely prepared and displayed always kept fresh.
My room was kept clean and fresh. The location is right there near everything.
Reviewed on Sep 18, 2025


Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,063, price is now $713 per person
$713
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,722 reviews)
my stay at this resort was good at first they gave me a room that I didn’t like I booked a suite with ocean view, they gave me a room seeing the mangrove was upset about that so they didn’t get to switch me out until the next day which they gave me a room which wasn’t a suite and then on the last day they gave me a different room that is a suite with Ocean view The staff were OK. Didn’t really like the bartender staff there weren’t nice. The food was good overall the hotel is clean and nice and concierge and some of the front desk. Staff were very nice and also the Butler was very nice and I love the shuttle driver He was so sweet.
Reviewed on Sep 17, 2025

The Grand Guesthouse
Old Town Key West
Save 100% on your flight
Price was $1,446, price is now $1,025 per person
$1,025
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,003 reviews)
When we arrived our room had the trash from the prior guests and no bath towels. Faucet had no pressure.
Reviewed on Aug 25, 2025
Don't see what you're looking for?
See all available trips from Columbus to Dredgers Key
View all tripsDredgers Key Hotel Deals

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
$192 nightly
The price is $216 total per night from Sep 28 to Sep 29
$216 total
Sep 28 - Sep 29
Total with taxes and fees
8.8/10 Excellent! (1,720 reviews)
"Excellent Property"
Reviewed on Sep 14, 2025

Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$195 nightly
The price is $219 total per night from Sep 24 to Sep 25
$219 total
Sep 24 - Sep 25
Total with taxes and fees
8.4/10 Very Good! (1,539 reviews)
"Pool could be colder!"
Reviewed on Sep 18, 2025

Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
$235 nightly
The price is $264 total per night from Oct 5 to Oct 6
$264 total
Oct 5 - Oct 6
Total with taxes and fees
8.6/10 Excellent! (1,780 reviews)
"Conveniently located hotel. SHUTTLE to Duvall Street & Airport"
Reviewed on Sep 14, 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.
More vacations you might like
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Key West Hotels
- All-inclusive Resorts in Key West
- Cheap Hotels in Key West
- Oceanfront Hotels in Key West
- Hotels near Duval Street
- Hotels near New Town
- Gay friendly Hotels in Monroe County
- Beach Hotels in Key West
- Hotels near Key West Historic District
- Fleming Key Hotels
- 4 Star Hotels in Fleming Key
- Resorts in Fleming Key
- Cabin Rentals in Fleming Key
- RV Parks in Fleming Key
- Houseboats in Fleming Key
- Condo Resorts in Fleming Key
- B&B in Fleming Key
- Hotels near Key West Tropical Forest and Botanical Garden
- Adults Only Resorts & in Key West
- Hotels near Key West Golf Club
- Hotels near Meadows
- Stock Island Hotels
- Hotels near Key West Burlesque Theater
- Hotels near Studios of Key West
- Flights to Key West
- Flights from Philadelphia (PHL) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Miami (MIA) to Key West (EYW)
- Flights from Boston (BOS) to Key West (EYW)
- Flights from New York (JFK) to Key West (EYW)
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Flights from Fort Myers (RSW) to Key West (EYW)
- Flights from Chicago (ORD) to Key West (EYW)
- Flights from Atlanta (ATL) to Key West (EYW)
- Flights from Baltimore (BWI) to Key West (EYW)
- Flights from Charlotte (CLT) to Key West (EYW)
- Flights from Key West Intl.
- Flights from Detroit (DTW) to Key West (EYW)
- Flights from Washington (DCA) to Key West (EYW)
- Flights from Jacksonville (JAX) to Key West (EYW)
- Flights from Dallas (DFW) to Key West (EYW)
- Flights from Raleigh (RDU) to Key West (EYW)
- Flights to Fleming Key
- Flights from Indianapolis (IND) to Key West (EYW)
- Flights from Minneapolis (MSP) to Key West (EYW)
- Flights from Pittsburgh (PIT) to Key West (EYW)
- Flights from St. Louis (STL) to Key West (EYW)
- Flights from Columbus (CMH) to Key West (EYW)
- Flights from Nashville (BNA) to Key West (EYW)
- Flights from Cleveland (CLE) to Key West (EYW)
- Flights from West Palm Beach (PBI) to Key West (EYW)
- Flights from Pensacola (PNS) to Key West (EYW)
- Flights from Cincinnati (CVG) to Key West (EYW)
- Flights from Houston (IAH) to Key West (EYW)
- Flights from New Orleans (MSY) to Key West (EYW)
- Flights from Charleston (CHS) to Key West (EYW)
- Flights from Kansas City (MCI) to Key West (EYW)
- Flights from Milwaukee (MKE) to Key West (EYW)
- Flights from Richmond (RIC) to Key West (EYW)
- Flights from Louisville (SDF) to Key West (EYW)
- Flights from Hartford (BDL) to Key West (EYW)
- Flights from Albany (ALB) to Key West (EYW)
- Flights from Sarasota (SRQ) to Key West (EYW)
- Flights from Grand Rapids (GRR) to Key West (EYW)
- Flights from Buffalo (BUF) to Key West (EYW)
- Flights from Norfolk (ORF) to Key West (EYW)
- Flights from Providence (PVD) to Key West (EYW)
- Flights from Denver (DEN) to Key West (EYW)
- Flights from St. Petersburg (PIE) to Key West (EYW)
- Flights from Memphis (MEM) to Key West (EYW)
- Key West Vacations
- All inclusive Vacation Packages Key West
- Visit New Town
- Ernest Hemingway Home and Museum
- Visit Monroe County
- Fleming Key Vacations
- Fort East Martello Museum and Gallery
- Key West Burlesque Theater
- Visit Fleming Key
- Duval Street
- Stock Island Vacations
- Sails To Rails Museum at Flagler Station
- Key West Cemetery
- Key West Art and Historical Society
- Saint Mary Star of the Sea
- Schooner Western Union
- The Kite House
- Raccoon Key Vacations
- Key West Historic District Vacations
- Donkey Milk House
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.