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Dredgers Key Vacation Packages

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Dredgers Key Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
Price was $1,022, price is now $714 per person
$714
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Southernmost Point and Duval Street are located nearby.

The Key West Hotel

The Key West Hotel

3 out of 5
Price was $1,878, price is now $1,160 per person
$1,160
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, room service, and daily housekeeping. Popular attractions Duval Street and Mallory Square are located nearby.
The location is amazing set back off Duvall. The staff was great and the room was excellent. The bar, pool, and entertainment were wonderful. We would stay there again!

Reviewed on Jul 24, 2026

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Price was $1,450, price is now $923 per person
$923
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
Excellent location, near Duval str, but far enough to not have the noise. Very large room, super comfortable bed and pillows. Room 8 is on the top floor requires 2 sets of stairs, it worked fine for us. Breakfast was good, staff friendly and helpful. Very enjoyable!

Reviewed on Jul 22, 2026

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Price was $1,578, price is now $1,049 per person
$1,049
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, parking (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.

Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $1,670, price is now $1,141 per person
$1,141
per person
Sep 11 - Sep 16
just found
Roundtrip non-stop flight included
Albany (ALB) to Key West (EYW)
Book a stay at this beach resort in Key West. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Southernmost Point and Duval Street are located nearby.

Bishop Hotel Key West

Bishop Hotel Key West

4 out of 5
Price was $1,346, price is now $920 per person
$920
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Popular attractions Duval Street and Southernmost Point are located nearby.
Great location! Wonderful staff and clean rooms

Reviewed on Jul 25, 2026

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

3 out of 5
Price was $1,465, price is now $1,019 per person
$1,019
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this beach cottage in Key West. Enjoy a beach locale, patios, and in-room washers/dryers. Popular attractions Duval Street and Southernmost Point are located nearby.

Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

3 out of 5
Price was $1,155, price is now $806 per person
$806
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this historic guesthouse in Key West. Enjoy free WiFi, beach cabanas (surcharge), and a business center. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
Excellent location. Right next to Duvall street and other attractions. Room was clean and the pool nice. There is a bar at the location and the prices are comparable to the other bars around town.

Reviewed on Jul 24, 2026

Dredgers Key Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Bishop Hotel Key West

Bishop Hotel Key West

4 out of 5
Old Town Key West
Price was $1,346, price is now $920 per person
$920
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was $1,878, price is now $1,160 per person
$1,160
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Key West Historic District
Price was $1,450, price is now $923 per person
$923
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
Price was $1,578, price is now $1,049 per person
$1,049
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)

Dredgers Key Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
Price was $1,022, price is now $730 per person
$730
per person
Sep 11 - Sep 16
just found
Roundtrip non-stop flight included
Albany (ALB) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was $4,093, price is now $2,486 per person
$2,486
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,670, price is now $1,141 per person
$1,141
per person
Sep 11 - Sep 16
just found
Roundtrip non-stop flight included
Albany (ALB) to Key West (EYW)
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
Save 100% on your flight
Price was $2,139, price is now $1,471 per person
$1,471
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Allegiant Air
Thu, Aug 20 - Sun, Aug 23
PIE
St. Petersburg-Clearwater Intl.
EYW
Key West Intl.
$121 Roundtrip, found 2 days ago
$121
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Thu, Aug 20 from St. Petersburg-Clearwater Intl. to Key West Intl., returning Sun, Aug 23, priced at $121 found 2 days ago
Breeze Airways
Thu, Aug 20 - Sun, Aug 23
TPA
Tampa Intl.
EYW
Key West Intl.
$146 Roundtrip, found 18 hours ago
$146
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Thu, Aug 20 from Tampa Intl. to Key West Intl., returning Sun, Aug 23, priced at $146 found 18 hours ago
Delta
Thu, Sep 17 - Fri, Oct 2
ATL
Hartsfield-Jackson Atlanta Intl.
EYW
Key West Intl.
$288 Roundtrip, found 15 hours ago
$288
Roundtrip
found 15 hours ago
Select Delta flight, departing Thu, Sep 17 from Hartsfield-Jackson Atlanta Intl. to Key West Intl., returning Fri, Oct 2, priced at $288 found 15 hours ago
United
Sat, Nov 7 - Wed, Nov 11
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$289 Roundtrip, found 4 days ago
$289
Roundtrip
found 4 days ago
Select United flight, departing Sat, Nov 7 from Newark Liberty Intl. Airport to Key West Intl., returning Wed, Nov 11, priced at $289 found 4 days ago