Dredgers Key Vacation Packages 2026 from $894

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The Latest Dredgers Key vacation packages

Price found within the past 48 hours. Click for updated prices.

Ella's Cottages - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$894

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (490 reviews)

Southernmost House - Adult Exclusive

Old Town Key West

Save 100% on your flight

$1,471

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Excellent place to stay and will absolutely stay there again! The staff was so helpful and friendly! The restaurant on the property has delicious food! I highly recommend staying at he Southern Most House, great pool, great location, great vacation!

Reviewed on Aug 16, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,907

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (561 reviews)

This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!

Reviewed on Jul 27, 2026

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$918

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,371 reviews)

Lighthouse Hotel - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$924

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (971 reviews)

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Dredgers Key Hotel Deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

$203 nightly

$228 total

Sep 1 - Sep 2

Total with taxes and fees

8.8/10 Excellent! (3,534 reviews)

"Part of the reason I booked this hotel was it had beach access? Well, the beach was completely covered in 3 to 6 feet of seaweed. No mention of it when booking the hotel. Or I would have made other arrangements The staff was excellent. The rooms were a little dated the room was clean, but some of ..."

Reviewed on Aug 18, 2026

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$200 nightly

$225 total

Sep 2 - Sep 3

Total with taxes and fees

9/10 Wonderful! (1,856 reviews)

"Love love love this hotel."

Reviewed on Aug 17, 2026

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$136 nightly

$153 total

Aug 19 - Aug 20

Total with taxes and fees

See all 2,765 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.