Saddlebunch Keys Vacations from $1,326

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The Latest Saddlebunch Keys vacation packages

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

Grand Maloney Hotel

Key West Historic District

$1,326

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

7.8/10 Good! (13 reviews)

Excellent location in old town. Quiet room away from street.

Reviewed on Jan 1, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$2,053

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (562 reviews)

The Gardens Hotel

Old Town Key West

$1,749

per person

Nov 12 - Nov 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,000 reviews)

It is a GREAT property in Key West, right in the center of the action.

Reviewed on Sep 28, 2026

Amelia Home by Avantstay In Historic Old Town w/ Pool

Old Town Key West

Save 100% on your flight

$2,695

per person

Dec 1 - Dec 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

10/10 Exceptional! (3 reviews)

Loved it

Reviewed on Mar 20, 2026

Duval s Duet on Duval by Brightwild

Old Town Key West

Save 100% on your flight

$7,219

per person

Nov 21 - Nov 27

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Key West (EYW)

No reviews

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Saddlebunch Keys Hotel Deals

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$160 nightly

$180 total

Oct 1 - Oct 2

Total with taxes and fees

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

$229 nightly

$258 total

Sep 30 - Oct 1

Total with taxes and fees

8.6/10 Excellent! (3,637 reviews)

"Property was amazing, our second time here. Staff was very accommodating! Pools were clean and the atmosphere at the pools was perfect. We will definitely be returning."

Reviewed on Sep 29, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$265 nightly

$298 total

Sep 30 - Oct 1

Total with taxes and fees

See all 3,412 properties in Saddlebunch Keys

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.