Saddlebunch Keys Vacations from $966
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The Latest Saddlebunch Keys vacation packages
Price found within the past 48 hours. Click for updated prices.
Ella's Cottages - Key West Historic Inns
Old Town Key West
$1,150
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (493 reviews)
Perfect location, quiet, but a short walk to everything fun. And I. August heat in the Keys, the only walks must be short. Cottages are small but well laid out, with super comfy bed, cold AC and hotter than hot shower. Staff was awesome and the 3 pm happy hour by the pool was laid back. Breakfast wasn't fancy, but it was abundant. We will definitely be back.
Reviewed on Aug 29, 2026
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Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$210 nightly
$237 total
Sep 8 - Sep 9
Total with taxes and fees
8.6/10 Excellent! (3,547 reviews)
"The first room was so dirty I had to tell staff. The shower and bathroom had hair the ac had actual hair hanging from it. Toothpast on the bathroom mirror , just disgusting. Second room was infested with ants. They got inside my laptop( I kept my laptop on top of the desk for work ) opened the laptop ..."
Reviewed on Aug 30, 2026
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$125 nightly
$141 total
Aug 31 - Sep 1
Total with taxes and fees
8.2/10 Very Good! (2,362 reviews)
"Todo Super bien; el personal que trabaja en la instalación te hacen sentir como en casa muy acogedor; tranquilo y un servicio increíble"
Reviewed on Aug 30, 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$195 nightly
$220 total
Aug 31 - Sep 1
Total with taxes and fees
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 Saddlebunch Keys Vacation Packages
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- Smathers Beach
- Old Town Key West Vacations
- Sombrero Beach
- Robbie's
- Key West Burlesque Theater
- Bahama Village Vacations
- Sunset Key Vacations
- Key West Vacations
- Waterfront Playhouse
- Sails To Rails Museum at Flagler Station
- Jackson Square
- Schooner Western Union
- Key West Butterfly and Nature Conservatory
- Stock Island Yacht Club & Marina
- South Beach
- Fort Zachary Taylor Historic State Park
- Key West Lighthouse and Keeper's Quarters Museum
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- Museum of Art & History at the Custom House
- Mallory Square
- Key West National Wildlife Refuge
- Duval Street
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- Visit Downtown Key West
- The Kite House
- Mallory Dock
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- Upper Sugarloaf Sound
- Visit Sugarloaf Key
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- Southernmost Point
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- Visit Big Pine Key
- Harry S. Truman Little White House
- Clarence S. Higgs Memorial Beach Park
- Saint Mary Star of the Sea
- San Carlos Institute - Casa Cuba
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
