Lower Keys Vacations from $667
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Your Lower Keys Vacation
Make planning your next big getaway quick and easy with a Lower Keys vacation package. Whether it's history, nature or something else entirely that brings you here, our package deals will help you discover the best of it. A trip to Lower Keys wouldn't be complete without spending a day or two in Cudjoe Key. This city is one of the most well-known places to visit here. When you're ready to stop dreaming and start packing, Expedia will help turn your Lower Keys vacation into reality.
The Latest Lower Keys 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 $1,064, price is now $667 per person
$667
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,016 reviews)
This property was accommodating, staff friendly, courteous, clean, and concierge was extremely helpful. Will visit again soon.
Reviewed on Sep 26, 2025
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,420, price is now $788 per person
$788
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,005 reviews)
Excellent hotel in every way, the gardens, the room, the breakfast, the location, we will definitely return.
Reviewed on Sep 25, 2025
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,323, price is now $747 per person
$747
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (791 reviews)
Second mother / daughter trip to Key West - first time staying at Lighthouse Hotel. We loved it! The hotel is charming and the location is perfect. The staff was super friendly and answered all of our questions. Pool area and bar is great and we enjoyed a nice breakfast every morning before venturing out for the day. We rented bikes to get around and this location was ideal - easy ride to everywhere we wanted to go. We had a great stay and will definitely book this hotel again!
Reviewed on Sep 22, 2025
Ridley House - Key West Historic Inns
Key West Historic District
Save 100% on your flight
Price was $1,231, price is now $806 per person
$806
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (819 reviews)
Everything was amazing.
we arrived early and in a rain storm my two kids and I were soaked head to toe and the water even entered our luggage. they let us check in early got us en upgrade to.
amazing staff and perfect spot close to all in Key West
Reviewed on Sep 25, 2025
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,257, price is now $850 per person
$850
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,025 reviews)
The condo was beautiful and had everything that we needed as well as a beautiful view of the sunset! Loved it and will be back again!!
Reviewed on Sep 25, 2025
Where to stay in Lower Keys
Find the best Lower Keys areas and neighborhoods for the activities you enjoy most. Learn more about Lower Keys
Cutthroat Harbor Estates
While Cutthroat Harbor Estates isn't home to many top sights, Venture Out Keys and Upper Sugarloaf Key are some notable places to visit nearby.
Discover the most popular places to visit in Lower Keys
Calusa Beach
Why not spend a lazy afternoon at Calusa Beach during your trip to Big Pine Key? While you're in the area, wander around the natural setting.
Boca Chica Beach
Why not spend a lazy afternoon at Boca Chica Beach during your trip to Key West? Stroll along the area's seaside, or simply savor its lively bars.
Upper Sugarloaf Sound
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.
What to do in Lower Keys
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
$50
per adult
92% of travellers recommend
Key West Sunset Sail with Live Music, Drinks and Appetizers!
$80
per adult
92% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
$27
per adult
80% of travellers recommend
Lower Keys Hotel Deals
Parmer's Resort
565 Barry Avenue, Summerland Key, FL
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $167 total per night from Sep 29 to Sep 30
$167 total
Sep 29 - Sep 30
Total with taxes and fees
9/10 Wonderful! (1,002 reviews)
"Clean room , many options for guests to do around property. Close to key west and marathon"
Reviewed on Sep 10, 2025
Sugar Loaf Lodge
17001 Overseas Hwy, Summerland Key, FL
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $111 total per night from Sep 29 to Sep 30
$111 total
Sep 29 - Sep 30
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"Good"
Reviewed on Sep 11, 2025
Old Wooden Bridge Resort and Marina
1791 Bogie Drive, Big Pine Key, FL
$204 nightly
The price is $230 total per night from Sep 30 to Oct 1
$230 total
Sep 30 - Oct 1
Total with taxes and fees
8.6/10 Excellent! (258 reviews)
"Really I have the best experience and soon I want to go again"
Reviewed on Sep 11, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
