Lower Keys Vacations from $683
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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 Beach House, Key West
Save 100% on your flight
Price was $1,121, price is now $683 per person
$683
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,010 reviews)
This was a perfect location for our visit to Key West. The property was above and beyond what we expected!
Reviewed on Oct 30, 2025
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,300, price is now $1,343 per person
$1,343
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (498 reviews)
Great location and friendly staff. They have remodeled a lot and are doing a super job. Nice decorations and LOVE the tiki bar and pool area. Key West Aloe products were a nice touch as well as the key lime cookies. The porch deck and handrail outside the Envy/Lust room needs a little attention. Overall, very comfortable and accommodating. I would definitely stay here again.
Reviewed on Oct 17, 2025
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,280, price is now $765 per person
$765
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,021 reviews)
Nice, walkable, safe
Reviewed on Oct 30, 2025
Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,156, price is now $692 per person
$692
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (378 reviews)
Loved it! Felt totally at home!!
Reviewed on Oct 30, 2025
Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
Save 100% on your flight
Price was $2,793, price is now $1,852 per person
$1,852
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.4/10 Very Good! (396 reviews)
Beautiful property far enough away from duval to be quiet but close enough to walk and right on its own private beach. You can rent bikes and jet skis and everything on site.
Reviewed on Oct 30, 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
Big Coppitt Key
If you're spending some time in Big Coppitt Key, Shark Key and Wilhelmina Harvey Park are top sights worth seeing.
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
Old Wooden Bridge Resort and Marina
1791 Bogie Drive, Big Pine Key, FL
$259 nightly
The price is $292 total per night from Nov 2 to Nov 3
$292 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (263 reviews)
We absolutely loved our stay here! I’ll be honest, when I saw the pictures online, I was a little nervous about the beds because they looked like they might be on the cheaper side… but wow, I was so wrong. The beds were unbelievably comfortable — high quality, cozy, supportive, and honestly some ...
Reviewed on Oct 27, 2025
Parmer's Resort
565 Barry Avenue, Summerland Key, FL
Fully refundableReserve now, pay when you stay
$158 nightly
The price is $178 total per night from Nov 16 to Nov 17
$178 total
Nov 16 - Nov 17
Total with taxes and fees
9/10 Wonderful! (1,005 reviews)
Excellent for relaxation
Reviewed on Oct 26, 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 Nov 30 to Dec 1
$111 total
Nov 30 - Dec 1
Total with taxes and fees
8/10 Very Good! (999 reviews)
This was an excellent value for the price - the room was spacious and clean, the property was quiet. There was a beautiful view with a balcony. I could not have been happier with my experience!
Reviewed on Oct 6, 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.
Find the Best Lower Keys Vacation Packages
Lower Keys Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Key West Intl. Airport (EYW) |
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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.