Lower Keys Vacations from $582
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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
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,024 reviews)
This property is fantastic a little drive from old Key West and all the shops in water activities but so beautiful. The little pool shack named Abby Road really has good food and the area is just so pretty to sit and take your food and watch the ocean or the pool or the iguanas. The staff was amazing. We would absolutely go back if we are going to visit Key West again.
Reviewed on Aug 1, 2025
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (1,668 reviews)
Liked everything. Food good. Bed comfortable. Clean everyday from employees. Nice pools. Staff good at desk. Fitness center great, maybe more weights?
Reviewed on Aug 2, 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
$40
per adult
92% of travellers recommend
Key West Sunset Sail with Live Music, Drinks and Appetizers!
$80
per adult
92% of travellers recommend
Lands End Sunset Cruise with Full Bar & Live Music
$75
per adult
90% of travellers recommend
Lower Keys Hotel Deals
Parmer's Resort
565 Barry Avenue, Summerland Key, FL
Fully refundableReserve now, pay when you stay
$163 nightly
The price is $183 total per night from Aug 26 to Aug 27
$183 total
Aug 26 - Aug 27
Total includes taxes and fees
8.8/10 Excellent! (1,001 reviews)
"Loved the property and all of the free activities! We definitely took advantage of the kayaks, paddle boards, pool and hammocks."
Reviewed on Jul 30, 2025
Old Wooden Bridge Resort and Marina
1791 Bogie Drive, Big Pine Key, FL
$232 nightly
The price is $262 total per night from Sep 1 to Sep 2
$262 total
Sep 1 - Sep 2
Total includes taxes and fees
8.6/10 Excellent! (253 reviews)
"Everything was good except the bathroom had a bath smell all the time and the boat ramp is broken . I"
Reviewed on Jul 25, 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 Aug 10 to Aug 11
$111 total
Aug 10 - Aug 11
Total includes taxes and fees
8/10 Very Good! (998 reviews)
"It was great"
Reviewed on Jul 27, 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.