Lower Keys Vacations from $781
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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 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Beautiful place ,the price incredible ,but the view from my balcony is the best , I fall in love with my apt/room .
Reviewed on Jul 30, 2025
Orchid Key Inn - Adults Only
Old Town Key West
Save 100% on your flight
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
great hotel in Key west ,friendly staff and old style 50's feel...rooms are on the small side ,however breakfast and water by the pool means rooms are for sleeping only
Reviewed on Aug 1, 2025
Almond Tree Inn Hotel - Adults Only
Old Town Key West
Save 100% on your flight
per person
Sep 1 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
10/10 Exceptional! (1,002 reviews)
It was just a all around grest place to stay. Clean, quiet, great staff snd walkable to nice restaurants and shopping.
Reviewed on Jul 31, 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
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
$27
per adult
78% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
$40
per adult
92% 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! (1,003 reviews)
"Sarah was AWESOME"
Reviewed on Jul 29, 2025
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939, Summerland Key, FL
9.6/10 Exceptional! (420 reviews)
"We stayed for July 4th and it was perfect! Loved the suite and as a family it was very convenient to have a kitchen, washer and dryer!"
Reviewed on Jul 29, 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! (1,003 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.