Lower Keys Vacations from $521
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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 $789, price is now $521 per person
$521
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,029 reviews)
Close to the airport
Reviewed on Sep 9, 2025
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,207, price is now $756 per person
$756
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,025 reviews)
Very nice master bathroom....
Pool area was very nice as well
Reviewed on Sep 16, 2025
Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,337, price is now $910 per person
$910
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (369 reviews)
This was a wonderful experience. It was everything we could ask for her rest and relaxation. We were celebrating our 25th and wedding anniversary and it did not disappoint.
Reviewed on Sep 12, 2025
The Perry Hotel & Marina Key West
Price was $754, price is now $524 per person
$524
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,083 reviews)
The staff was great. The rooms all have balconies and we choose the Perry view. Guests all seemed jovial. Perfect for a fun getaway. Complimentary champagne upon arrival was great too!
Reviewed on Sep 15, 2025
Ridley House - Key West Historic Inns
Key West Historic District
Price was $2,153, price is now $1,502 per person
$1,502
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (815 reviews)
The room we were in was directly attached to the kitchen area so it was very noisy starting at 6am every morning. Other than the noise in the morning the stay was fine. I would say it would be nice if the people making breakfast could have been a little quieter in the morning.
Reviewed on Sep 10, 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
$148 nightly
The price is $167 total per night from Sep 17 to Sep 18
$167 total
Sep 17 - Sep 18
Total with taxes and fees
9/10 Wonderful! (1,001 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 17 to Sep 18
$111 total
Sep 17 - Sep 18
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
"Good"
Reviewed on Sep 11, 2025
Looe Key Reef Resort
27340 Overseas Highway, Summerland Key, FL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $123 total per night from Sep 27 to Sep 28
$123 total
Sep 27 - Sep 28
Total with taxes and fees
7.4/10 Good! (1,002 reviews)
"This is a very REASONABLY priced lodging for the FL Keys so expect simple things. We had a great stay, room was clean, the young gent at the front desk was exceptionally friendly and helpful, ditto at checkout. The beds are comfortable. The shower head had great pressure and the onsite tiki bar is ..."
Reviewed on Sep 15, 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.
