Lower Florida Keys Vacations from $722
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Your Lower Florida Keys Vacation
With a Lower Florida Keys vacation package, you can forget about the hassle of planning and instead focus on experiencing everything this amazing destination has on offer. Your trip to Lower Florida Keys wouldn't be complete without experiencing some of its most well-known cities, starting with Key West. Two of the top attractions here include Smathers Beach and Mallory Square. Cudjoe Key is another favorite with Lower Florida Keys travelers. Visitors to this city love Florida Keys Beaches and Sugarloaf Beach. When it's time to stop dreaming and start discovering, Expedia will help turn your Lower Florida Keys vacation into a reality.
The Latest Lower Florida 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 $1,128, price is now $722 per person
$722
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip 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
Ridley House - Key West Historic Inns
Key West Historic District
Price was $2,415, price is now $1,214 per person
$1,214
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip 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
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,729, price is now $963 per person
$963
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,005 reviews)
Everyone and everything was great, such a great location to enjoy the whole island!
Reviewed on Sep 28, 2025
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $1,908, price is now $1,165 per person
$1,165
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (496 reviews)
Excellent location right in the heart of town super friendly staff and very nice property
Reviewed on Aug 3, 2025
Don't see what you're looking for?
See all available trips from Columbus to Lower Florida Keys
View all tripsWhere to stay in Lower Florida Keys
Find the best Lower Florida Keys areas and neighborhoods for the activities you enjoy most. Learn more about Lower Florida Keys
Old Town Key West
3 out of top 10 points of interest in this area
4.5/5(226 area reviews)
Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.
Discover the most popular places to visit in Lower Florida Keys
Duval Street
Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.
Southernmost Point
Snap a memorable photograph from the edge of North America at this monumental landmark.
Mallory Square
Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.
What to do in Lower Florida 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 Florida 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 Oct 1 to Oct 2
$167 total
Oct 1 - Oct 2
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 Oct 1 to Oct 2
$111 total
Oct 1 - Oct 2
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"Good"
Reviewed on Sep 11, 2025
Looe Key Reef Resort
27340 Overseas Highway, Summerland Key, FL
Fully refundableReserve now, pay when you stay
$117 nightly
The price is $132 total per night from Oct 2 to Oct 3
$132 total
Oct 2 - Oct 3
Total with taxes and fees
7.4/10 Good! (1,004 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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- Apartments in Raccoon Key
- Hotels near Stock Island Yacht Club & Marina
- Stock Island Hotels
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- RV Parks in Cudjoe Key
- Cottages in Cudjoe Key
- Resorts in Cudjoe Key
- Beach Hotels in Cudjoe Key
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- Villas in Cudjoe Key
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- Flights to Key West
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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.
