
Lower Keys Vacations from $1,906
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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.

Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $2,618, price is now $1,906 per person
$1,906
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (3,630 reviews)
Our balcony room was beautiful.
Reviewed on Oct 28, 2026

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $3,956, price is now $2,454 per person
$2,454
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (564 reviews)
Property was everything as described, clean, in the heart of the excitement that is Key West
Pool was refreshing and close to tiki bar and local entertainment.
The room was spacious, clean and comfy beds. There were issues and there was really no staff to address. Most impactive was the fire alarm. First started going off rang for a min or two, then reset. Happened a dozen times, each causing us to avoid sleep, leave room to make sure nothing was wrong. It wasn't. Then around 10 PM it went off and would not stop. Tried to call office, but nobody there after 6pm. Freaking insane, no emergency contact, maintenance number, nothing. We sent email in hopes it w
May have been monitored... nope. Been 2 days and heard nothing back at all. Found the bartender at on site tici bar and though he abd is barback wete busy they found a ladder, called someone who told them to remove the devise. Eureka after almost 3 hours problem solved. Safety device removed and left peace and quite, perhaps fo fire warning, buy fine
Also internet and this TV / entertainment no work. No maintenance, no visible router to reboot, be gave up and ended the insanity
Maintenance guy was at the door early morning to properly troubleshoot or replace fire annunciator
We only were booked for a night so when we checked out in morning front desk girl simply apologized and was actually sort of blowing us off as she was leaving the desk empty the service a near $600 o/n should offer
Reviewed on Oct 6, 2026


The Marker Key West Harbor Resort
Key West Historic District
Save 100% on your flight
Price was $2,885, price is now $2,084 per person
$2,084
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,033 reviews)
needs to be refurbished
Reviewed on Oct 27, 2026

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 Key and Venture Out Keys are some notable places to visit nearby.
Stay near popular Lower Keys attractions
What to do in Lower Keys

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
94% of travellers recommend

Champagne and Sunsets: A Key West Catamaran Adventure
$59
per adult
94% of travellers recommend
Lower Keys Hotel Deals

Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
$178 nightly
The price is $200 total per night from Nov 1 to Nov 2
$200 total
Nov 1 - Nov 2
Total with taxes and fees
9/10 Wonderful! (1,005 reviews)
"The privacy was fantastic, the staff was helpful and we were right down the street from Robbie’s"
Reviewed on Oct 28, 2026

Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (660 reviews)
"The property is well maintained with a beautiful pool and bar area. The bed was comfortable and private We enjoyed sitting out on our balcony while watching the sun set. The staff kept us informed of the daily activities and answered any questions. The kitchenette afforded us family meals and family ..."
Reviewed on Oct 27, 2026

Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $167 total per night from Nov 20 to Nov 21
$167 total
Nov 20 - Nov 21
Total with taxes and fees
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.






























