Lower Keys Vacations from $1,628

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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.
The Gardens Hotel

The Gardens Hotel

Old Town Key West
Save 100% on your flight
$1,628
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
N/a

Reviewed on Oct 11, 2026

The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
$2,757
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (563 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

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Old Town Key West
$5,470
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
10/10 Exceptional! (1 review)
Loved the closeness to Duval st and the privacy

Reviewed on Oct 17, 2025

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

Old Town Key West
$4,610
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
10/10 Exceptional! (1 review)
Location, comfort and great customer service! A great place for a family to stay and share in some fun together!!

Reviewed on Jul 26, 2026

Amelia Home by Avantstay In Historic Old Town w/ Pool

Amelia Home by Avantstay In Historic Old Town w/ Pool

Old Town Key West
Save 100% on your flight
$3,242
per person
Dec 13 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
10/10 Exceptional! (3 reviews)
Loved it

Reviewed on Mar 20, 2026

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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
A calm lake with several white birds, including herons and pelicans, on the water's edge.

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.

A coastal landscape with a beach, a pier, and dense greenery.

Big Coppitt Key

If you're spending some time in Big Coppitt Key, Shark Key and Wilhelmina Harvey Park are top sights worth seeing.

A waterfront property with a pool, palm trees, and a building with a white roof.

Sugarloaf Shores

While Sugarloaf Shores isn't home to many top sights, Florida Keys Beaches and Sugarloaf Beach are some notable places to visit nearby.

An aerial view of a bridge over turquoise water.

Cudjoe Gardens

When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Florida Keys Beaches, some noteworthy sights in the nearby area.

A fence with numerous lost shoes hanging on it.

Geiger Key

While there might not be top attractions in Geiger Key, you can explore the larger area and discover places like Boca Chica Beach and Boca Chica Nude Beach.

Stay near popular Lower Keys attractions

A beach with clear turquoise water, a sandy shore, palm trees, and a steel bridge over the water.

Bahia Honda State Park

9.4/10 (50 reviews)
You can take time to visit Bahia Honda State Park during your travels to Big Pine Key. While you're in the area, wander around the natural setting.
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A beach with clear turquoise water, a sandy shore, and a long pier extending into the water.
Photo by Sérgio Veludo

Calusa Beach

7.8/10 (9 reviews)
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.
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A beach with a thatched hut, palm trees, and boats in the water.

Boca Chica Beach

8.0/10 (1 review)
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.
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A motorcycle parked on a beach with palm trees and a clear sky.
Photo by Paul Devall

Sugarloaf Beach

8.4/10 (38 reviews)
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
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A clear blue sky, calm sea, and a tree with exposed roots on a sandy beach.

Sandspur Beach

10.0/10 (1 review)
Why not spend a lazy afternoon at Sandspur Beach during your trip to Big Pine Key? While you're in the area, wander around the natural setting.
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Upper Sugarloaf Key

8.6/10 (54 reviews)
Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.
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Key West Visitors Center

8.4/10 (85 reviews)
After visiting Key West Visitors Center, make a plan to see the other sights and activities in Big Pine Key. Amble around this relaxing area's marina, or seek out the fishing spots.
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National Key Deer Refuge Visitor Center

8.4/10 (50 reviews)
National Key Deer Refuge Visitor Center is just one of the places to see in Big Pine Key, so why not enjoy the other things to explore during your travels? While you're in the area, stroll along the beaches.
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What to do in Lower Keys

Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

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

Champagne and Sunsets: A Key West Catamaran Adventure

$59
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$41
per adult
88% of travellers recommend
Key West Conch Tour Train
See all activities in Lower Keys

Lower Keys Hotel Deals

Parmer's Resort

Parmer's Resort

565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
$198 nightly
$223 total
Nov 1 - Nov 2
Total with taxes and fees
9/10 Wonderful! (1,002 reviews)
"Was a beautiful property. We only needed to stay one night and did not get to enjoy all of the amenities. Breakfast was wonderful. We had stayed many years so and looked forward to going back. The sunrise was spectacular! Nice beach, pool, area and the grounds very well maintained."

Reviewed on Oct 11, 2026

Parmer's Resort
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

251 Co Rd 939 Summerland Key FL
Sugarloaf Key Hotel at KOA Resort
Looe Key Reef Resort

Looe Key Reef Resort

27340 Overseas Highway Summerland Key FL
Fully refundableReserve now, pay when you stay
$104 nightly
$117 total
Oct 14 - Oct 15
Total with taxes and fees
7.8/10 Good! (1,003 reviews)
"They had a nice pool you could park your boat in the channel they also had a very nice tiki bar and grill it was an ok place to stay but parking sucked"

Reviewed on Oct 11, 2026

Looe Key Reef Resort
See all 842 properties in Lower Keys
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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