Lower Florida Keys Vacations from $1,152

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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.
The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
$1,152
per person
Dec 13 - Dec 16
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
Save 100% on your flight
$4,579
per person
Dec 30 - Jan 4
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

Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay

Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay

Beachside
Save 100% on your flight
$2,133
per person
Dec 9 - Dec 16
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
No reviews
Bananas Foster by Brightwild Epic Guesthouse

Bananas Foster by Brightwild Epic Guesthouse

Key West Historic District
$25,427
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
No reviews
Commodore s Compound by Brightwild Huge Home

Commodore s Compound by Brightwild Huge Home

Key West Historic District
$22,240
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
No reviews
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Where 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
A white building with shutters, palm trees, and a lawn.

Old Town Key West

4 out of top 10 points of interest in this area

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.

A coastal town with a prominent building featuring a blue awning, a chicken shack, and a store with colorful merchandise.

Downtown Key West

If you're spending some time in Downtown Key West, Duval Street and Ernest Hemingway Home and Museum are top sights worth seeing.

A two-story house with green shutters and a wooden balcony.

Key West Historic District

2 out of top 10 points of interest in this area

Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.

A marina with yachts docked, a prominent red building, and a coastal cityscape in the background.

New Town

Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Fort East Martello Museum and Gallery.

A sunset over the ocean with scattered clouds.

Uptown - Upper Duval

If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.

Stay near popular Lower Florida Keys attractions

A street with a pharmacy, a theater, and a yellow building.

Duval Street

9.2/10 (20,928 reviews)
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.
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A wooden signpost with city names and distances, a beach with umbrellas, and lounge chairs.

Florida Keys Beaches

8.4/10 (858 reviews)
Nothing says vacation like spending a carefree day at Florida Keys Beaches, a popular beach in Long Beach Estates.
See properties
A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.

Southernmost Point

8.8/10 (17,214 reviews)
Snap a memorable photograph from the edge of North America at this monumental landmark.
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A sign reading "Welcome to Mallory Square" with an American flag, a red and white striped awning, and a statue of a man in a blue shirt and straw hat.

Mallory Square

9.2/10 (15,939 reviews)
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.
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A beach with white sand, palm trees, and a building in the background.

Smathers Beach

8.4/10 (8,320 reviews)
Key West’s popular party beach has an electric atmosphere on the weekends and is a destination for water sports lovers.
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A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.

Ernest Hemingway Home and Museum

9.2/10 (8,543 reviews)
Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.
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A coastal fortification with a staircase leading to a higher platform, overlooking the sea.

Fort Zachary Taylor Historic State Park

9.0/10 (4,544 reviews)
The displays of old weapons and interpretive panels in a fort at the heart of the southernmost state park in the continental U.S. provide information about the Civil War.
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A wooden sign with information about South Beach, Key West, Florida, including public beach status, restaurant hours, and beach chair rental.

South Beach

8.4/10 (5,461 reviews)
Head to the southernmost beach of the continental United States to relax and swim in the waters where famous writer Tennessee Williams once took his daily swim.
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What to do in Lower Florida 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 Florida Keys

Lower Florida 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! (1,001 reviews)
"Fishing charter guide pick up from dock every morning. G"

Reviewed on Oct 8, 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
$102 nightly
$115 total
Oct 14 - Oct 15
Total with taxes and fees
7.8/10 Good! (1,000 reviews)
"This is a great inexpensive place to stay. Room was clean. Resort is showing some wear but is still good. Staff are very helpful with local recommendations. There is a great gas station next door with some items for sale in case you forget something. I would stay again."

Reviewed on Oct 5, 2026

Looe Key Reef Resort
See all 3,439 properties in Lower Florida 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 Florida Keys Vacation Packages

Lower Florida Keys Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Miami Intl. Airport (MIA)

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