Lower Florida Keys Vacation Packages 2026 from $1,060

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 Gardens Hotel

Old Town Key West

Save 100% on your flight

$1,060

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,003 reviews)

This is a lovely hotel. We stayed in on of the garden "cottages". It was a perfect room and offered a little privacy. I would definitely stay there again. It was a quiet area, but close to everything for walkability.

Reviewed on Sep 20, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$3,269

per person

Nov 5 - Nov 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (562 reviews)

Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

Coconut Beach Resort

Old Town Key West

Save 100% on your flight

$1,261

per person

Oct 25 - Oct 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.8/10 Excellent! (219 reviews)

Maintenance people were so nice and helpful Place was clean Blanket on the bed was paper thin like a sheet Could not get both TVs to work said no service Room was on Third floor all stairs no elevator a bit difficult with luggage

Reviewed on Sep 11, 2026

Beachside Resort & Residences

Save 100% on your flight

$1,554

per person

Oct 21 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (2,487 reviews)

The room was clean and nice amenities. The staffs were nice. The elevator for our building was out of service when we were there. We had to use the elevator of the next building.

Reviewed on Sep 21, 2026

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

Old Town Key West

Save 100% on your flight

$3,410

per person

Dec 1 - Dec 7

found 1 day ago

Roundtrip 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

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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 Key West Tropical Forest and Botanical Garden.

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 beach with a pier extending into the ocean during sunset.

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.

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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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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 vintage typewriter on a wooden table with a notebook and pen beside it.

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 brick corridor with arched ceilings and benches.

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 beachside resort with palm trees, a large white building, and a checkered pattern on the sand.

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

Key West Rum & Reggae: Snorkel & Sunset Sail Combo

$69

per adult

88% of travellers recommend

Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$41

per adult

88% of travellers recommend

See all activities in Lower Florida Keys

Lower Florida Keys Hotel Deals

Parmer's Resort

565 Barry Avenue Summerland Key FL

Fully refundableReserve now, pay when you stay

$173 nightly

$194 total

Oct 4 - Oct 5

Total with taxes and fees

9/10 Wonderful! (1,002 reviews)

"The location is nice and staff was friendly and helpful. Breakfast was OK. The rooms are in need of updating and the beds are frumpy/uncomfortable. Nice to have KIKI's Tiki Bar & restaurant nearby and on the water!"

Reviewed on Sep 21, 2026

Sugarloaf Key Hotel at KOA Resort

251 Co Rd 939 Summerland Key FL

9.8/10 Exceptional! (635 reviews)

"Extraordinarily clean and well maintained. We stayed in the hotel which was well thought out"

Reviewed on Sep 19, 2026

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Sugarloaf Key RV Resort & Cottages

311 Johnson Rd Summerland Key FL

9.2/10 Wonderful! (31 reviews)

"Make sure to meet Lena and get the right place and deal from her"

Reviewed on Sep 10, 2026

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See all 3,415 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.