Lower Keys Vacation Packages 2026 from $1,656

Photo by Rick Tuers

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 Perry Hotel & Marina Key West

Save 100% on your flight

$1,656

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,335 reviews)

Stayed just one night and wished we had stayed longer. Phil on the reception desk was so helpful. The property is like new and so tranquil, with a shuttle bus every hour into the town centre. We were given an allowance of 20% off food at the restaurants which we did not use so Phil, without asking, waived our parking fee to make up. Now that's something I have never experienced at any other hotel. Please visist this hotel, you will not be disappointed.

Reviewed on Aug 27, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$3,450

per person

Oct 31 - Nov 7

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

Southernmost House - Adult Exclusive

Old Town Key West

Save 100% on your flight

$1,873

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,004 reviews)

Super nice and clean, staff was wonderful w knowledge of the history of the mansion

Reviewed on Aug 24, 2026

Ridley House - Key West Historic Inns

Key West Historic District

Save 100% on your flight

$1,973

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (951 reviews)

Ella's Cottages - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$1,733

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (493 reviews)

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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 Out Keys and Venture Key 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 Upper Sugarloaf Sound are some notable places to visit nearby.

Boat traveling under the Seven Mile Bridge, Florida Keys, USA

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.

Aerial view of scenic coastal road with turquoise water and bridge, Summerland Key, Florida, United States.

Bay Point

Bay Point might not have many top sights, but Lower Sugarloaf Sound and Florida Keys Beaches are two attractions nearby that you can check out.

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.

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 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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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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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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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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Cook Island

9.2/10 (5 reviews)

Commune with nature and explore the great outdoors at Cook Island during your travels in Big Pine Key. While you're in the area, wander around the natural setting.

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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

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

$45

per adult

88% of travellers recommend

See all activities in Lower Keys

Lower Keys Hotel Deals

Parmer's Resort

565 Barry Avenue Summerland Key FL

Fully refundableReserve now, pay when you stay

$148 nightly

$167 total

Aug 30 - Aug 31

Total with taxes and fees

9/10 Wonderful! (1,000 reviews)

"Though it's an older property that does not take away from the fact the rooms are clean, the views amazing and staff wonderful. If you are looking to relax and enjoy the Florida Keys laid back style then this is the place to stay. Great for singles, couples and families. Close to Key West too."

Reviewed on Aug 26, 2026

Sugarloaf Key Hotel at KOA Resort

251 Co Rd 939 Summerland Key FL

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Old Wooden Bridge Resort and Marina

1791 Bogie Drive Big Pine Key FL

$225 nightly

$253 total

Sep 1 - Sep 2

Total with taxes and fees

8.6/10 Excellent! (367 reviews)

"Bad. Will not return to this property"

Reviewed on Aug 26, 2026

See all 825 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.