Top Beach vacation packages in Key West

Price found within the past 48 hours. Click for updated prices.

Southernmost Beach Resort and Guesthouses

Old Town Key West

$605

per person

Jul 18 - Jul 20

found 2 hours ago

Roundtrip flight included

Washington (WAS) to Key West (EYW)

8.8/10 Excellent! (3,304 reviews)

Our room was not far from the beach, pool and beach club. Luckily, there was a dehumidifier in our room as without it, counters were wet with humidity. Room was cute and comfortable but there was too much stuff for sale in the room with took up space that would have been better left available for guests to us. Parking is quite pricey at $50 per day. Public beach was loaded with big mounds of seaweed

Reviewed on May 18, 2026

Pier House Resort & Spa

Key West Historic District

$638

per person

Jul 18 - Jul 20

found 2 hours ago

Roundtrip flight included

Washington (WAS) to Key West (EYW)

9/10 Wonderful! (1,115 reviews)

the location is great and the pool and gulf areas are really nice, clean and the staff is excellent

Reviewed on May 18, 2026

Blue Flamingo Resort Key West

New Town

$822

per person

Jun 17 - Jun 20

found 20 hours ago

Roundtrip non-stop flight included

Greensboro (GSO) to Key West (EYW)

8.4/10 Very Good! (2,190 reviews)

We had a great time at the Blue Flamingo. Pool was great. The bartenders were great. The shuttle down to Duval area was so nice to have. Only issue was with the room. Beds we not comfortable and the walls are paper thin. Could hear everything from side rooms, rooms above, and the outside.

Reviewed on May 18, 2026

La Concha Key West, Autograph Collection

Key West Historic District

$613

per person

Jul 18 - Jul 20

found 2 hours ago

Roundtrip flight included

Washington (WAS) to Key West (EYW)

8.8/10 Excellent! (388 reviews)

We love staying here it’s so close to everything!

Reviewed on May 18, 2026

Southernmost House - Adult Exclusive

Old Town Key West

$732

per person

Jul 18 - Jul 20

found 2 hours ago

Roundtrip flight included

Washington (WAS) to Key West (EYW)

9.4/10 Exceptional! (1,006 reviews)

Beautiful property. Excellent service.

Reviewed on May 15, 2026

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3 Night Beach vacations in Key West

Price found within the past 48 hours. Click for updated prices.

Blue Flamingo Resort Key West

New Town

$767

per person

Jul 18 - Jul 21

found 5 hours ago

Roundtrip flight included

Waterloo (ALO) to Key West (EYW)

8.4/10 Very Good! (2,190 reviews)

We had a great time at the Blue Flamingo. Pool was great. The bartenders were great. The shuttle down to Duval area was so nice to have. Only issue was with the room. Beds we not comfortable and the walls are paper thin. Could hear everything from side rooms, rooms above, and the outside.

Reviewed on May 18, 2026

Pier House Resort & Spa

Key West Historic District

$945

per person

Jul 18 - Jul 21

found 5 hours ago

Roundtrip flight included

Waterloo (ALO) to Key West (EYW)

9/10 Wonderful! (1,115 reviews)

the location is great and the pool and gulf areas are really nice, clean and the staff is excellent

Reviewed on May 18, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

$926

per person

Jul 18 - Jul 21

found 5 hours ago

Roundtrip flight included

Waterloo (ALO) to Key West (EYW)

8.8/10 Excellent! (3,304 reviews)

Our room was not far from the beach, pool and beach club. Luckily, there was a dehumidifier in our room as without it, counters were wet with humidity. Room was cute and comfortable but there was too much stuff for sale in the room with took up space that would have been better left available for guests to us. Parking is quite pricey at $50 per day. Public beach was loaded with big mounds of seaweed

Reviewed on May 18, 2026

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See all available trips from Columbus to Key West

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4 Night Beach vacations in Key West

Price found within the past 48 hours. Click for updated prices.

The Reach Key West, Curio Collection by Hilton

Old Town Key West

$1,060

per person

Jul 19 - Jul 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

8.6/10 Excellent! (1,013 reviews)

Amazing staff, clean buildings and great facilities

Reviewed on May 18, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

$1,162

per person

Jul 18 - Jul 22

found 24 hours ago

Roundtrip non-stop flight included

Erie (ERI) to Key West (EYW)

8.8/10 Excellent! (3,304 reviews)

Our room was not far from the beach, pool and beach club. Luckily, there was a dehumidifier in our room as without it, counters were wet with humidity. Room was cute and comfortable but there was too much stuff for sale in the room with took up space that would have been better left available for guests to us. Parking is quite pricey at $50 per day. Public beach was loaded with big mounds of seaweed

Reviewed on May 18, 2026

The Grand Guesthouse

Old Town Key West

$1,456

per person

Jul 18 - Jul 22

found 24 hours ago

Roundtrip non-stop flight included

Erie (ERI) to Key West (EYW)

9.6/10 Exceptional! (1,003 reviews)

The staff was very helpful and great to work with.

Reviewed on May 1, 2026

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How do I book the best Key West beach vacation packages?

Life’s a beach when you dive into our brilliant Key West beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Key West?

A rental steps from the shore creates an amazingly affordable Key West beach vacation. Seaside sojourns during low season start from $605. Prices and availability are subject to change. Additional terms may apply.

When should I book a Key West beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

How can I book the best family beach vacations in Key West?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Key West beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Key West vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Key West beach vacation deals?

Sort your search results by deals to delight in amazing Key West beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Key West beach trip with free cancellation and/or flexible dates?

Just like the Key West tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Key West beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Key West. (OK, maybe not that last part.)

Top Beach Key West Hotels

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard Key West FL

4 min drive from Duval Street

At this hotel, get ready to stroll along the shoreline in Key West, as you'll be close to Florida Keys Beaches. Amenities at Margaritaville Beach House Key West ...

8.8/10 Excellent! (1,797 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...

"Wonderful to be away from the chaos of the main Key West attractions. Amazing view and access to Smathers beach. Clean and well maintained property."

Reviewed on May 17, 2026

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

16 min walk from Duval Street

Feel the sand between your toes at this spa resort, the perfect choice for watching the sunset on Florida Keys Beaches if you're looking for a getaway in Key ...

8.4/10 Very Good! (660 reviews)

Travelers like: on the beach, sun loungers, beach bars, massages on beach

Travelers say...

"Room smells"

Reviewed on May 18, 2026

DoubleTree Resort by Hilton Grand Key - Key West

3990 S Roosevelt Blvd Key West FL

7 min drive from Duval Street

At this resort, get ready to enjoy the sunsets on the beach in Key West, as you'll be not far from the beach. A free beach shuttle, an outdoor pool, and a poolside ...

8.4/10 Very Good! (1,025 reviews)

Travelers like: close to beach, sun loungers, beach umbrellas, outdoor pool

Travelers say...

"Great service from staff"

Reviewed on May 18, 2026

See all 2,687 properties in Key West

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.