Florida Keys Beach Vacations

Book a Beach Hotel + Flight or Car together to unlock savings

Top Beach vacation packages in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Pier House Resort & Spa
Cheeca Lodge & Spa
La Siesta Resort & Villas
Tranquility Bay Beachfront Hotel and Resort
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5* Beach vacations in Florida Keys

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Cheeca Lodge & Spa
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3 Night Beach vacations in Florida Keys

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Hawks Cay Resort
La Siesta Resort & Villas
Cheeca Lodge & Spa
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4 Night Beach vacations in Florida Keys

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Lime Tree Bay Resort
La Siesta Resort & Villas
Pier House Resort & Spa
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Find your perfect Florida Keys beach vacation

How do I book the best Florida Keys beach vacation packages?

Life’s a beach when you dive into our brilliant Florida Keys 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 Florida Keys?

A rental steps from the shore creates an amazingly affordable Florida Keys beach vacation. Seaside sojourns during low season start from $530. Prices and availability are subject to change. Additional terms may apply.

When should I book a Florida Keys 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 Florida Keys?

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 Florida Keys 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 Florida Keys 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 Florida Keys beach vacation deals?

Sort your search results by deals to delight in amazing Florida Keys 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 Florida Keys beach trip with free cancellation and/or flexible dates?

Just like the Florida Keys 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 Florida Keys 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 Florida Keys. (OK, maybe not that last part.)

Top Beach Florida Keys Hotels

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
  • 11 min walk from Duval Street
This spa hotel is a few steps from South Beach, where you can watch the sunset on your beach trip. Amenities at Southernmost Beach Resort and Guesthouses include ...
8.8/10 Excellent! (3,112 reviews)

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

Travelers say...
Too many children!! No repeat rewards!!

Reviewed on Feb 26, 2026

Southernmost Beach Resort and Guesthouses
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
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! (1,802 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...
Staff very friendly and helpful, received daily texts for anything we needed, room accommodations excellent, hotel restaurant food very good and really no complaints. Will definitely stay there again!

Reviewed on Feb 24, 2026

Margaritaville Beach House Key West
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
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 ...
8.2/10 Very Good! (1,000 reviews)

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

Travelers say...
Nice clean hotel. Smathers beach right down the road. Shuttle to Duval and the airport were very nice.

Reviewed on Feb 24, 2026

DoubleTree Resort by Hilton Grand Key - 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.