Florida Keys Beach Vacations

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Top Beach vacation packages in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

Northside Resort
$692
per person
Dec 13 - Dec 16
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,468 reviews)
We loved this resort! We will definitely be returning here in the future. Great location- not far from Duvall St but close enough that it’s only a 10 minute drive.

Reviewed on Oct 12, 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

$718
per person
Dec 13 - Dec 16
found 15 hours ago
Roundtrip non-stop flight included
Fresno (FAT) to Miami (MIA)
9/10 Wonderful! (281 reviews)
this was the nicest place i have ever stayed. the staff was so incredibly helpful and the amenities they provide are amazing. will definitely stay here again. 10/10

Reviewed on Oct 12, 2026

Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
$726
per person
Dec 13 - Dec 16
found 15 hours ago
Roundtrip non-stop flight included
Fresno (FAT) to Miami (MIA)
9.2/10 Wonderful! (1,471 reviews)
Islander Resort

Islander Resort

Matecumbe
$1,110
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
9.4/10 Exceptional! (1,132 reviews)
Fabulous bedroom cozy bed and awesome hot shower. Couch was sorta cheap and no fridge but we loved the ice maker and kitchenette. We loved the pool and the staff. Weak drinks but good food. The feeling there is soooo great. Will 100% come back.

Reviewed on Oct 13, 2026

Pier House Resort & Spa

Pier House Resort & Spa

Key West Historic District
$1,016
per person
Dec 13 - Dec 16
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,340 reviews)
After offering us an upgraded room for 100 a night with a water view, we accepted. Guess we should have asked how much of a view, because we were 1 room away from end of hotel property with a partial view of water but a lovely view of a wooden fence. This was our 8th stay with The Pier House. Usually get a little welcome back gift. Not anymore. What ever company bought out the Pier House has certainly made changes, and not for the better. Beach chairs are overcrowded, too close together and the pool itself needs repairs, refinishing and a good coat of paint. Darn shame, this use to be our go to happy vacation spot.

Reviewed on Oct 12, 2026

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5* Beach vacations in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
$726
per person
Dec 13 - Dec 16
found 15 hours ago
Roundtrip non-stop flight included
Fresno (FAT) to Miami (MIA)
9.2/10 Wonderful! (1,471 reviews)
Don't see what you're looking for?
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3 Night Beach vacations in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

$718
per person
Dec 13 - Dec 16
found 15 hours ago
Roundtrip non-stop flight included
Fresno (FAT) to Miami (MIA)
9/10 Wonderful! (281 reviews)
this was the nicest place i have ever stayed. the staff was so incredibly helpful and the amenities they provide are amazing. will definitely stay here again. 10/10

Reviewed on Oct 12, 2026

Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
Save 100% on your flight
$992
per person
Nov 13 - Nov 16
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9.2/10 Wonderful! (1,471 reviews)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
$791
per person
Dec 13 - Dec 16
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (3,636 reviews)
We went with 2 other couples 2nd year in a row at Southern Most, that should tell you how much we enjoyed it! Great location, food rooms were always cleaned.

Reviewed on Oct 12, 2026

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4 Night Beach vacations in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
Save 100% on your flight
$528
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Miami (MIA)
9.2/10 Wonderful! (1,471 reviews)
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Save 100% on your flight
$552
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Miami (MIA)
9/10 Wonderful! (281 reviews)
this was the nicest place i have ever stayed. the staff was so incredibly helpful and the amenities they provide are amazing. will definitely stay here again. 10/10

Reviewed on Oct 12, 2026

Hawks Cay Resort

Hawks Cay Resort

Save 100% on your flight
$629
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Miami (MIA)
8.2/10 Very Good! (1,006 reviews)
Loved every moment

Reviewed on Oct 12, 2026

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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 $528. 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

Margaritaville Beach House Key West

Margaritaville Beach House Key West

2001 South Roosevelt Blvd 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 ...
Margaritaville Beach House Key West
Casa Marina Key West, Curio Collection by Hilton

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! (966 reviews)

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

Travelers say...
"Will not return again poor service room was dirty"

Reviewed on Oct 13, 2026

Casa Marina Key West, Curio Collection by Hilton
DoubleTree Resort by Hilton Grand Key - Key West

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! (1,116 reviews)

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

Travelers say...
"Staff was great"

Reviewed on Oct 13, 2026

DoubleTree Resort by Hilton Grand Key - Key West
See all 8,242 properties in 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.

Things to do

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
Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

$79
per adult
98% of travellers recommend
Sunset Sail in Key West with Beverages Included
See all activities in Florida Keys

More vacations you might like

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