Florida Keys Beach Vacations 2026

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Top Beach vacation packages in Florida Keys

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton

$572

per person

Sep 27 - Sep 30

found 23 hours ago

Roundtrip flight included

Dallas (DFW) to Miami (MIA)

8.6/10 Excellent! (1,157 reviews)

This is our second visit to Baker's Cay, and it's a total go-to resort for our family. Highly recommend!

Reviewed on Aug 27, 2026

Hawks Cay Resort

Save 100% on your flight

$903

per person

Oct 30 - Nov 2

found 16 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

8.2/10 Very Good! (1,003 reviews)

I was really enjoying my time at Hawks Cay Resort. The views here were absolutely breathtaking! 🌴🌊😍 I just wanted to relax, enjoy the beautiful scenery, and make the most of every moment of my vacation.

Reviewed on Aug 26, 2026

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$967

per person

Oct 28 - Nov 1

found 3 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

9.2/10 Wonderful! (1,402 reviews)

Cheeca was an amazing experience.

Reviewed on Aug 28, 2026

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

Save 100% on your flight

$949

per person

Oct 28 - Nov 1

found 3 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

9/10 Wonderful! (250 reviews)

I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff.

Reviewed on Aug 23, 2026

Tranquility Bay Beachfront Hotel and Resort

$711

per person

Oct 30 - Nov 2

found 16 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

8.8/10 Excellent! (1,011 reviews)

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5* Beach vacations in Florida Keys

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

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$967

per person

Oct 28 - Nov 1

found 3 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

9.2/10 Wonderful! (1,402 reviews)

Cheeca was an amazing experience.

Reviewed on Aug 28, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

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3 Night Beach vacations in Florida Keys

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

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$742

per person

Oct 29 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Miami (MIA)

9.2/10 Wonderful! (1,402 reviews)

Cheeca was an amazing experience.

Reviewed on Aug 28, 2026

Hawks Cay Resort

Save 100% on your flight

$903

per person

Oct 30 - Nov 2

found 16 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

8.2/10 Very Good! (1,003 reviews)

Reviewed on Aug 26, 2026

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

$866

per person

Oct 30 - Nov 2

found 1 day ago

Roundtrip flight included

St. Louis (STL) to Miami (MIA)

9/10 Wonderful! (250 reviews)

I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff.

Reviewed on Aug 23, 2026

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4 Night Beach vacations in Florida Keys

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

Pier House Resort & Spa

Key West Historic District

$952

per person

Oct 28 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Key West (EYW)

9/10 Wonderful! (1,288 reviews)

i stayed in the king room with accessible lanai. the bathroom was spacious, easily accessible shower stall. i liked the bar near the private beach, the food and drinks were good. i had delicious filet mignon for dinner, for breakfast which was included i had the spectacular lobster benedict, soooo delicious. i’ll stay here again, it’s right on Duval street, walking distance to the bars and shops and boating trips, jet ski rentals

Reviewed on Aug 27, 2026

Hawks Cay Resort

Save 100% on your flight

$1,120

per person

Nov 5 - Nov 9

found 23 hours ago

Roundtrip flight included

Denver (DEN) to Miami (MIA)

8.2/10 Very Good! (1,003 reviews)

Reviewed on Aug 26, 2026

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$967

per person

Oct 28 - Nov 1

found 3 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

9.2/10 Wonderful! (1,402 reviews)

Cheeca was an amazing experience.

Reviewed on Aug 28, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

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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 $572. 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

1319 Duval Street Key West FL

10 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 ...

Hyatt Vacation Club at Windward Pointe, Key West

3675 South Roosevelt Boulevard Key West FL

7 min drive from Duval Street

Recharge at this hotel and watch the sunset on the beach in Key West, as you'll be not far from the beach. An outdoor pool, a restaurant, and a hot tub are just ...

9.4/10 Exceptional! (1,261 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...

"We had the BEST time here! The room was perfect for traveling with an adult son and minor son. We all had our own areas. The kitchen was beyond helpful and cut the cost of our stay since we didn't have to eat out every meal. The grounds were absolutely gorgeous and sitting on the balcony overlooking ..."

Reviewed on Aug 28, 2026

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 ...

8.8/10 Excellent! (1,795 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...

"This hotel is beautiful, and the service is outstanding. From the moment you approach the front desk, they offer you a drink. I've been encouraging all my friends to visit. I can't wait to return and stay for a few days longer!"

Reviewed on Aug 28, 2026

See all 8,256 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.