Top Beach vacation packages in Florida Keys

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

Hawks Cay Resort

Save 100% on your flight

$637

per person

Nov 18 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Miami (MIA)

8/10 Very Good! (1,011 reviews)

Only stayed one night. Dinner was very good.

Reviewed on Oct 17, 2025

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

$680

per person

Nov 17 - Nov 20

found 11 hours ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

8.4/10 Very Good! (347 reviews)

The views were great! Water access was perfect! Had a lot of issues with house keeping? We stayed 8 nights and had no housekeeping 3 of those days, even after I complained the first time? No towels, washclothes, bed not made. Normal housekeeping duties were not done? After the last time I had to go speak with the front desk and they did refund me $200.00. It was something but I expected a lot more for what we paid for our stay. Staff was very polite!

Reviewed on Oct 14, 2025

Pier House Resort & Spa

Key West Historic District

Save 100% on your flight

$902

per person

Dec 18 - Dec 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

9/10 Wonderful! (1,005 reviews)

Enjoyed the stay. Property and proximity both very good. Staff friendly. Beautiful views

Reviewed on Oct 17, 2025

Tranquility Bay Beachfront Hotel and Resort

Save 100% on your flight

$721

per person

Nov 18 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Miami (MIA)

8.8/10 Excellent! (1,000 reviews)

Clean, large rooms with a comfortable bed and nice balcony.

Reviewed on Oct 16, 2025

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

Save 100% on your flight

$766

per person

Nov 17 - Nov 21

found 7 hours ago

Roundtrip flight included

Dallas (DFW) to Miami (MIA)

8.6/10 Excellent! (1,015 reviews)

Clean room, nice staff and facilities

Reviewed on Oct 12, 2025

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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

$600

per person

Nov 17 - Nov 21

found 7 hours ago

Roundtrip flight included

Dallas (DFW) to Miami (MIA)

9.2/10 Wonderful! (1,201 reviews)

This resort was amazing!

Reviewed on Oct 17, 2025

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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.

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

$680

per person

Nov 17 - Nov 20

found 11 hours ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

8.4/10 Very Good! (347 reviews)

The views were great! Water access was perfect! Had a lot of issues with house keeping? We stayed 8 nights and had no housekeeping 3 of those days, even after I complained the first time? No towels, washclothes, bed not made. Normal housekeeping duties were not done? After the last time I had to go speak with the front desk and they did refund me $200.00. It was something but I expected a lot more for what we paid for our stay. Staff was very polite!

Reviewed on Oct 14, 2025

Hawks Cay Resort

Save 100% on your flight

$1,150

per person

Dec 24 - Dec 27

found 6 hours ago

Roundtrip non-stop flight included

Fort Wayne (FWA) to Miami (MIA)

8/10 Very Good! (1,011 reviews)

Only stayed one night. Dinner was very good.

Reviewed on Oct 17, 2025

Pier House Resort & Spa

Key West Historic District

Save 100% on your flight

$902

per person

Dec 18 - Dec 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

9/10 Wonderful! (1,005 reviews)

Enjoyed the stay. Property and proximity both very good. Staff friendly. Beautiful views

Reviewed on Oct 17, 2025

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

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4 Night Beach vacations in Florida Keys

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

Sunset Cove Beach Resort

Save 100% on your flight

$485

per person

Nov 17 - Nov 21

found 7 hours ago

Roundtrip flight included

Dallas (DFW) to Miami (MIA)

9/10 Wonderful! (1,001 reviews)

Was a quiet pleasurable experience

Reviewed on Oct 15, 2025

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$771

per person

Dec 18 - Dec 22

found 15 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Miami (MIA)

9.2/10 Wonderful! (1,201 reviews)

This resort was amazing!

Reviewed on Oct 17, 2025

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

$771

per person

Nov 17 - Nov 21

found 13 hours ago

Roundtrip non-stop flight included

Akron (CAK) to Key West (EYW)

8.4/10 Very Good! (347 reviews)

The views were great! Water access was perfect! Had a lot of issues with house keeping? We stayed 8 nights and had no housekeeping 3 of those days, even after I complained the first time? No towels, washclothes, bed not made. Normal housekeeping duties were not done? After the last time I had to go speak with the front desk and they did refund me $200.00. It was something but I expected a lot more for what we paid for our stay. Staff was very polite!

Reviewed on Oct 14, 2025

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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 $485. Prices and availability are subject to change. Additional terms may apply.

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

2001 South Roosevelt Boulevard, Key West, FL

4 min drive from Duval Street

Relax and unwind at this hotel and walk along the waves in Key West, as you'll be close to the beach. Amenities at Margaritaville Beach House Key West include ...

8.6/10 Excellent! (1,777 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...

"Excellent experience"

Reviewed on Oct 12, 2025

Parrot Key Hotel & Villas

2801 N Roosevelt Blvd, Key West, FL

5 min drive from Duval Street

Book a stay at this beach hotel in Key West. Enjoy free WiFi, 4 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. ...

9/10 Wonderful! (1,125 reviews)

"We had a great visit. The staff was amazing & very accommodating. The rooms were clean & bed was comfy! Will stay again"

Reviewed on Oct 17, 2025

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! (1,012 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...

"The staff was great. We checked in around 8pm and discovered there was a problem with our air conditioner. They came to the room that night to attempt to fix it and offered us another room for the night when they couldn’t. Then the next morning they got a technician to come and work on it. We went ..."

Reviewed on Oct 13, 2025

See all 8,380 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.