Top Beach vacation packages in Florida Keys

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

Amara Cay Resort

Matecumbe

Save 100% on your flight

$302

per person

Sep 13 - Sep 16

found 18 hours ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

8.8/10 Excellent! (1,288 reviews)

The rooms were clean, staff was attentive but property had trash laying around and

Reviewed on Jul 9, 2026

La Siesta Resort & Villas

Matecumbe

$524

per person

Aug 9 - Aug 12

found 7 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,007 reviews)

The room was very dirty when we arrived. The location and view from the room was amazing. The pool was great except it had black spots all over, which looked like black mold. There were also metal brush bristles from the staff cleaning the pool, on the bottom of the pool and a few people were cut while swimming. The pool attendant told us that the amenities were closed because of the wind being over 10 knots, including the Rum Runner, which wasn’t and shouldn’t have been the case. We later saw the rum runner dropping people off. We were very upset because we were looking forward to going on it one last time before the end of our trip. We lost a full day of using the paddle boards and kayaks and the Rum Runner. The staff was very friendly and accommodating when we talked to them about our issues.

Reviewed on Jul 9, 2026

Tranquility Bay Beachfront Hotel and Resort

$491

per person

Sep 10 - Sep 13

found 16 hours ago

Roundtrip flight included

Dallas (DFW) to Miami (MIA)

8.8/10 Excellent! (1,004 reviews)

Great place and would stay again. The staff works tirelessly to make everyone welcome. The housekeeping staff is simply amazing... there are so many rooms to clean and in short time and they bust it out. The Tiki Bar food is DELICIOUS and big portions... and the drinks are great! Well maintained beach area (bring your snorkels!) and the pool is very nice. Water does get "warm" in the summer in both, but its beautiful. Location is fabulous as well. Spacious villas and has everything you need to relax and unwind.

Reviewed on Jul 9, 2026

Hawks Cay Resort

Save 100% on your flight

$506

per person

Aug 9 - Aug 12

found 9 hours ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

8.2/10 Very Good! (1,006 reviews)

We have a second part of staying The first part was NOT GOOD Refrigerator broken AC broken They tried and corrected by moving to another room 11pm doing the whole work again But we still here for another reservation done Let’s see !!!

Reviewed on Jul 8, 2026

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$354

per person

Aug 9 - Aug 12

found 9 hours ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9.2/10 Wonderful! (1,330 reviews)

Super lindo y tranquilo

Reviewed on Jul 7, 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

Matecumbe

Save 100% on your flight

$354

per person

Aug 9 - Aug 12

found 9 hours ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9.2/10 Wonderful! (1,330 reviews)

Super lindo y tranquilo

Reviewed on Jul 7, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

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

$301

per person

Sep 13 - Sep 16

found 18 hours ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9.2/10 Wonderful! (1,330 reviews)

Super lindo y tranquilo

Reviewed on Jul 7, 2026

Amara Cay Resort

Matecumbe

Save 100% on your flight

$302

per person

Sep 13 - Sep 16

found 18 hours ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

8.8/10 Excellent! (1,288 reviews)

The rooms were clean, staff was attentive but property had trash laying around and

Reviewed on Jul 9, 2026

La Siesta Resort & Villas

Matecumbe

$524

per person

Aug 9 - Aug 12

found 7 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,007 reviews)

The room was very dirty when we arrived. The location and view from the room was amazing. The pool was great except it had black spots all over, which looked like black mold. There were also metal brush bristles from the staff cleaning the pool, on the bottom of the pool and a few people were cut while swimming. The pool attendant told us that the amenities were closed because of the wind being over 10 knots, including the Rum Runner, which wasn’t and shouldn’t have been the case. We later saw the rum runner dropping people off. We were very upset because we were looking forward to going on it one last time before the end of our trip. We lost a full day of using the paddle boards and kayaks and the Rum Runner. The staff was very friendly and accommodating when we talked to them about our issues.

Reviewed on Jul 9, 2026

Don't see what you're looking for?

See all available trips from Columbus to Florida Keys

View all trips

4 Night Beach vacations in Florida Keys

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

Ibis Bay Beach Resort

Northside Resort

$707

per person

Sep 9 - Sep 13

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to Key West (EYW)

8.2/10 Very Good! (2,289 reviews)

Great property and excellent value. The place was clean and very nice. Really appreciated how clean and well kept everything was.

Reviewed on Jul 9, 2026

Amara Cay Resort

Matecumbe

Save 100% on your flight

$801

per person

Sep 17 - Sep 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

8.8/10 Excellent! (1,288 reviews)

The rooms were clean, staff was attentive but property had trash laying around and

Reviewed on Jul 9, 2026

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$2,083

per person

Sep 14 - Sep 18

found 1 hour ago

Roundtrip non-stop flight included

Lafayette (LFT) to Miami (MIA)

9.2/10 Wonderful! (1,330 reviews)

Super lindo y tranquilo

Reviewed on Jul 7, 2026

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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 $301. 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

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

29 min drive from Florida Keys Beaches

Make the most of this fantastic location, as you'll be close to a private beach with a stay at this hotel. 2 restaurants, 2 bars, and an outdoor pool are just ...

8.6/10 Excellent! (2,336 reviews)

Travelers like: on the beach, sun loungers, beach towels, outdoor pool

Travelers say...

"Perfect place to stay. We would have had so much fun if we had known about that place last year. We definitely will come back"

Reviewed on Jul 9, 2026

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

36 min drive from Florida Keys Beaches

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! (3,438 reviews)

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

Travelers say...

"found dirty ice bucket in room and every night the ceiling fan and light would come on and stay on or flash on and off. Told the office staff two days in a row and they only wanted to give me resort credit. Not concerned at all that our nights were disrupted at midnight every night! Seems by reading ..."

Reviewed on Jul 9, 2026

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard Key West FL

33 min drive from Florida Keys Beaches

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! (1,820 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...

"The room had a terrible order to it and the furniture looked very worn out. We didn't even unpacked, and went down and checked out"

Reviewed on Jul 8, 2026

See all 8,283 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.