Top Beach vacation packages in Florida Keys

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

Amara Cay Resort

Matecumbe

$562

per person

Aug 1 - Aug 3

found 4 hours ago

Roundtrip flight included

Pittsburgh (PIT) to Miami (MIA)

8.8/10 Excellent! (1,269 reviews)

Beautiful location, very helpful staff and just an exquisite experience. Food was excellent. Loved every second.

Reviewed on May 13, 2026

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

Save 100% on your flight

$638

per person

Jul 16 - Jul 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9/10 Wonderful! (192 reviews)

Beautiful property, lots to do on the property. We found lighting in the rooms to be a little lacking, especially in the coffee bar area. The rooms are really small but we kind of knew that going in, the balcony was a great extension of space. Clean and lots of staff around to help with anything.

Reviewed on May 14, 2026

Islander Resort

Matecumbe

Save 100% on your flight

$767

per person

Jul 16 - Jul 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9.2/10 Wonderful! (1,004 reviews)

I think some of the outdoor cushions could be updated.

Reviewed on May 13, 2026

Cheeca Lodge & Spa

Matecumbe

$808

per person

Jun 14 - Jun 17

found 1 day ago

Roundtrip non-stop flight included

Indianapolis (IND) to Miami (MIA)

9.2/10 Wonderful! (1,323 reviews)

Exelente service but the room need more clean and attention

Reviewed on May 11, 2026

Hawks Cay Resort

$848

per person

Jun 14 - Jun 17

found 1 hour ago

Roundtrip non-stop flight included

Allentown (ABE) to Miami (MIA)

8.2/10 Very Good! (1,008 reviews)

Perfect for our family, staff was amazing and the property is beautiful

Reviewed on May 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

Matecumbe

$808

per person

Jun 14 - Jun 17

found 1 day ago

Roundtrip non-stop flight included

Indianapolis (IND) to Miami (MIA)

9.2/10 Wonderful! (1,323 reviews)

Exelente service but the room need more clean and attention

Reviewed on May 11, 2026

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3 Night Beach vacations in Florida Keys

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

Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

$531

per person

Jun 14 - Jun 17

found 6 hours ago

Roundtrip non-stop flight included

Indianapolis (IND) to Miami (MIA)

8.8/10 Excellent! (1,174 reviews)

There are two pools. We found that the pool closest to the hotel was more kid friendly than the other one by the restaurant. We had a wonderful time, but it was hard to get a hold of the front desk when we needed them and it was a pain to walk all the way there from the hotel rooms which is a separate building.

Reviewed on May 13, 2026

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

Save 100% on your flight

$638

per person

Jul 16 - Jul 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9/10 Wonderful! (192 reviews)

Beautiful property, lots to do on the property. We found lighting in the rooms to be a little lacking, especially in the coffee bar area. The rooms are really small but we kind of knew that going in, the balcony was a great extension of space. Clean and lots of staff around to help with anything.

Reviewed on May 14, 2026

Islander Resort

Matecumbe

Save 100% on your flight

$767

per person

Jul 16 - Jul 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

9.2/10 Wonderful! (1,004 reviews)

I think some of the outdoor cushions could be updated.

Reviewed on May 13, 2026

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4 Night Beach vacations in Florida Keys

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

Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

Save 100% on your flight

$409

per person

Jul 18 - Jul 22

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Miami (MIA)

8.8/10 Excellent! (1,174 reviews)

There are two pools. We found that the pool closest to the hotel was more kid friendly than the other one by the restaurant. We had a wonderful time, but it was hard to get a hold of the front desk when we needed them and it was a pain to walk all the way there from the hotel rooms which is a separate building.

Reviewed on May 13, 2026

Lime Tree Bay Resort

Save 100% on your flight

$426

per person

Jul 18 - Jul 22

found 8 hours ago

Roundtrip flight included

Baltimore (BWI) to Miami (MIA)

9.2/10 Wonderful! (1,264 reviews)

Our first trip down the Keys and we picked this location based on photos/comments from the internet. It did not disappoint. Staff was friendly and helpful. Location was outstanding. Beautiful water (and easy access). Small resort feel and a nice studio beach level room. Bathrooms are small.. but don’t spend too much time in them so not an issue! Easy access to amenities such as pool, paddle boards, kayaks etc.. Would definitely stay here again if we returned.

Reviewed on May 14, 2026

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

Save 100% on your flight

$883

per person

Jul 16 - Jul 20

found 4 hours ago

Roundtrip flight included

Cleveland (CLE) to Miami (MIA)

9/10 Wonderful! (192 reviews)

Beautiful property, lots to do on the property. We found lighting in the rooms to be a little lacking, especially in the coffee bar area. The rooms are really small but we kind of knew that going in, the balcony was a great extension of space. Clean and lots of staff around to help with anything.

Reviewed on May 14, 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 $409. 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

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! (1,791 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...

Very overpriced the pool was small, no balcony views

Reviewed on May 14, 2026

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! (651 reviews)

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

Travelers say...

Amazing location with private beach and awesome restaurant. We would definitely stay here again.

Reviewed on May 13, 2026

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! (1,021 reviews)

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

Travelers say...

Dear Double Tree, This was our first trip to Key West and our first experience with a Hilton resort. You met and exceeded any expectations that we could have had. The friendliness, helpfulness and professionalism of each member of your staff was outstanding. The facility was immaculate and well maintained. ...

Reviewed on May 14, 2026

See all 8,335 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.