Top Beach vacation packages 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

$567

per person

Jun 30 - Jul 4

found 1 day ago

Roundtrip flight included

New York (NYC) to Miami (MIA)

8.6/10 Excellent! (1,163 reviews)

The location was okay, but not any place we'd revisit. There's a pool in the main lobby area and another that is where the rooms are. That one doesn't have pool service and this is the first resort that we've been to that doesn't have towels available at the pool. Unknowingly to us, there were towels in the cabinet but we never opened that. They have a coffee/snack bar that I was told closed at 11. I was really looking forward to an iced coffee and just thought it was strange that the hours weren't longer.

Reviewed on May 29, 2026

La Siesta Resort & Villas

Matecumbe

$780

per person

Jun 29 - Jul 2

found 1 hour ago

Roundtrip non-stop flight included

Myrtle Beach (MYR) to Miami (MIA)

8.6/10 Excellent! (1,003 reviews)

Room was nice with balcony but not what I expected. Thought I was booking the room that was in the picture. All the pictures of my room at time of reservation appeared like the photos shown on the site, but this was not in fact the room we received. Overall the property is pretty nice with bikes, kayaks and paddleboards available at no extra charge. There was a free shuttle to the sister resorts Amara Cay and Three Waters Resorts. We went to the Three Waters Resort and this resort was a bit nicer than La Siesta and the staff there was amazing. The staff a La Siesta, not so much often hard to find, even at the pool bar and beach/kayak area.

Reviewed on May 14, 2026

Cheeca Lodge & Spa

Matecumbe

$858

per person

Jun 29 - Jul 2

found 1 hour ago

Roundtrip non-stop flight included

Myrtle Beach (MYR) to Miami (MIA)

9.2/10 Wonderful! (1,315 reviews)

My wife and I had an amazing experience. The staff were very friendly and helpful. We loved our room with the screened patio, we had our coffee there every morning overlooking the tennis courts. There’s so many things to do that are included, I don’t think we’ve ever stayed at a resort that had so many amenities included at no charge. We will definitely visit again on our next trip to the Keys.

Reviewed on May 28, 2026

Tranquility Bay Beachfront Hotel and Resort

Save 100% on your flight

$729

per person

Jul 1 - Jul 4

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Miami (MIA)

8.8/10 Excellent! (1,007 reviews)

Very clean and staff was amazing and helpful. Definable would come back!

Reviewed on May 27, 2026

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

$627

per person

Jul 30 - Aug 1

found 1 day ago

Roundtrip flight included

Memphis (MEM) to Miami (MIA)

9/10 Wonderful! (198 reviews)

The property was beautiful as soon as we pulled up we were greeted by a woman on a golf cart. She was so happy and helpful. It made us feel comfortable right away, showed us to the front desk and she was also so very friendly. I wish I remembered their names. We got an ocean view. It also overlooked the pool and tiki bar and beach. The rooms were clean. Our balcony had very comfortable seating. We sat outside all night and walked to the property around the marina. I would definitely come back.

Reviewed on May 30, 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

$858

per person

Jun 29 - Jul 2

found 1 hour ago

Roundtrip non-stop flight included

Myrtle Beach (MYR) to Miami (MIA)

9.2/10 Wonderful! (1,315 reviews)

My wife and I had an amazing experience. The staff were very friendly and helpful. We loved our room with the screened patio, we had our coffee there every morning overlooking the tennis courts. There’s so many things to do that are included, I don’t think we’ve ever stayed at a resort that had so many amenities included at no charge. We will definitely visit again on our next trip to the Keys.

Reviewed on May 28, 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

Save 100% on your flight

$471

per person

Jul 1 - Jul 4

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Miami (MIA)

8.6/10 Excellent! (1,163 reviews)

The location was okay, but not any place we'd revisit. There's a pool in the main lobby area and another that is where the rooms are. That one doesn't have pool service and this is the first resort that we've been to that doesn't have towels available at the pool. Unknowingly to us, there were towels in the cabinet but we never opened that. They have a coffee/snack bar that I was told closed at 11. I was really looking forward to an iced coffee and just thought it was strange that the hours weren't longer.

Reviewed on May 29, 2026

La Siesta Resort & Villas

Matecumbe

$780

per person

Jun 29 - Jul 2

found 1 hour ago

Roundtrip non-stop flight included

Myrtle Beach (MYR) to Miami (MIA)

8.6/10 Excellent! (1,003 reviews)

Room was nice with balcony but not what I expected. Thought I was booking the room that was in the picture. All the pictures of my room at time of reservation appeared like the photos shown on the site, but this was not in fact the room we received. Overall the property is pretty nice with bikes, kayaks and paddleboards available at no extra charge. There was a free shuttle to the sister resorts Amara Cay and Three Waters Resorts. We went to the Three Waters Resort and this resort was a bit nicer than La Siesta and the staff there was amazing. The staff a La Siesta, not so much often hard to find, even at the pool bar and beach/kayak area.

Reviewed on May 14, 2026

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$873

per person

Jul 30 - Aug 2

found 1 day ago

Roundtrip flight included

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

9.2/10 Wonderful! (1,315 reviews)

My wife and I had an amazing experience. The staff were very friendly and helpful. We loved our room with the screened patio, we had our coffee there every morning overlooking the tennis courts. There’s so many things to do that are included, I don’t think we’ve ever stayed at a resort that had so many amenities included at no charge. We will definitely visit again on our next trip to the Keys.

Reviewed on May 28, 2026

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4 Night Beach vacations in Florida Keys

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

Lime Tree Bay Resort

Save 100% on your flight

$660

per person

Jul 30 - Aug 3

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Miami (MIA)

9.2/10 Wonderful! (1,288 reviews)

Booked online, initially expecting all facilities "one footprint". Three pools were advertised w/canal, garden, and water access. Room 5 faced open water, w/o 'beach' access. Pool was great, loved gradual shallow 8" to 5'. Tiki-style umbrellas at pool/water areas, provide shade. Chairs comfortable, beach towels accessible, large, clean & striped blue. Check-in staff helpful and friendly. Yoga offering 2x weekly. Attempt to book a massage was a dead end. The kayaks, paddle boards and bikes are included, limited due to wind conditions. This was disappointing. Bar drinks were strong, yet tasty. Onsite conch fritters were as expected, homemade and crispy. Ice is available, although we did not use. We did not embark on cleaning, although when requested clean towels, paper towels, toilet tissue were obtained through office/housekeeping. King room could use a full length mirror. The bed was comfortable, although not firm. Full kitchen-I deep cleaned upon arrival as mold was growing over microwave. Refrigerator full size. Coffee pot-too small. Knives not sharp, we bought our own. We cooked daily, shopped Publix/Winn Dixie. Tile floor, left our feet BLACK, and bathroom could have been cleaner-brought lysol! AC & fan COOL. Front porch was our favorite. Safe in room. Parking provided and convenient. Both rolling cart/wagon for self checkin/out use. WE loved 1st floor-palm trees & geckos. Bring snorkel-nurse shark, lobster, and fish to see! Staff friendly! Breakfast onsite not tried.

Reviewed on May 28, 2026

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$1,340

per person

Jul 1 - Jul 5

found 15 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,315 reviews)

My wife and I had an amazing experience. The staff were very friendly and helpful. We loved our room with the screened patio, we had our coffee there every morning overlooking the tennis courts. There’s so many things to do that are included, I don’t think we’ve ever stayed at a resort that had so many amenities included at no charge. We will definitely visit again on our next trip to the Keys.

Reviewed on May 28, 2026

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

Save 100% on your flight

$767

per person

Jul 30 - Aug 3

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Miami (MIA)

9/10 Wonderful! (198 reviews)

The property was beautiful as soon as we pulled up we were greeted by a woman on a golf cart. She was so happy and helpful. It made us feel comfortable right away, showed us to the front desk and she was also so very friendly. I wish I remembered their names. We got an ocean view. It also overlooked the pool and tiki bar and beach. The rooms were clean. Our balcony had very comfortable seating. We sat outside all night and walked to the property around the marina. I would definitely come back.

Reviewed on May 30, 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 $471. 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! (1,803 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...

"We loved our stay! Would definitely be back again!"

Reviewed on May 29, 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! (1,027 reviews)

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

Travelers say...

"S"

Reviewed on May 29, 2026

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

5 min drive from Duval Street

Watch the sunset on the beach in Key West, as you'll be near a private beach when booking a getaway at this hotel. Amenities at Ibis Bay Beach Resort include ...

8/10 Very Good! (2,284 reviews)

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

Travelers say...

"We checked in 45 minutes early which they allowed and was great. The room itself was big and had 2 nice beds, a cute fridge/freezer and dresser. The doorwalls only had a bar and no lock. The bathroom shower was small with no shelves and no bathroom counter to speak of. The shower had dead bugs all ..."

Reviewed on May 28, 2026

See all 8,386 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.