Top Beach vacation packages in Islamorada

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

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

Save 100% on your flight

$850

per person

Feb 16 - Feb 19

found 1 day ago

Roundtrip flight included

Washington (WAS) to Miami (MIA)

9/10 Wonderful! (108 reviews)

Room very clean; staff very friendly and helpful. The location stunning!

Reviewed on Jan 15, 2026

Amara Cay Resort

Matecumbe

Save 100% on your flight

$1,002

per person

Feb 16 - Feb 19

found 1 day ago

Roundtrip non-stop flight included

Atlantic City (ACY) to Miami (MIA)

8.8/10 Excellent! (1,252 reviews)

Great Location, Friendly Staff

Reviewed on Jan 12, 2026

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$1,746

per person

Mar 19 - Mar 22

found 13 hours ago

Roundtrip non-stop flight included

Bangor (BGR) to Miami (MIA)

9.2/10 Wonderful! (1,262 reviews)

Overall our stay was fabulous. Some small gripes are the shower heads were built up with mineral deposits and didn’t spray properly and there was a leak in our ceiling above the toilet. However it is a beautiful resort. Lots of amenities, fun for the whole family

Reviewed on Jan 11, 2026

La Siesta Resort & Villas

Matecumbe

Save 100% on your flight

$1,030

per person

Feb 16 - Feb 19

found 1 day ago

Roundtrip non-stop flight included

Atlantic City (ACY) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

The kitchen had nothing in it, so plan ahead. No silverware at all. The room was as pictured, and the pool.and beach areas were very nice. Lots of restaurants super close. Shopping nearby as well

Reviewed on Jan 12, 2026

Islander Resort

Matecumbe

$1,667

per person

Mar 19 - Mar 22

found 13 hours ago

Roundtrip non-stop flight included

Bangor (BGR) to Miami (MIA)

9.2/10 Wonderful! (1,005 reviews)

Really liked this place! Had a few issues with hot water and the shower. They were definitely responsive about fixing but there were some language barriers which made that a little difficult. Some of the furniture around the pool needed some love. And there was a lot of empty space on the property that felt a little too empty? But would recommend it to others!

Reviewed on Jan 13, 2026

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5* Beach vacations in Islamorada

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

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$1,746

per person

Mar 19 - Mar 22

found 13 hours ago

Roundtrip non-stop flight included

Bangor (BGR) to Miami (MIA)

9.2/10 Wonderful! (1,262 reviews)

Overall our stay was fabulous. Some small gripes are the shower heads were built up with mineral deposits and didn’t spray properly and there was a leak in our ceiling above the toilet. However it is a beautiful resort. Lots of amenities, fun for the whole family

Reviewed on Jan 11, 2026

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3 Night Beach vacations in Islamorada

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

Amara Cay Resort

Matecumbe

Save 100% on your flight

$1,002

per person

Feb 16 - Feb 19

found 1 day ago

Roundtrip non-stop flight included

Atlantic City (ACY) to Miami (MIA)

8.8/10 Excellent! (1,252 reviews)

Great Location, Friendly Staff

Reviewed on Jan 12, 2026

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$1,746

per person

Mar 19 - Mar 22

found 13 hours ago

Roundtrip non-stop flight included

Bangor (BGR) to Miami (MIA)

9.2/10 Wonderful! (1,262 reviews)

Overall our stay was fabulous. Some small gripes are the shower heads were built up with mineral deposits and didn’t spray properly and there was a leak in our ceiling above the toilet. However it is a beautiful resort. Lots of amenities, fun for the whole family

Reviewed on Jan 11, 2026

La Siesta Resort & Villas

Matecumbe

Save 100% on your flight

$1,030

per person

Feb 16 - Feb 19

found 1 day ago

Roundtrip non-stop flight included

Atlantic City (ACY) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

The kitchen had nothing in it, so plan ahead. No silverware at all. The room was as pictured, and the pool.and beach areas were very nice. Lots of restaurants super close. Shopping nearby as well

Reviewed on Jan 12, 2026

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4 Night Beach vacations in Islamorada

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

Creekside Inn

$587

per person

Mar 19 - Mar 23

found 22 hours ago

Roundtrip flight included

Atlanta (ATL) to Miami (MIA)

8/10 Very Good! (1,004 reviews)

Excelente personal muy amable

Reviewed on Jan 16, 2026

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$2,129

per person

Mar 19 - Mar 23

found 1 day ago

Roundtrip flight included

Des Moines (DSM) to Miami (MIA)

9.2/10 Wonderful! (1,262 reviews)

Overall our stay was fabulous. Some small gripes are the shower heads were built up with mineral deposits and didn’t spray properly and there was a leak in our ceiling above the toilet. However it is a beautiful resort. Lots of amenities, fun for the whole family

Reviewed on Jan 11, 2026

La Siesta Resort & Villas

Matecumbe

Save 100% on your flight

$1,051

per person

Feb 16 - Feb 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,000 reviews)

The kitchen had nothing in it, so plan ahead. No silverware at all. The room was as pictured, and the pool.and beach areas were very nice. Lots of restaurants super close. Shopping nearby as well

Reviewed on Jan 12, 2026

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See all available trips from Columbus to Islamorada

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How do I book the best Islamorada beach vacation packages?

Life’s a beach when you dive into our brilliant Islamorada 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 Islamorada?

A rental steps from the shore creates an amazingly affordable Islamorada beach vacation. Seaside sojourns during low season start from $587. Prices and availability are subject to change. Additional terms may apply.

When should I book a Islamorada 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 Islamorada?

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 Islamorada 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 Islamorada 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 Islamorada beach vacation deals?

Sort your search results by deals to delight in amazing Islamorada 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 Islamorada beach trip with free cancellation and/or flexible dates?

Just like the Islamorada 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 Islamorada 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 Islamorada. (OK, maybe not that last part.)

Top Beach Islamorada Hotels

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

22 min walk from Theater of the Sea

At this hotel, get ready to watch the sunset on the beach in Islamorada, as you'll be close to a private beach. 2 outdoor pools, a bar, and beach towels are ...

9.2/10 Wonderful! (1,631 reviews)

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

Travelers say...

The check in was easy. The front desk employee was very kind. Our room was spotless. We spent the afternoon on the beach and used the kayak. We enjoyed breakfast. The omelet chef was awesome. Overall I was very happy with my stay

Reviewed on Jan 12, 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

8 min drive from Theater of the Sea

Relax at this luxury spa resort and get ready to watch the sunset on the beach in Islamorada, as you'll be near a private beach. 3 outdoor pools, 10 outdoor ...

9.2/10 Wonderful! (1,288 reviews)

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

Travelers say...

Overall our stay was fabulous. Some small gripes are the shower heads were built up with mineral deposits and didn’t spray properly and there was a leak in our ceiling above the toilet. However it is a beautiful resort. Lots of amenities, fun for the whole family

Reviewed on Jan 11, 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

12 min drive from Theater of the Sea

You will love your stay at this resort and get ready to walk along the waves in Islamorada, as you'll be a short walk from a private beach. Amenities at Amara ...

8.8/10 Excellent! (1,260 reviews)

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

Travelers say...

This resort exceed our expectations. Wonderful for families , very clean and amazing staff. We did a free fishing lesson with captain Patrick and he was wonderful-also great with kids. Loved the free water taxi to visit the sister resorts . We will definitely be back

Reviewed on Jan 10, 2026

See all 2,213 properties in Islamorada

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.