Top Beach vacation packages in Islamorada

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

La Siesta Resort & Villas

Matecumbe

$415

per person

Nov 17 - Nov 21

found 2 hours ago

Roundtrip flight included

Dallas (DFW) to Miami (MIA)

8.6/10 Excellent! (1,005 reviews)

too many small ants in my room an all over us

Reviewed on Oct 16, 2025

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$771

per person

Dec 18 - Dec 22

found 9 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

Islander Resort

Matecumbe

Save 100% on your flight

$531

per person

Nov 17 - Nov 21

found 2 hours ago

Roundtrip flight included

Dallas (DFW) to Miami (MIA)

9.2/10 Wonderful! (1,002 reviews)

We loved staying at the Islander! The staff was very welcoming and responded instantly to texts. It was nice that they offered a shuttled so we could experience other places close to the resort. The rooms were beautiful along with the beach and pool areas! So many seating/lounging options with the cutest furniture. I would highly recommend this resort, well done!

Reviewed on Oct 14, 2025

Amara Cay Resort

Matecumbe

$1,055

per person

Dec 20 - Dec 24

found 1 day ago

Roundtrip flight included

Nashville (BNA) to Miami (MIA)

8.8/10 Excellent! (1,247 reviews)

Excellent! I’ll recommend

Reviewed on Oct 13, 2025

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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

$771

per person

Dec 18 - Dec 22

found 9 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

Don't see what you're looking for?

See all available trips from Columbus to Islamorada

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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

$512

per person

Nov 19 - Nov 22

found 4 hours ago

Roundtrip flight included

Nashville (BNA) to Miami (MIA)

8.8/10 Excellent! (1,247 reviews)

Excellent! I’ll recommend

Reviewed on Oct 13, 2025

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$1,215

per person

Dec 19 - Dec 22

found 12 hours ago

Roundtrip non-stop flight included

Hartford (BDL) to Miami (MIA)

9.2/10 Wonderful! (1,201 reviews)

This resort was amazing!

Reviewed on Oct 17, 2025

Islander Resort

Matecumbe

Save 100% on your flight

$610

per person

Nov 19 - Nov 22

found 4 hours ago

Roundtrip flight included

Nashville (BNA) to Miami (MIA)

9.2/10 Wonderful! (1,002 reviews)

We loved staying at the Islander! The staff was very welcoming and responded instantly to texts. It was nice that they offered a shuttled so we could experience other places close to the resort. The rooms were beautiful along with the beach and pool areas! So many seating/lounging options with the cutest furniture. I would highly recommend this resort, well done!

Reviewed on Oct 14, 2025

Don't see what you're looking for?

See all available trips from Columbus to Islamorada

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4 Night Beach vacations in Islamorada

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

Creekside Inn

Save 100% on your flight

$321

per person

Nov 17 - Nov 21

found 2 hours ago

Roundtrip flight included

Dallas (DFW) to Miami (MIA)

8/10 Very Good! (1,009 reviews)

Clean room,feiendly staff wben available; difficulties contacting front desk personel and getting the room serviced when serviced done well

Reviewed on Oct 14, 2025

Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$771

per person

Dec 18 - Dec 22

found 9 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 Morada

Matecumbe

Save 100% on your flight

$802

per person

Dec 18 - Dec 22

found 9 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Miami (MIA)

9.4/10 Exceptional! (409 reviews)

The marina was clean and convenient.

Reviewed on Aug 3, 2025

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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 $321. Prices and availability are subject to change. Additional terms may apply.

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

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, 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 ...

9/10 Wonderful! (1,221 reviews)

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

Travelers say...

"room were cleaned every morning; we were able to park under the room drinks were pricy"

Reviewed on Oct 9, 2025

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! (1,254 reviews)

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

Travelers say...

"Room was spacious, clean with a great balcony."

Reviewed on Oct 7, 2025

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! (1,543 reviews)

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

Travelers say...

"Love this place. Great beach/pool. Lovely room with great bathroom. Unbelievable view of the sunrise over the water from our balcony"

Reviewed on Oct 14, 2025

See all 2,217 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.