Windley Key Beach Vacations 2026

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Top Beach vacation packages in Windley Key

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

Miami Vacation Rentals - Downtown

Downtown Miami

Save 100% on your flight

$973

per person

Oct 24 - Oct 31

found 8 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (81 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$12,309

per person

Oct 24 - Oct 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

EAST Miami Residences

Brickell

$1,933

per person

Oct 24 - Oct 31

found 13 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (143 reviews)

Great staff. Really try to sort out any issues and requests.

Reviewed on Aug 20, 2026

1 Hotel South Beach

South Beach

$3,613

per person

Oct 1 - Oct 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,613 reviews)

Kimpton Surfcomber Hotel by IHG

South Beach

Save 100% on your flight

$1,323

per person

Oct 24 - Oct 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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

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See all available trips from Columbus to Windley Key

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5* Beach vacations in Windley Key

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

EAST Miami Residences

Brickell

$1,933

per person

Oct 24 - Oct 31

found 13 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (143 reviews)

Great staff. Really try to sort out any issues and requests.

Reviewed on Aug 20, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$12,309

per person

Oct 24 - Oct 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

1 Hotel South Beach

South Beach

$3,613

per person

Oct 1 - Oct 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,613 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

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3 Night Beach vacations in Windley Key

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

Pelican Hotel

South Beach

Save 100% on your flight

$555

per person

Nov 17 - Nov 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (492 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$7,348

per person

Oct 9 - Oct 12

found 21 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

The Marlin Hotel

South Beach

Save 100% on your flight

$610

per person

Oct 29 - Nov 1

found 20 hours ago

Roundtrip flight included

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

9.2/10 Wonderful! (1,004 reviews)

Corner suite was great. Staff were very helpful. Great weekend stay!

Reviewed on Aug 24, 2026

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

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4 Night Beach vacations in Windley Key

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

President Hotel Villa

South Beach

Save 100% on your flight

$565

per person

Nov 12 - Nov 16

found 7 hours ago

Roundtrip flight included

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

8.2/10 Very Good! (1,005 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$8,222

per person

Oct 8 - Oct 12

found 9 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

1 Hotel South Beach

South Beach

Save 100% on your flight

$1,322

per person

Oct 28 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,613 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

View all trips

How do I book the best Windley Key beach vacation packages?

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

A rental steps from the shore creates an amazingly affordable Windley Key beach vacation. Seaside sojourns during low season start from $555. Prices and availability are subject to change. Additional terms may apply.

How can I book the best family beach vacations in Windley Key?

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 Windley Key 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 Windley Key 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 Windley Key beach vacation deals?

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

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

Top Beach Windley Key Hotels

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

84001 Overseas Hwy Islamorada FL

10 min walk from Theater of the Sea

Make the most of this fantastic location, as you'll be within walking distance of a private beach with a holiday at this resort. Amenities at Three Waters Resort ...

9/10 Wonderful! (255 reviews)

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

Travelers say...

"I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff."

Reviewed on Aug 23, 2026

Fisher Inn Resort & Marina

84951 Overseas Hwy Islamorada FL

5 min walk from Theater of the Sea

You will love your stay at this motel and stroll along the shore in Islamorada, as you'll be close to a private beach. An outdoor pool, beach towels, and beach ...

8.2/10 Very Good! (1,015 reviews)

Travelers like: on the beach, sun loungers, beach umbrellas, beach towels

Travelers say...

"Was Great! Everyone was super nice and helpful!"

Reviewed on Aug 23, 2026

Coconut Cove Resort and Marina

84801 Overseas Highway Islamorada FL

2 min walk from Theater of the Sea

Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free parking, and a marina. Our guests praise the pool and the helpful staff in our reviews. ...

See all 2,710 properties in Windley Key

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.