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.

Bahama Beach Club Pompano

Save 100% on your flight

$592

per person

Jan 5 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.8/10 Exceptional! (49 reviews)

I have just returned from a fabulous stay at Bahama Beach Club. This wonderful property provided an immaculately clean and comfortable unit for my stay. I had a full kitchen, living room and a very comfortable large bed. The air conditioning was great, along with easy parking too. There was even a tea kettle, I’ve never seen one in Florida before! I had everything that I needed to make life easy away from home. It is a lovely, peaceful place and the location was fantastic. I walked across to the beach in under a few minutes. The owners have great attention to detail, and even provided chairs and umbrellas for the beach. I am so glad to have stayed here and found such a lovely place to come back to again and again. I can’t wait to return again soon!

Reviewed on Oct 17, 2026

Avi Lux Stay

East Fort Lauderdale

$721

per person

Dec 7 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.6/10 Good! (10 reviews)

If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.

Reviewed on Aug 28, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$12,496

per person

Nov 29 - Dec 4

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

Lyfe Resort & Residences

Hollywood Beach

Save 100% on your flight

$769

per person

Jan 9 - Jan 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.8/10 Good! (37 reviews)

We stay here every time. We really like everything.

Reviewed on Oct 22, 2026

Hotel Riu Plaza Miami Beach

Mid Beach

$766

per person

Jan 11 - Jan 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,199 reviews)

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5* Beach vacations in Windley Key

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

Miami Vacation Rentals - Downtown

Downtown Miami

$1,029

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (92 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$12,496

per person

Nov 29 - Dec 4

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

Save 100% on your flight

$4,038

per person

Nov 30 - Dec 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,654 reviews)

Loved

Reviewed on Oct 21, 2026

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.

Avi Lux Stay

East Fort Lauderdale

$575

per person

Dec 3 - Dec 6

found 1 hour ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.6/10 Good! (10 reviews)

Reviewed on Aug 28, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$8,161

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip non-stop 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

Hotel Riu Plaza Miami Beach

Mid Beach

Save 100% on your flight

$1,442

per person

Dec 30 - Jan 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,199 reviews)

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.

Hotel Riu Plaza Miami Beach

Mid Beach

$766

per person

Jan 11 - Jan 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,199 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$16,565

per person

Dec 30 - Jan 3

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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

$1,088

per person

Dec 6 - Dec 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (163 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

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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 $575. Prices and availability are subject to change. Additional terms may apply.

When should I book a Windley Key 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 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! (297 reviews)

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

Travelers say...

"Beautiful property, would stay there again"

Reviewed on Oct 22, 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! (1,000 reviews)

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

Travelers say...

"We had a nice stay at Fisher Inn. The location was great, the rooms were spacious, and having two king beds was a bonus. The bathroom was on the small side, but it was clean. We also appreciated the Keurig coffee maker in the room, especially having dark roast coffee available, and there were some ..."

Reviewed on Oct 21, 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. ...

9/10 Wonderful! (302 reviews)

"Our stay here was wonderful. Though some things may need updated the overall ambiance of the resort over rode that. The managing staff are very helpful & hardworking. It’s a beautiful piece of oceanfront property & so easy to navigate whether you want to swim, boat, fish or just relax."

Reviewed on Oct 21, 2026

See all 2,688 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.