Top Beach vacation packages in Windley Key

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

Hotel Colonnade Coral Gables, Autograph Collection

Coral Gables Section

$521

per person

Nov 21 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,006 reviews)

Es un hotel estupendo muy bien situado y el personal es fantástico!!

Reviewed on Oct 14, 2025

The Shelborne By Proper, a Member of Design Hotels

South Beach

$1,335

per person

Dec 31 - Jan 4

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

9.8/10 Exceptional! (31 reviews)

Great hotel. Clearly freshly refurbished and excellent facilities. Staff were extremely attentive - everyone we bumped into in the lift, for example, even junior team members, asked how we were and whether there was anything that they could do to improve our stay. Shows a great culture! Only downsides are a bar that shuts very early (10pm) and a LOT of mosquitoes in the outdoor pool area - they give bug spray it we had to retreat late afternoon or after rain.

Reviewed on Oct 6, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$13,533

per person

Dec 3 - Dec 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Bahama Beach Club Pompano

$632

per person

Jan 1 - Jan 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

10/10 Exceptional! (12 reviews)

Such a cute property with lots of charm and a great pool. We loved being able to walk to absolutely everything! The owners were so helpful in guiding us in things to do and how to best get around. We can’t wait to return.

Reviewed on Oct 15, 2025

Bentley Hotel South Beach

South Beach

$703

per person

Jan 10 - Jan 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (334 reviews)

The staff very friendly and helpful,

Reviewed on Oct 15, 2025

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5* Beach vacations in Windley Key

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

EAST Miami

Downtown Miami

$790

per person

Jan 10 - Jan 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (3,369 reviews)

I spend two days there everything was perfect clean and nice I love it can’t wait to go back there

Reviewed on Oct 14, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$13,533

per person

Dec 3 - Dec 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

1 Hotel South Beach

South Beach

$4,067

per person

Dec 30 - Jan 4

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,307 reviews)

Great stay, well get back

Reviewed on Oct 10, 2025

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3 Night Beach vacations in Windley Key

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

The Shelborne By Proper, a Member of Design Hotels

South Beach

Save 100% on your flight

$664

per person

Nov 15 - Nov 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.8/10 Exceptional! (31 reviews)

Great hotel. Clearly freshly refurbished and excellent facilities. Staff were extremely attentive - everyone we bumped into in the lift, for example, even junior team members, asked how we were and whether there was anything that they could do to improve our stay. Shows a great culture! Only downsides are a bar that shuts very early (10pm) and a LOT of mosquitoes in the outdoor pool area - they give bug spray it we had to retreat late afternoon or after rain.

Reviewed on Oct 6, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$8,645

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip flight included

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

8/10 Very Good! (1 review)

Fox Garden Home Near Downtown & Beach

Central Fort Lauderdale

$1,581

per person

Dec 17 - Dec 20

found 1 day ago

Roundtrip flight included

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

No reviews

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4 Night Beach vacations in Windley Key

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

Bentley Hotel South Beach

South Beach

$703

per person

Jan 10 - Jan 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (334 reviews)

The staff very friendly and helpful,

Reviewed on Oct 15, 2025

The Shelborne By Proper, a Member of Design Hotels

South Beach

$1,335

per person

Dec 31 - Jan 4

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

9.8/10 Exceptional! (31 reviews)

Great hotel. Clearly freshly refurbished and excellent facilities. Staff were extremely attentive - everyone we bumped into in the lift, for example, even junior team members, asked how we were and whether there was anything that they could do to improve our stay. Shows a great culture! Only downsides are a bar that shuts very early (10pm) and a LOT of mosquitoes in the outdoor pool area - they give bug spray it we had to retreat late afternoon or after rain.

Reviewed on Oct 6, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$8,449

per person

Jan 2 - Jan 6

found 19 hours ago

Roundtrip flight included

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

8/10 Very Good! (1 review)

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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 $521. 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 ...

8.8/10 Excellent! (95 reviews)

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

Travelers say...

"view was great ,service was great also"

Reviewed on Oct 9, 2025

Fisher Inn Resort & Marina

84951 Overseas Hwy, Islamorada, FL

6 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 ...

8/10 Very Good! (1,002 reviews)

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

Travelers say...

"While we did like our stay and the staff was helpful and friendly, we have two things we would like to mention. First off, it was difficult to relax in the pool or along the water because the facility’s music was always playing at a loud volume through the fake rock speakers. The one time we were ..."

Reviewed on Oct 11, 2025

Coconut Cove Resort and Marina

84801 Overseas Highway, Islamorada, FL

2 min walk from Theater of the Sea

Stay at this 3-star beach hotel in Islamorada. Enjoy free breakfast, free parking, and a marina. Our guests praise the pool and the helpful staff in our reviews. ...

7.6/10 Good! (823 reviews)

"What a true florida gem. Real old Florida"

Reviewed on Oct 11, 2025

See all 2,757 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.