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 - Brickell

Brickell

Save 100% on your flight

$1,091

per person

Nov 4 - Nov 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.8/10 Excellent! (567 reviews)

I was very disappointed with my stay at Icon Brickell, especially as a parent traveling with children. The apartment and overall property did not match what was presented in the photos, which was disappointing from the start. At the pool, I was supervising three children at all times, but we were repeatedly approached about rules that had not been clearly communicated. I was first told I had to be inside the pool with the children, which I did. Then, one child was told he could not jump in, even though he was wearing a life jacket and I was supervising him. Later, we entered the hot pool and were only then told that children must be over 5 years old. I understand that safety rules are necessary, but they should be clearly posted and explained in advance. Families should know these restrictions before entering the pool area. What was supposed to be an enjoyable family stay became stressful and uncomfortable. Based on my experience, I would not recommend Icon Brickell to families with young children.

Reviewed on Sep 7, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,995

per person

Nov 19 - Nov 22

found 14 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

EAST Miami Residences

Brickell

Save 100% on your flight

$1,743

per person

Nov 4 - Nov 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (150 reviews)

The room was really nice, there are small things that can be improved but overall nice.

Reviewed on Aug 25, 2026

Miami Vacation Rentals - Downtown

Downtown Miami

Save 100% on your flight

$1,158

per person

Nov 4 - Nov 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (83 reviews)

💯

Reviewed on Sep 6, 2026

1 Hotel South Beach

South Beach

Save 100% on your flight

$1,387

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,617 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

Save 100% on your flight

$1,158

per person

Nov 4 - Nov 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9/10 Wonderful! (83 reviews)

💯

Reviewed on Sep 6, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,995

per person

Nov 19 - Nov 22

found 14 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

EAST Miami Residences

Brickell

Save 100% on your flight

$1,743

per person

Nov 4 - Nov 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (150 reviews)

The room was really nice, there are small things that can be improved but overall nice.

Reviewed on Aug 25, 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.

EAST Miami Residences

Brickell

Save 100% on your flight

$1,047

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (150 reviews)

The room was really nice, there are small things that can be improved but overall nice.

Reviewed on Aug 25, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,995

per person

Nov 19 - Nov 22

found 14 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

$1,387

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,617 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

View all trips

4 Night Beach vacations in Windley Key

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

Barcelona Studios Guesthouse

South Beach

Save 100% on your flight

$310

per person

Oct 20 - Oct 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (258 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$5,862

per person

Nov 1 - Nov 5

found 1 day ago

Roundtrip flight included

New York (NYC) 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

Pelican Hotel

South Beach

Save 100% on your flight

$573

per person

Nov 18 - Nov 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (506 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 $310. 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 ...

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...

"Everything was great!"

Reviewed on Sep 8, 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! (287 reviews)

"Amazing customer service"

Reviewed on Sep 6, 2026

See all 2,714 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.