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Windley Key Beach Vacations

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Top Beach vacation packages in Windley Key

Price found within the past 48 hours. Click for updated prices.
  • Room, 1 King Bed, Balcony, Ocean View (Balcony) | Premium bedding, in-room safe, laptop workspace, iron/ironing board
    Aug 23 - Aug 25

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

    Islamorada
    2 nights
    4.0 star property
    9.0/10 - Wonderful (235 reviews)
    "Great place to relax"
    Reviewed July 23, 2026
    Roundtrip • New York (NYC) - Miami (MIA)
    LGA - MIA • Nonstop MIA - EWR • 1 stop
    $606
    $526
    per traveler
    found 20 hours ago
    Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
  • Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view
    Aug 29 - Sep 2

    Drop Anchor + Flight

    Islamorada
    4 nights
    3.0 star property
    8.8/10 - Excellent (1,007 reviews)
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • Nonstop MIA - BOS • Nonstop
    $699
    $578
    per traveler
    found 1 day ago
    Drop Anchor
  • Exterior
    Aug 29 - Sep 2

    Fisher Inn Resort & Marina + Flight

    Islamorada
    4 nights
    3.5 star property
    8.2/10 - Very Good (1,003 reviews)
    "We had an ocean front view which is what we were looking for...espectacular view from our room balcony... Loved the little beach set up with chairs and kiosks facing the ocean, great for evenings moonrise. Only one thing that needs upgrade is the floor tiles in between bathroom and kichen counters...currently a floor mat is on top of the broken tiles but it poses a safety hazard if you are batefoot... Overall a nice and cozy quiet place, perfect for relaxing....restaurants are close by...i..."
    Reviewed July 23, 2026
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • Nonstop MIA - BOS • Nonstop
    $599
    $541
    per traveler
    found 1 day ago
    Fisher Inn Resort & Marina
  • Exterior
    Sep 1 - Sep 6

    Coconut Cove Resort and Marina + Flight

    Islamorada
    5 nights
    3.0 star property
    9.0/10 - Wonderful (278 reviews)
    "Amazing staff! Clancy is great! This place is so cute family oriented and friendly! I cant wait to stay here again!"
    Reviewed July 23, 2026
    Roundtrip • New York (JFK) - Miami (MIA)
    JFK - MIA • Nonstop MIA - JFK • 1 stop
    $853
    $819
    per traveler
    found 18 hours ago
    Coconut Cove Resort and Marina

Top Beach Windley Key Hotels

Exterior

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
0.5 mi from Windley Key
8.2 out of 10, Very Good, (1,003 reviews)
"We had an ocean front view which is what we were looking for...espectacular view from our room balcony... Loved the little beach set up with chairs and kiosks facing the ocean, great for evenings moonrise. Only one thing that needs upgrade is the floor tiles in between bathroom and kichen counters...currently a floor mat is on top of the broken tiles but it poses a safety hazard if you are batefoot... Overall a nice and cozy quiet place, perfect for relaxing....restaurants are close by...i...
$168 nightly
The price is $189
Aug 9 - Aug 10
Total with taxes and fees
Fisher Inn Resort & Marina
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.
See all properties in Windley Key

Find your perfect Windley Key beach vacation

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 $526. 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.)