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.
Hotel Riu Plaza Miami Beach
Mid Beach
$860
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,180 reviews)
Overall stay was pleasant. Great views and access to the public beach. Free shuttle which runs up and down Collins Ave. Buffet breakfast has a nice selection of tasty items. My only gripe was the elevators. Elevators are small and it can get pretty busy depending on the season. The elevators get bogged down easily and can take pretty long to come. Lastly, your room key card only allows you access to the floor that you're staying on. I traveled with family and we were all on different floors. This made it difficult to visit other rooms; however, from a safety precaution I can understand why they do it. Overall great stay!
Reviewed on Sep 10, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$11,624
per person
Nov 11 - Nov 18
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
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View all trips5* Beach vacations in Windley Key
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$11,624
per person
Nov 11 - Nov 18
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
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See all available trips from Columbus to Windley Key
View all trips3 Night Beach vacations in Windley Key
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Miami Beach
Mid Beach
$539
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,180 reviews)
Overall stay was pleasant. Great views and access to the public beach. Free shuttle which runs up and down Collins Ave. Buffet breakfast has a nice selection of tasty items. My only gripe was the elevators. Elevators are small and it can get pretty busy depending on the season. The elevators get bogged down easily and can take pretty long to come. Lastly, your room key card only allows you access to the floor that you're staying on. I traveled with family and we were all on different floors. This made it difficult to visit other rooms; however, from a safety precaution I can understand why they do it. Overall great stay!
Reviewed on Sep 10, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$7,230
per person
Nov 26 - Nov 29
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
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View all trips4 Night Beach vacations in Windley Key
Price found within the past 48 hours. Click for updated prices.
Park Royal Miami Beach managed by Accor
North Beach
$484
per person
Oct 15 - Oct 19
found 11 hours ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
8.8/10 Excellent! (193 reviews)
Had been to Ft. Lauderdale and wanted to check for a decent none night stay in Miami and found this hotel Thro Expedia . Expedia rated this high and happy that we chose this place . Nice location. 5 mins off the beach . The beach is just walkable from this hotel. Very good service . The guy in lobby was very helpful . There was a donminos pizza next door , which was very useful for kids.
Amenities were decent . They had an outdoor swimming pool . Slightly smaller .. there were 2-3 families swimming and it was almost full :) washer dryer worked but it was good .. elevator was small and sometimes slow . We didn’t find a gym. No complimentary breakfast.. parking was a bit wierd and cramped ! They charged per night which was slightly expensive .
The rooms were awesome ! It was good sized for the price . Also had a kitchen.. though we didn’t use the kitchen , it is very good to have , just incase . Bed was comfortable .. bathrooms were neat . Price wise I think this room was very good and value for money . Wanted to give 3 , but just for the room and pricing , I’m giving it a 4 . Good experience overall .
Reviewed on Sep 1, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$5,862
per person
Nov 1 - Nov 5
found 11 hours 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
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View all tripsFind 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 $484. 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
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
