Windley Key Adventure Vacations

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Top Adventure vacation packages in Windley Key

Price found within the past 48 hours. Click for updated prices.
Angler’s Hotel – Miami Beach

Angler’s Hotel – Miami Beach

4 out of 5
South Beach
Save 100% on your flight
Price was $1,360, price is now $783 per person
$783
per person
Jul 2 - Jul 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (1,010 reviews)
We live in miami. Just went to get away from our adult kuds who are home from college. The hotel was perfect. The room was clean and the property was really nice and elegant. Great location and easy walk to beach.

Reviewed on Apr 27, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $19,369, price is now $8,858 per person
$8,858
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
Price was $3,231, price is now $1,796 per person
$1,796
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,483 reviews)
This is an exceptional hotel! Everything is exactly as you would expect. Definitely highly recommend.

Reviewed on Apr 27, 2026

Bay Breeze Premium Apartments By Eskape Collection

Bay Breeze Premium Apartments By Eskape Collection

4 out of 5
Save 100% on your flight
Price was $1,756, price is now $1,022 per person
$1,022
per person
Jul 12 - Jul 19
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (213 reviews)
The apartment was well equipped and comfortable. The management did everything they could to make us comfortable and even were very flexible when we had to extend our trip because of a snowstorm back home..

Reviewed on Apr 26, 2026

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
Price was $1,460, price is now $864 per person
$864
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (8,099 reviews)
Hot tub was cold the first two days and the rental vouchers were not working (so we had to pay for the bikes and seek reimbursement which is a pain, bikes were meant to be free to hotel guests 2 hours/day.

Reviewed on Apr 27, 2026

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5* Adventure vacations in Windley Key

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

EAST Miami

5 out of 5
Brickell
Save 100% on your flight
Price was $1,571, price is now $978 per person
$978
per person
Jul 21 - Jul 26
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (3,729 reviews)
Waooo, staying here was an absolute blast! This hotel is easily 1A. From the exceptional staff to the high quality of the rooms, everything was perfect. The location is unbeatable, with so many great shops and restaurants just steps away. I also loved the pool area—it's a great spot to relax. For me, this is a 20/10 rating. I highly recommend it!

Reviewed on Apr 27, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $19,369, price is now $8,858 per person
$8,858
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
Price was $3,231, price is now $1,796 per person
$1,796
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,483 reviews)
This is an exceptional hotel! Everything is exactly as you would expect. Definitely highly recommend.

Reviewed on Apr 27, 2026

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3 Night Adventure vacations in Windley Key

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

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
Price was $1,487, price is now $903 per person
$903
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (8,099 reviews)
Hot tub was cold the first two days and the rental vouchers were not working (so we had to pay for the bikes and seek reimbursement which is a pain, bikes were meant to be free to hotel guests 2 hours/day.

Reviewed on Apr 27, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $17,749, price is now $8,949 per person
$8,949
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
iCoconutGrove Vacation Rentals

iCoconutGrove Vacation Rentals

4 out of 5
Coconut Grove
Save 100% on your flight
Price was $2,698, price is now $1,632 per person
$1,632
per person
Jun 27 - Jun 30
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
9.2/10 Wonderful! (1,001 reviews)
Beautiful and very well Located property. Lacks a proper restaurant in the location to be perfect. Otherwise, outstanding

Reviewed on Apr 27, 2026

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4 Night Adventure vacations in Windley Key

Price found within the past 48 hours. Click for updated prices.
Brickell Bay 3304

Brickell Bay 3304

3 out of 5
Brickell
Price was $1,697, price is now $558 per person
$558
per person
Jul 8 - Jul 12
found 19 hours ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
No reviews
Brickell Bay 3505

Brickell Bay 3505

3 out of 5
Brickell
Price was $1,874, price is now $596 per person
$596
per person
Jul 7 - Jul 11
found 15 hours ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
9/10 Wonderful! (2 reviews)
The room was clean, there was a problem at the check out time as all the guest have the same check out and all the elevators collapse, it took us more than an hour to get down. The parking is really a problem as we had to go up almost 20 floors. Location is pretty good.

Reviewed on Apr 14, 2026

Brickell Bay 3318

Brickell Bay 3318

3 out of 5
Brickell
Price was $1,697, price is now $558 per person
$558
per person
Jul 8 - Jul 12
found 19 hours ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
No reviews
Don't see what you're looking for?
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Find awesome Windley Key adventure vacations

How can I book the best Windley Key adventure trips?

Choose your own adventure in Windley Key, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun.

How can I plan the perfect Windley Key family adventure vacation?

Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Windley Key. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning.

Can I book all-inclusive Windley Key adventure vacation packages?

By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway.

Why should I book a Windley Key adventure vacation for couples?

Book a Windley Key couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.

How can I find the best deals on adventure packages in Windley Key?

It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals.

Can I book an adventure vacation package in Windley Key with free cancellation and/or flexible dates?

Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility.

Why should I book a Windley Key adventure trip with Expedia?

Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A.

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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.