
Windley Key Vacations from $363
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The Latest Windley Key vacation packages
Price found within the past 48 hours. Click for updated prices.


Riverside Hotel
East Fort Lauderdale
Price was $1,376, price is now $447 per person
$447
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (2,528 reviews)
It’s at the center of Las Olas with so many options for drinking and dining. There’s also the access to the river and boat rides. The airport is less than 10 minutes away.
Reviewed on Sep 14, 2025


President Villa
South Beach
Save 100% on your flight
Price was $1,195, price is now $610 per person
$610
per person
Dec 5 - Dec 9
found 13 hours ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
Breakfast was tasty but the lady in the ams was a grump all 3 days she served us, lighten up girl you are servings Breakfast for guests . Room was clean and patio was great, not too much privacy but still enjoyed it. The bartender Michael, i believe was his name was awesome and very helpful and drinks were great ! Cons hardly had cold water which was a bit annoying and our tv was not working completely. Was a bit disappointed with the pool being out of service. When i booked room it stated pool would be ok on my day 2 of stay then it said 1 more day n then it said weeks to be repaired. Daily fee said it basically covered a few things including pool but we had no pool....
Reviewed on Sep 7, 2025

1 Hotel South Beach
South Beach
Price was $2,968, price is now $1,558 per person
$1,558
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,295 reviews)
Couldn’t have asked for a better stay. The friendly and kind staff went above and beyond in every possible way to make sure our needs were met. The amenities (restaurants, pools, beach, soups, common areas) are first-rate. True value for money.
Reviewed on Sep 15, 2025
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See all available trips from Columbus to Windley Key
View all tripsDiscover the most popular places to visit in Windley Key

Windley Key Fossil Reef Geological State Park
4.5/5(20 reviews)
Explore the fossilized reef of a former quarry in this island park, as you learn about the history and ecology from the interpretive trails.
What to do in Windley Key

Explore Mangrove Creeks with an All Day SUP/single kayak Rental
$47
per adult

Ft. Lauderdale to Key West Day Trip Quality Day Tours
$225
per adult

Explore the Mangrove Creeks with an ALL Day Tandem Kayak Rental
$65
per adult
Windley Key Hotel Deals

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$220 nightly
The price is $247 total per night from Sep 30 to Oct 1
$247 total
Sep 30 - Oct 1
Total with taxes and fees
9/10 Wonderful! (76 reviews)
"We had a fantastic time here! The room was spotless- clean bed, fresh towels, and a great shower. Room service breakfast was delicious. The resort has everything you need, so no need to leave. We loved all the onsite restaurants, and the tiki bar was a total vibe. Big shoutout to our favorite bartender, ..."
Reviewed on Sep 8, 2025

Fisher Inn Resort & Marina
84951 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $146 total per night from Sep 25 to Sep 26
$146 total
Sep 25 - Sep 26
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
"Great views manatees cruising by very relaxing"
Reviewed on Aug 23, 2025

Coconut Cove Resort and Marina
84801 Overseas Highway, Islamorada, FL
$119 nightly
The price is $134 total per night from Sep 18 to Sep 19
$134 total
Sep 18 - Sep 19
Total with taxes and fees
7.6/10 Good! (816 reviews)
"Staff were very nice and welcoming. Nice pool and view. Room was nice clean and comfortable. Definitely would stay again"
Reviewed on Aug 15, 2025
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.