Windley Key Vacations from $536

Book a Hotel + Flight or Car together to unlock savings

The Latest Windley Key vacation packages

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

South Beach
Save 100% on your flight
$536
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (1,005 reviews)
I had a great stay! Thank you!

Reviewed on Sep 18, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach
$9,348
per person
Nov 10 - Nov 15
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

Pelican Hotel

Pelican Hotel

South Beach
$746
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (506 reviews)
Miami Vacation Rentals - Brickell

Miami Vacation Rentals - Brickell

Brickell
$1,319
per person
Dec 2 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Miami (MIA)
8.8/10 Excellent! (567 reviews)
Is a very nice property. SPA and Gym are very good. Very clean rooms with everything you need to make an apartment work (cleaning products, toiletries). The only bad thing was that the pool is closed an it will probably be by the entire year, they compensated with free wine and activites.

Reviewed on Sep 14, 2026

President Hotel Villa

President Hotel Villa

South Beach
Save 100% on your flight
$672
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,004 reviews)
I love the room. I would definitely stay again. The only thing I would say is the showers are definitely not hot enough for me. I don’t know if I just like it too hot but that’s the only issue I really had.

Reviewed on Sep 7, 2026

Don't see what you're looking for?
See all available trips from Columbus to Windley Key
View all trips

Stay near popular Windley Key attractions

Windley Key Fossil Reef Geological State Park

8.8/10 (184 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.
See properties

Hog Heaven

After visiting Hog Heaven, make a plan to see the other sights and activities in Islamorada. Discover the beautiful sunsets in this relaxing area, or enjoy its fishing spots.
See properties

Windley Key Hotel Deals

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

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

84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$264 nightly
$297 total
Sep 27 - Sep 28
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

84951 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$139 nightly
$156 total
Sep 21 - Sep 22
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
"Clean and comfortable rooms. I love the location relative to things to do in the Keys. We used the bikes while there and have used kayak/paddleboards in past. The staff is absolutely amazing. I had messed up the dates of the reservation. Jamal worked really hard to get me a room at a rate i could ..."

Reviewed on Sep 18, 2026

Fisher Inn Resort & Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

84801 Overseas Highway Islamorada FL
$149 nightly
$168 total
Sep 21 - Sep 22
Total with taxes and fees
9/10 Wonderful! (293 reviews)
"Excellent stay! Love this place and will definitely be back!"

Reviewed on Sep 18, 2026

Coconut Cove Resort and Marina
See all 2,707 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.

Find the Best Windley Key Vacation Packages

Windley Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)

More vacations you might like

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.