Windley Key Vacations from $423

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Windley Key vacation packages

Price found within the past 48 hours. Click for updated prices.
Pelican Hotel

Pelican Hotel

South Beach
Save 100% on your flight
$423
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (499 reviews)
Location is fantastic, as it the restaurant. Staff was great. The room was very small, and the bed felt like concrete.

Reviewed on Sep 1, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach
$5,807
per person
Nov 17 - Nov 20
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

Park Royal Miami Beach managed by Accor

Park Royal Miami Beach managed by Accor

North Beach
Save 100% on your flight
$603
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (191 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

President Hotel

President Hotel

South Beach
Save 100% on your flight
$572
per person
Nov 11 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (2,718 reviews)
Staff was great.

Reviewed on Sep 2, 2026

The Penguin Hotel

The Penguin Hotel

South Beach
Save 100% on your flight
$533
per person
Nov 11 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,951 reviews)
From a-z excellent,my favorite place

Reviewed on Sep 1, 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
$240 nightly
$270 total
Sep 9 - Sep 10
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
$156 nightly
$175 total
Sep 21 - Sep 22
Total with taxes and fees
Fisher Inn Resort & Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

84801 Overseas Highway Islamorada FL
$105 nightly
$118 total
Sep 8 - Sep 9
Total with taxes and fees
9/10 Wonderful! (285 reviews)
"La propiedad en general estaba muy limpia, el personal bien atento, la piscina increíble, tiene una vista al mar espectacular y un desayuno estupendo, lo recomiendo"

Reviewed on Aug 31, 2026

Coconut Cove Resort and Marina
See all 2,711 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.