
Windley Key Vacations from $423
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The Latest Windley Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Pelican Hotel
South Beach
$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
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
North Beach
$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


Don't see what you're looking for?
See all available trips from Columbus to Windley Key
View all tripsStay 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.
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.
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
$240 nightly
$270 total
Sep 9 - Sep 10
Total with taxes and fees

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

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
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) |
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- Bluefin Rock Harbor Marina
- Shops at Sunset Place
- Anne's Beach
- Florida Keys Dive Center
- Mayfair in the Grove
- Coconut Grove Vacations
- Coral Gables Congregational Church
- Cocowalk Shopping Center
- Coconut Grove Convention Center
- Caribbean Club Bar
- Pigeon Key
- Marinelab Undersea Laboratory
- Visit Islamorada
- Coral Way Shopping Area
- History of Diving Museum
- Matecumbe United Methodist Church
- Galleria Shopping Center
- Jimmy Johnson's Big Chill
- Barnacle State Historic Park
- Shops at Merrick Park
- Coral Castle Museum
- All inclusive Vacation Packages Key Largo
- Venetian Pool
- Marathon Vacations
- University of Miami
- Key Largo Vacations
- Islamorada County Park
- Tavernier Vacations
- Bud n' Mary's Dive Center
- Windley Key Fossil Reef Geological State Park
- Biscayne Community Center & Village Green Park
- Jerry Herman Ring Theater
- Florida Keys Brewing Co.
- Salvadore Park Tennis Center
- Jacob's Aquatic Center
- Baker's Cay Resort Beach
- Islamorada Vacations
- Everglades National Park
- Long Key Vacations
- Long Key State Park
- West Miami Vacations
- Coconut Grove Bike Path
- Pinecrest Vacations
- Hurricane Monument
- Biltmore Hotel
- Sombrero Beach
- Old Cutler Trail
- Merrick House
- Larkin Community Hospital
- Fiesta Key
- Founders Park
- Visit Upper Matecumbe Key
- Visit Key Largo
- Sunset Drive Beach
- Harry Harris Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















