Windley Key Vacations from $536
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The Latest Windley Key vacation packages
Price found within the past 48 hours. Click for updated prices.
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
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
South Beach
$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
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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
$264 nightly
$297 total
Sep 27 - Sep 28
Total with taxes and fees
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
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
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
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- 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.