Windley Key Vacations from $552
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The Latest Windley Key Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Pantera Rosa
Sep 4 - Sep 7Pantera Rosa + Flight
South Beach3 nights4.0 star property8.8/10 - Excellent (74 reviews)"The property is great. The location is perfect. The room was outstanding. Checkin is an absolute nightmare!!! Took us an hour from arrival to get our room. It's all done online, nobody to greet you. I saw one person in 4 days on the property. Requested fresh towels sent a text message had to send it again 8 hours later. Finally, got our towels."Reviewed June 26, 2026Roundtrip • Boston (BOS) - Miami (MIA)BOS - MIA • 1 stop MIA - BOS • Nonstop - Casablanca Miami Beach
Oct 8 - Oct 12Casablanca Miami Beach + Flight
North Beach4 nights3.0 star property5.8/10 - (327 reviews)"Pleas don’t book the apartment in this hotel. It’s not associated with the hotel services. The 2nd room has 3 beds all bed sheets were dirty. The has prior hair from guest before us. Behind the headboard I found a dirty t-shirt. Hall restroom tub was rusted and peeling, I was disgusted to see that. The other restroom still had a long hair in the tub. Sanitary is NOT a priority for the owner of this apartment. The price I paid for my 4 day was a steel. Also, beach gear was a laugh in the face. No..."Reviewed July 23, 2026Roundtrip • Boston (BOS) - Miami (MIA)BOS - MIA • Nonstop MIA - BOS • Nonstop$9,569$4,284found 19 hours agoper traveler - The Retreat Collection at 1 Hotel & Homes South Beach
Oct 23 - Oct 28The Retreat Collection at 1 Hotel & Homes South Beach + Flight
South Beach5 nights5.0 star property8.0/10 - 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 June 22, 2016Roundtrip • Boston (BOS) - Miami (MIA)BOS - MIA • Nonstop MIA - BOS • Nonstop$20,011$9,643found 1 day agoper traveler - The Marlin Hotel
Oct 5 - Oct 10The Marlin Hotel + Flight
South Beach5 nights4.0 star property9.2/10 - Wonderful (1,004 reviews)"The location was great, the bar convenient, the restaurant downstairs was great. Overnight parking was reasonable."Reviewed August 2, 2026Roundtrip • Boston (BOS) - Miami (MIA)BOS - MIA • Nonstop MIA - BOS • Nonstop - The Key West Hotel
Oct 18 - Oct 24The Key West Hotel + Flight
Key West Historic District6 nights3.0 star property9.2/10 - Wonderful (561 reviews)"This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!"Reviewed July 27, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • Nonstop EYW - BOS • 1 stop$8,918$4,862found 2 days agoper traveler
Windley Key Hotel Deals
8.2 out of 10, Very Good, (1,008 reviews)
8.2/10
Very Good
(1,008 reviews)
$147 nightly
The price is $166
$166 total
Aug 30 - Aug 31
Total with taxes and fees
8.8 out of 10, Excellent, (1,005 reviews)
8.8/10
Excellent
(1,005 reviews)
"Drop Anchor was a nice experience. We stayed for two nights..no major issues except for the air-conditioning in our room wasn't covering the space inside enough, it was a small a/c unit and i think it's capacity wasn't enough to cool the room. So we were a bit uncomfortable based on that. But otherwise everything else was up to standard. I would consider visiting there again in the future tho. Staff very helpful and friendly, amenities nice and access to restaurants and other activities near by."
$163 nightly
The price is $178
$178 total
Aug 6 - Aug 7
Total with taxes and fees
Coconut Cove Resort and Marina
Coconut Cove Resort and Marina3.0 star property
0.7 mi from Windley Key
9.0 out of 10, Wonderful, (279 reviews)
9.0/10
Wonderful
(279 reviews)
"Wow! I stayed there for a week and I really felt like I was in my little slice of heaven! The resort is decorated beautifully. The room definitely has the Florida keys vibe and the staff were so awesome. I would have loved to stay there forever. I can't wait to go back!!!"
$149 nightly
The price is $168
$168 total
Aug 30 - Aug 31
Total with taxes and fees
9.0 out of 10, Wonderful, (26 reviews)
9.0/10
Wonderful
(26 reviews)
"Food was excellent and the staff was delightful. Very accommodating"
$186 nightly
The price is $210
$210 total
Aug 18 - Aug 19
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort4.0 star property
1.2 mi from Windley Key
9.0 out of 10, Wonderful, (246 reviews)
9.0/10
Wonderful
(246 reviews)
$272 nightly
The price is $306
$306 total
Aug 12 - Aug 13
Total with taxes and fees
9.2 out of 10, Wonderful, (1,762 reviews)
9.2/10
Wonderful
(1,762 reviews)
"Room was clean, breakfast was mediocre, especially for the “resort fee” beach was fine as long as you didn’t want to swim. Foul smelling seaweed was in the water at the beach."
$209 nightly
The price is $235
$235 total
Aug 11 - Aug 12
Total with taxes and fees
9.6 out of 10, Exceptional, (261 reviews)
9.6/10
Exceptional
(261 reviews)
"Clean and quiet"
$181 nightly
The price is $204
$204 total
Aug 13 - Aug 14
Total with taxes and fees
7.6 out of 10, Good, (1,001 reviews)
7.6/10
Good
(1,001 reviews)
$138 nightly
The price is $155
$155 total
Aug 12 - Aug 13
Total with taxes and fees
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.