Windley Key Vacations from $394
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The Latest Windley Key Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Luxuri Suites
Sep 7 - Sep 11Luxuri Suites + Flight
South Beach4 nights3.0 star property6.8/10 - (57 reviews)"Ok the fact we had no desk for check was terrible. I could not check in due to a code for door and room acess never being sent to my email resulted in me not checking for 3hours until I was told about a sister property 3 blocks from where I was stay had to walk in the rain to the siater property for thwm to grant me acess codes to get into my room now at 3am. I wouls likw to be reemburst for that night and day. My TV had no working batteries and once I go batteries the TV volum did not work."Reviewed July 9, 2026Roundtrip • New York (EWR) - Miami (MIA)EWR - FLL • Nonstop FLL - EWR • Nonstop - Casablanca Miami Beach
Oct 13 - Oct 16Casablanca Miami Beach + Flight
North Beach3 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 • New York (EWR) - Miami (MIA)EWR - FLL • Nonstop FLL - EWR • Nonstop$7,117$2,797found 1 day agoper traveler - The Retreat Collection at 1 Hotel & Homes South Beach
Oct 10 - Oct 14The Retreat Collection at 1 Hotel & Homes South Beach + Flight
South Beach4 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$14,195$6,878found 1 day agoper traveler - 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 - The Local House
Sep 9 - Sep 14The Local House + Flight
South Beach5 nights3.5 star property9.2/10 - Wonderful (1,000 reviews)Roundtrip • Boston (BOS) - Miami (MIA)BOS - MIA • Nonstop MIA - BOS • 1 stop
Windley Key Hotel Deals
8.2 out of 10, Very Good, (1,007 reviews)
8.2/10
Very Good
(1,007 reviews)
"Usually they have kayaks to use but they had none but still had to pay $90 resort fee"
$139 nightly
The price is $156
$156 total
Aug 9 - Aug 10
Total with taxes and fees
8.8 out of 10, Excellent, (1,004 reviews)
8.8/10
Excellent
(1,004 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."
$169 nightly
The price is $186
$186 total
Aug 9 - Aug 10
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 11 - Aug 12
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, (278 reviews)
9.0/10
Wonderful
(278 reviews)
"Amazing staff! Clancy is great! This place is so cute family oriented and friendly! I cant wait to stay here again!"
$146 nightly
The price is $164
$164 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 19 - Aug 20
Total with taxes and fees
9.2 out of 10, Wonderful, (1,760 reviews)
9.2/10
Wonderful
(1,760 reviews)
$197 nightly
The price is $221
$221 total
Aug 11 - Aug 12
Total with taxes and fees
9.2 out of 10, Wonderful, (1,360 reviews)
9.2/10
Wonderful
(1,360 reviews)
"Place is a bit worn, overall it held its charm and the staff was friendly"
$204 nightly
The price is $229
$229 total
Aug 18 - Aug 19
Total with taxes and fees
7.6 out of 10, Good, (1,004 reviews)
7.6/10
Good
(1,004 reviews)
"Wanted to stay at this property for a few years and finally booked for a quick weekend trip. If we would have had a boat to make use of the ramp and marina, that’s the best use of the property. Property has potential. Room: The bath towels smelled musty and there weren’t blankets or heavy covers for the beds. We had two flat sheets that’s it. AC worked well and fridge kept cold and even refroze my ice packs for the cooler. Shower pressure was good, water temp had enough hot water for three...
$130 nightly
The price is $146
$146 total
Aug 5 - Aug 6
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.