Windley Key Vacations from $288
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The Latest Windley Key Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Private Apartment at the Congress
Aug 28 - Aug 31Private Apartment at the Congress + Flight
South Beach3 nights4.0 star property5.6/10 - (11 reviews)"Really friendly staff, easy check in and even accommodated early check in. Roof top pool was clean and spacious with a nice bar."Reviewed July 9, 2026Roundtrip • Atlanta (ATL) - Miami (MIA)ATL - MIA • Nonstop MIA - ATL • 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$6,822$2,833found 1 day agoper traveler - The Retreat Collection at 1 Hotel & Homes South Beach
Sep 25 - Sep 28The Retreat Collection at 1 Hotel & Homes South Beach + Flight
South Beach3 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 • Atlanta (ATL) - Miami (MIA)ATL - MIA • Nonstop MIA - ATL • Nonstop$12,100$6,070found 1 day agoper traveler - Nobu Hotel Miami Beach
Oct 2 - Oct 5Nobu Hotel Miami Beach + Flight
Mid Beach3 nights5.0 star property8.6/10 - Excellent (1,427 reviews)Roundtrip • Atlanta (ATL) - Miami (MIA)ATL - MIA • Nonstop MIA - ATL • Nonstop$900$453found 1 day agoper traveler - The Local House
Oct 1 - Oct 6The Local House + Flight
South Beach5 nights3.5 star property9.2/10 - Wonderful (1,000 reviews)Roundtrip • Atlanta (ATL) - Miami (MIA)ATL - MIA • Nonstop MIA - ATL • Nonstop$1,182$616found 1 day agoper traveler
Windley Key Hotel Deals
8.2 out of 10, Very Good, (1,004 reviews)
8.2/10
Very Good
(1,004 reviews)
"We had an ocean front view which is what we were looking for...espectacular view from our room balcony...
Loved the little beach set up with chairs and kiosks facing the ocean, great for evenings moonrise.
Only one thing that needs upgrade is the floor tiles in between bathroom and kichen counters...currently a floor mat is on top of the broken tiles but it poses a safety hazard if you are batefoot...
Overall a nice and cozy quiet place, perfect for relaxing....restaurants are close by...i...
$155 nightly
The price is $174
$174 total
Aug 12 - Aug 13
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, (236 reviews)
9.0/10
Wonderful
(236 reviews)
"Todo bien"
$272 nightly
The price is $306
$306 total
Aug 5 - Aug 6
Total with taxes and fees
8.8 out of 10, Excellent, (1,009 reviews)
8.8/10
Excellent
(1,009 reviews)
"I did not like that. The room had windows with no coverings. It woke me up too early and I needed to be able to sleep late. Other than that the room was beautiful in the shower was awesome."
$180 nightly
The price is $198
$198 total
Jul 26 - Jul 27
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!"
$184 nightly
The price is $207
$207 total
Aug 3 - Aug 4
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 12 - Aug 13
Total with taxes and fees
9.2 out of 10, Wonderful, (1,759 reviews)
9.2/10
Wonderful
(1,759 reviews)
$197 nightly
The price is $221
$221 total
Aug 3 - Aug 4
Total with taxes and fees
9.2 out of 10, Wonderful, (1,350 reviews)
9.2/10
Wonderful
(1,350 reviews)
$232 nightly
The price is $261
$261 total
Aug 18 - Aug 19
Total with taxes and fees
8.8 out of 10, Excellent, (711 reviews)
8.8/10
Excellent
(711 reviews)
"my 2nd time staying here and i will be back for a 3rd"
$116 nightly
The price is $131
$131 total
Aug 18 - Aug 19
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.