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$7,135$2,815found 1 day 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 (1,002 reviews)Roundtrip • Boston (BOS) - Miami (MIA)BOS - MIA • Nonstop MIA - BOS • Nonstop - 1 Hotel South Beach
Oct 5 - Oct 101 Hotel South Beach + Flight
South Beach5 nights5.0 star property9.4/10 - Exceptional (1,583 reviews)Roundtrip • Boston (BOS) - Miami (MIA)BOS - MIA • Nonstop MIA - BOS • Nonstop
What to do in Windley Key
Snorkel and Sandbar Combo Adventure in Islamorada
$111
per adult
0% of travelers recommend
Tavernier, FL: Mangrove and Manatees Guided Kayak Eco Tour
$69
per adult
0% of travelers recommend
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
$49
per adult
80% of travelers recommend
Windley Key Hotel Deals
8.2 out of 10, Very Good, (1,004 reviews)
8.2/10
Very Good
(1,004 reviews)
$145 nightly
The price is $163
$163 total
Aug 31 - Sep 1
Total with taxes and fees
8.8 out of 10, Excellent, (1,003 reviews)
8.8/10
Excellent
(1,003 reviews)
$161 nightly
The price is $177
$177 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, (243 reviews)
9.0/10
Wonderful
(243 reviews)
$272 nightly
The price is $306
$306 total
Aug 10 - Aug 11
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!"
$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 12 - Aug 13
Total with taxes and fees
9.2 out of 10, Wonderful, (1,752 reviews)
9.2/10
Wonderful
(1,752 reviews)
$200 nightly
The price is $224
$224 total
Aug 6 - Aug 7
Total with taxes and fees
9.2 out of 10, Wonderful, (1,357 reviews)
9.2/10
Wonderful
(1,357 reviews)
$225 nightly
The price is $254
$254 total
Aug 18 - Aug 19
Total with taxes and fees
7.6 out of 10, Good, (1,001 reviews)
7.6/10
Good
(1,001 reviews)
$144 nightly
The price is $162
$162 total
Aug 10 - Aug 11
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.