Windley Key Vacations from $674
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The Latest Windley Key Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Loews Miami Beach Hotel – South Beach
Sep 23 - Sep 27Loews Miami Beach Hotel – South Beach + Flight
South Beach4 nights4.5 star property9.4/10 - Exceptional (1,166 reviews)Roundtrip • Boston (BOS) - Miami (MIA)BOS - MIA • Nonstop MIA - BOS • 1 stop - 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 - 1 Hotel South Beach
Oct 5 - Oct 101 Hotel South Beach + Flight
South Beach5 nights5.0 star property9.4/10 - Exceptional (1,582 reviews)"Great place"Reviewed July 31, 2026Roundtrip • Boston (BOS) - Miami (MIA)BOS - MIA • Nonstop MIA - BOS • Nonstop - EAST Miami Residences
Oct 9 - Oct 14EAST Miami Residences + Flight
Brickell5 nights5.0 star property9.2/10 - Wonderful (142 reviews)"Ji"Reviewed August 1, 2026Roundtrip • New York (JFK) - Miami (MIA)JFK - MIA • Nonstop MIA - JFK • 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, (1,003 reviews)
8.2/10
Very Good
(1,003 reviews)
"We stay here once or twice a year, the staff is very friendly. The amenities are perfect and the location is right where you want to be."
$145 nightly
The price is $163
$163 total
Aug 31 - Sep 1
Total with taxes and fees
8.8 out of 10, Excellent, (1,002 reviews)
8.8/10
Excellent
(1,002 reviews)
"The hotel it’s nice but they don’t have beach . Not beach … they just have pool."
$170 nightly
The price is $187
$187 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 4 - Aug 5
Total with taxes and fees
9.2 out of 10, Wonderful, (1,752 reviews)
9.2/10
Wonderful
(1,752 reviews)
$204 nightly
The price is $230
$230 total
Aug 11 - Aug 12
Total with taxes and fees
9.2 out of 10, Wonderful, (1,356 reviews)
9.2/10
Wonderful
(1,356 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)
$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.