Windley Key Vacations from $446
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The Latest Windley Key Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- President Hotel Villa
Jan 16 - Jan 21President Hotel Villa + Flight
South Beach5 nights3.5 star property8.2/10 - Very good (1,002 reviews)"Good stay for a night"Reviewed November 3, 2026Roundtrip • Boston (BOS) - Miami (MIA)BOS - FLL • Nonstop FLL - BOS • Nonstop$888$446found 1 day agoper traveler - The Retreat Collection at 1 Hotel & Homes South Beach
Jan 28 - Feb 2The 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 - FLL • Nonstop MIA - BOS • Nonstop$21,550$10,090found 7 hours agoper traveler - Avi Lux Stay
Dec 10 - Dec 13Avi Lux Stay + Flight
East Fort Lauderdale3 nights4.5 star property7.6/10 - Good (10 reviews)"If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE. "Reviewed August 28, 2025Roundtrip • Boston (BOS) - Miami (MIA)BOS - FLL • Nonstop FLL - BOS • Nonstop$1,184$569found 1 day agoper traveler - Henrosa Hotel
Jan 16 - Jan 21Henrosa Hotel + Flight
South Beach5 nights3.5 star property8.4/10 - Very good (962 reviews)Roundtrip • Boston (BOS) - Miami (MIA)BOS - FLL • Nonstop FLL - BOS • Nonstop$1,084$525found 1 day agoper traveler - 72 Park Miami Beach Boutique Residences by IliosRentals
Jan 28 - Feb 272 Park Miami Beach Boutique Residences by IliosRentals + Flight
North Beach5 nights4.5 star property8.2/10 - Very good (19 reviews)"We had a wonderful stay with our group of three adults and three children! Everything was very comfortable, and the apartment was beautiful, clean, and well-maintained. There is a convenient shuttle service to the beach, but the 10-minute walk is also perfectly fine, even with children. Communication was excellent, and any questions we had were answered quickly. Overall, a very pleasant experience for the whole family. We would definitely recommend this place and would happily stay here again!"Reviewed October 17, 2026Roundtrip • Boston (BOS) - Miami (MIA)BOS - FLL • Nonstop MIA - BOS • Nonstop$2,290$1,141found 1 day agoper traveler
Discover the most popular places to visit in Windley Key
What to do in Windley Key
Tavernier, FL: Mangrove and Manatees Guided Kayak Eco Tour
$69
per adult
100% of travelers recommend
Islamorada Sunset Cruise with Champagne Toast and Snacks
$84
per adult
80% of travelers recommend
Kayak through Mangrove Forests in the Florida Keys
$65
per adult
100% of travelers recommend
Windley Key Hotel Deals
8.6 out of 10, Excellent, (1,000 reviews)
8.6/10
Excellent
(1,000 reviews)
$159 nightly
The price is $174
$174 total
Nov 8 - Nov 9
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, (307 reviews)
9.0/10
Wonderful
(307 reviews)
$272 nightly
The price is $306
$306 total
Nov 29 - Nov 30
Total with taxes and fees
8.2 out of 10, Very good, (1,000 reviews)
8.2/10
Very good
(1,000 reviews)
"We enjoyed everything!"
$188 nightly
The price is $212
$212 total
Nov 5 - Nov 6
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, (305 reviews)
9.0/10
Wonderful
(305 reviews)
$169 nightly
The price is $190
$190 total
Nov 15 - Nov 16
Total with taxes and fees
9.2 out of 10, Wonderful, (34 reviews)
9.2/10
Wonderful
(34 reviews)
"Great clean room. Staff was great. Ive wanted to stay there for years and wasn't disappointed"
$207 nightly
The price is $233
$233 total
Nov 16 - Nov 17
Total with taxes and fees
Hampton Inn Key Largo Manatee Bay
Hampton Inn Key Largo Manatee Bay2.5 star property
16 mi from Windley Key
8.8 out of 10, Excellent, (1,126 reviews)
8.8/10
Excellent
(1,126 reviews)
"Good breakfast Good mattress Shower was fair Parking was easy Nice staff"
$130 nightly
The price is $147
$147 total
Nov 16 - Nov 17
Total with taxes and fees
9.2 out of 10, Wonderful, (1,205 reviews)
9.2/10
Wonderful
(1,205 reviews)
"Very neat and clean property."
$103 nightly
The price is $116
$116 total
Nov 15 - Nov 16
Total with taxes and fees
9.0 out of 10, Wonderful, (1,001 reviews)
9.0/10
Wonderful
(1,001 reviews)
"Excellent"
$128 nightly
The price is $144
$144 total
Nov 9 - Nov 10
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.