Windley Key Vacation Packages
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Top Windley Key vacation package deals
Price found within the past 48 hours. Click for updated prices.
2.5-star property
Lexington by Hotel RL Miami Beach
Mid Beach
7.4/10 Good! (1,332 reviews)
Dec 1 - Dec 6
5 night stay
Detroit (DTW) to Miami (MIA)
Delta • Coach
Miami (MIA) to Detroit (DTW)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,199, price is now $639 per person
$639
per person
found 1 day ago
Room was just ok,but wasnt worth the money,staff was non chalant or rarely at the front desk to help out with questions.Beach View was the highlight being that it was beachfront.The outdoor pool was also ok but not worth the price. Saw 2-3 huge cockroaches in the main lobby.Also apparently there is a certain amount of times you can come and go in the paid parking lot but you find out at the gate when you’re asked to pay for more time eventhough you thought you paid per full day.Overall experience was a waste and horrible experience never going back and wont dare refer anyone to go there.
Reviewed on Sep 14, 2026
5.0-star property
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
8/10 Very Good! (1 review)
Nov 3 - Nov 8
5 night stay
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
United • Non-stop • Coach
Miami (MIA) to Newark Liberty Intl. Airport (EWR)
Frontier Airlines • Non-stop • Coach
Price was $19,399, price is now $9,286 per person
$9,286
per person
found 1 day ago
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 on Jun 22, 2016
4.0-star property
Pelican Hotel
South Beach
9.2/10 Wonderful! (506 reviews)
Dec 3 - Dec 6
3 night stay
Detroit (DTW) to Miami (MIA)
American Airlines • Coach
Miami (MIA) to Detroit (DTW)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,650, price is now $837 per person
$837
per person
found 1 day ago
nanana
Reviewed on Sep 14, 2026
4.0-star property
Pelican Grand Beach Resort - A Noble House Resort
East Fort Lauderdale
8.8/10 Excellent! (1,708 reviews)
Dec 2 - Dec 8
6 night stay
Detroit (DTW) to Miami (MIA)
Frontier Airlines • Roundtrip • Coach
Price was $2,245, price is now $1,142 per person
$1,142
per person
found 1 day ago
.
Reviewed on Sep 15, 2026
5.0-star property
EAST Miami Residences
Brickell
9.2/10 Wonderful! (150 reviews)
Dec 2 - Dec 6
4 night stay
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $3,218, price is now $1,801 per person
$1,801
per person
found 20 hours ago
The room was really nice, there are small things that can be improved but overall nice.
Reviewed on Aug 25, 2026
Top rated hotels for your Windley Key vacation package
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
1.23 mi from city center
$248 nightly
The price is $279 total per night
$279 total
Sep 27 - Sep 28
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort features a private beach, a marina, and 3 outdoor pools. Transportation is made easy with a free area shuttle. The 24-hour front desk has multilingual staff ready to assist with tours/tickets and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a 24-hour gym, free WiFi in public areas, and meeting rooms.
On private beach
Pool
Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Free Cancellation
Reserve now, pay when you stay
0.54 mi from city center
$139 nightly
The price is $156 total per night
$156 total
Sep 21 - Sep 22
Total with taxes and fees
Guests staying at Fisher Inn Resort & Marina enjoy access to a private beach, an outdoor pool, and free WiFi in public areas. Free parking is available if you drive. Front-desk staff can assist with concierge services and luggage storage. Other amenities at this beach motel include coffee/tea in a common area, a microwave in a common area, and a refrigerator in a common area.
On private beach
Pool
Coconut Cove Resort and Marina
84801 Overseas Highway Islamorada FL
0.67 mi from city center
$149 nightly
The price is $168 total per night
$168 total
Sep 17 - Sep 18
Total with taxes and fees
Guests of Coconut Cove Resort and Marina enjoy a marina, an outdoor pool, and a children's pool. If you plan to drive, free parking is available. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. Other amenities at this beach hotel include a gym, free WiFi in public areas, and a business center.
Pool
Breakfast included
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.
Things to do
Private 3-Hour Islamorada Sandbar Tour
$500
per traveler
100% of travellers recommend
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