Have I mentioned that this listing is for celebrating Fantasy Fest in sunny Key West, FL? You will be staying at the Hyatt Windward Pointe; 7 nights; fully furnished condo style residence; sleeps 6; 2 bedrooms; king bed in master bedroom; queen bed in guest bedroom; sofa bed in living room; 2 bathrooms; whirlpool tub in master bath, kitchen; dining area; living room; princess balcony w/ Atlantic Ocean, swimming pool, and courtyard views; ocean front infinity pool and hot tub. Check-in Saturday, October 18, 2025; check-out Saturday, October 25, 2025.
Fantasy Fest -
For those who are not familiar with Fantasy Fest, Fantasy Fest is an annual 10-day party in paradise for grown-ups. Started in 1979 by a small group of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful season. It worked. Fantasy Fest has grown every year since its inception and is now the wildest extravaganza around! Fun-loving revelers from around the globe bring their creativity and imaginations as they descend upon Key West each year in October for 10 days filled with costuming, parades, libations, and excitement! Checkout the photos.
The prime 7 days of Fantasy Fest are Sunday, October 19 to Sunday, October 26, 2025. Fantasy Fest builds up as the 10 days go on to its climax on the final Saturday night. This listing includes 6 of the 7 prime nights, but does not include the final Saturday night.
Be forewarned: Fantasy Fest is a party for adults. It is not "PG" rated.
Hyatt Windward Pointe -
Welcome to the Hyatt Windward Pointe, a Hyatt Vacation Club. Set along the Atlantic Ocean, the Hyatt Windward Pointe blends the laid-back Key West style with a modern, upscale resort ambiance. Here is a retreat where you can slow down and forget the rush and stress of your day-to-day life. Bask beside the lushly landscaped ocean front pool or hot tub that gives you the illusion that you’re softly floating on the open sea or grab a snack at Abbey Road poolside sandwich and snack bar.
Perfectly situated on the eastern side of the island, this gracious retreat directly overlooks the Atlantic Ocean, offering magnificent water views and Key West sunrises! All residences at the Hyatt Windward Pointe are ocean front or ocean view (see the marked-up resort layout in the photos in this listing for the differentiation). All residences also have swimming pool, hot tub, and/ or lush courtyard views.
Cherish the lavish plantation-style décor while taking advantage of the convenience offered by a fully equipped kitchen, dining area, living room, 3 flat screen TVs, DVD player, private furnished balcony, heated infinity edge pool, and hot tub, BBQ grills, pool bar/ grille, etc. Complimentary Wi-Fi access, in-room washer and dryer, and on-site parking are also included.
All 93 ultra-spacious, ultra-plush residences at Hyatt Windward Pointe feature two bedrooms - an oceanfront (or ocean view) master suite with a king bed and adjoining bathroom outfitted with a walk-in shower and spa tub, a guest bedroom with a queen bed and full bath, and a sleep sofa in the living room. All residences sleep 6 adults.
Hyatt typically offers complimentary, freshly brewed Starbucks coffee and an assortment of teas from 7:00 to 9:00 AM each morning in the lobby.
The Hyatt Windward Pointe also features the Abby Road Pool Bar and Grill, shuffleboard courts, volleyball courts, a pool table, ping-pong and foosball tables, barbecue grills.
Electric car charging stations may be available at the Hyatt Windward Pointe. Boat and trailer parking may also be available. I do not get involved with the charging stations or the boat and trailer parking. Please coordinate use of these facilities by calling the Hyatt Windward Pointe's front desk after making your reservation and after receiving your Hyatt Guest Certificate. Advance booking may be required.
The Hyatt Windward Pointe's convenient location puts you just minutes from the free-spirited art, music and entertainment scene of Old Town. Or head over to nearby Smathers Beach, the biggest white sand beach in Key West to rent windsurfers or go parasailing. The Keys are also a haven for anglers - shallow flats, mangrove islands, inland channels and open blue waters offer world-class fishing opportunities. Hoping to test your skills on the green? You're in luck - Key West Golf Club is located nearby and is the only Caribbean inspired course in the U.S.
Whether you choose to spend your days simply relaxing by the infinity pool or setting off on a dive adventure, Key West delivers a dream vacation of your own design. Your island home is just minutes away from celebrating the sunset each evening at Mallory Square and taking in the renowned dining, shopping and nightlife of Duval Street.
The Hyatt Windward Pointe is located about 3 Miles from Key West's Historic Seaport District, Duval Street’s dining, shopping, and nightlife, Mallory Square sunsets, and the Sunset Pier.
The following residences are included in this listing along with their time periods, their unit number, and their floor number.
October 18 to October 25, 2025, Hyatt Windward Pointe, Unit # 5621, 2nd floor
o Celebrate Fantasy Fest 2025 in Key West
o Awesome corner unit, Princess balcony, Great views
o Note: Fantasy Fest runs for 10 nights from October 17 to October 26, 2025. This listing is for 7 of the 10 nights.
o Key West’s Goombay Fest 2025 may be held October 17, 18, and 19, 2025. It was not yet scheduled at the time of this listing.
See the attached annotated photo of the Hyatt Windward Pointe layout for your residence location.
The photos in this listing are stock photos and do not show the actual residence listed.
Of course, if you're looking for more natural pursuits, you have plenty of options - Key West is a haven for fishers, and the unique ecosystem is well-suited to those seeking to explore by foot or bike. Plenty of unique attractions await those looking for a change of pace - check out the Harry S. Truman Little White House, Key West Aquarium, Key West Lighthouse Museum and Mel Fisher Maritime Heritage Museum; all within walking distance of the Hyatt Sunset Harbor.
Sights and Attractions Unique to Key West -
(that you may not want to miss)
Attractions:
o Mile Marker 0 (US Hwy 1),
o the Southernmost Point Buoy,
o the Little Whitehouse,
o Ernest Hemingway’s Home,
o the Butterfly and Nature Conservatory,
o Mel Fisher’s Maritime Museum,
o Sunset Celebration at Mallory Square and the Sunset Pier,
o Sunset Sail or Day Sail Adventures (my favorite is Danger Charters),
o Day Trip to the Dry Tortugas National Park & Fort Jefferson (70 miles West of Key West by Boat or Seaplane; Tour the Historic Fort, Swim, Snorkel, and/ or Dive),
o Fort Zackary Taylor State Park (swim (possibly the best beach on Key West), snorkel, fish, nature trails, cookout, or bike), and
o Mangrove Eco Tour, Paddleboarding, Kayaking, etc. at Lazy Dog adventures.
Happy Hours at the Historic Seaport (from 4:00 to 6:30 daily). My favorites are:
o The Boathouse at Turtle Kraal (½ price appetizers and drinks)
o Alonzo’s Oyster Bar (Special priced oysters, appetizers and drinks).
Local’s Hangouts:
o Captain Tony’s Bar (Yes, Captain Tony did not just exist in a Jimmy Buffett song. He was a real person, and I did meet him.),
o Green Parrot Bar (Key West institution since 1890), and the
o Schooner Wharf Bar (open air rustic Key West institution).
Breakfast & Brunch Spots:
o Pepe’s Café (the oldest eatery in the Keys, uses fresh squeezed juices),
o Blue Heaven (open air restaurant, share your breakfast with the free-range chickens),
o Harpoon Harry’s, and
o The Breakfast Club, Too.
Popular Watering Holes & Eateries:
o Sloppy Joe’s Bar,
o Hog’s Breath Saloon,
o Margaritaville,
and many, many more.
2024 Bubba Awards Marked Another Banner Year -
Key West People’s Choice Awards celebrated its 11th year in 2024 honoring 91 local businesses, people and nonprofits for their commitment and contributions to the Key West community. More than a quarter-million votes were cast in the nomination and final voting phases of the awards that truly are the people’s choice.
Key West’s People’s Choice Awards were announced by “Keys Weekly” in July 2024. Here are the 2024, 2023 and 2022 winners (listed 1st and showing the year) and 2024, 2023 and 2022 runners up in the “Food & Drink” category (W Indicates Winner, R indicates Runners up).
o Best Key Lime Pie: Blue Heaven (22R, 23R, 24W), Kermit’s Key Lime Shoppe (22W, 23W, 24R), Red Shoe Island Bistro (24R), Square Grouper (22R, 23R)
o Best Cuban Sandwich: Sandy’s Café (22R, 23W, 24W), Kim's Kuban (22W, 23R, 24R), Fritas Cuban Burger Cafe (24R), 5 Brothers (22R, 23R)
o Best International Restaurant: Benihana (23W, 24W), El Siboney (22W, 23R, 24R), Atlas Izakaya (24R) Bel Mare (23R), Fritas Cuban Café (22R), Tikka Bar (22R)
o Best Cup of Coffee: Cuban Coffee Queen (22W, 23W, 24W), Key’s Coffee Co (22R, 23R, 24R), Sandy’s Cafe (24R), Baby’s Coffee (22R, 23R, on US-1)
o Best Breakfast: Goldman’s Deli (22W, 23W, 24W), Harpoon Harry's (22R, 23R, 24R), Blue Heaven (23R, 24R), Two Friends (22R, 23R)
o Best Brunch: Hot Tin Roof (23R, 24W), Azur (22R, 23R, 24R), Morning Joint (24R), Blue Heaven (22W, 23W), Matt’s Stock Island Kitchen (22R)
o Best Lunch: Hogfish Bar & Grill (23R, 24W), Moondog Café (22R, 23W, 24R), Miami Subs (24R0, Little Whitehouse Subs (23R), Hogfish Bar & Grill (23R), Fritas Cuban Burger Café (22R), Pepe’s Café (22W)
o Best Bar: Green Parrot (22W, 23W, 24W), General Horseplay (24R), Bearded Lady (24R), Hank’s Hair of the Dog (22R, 23R), Virgilios (23R), Tattoos & Scars (22R)
o Best Gay Bar: 22&Co (22W, 23W, 24W), Aqua Bar and Nightclub (22R, 23R, 24R), 801 Bourbon Bar (22R, 23R, 24R)
Cont'd below -
