Waterfront Resort, Fantasy Fest, Old Town, 7 Nights, Pool, Hot Tub, Hyatt | Resort in Key West

Have I mentioned that this listing is for celebrating Fantasy Fest in sunny Key West, FL? You will be staying at the Hyatt Sunset Harbor; 7 nights; fully furnished condo style residence; sleeps 6; 2 bedrooms; queen bed in master bedroom; king bed in guest bedroom; sofa bed in living room; 2 bathrooms; kitchen; dining area; living room; balcony w/ Gulf of Mexico, swimming pool, and courtyard views; Gulf front outdoor pool and whirlpool hot tub. Check-in Sunday, October 19, 2025; check-out Sunday, October 26, 2025.
Fantasy Fest -
Those who are familiar with Key West and familiar with Fantasy Fest know it doesn't get much better than enjoying Fantasy Fest while staying at the Hyatt Sunset Harbor; within walking distance of all the Festivities that Mallory Square, the Sunset Pier, the Historic District, and Duval Street hold.
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 the Sunday to Sunday that I have listed. Fantasy Fest builds up as the 10 days go on to its climax on the final Saturday night.
Be forewarned: Fantasy Fest is a party for adults. It is not "PG" rated.
Hyatt Sunset Harbor -
Location, it matters where you stay in Key West!
Imbibe in the relaxed Key West lifestyle from a coveted location nestled in the heart of Key West’s famed Old Town at the Hyatt Sunset Harbor, a Hyatt Vacation Club. The right size, the perfect view and the must-have amenities. Lush, verdant foliage surrounds the courtyard, and a beautiful contemporary design creates an environment of relaxation and restoration. Guests are encouraged to slow down, relax and dip into the outdoor pool and whirlpool hot tub while soaking up some famed Floridian rays.
Hyatt’s Sunset Harbor is not just another Key West property; it is nestled deep in the heart of Old Town, the heart and soul of one of America’s most treasured vacation destinations. Nearby, you can enjoy the charms of Duval Street shopping or nightlife, the nightly sunset celebration at Mallory Square, entertainment and refreshments at the Sunset Pier, and the many happy hours at Key West’s Historic Seaport and throughout Key West.
Perfectly situated on the western side of the island, this gracious retreat directly overlooks the Gulf of Mexico, offering magnificent water views and Key West sunsets! Hyatt Sunset Harbor's residences become the perfect home-away-from-home during your stay in Key West!
The Hyatt Sunset Harbor’s 40 residential-style retreats offer well-appointed comforts of home and signature Hyatt care. 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.
Hyatt Sunset Harbor's courtyard, swimming pool, and hot tub are waterfront!
Two-bedroom tropical-style residences feature a master suite with a deluxe king-size bed and connecting full bath with separate shower and tub; a guest suite with queen-size bed and full bath; a fully equipped kitchen; dining area; living area with TV, sleep sofa, stereo, and DVD player; and a private balcony with pool and harbor views. Amenities include a coffeemaker, ceiling fans, wireless internet, and onsite laundry facilities. Two-bedroom residences sleep up to 6 adult guests. Some two-bedroom residences are multi-level; you must climb stairs to get to the bedrooms and bathrooms.
All two-bedroom condo style residences at the Hyatt Sunset Harbor are Gulf front or Gulf view (see the marked-up resort layout in the photos in this listing for the differentiation). Most two-bedroom residences also have pool, spa, and/ or lush courtyard views. Hyatt Sunset Harbor's courtyard, swimming pool, and hot tub are waterfront! Key West is a tropical paradise. Some water views may be partially obstructed by palm trees or other vegetation. Cruise ships have returned to Key West. Some water views may be partially obstructed at times by cruise ships.
This listing is for a top floor corner unit with Gulf, courtyard, swimming pool, and hot tub views.
The photos in this listing are stock photos and do not show the actual room 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)
o Best Wine Selection: La Trattoria (24W, 23R), Grand Vin Wine Bar (22W, 23W, 24R), ViV Wine Bistro (24R, 22R), A&B Lobster House (23R), Vinos on Duval (22R)
o Best Mojito: Pepe’s (24W), El Meson del Pepe’s (22W, 23W, 24R), Willie T’s (22R, 23R, 24R), Seaside Café (23R), Two Friends (22R)
o Best Beer Selection: Bearded Lady (24W, 23R, 22W), My New Joint (22R, 23W, 24R) on Cudjoe Key), Cayo Hueso Brewing (24R), The Retro Room (22R, 23R)
o Best Bartender: Micela Elechko (@ Green Parrot) (23W, 24W), Alex Tolmachenko (@ Virgilio’s) (23R, 24R), Neil Lindley (@Orchard Key Inn) (24R), Carlos Home (@22 & Co) (22W, 23R), Fabiola Azuaje (@Two Friends) (22R), Joan Kongos (@ Rams Head Southernmost) (22R)
Cont'd below -

Waterfront Resort, Fantasy Fest, Old Town, 7 Nights, Pool, Hot Tub, Hyatt is located in Truman Annex. Waterfront Resort, Fantasy Fest, Old Town, 7 Nights, Pool, Hot Tub, Hyatt provides accommodation, featuring View, Wheelchair Accessible, Ocean View, among other amenities. This Resort features View, Wheelchair Accessible, Ocean View, to make your stay a comfortable one.

Waterfront Resort, Fantasy Fest, Old Town, 7 Nights, Pool, Hot Tub, Hyatt has 2 Bedrooms , 2 Bathrooms, and max occupancy of 6 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Resort because of the excellent services rendered by the owner or manager of this Resort, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Resort has a friendly neighborhood, and the Truman Annex has interesting places to visit. If you want to learn more about the Resort in Truman Annex, such as places to visit and things to do nearby, you can check below to learn more.