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2 Rooms Left
Charming
DAILY DROP
Winslow's Bungalows - Key West Historic Inns
92%
|
–
Old Town Key West
per night
Includes all fees
Smack dab in the middle of historic Old Town, two blocks from Duval Street and half a mile from the beach.
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1 Room Left
Luxe
DEAL
Cheeca Lodge & Spa
94%
|
–
Islamorada
per night
Includes all fees
Borrowable bikes, sea kayaks & paddleboats make the most of this scenic + explorable locale.
Solid
DEAL
Faro Blanco Resort & Yacht Club
92%
|
–
Florida Keys
per night
Includes all fees
In the mood for a leisurely lunch? Look no further than the hotel’s own eatery.
2 Rooms Left
Hip
DEAL
Amara Cay Resort
93%
|
–
Islamorada
per night
Includes all fees
We’ll be in a hammock on the private beach all day (right after we Instagram it).
1 Room Left
Luxe
DEAL
Baker's Cay Resort Key Largo, Curio Collection by Hilton
91%
|
–
Key Largo
per night
Includes all fees
Two words: private beach. Snorkel, paddleboard, kayak, fish or just kick back and relax.
1 Room Left
Basic
DEAL
Seashell Motel
75%
|
–
Florida Keys
per night
Includes all fees
Free parking means you're not stuck tracking down a spot.
1 Room Left
Basic
Westwinds Inn
86%
|
–
Key West
per night
Includes all fees
The main house is a stately white-pillared affair, with smaller bungalows around the tropical gardens and pools.
Basic
DEAL
Southwinds Motel
88%
|
–
Florida Keys
per night
Includes all fees
Steps from Duval Street as well as the ocean, it's a perfect little motel in all its aquamarine glory.
1 Room Left
Charming
The Garden House - Adults Only
95%
|
–
Florida Keys
per night
Includes all fees
Quaint and quiet historic ‘hood, but an easy 8-min stroll to the world-famous dining/nightlife action on Duval Street.
2 Rooms Left
Basic
Bayside Inn Key Largo
91%
|
–
Florida Keys
per night
Includes all fees
On a private stretch of sand overlooking the bay, plus a pool with views, swimming lagoon and fishing pier.
2 Rooms Left
Charming
Winslow's Bungalows - Key West Historic Inns
92%
|
–
Old Town Key West
per night
Includes all fees
Smack dab in the middle of historic Old Town, two blocks from Duval Street and half a mile from the beach.
Hip
Blue Flamingo Resort Key West
88%
|
–
Key West
per night
Includes all fees
Awesome outdoor pool with plenty of space. Kick back with a drink from the poolside bar.
2 Rooms Left
Solid
Margaritaville Beach House Key West
90%
|
–
Key West
per night
Includes all fees
Yup, all rooms are spacious with Sweet Sleeper beds as deliciously comfortable as they sound.
Solid
Skipjack Resort Suites & Marina
85%
|
–
Florida Keys
per night
Includes all fees
All-suite escape complete with galley kitchens for whipping up whatever it is you like to whip up on vaycay.
2 Rooms Left
Luxe
H2O Suites
98%
|
–
Florida Keys
per night
Includes all fees
Stunning modern décor throughout. Living room rocks a sofa and wet bar for an awesome getaway.
2 Rooms Left
Hip
La Siesta Resort & Villas
93%
|
–
Islamorada
per night
Includes all fees
Nicknamed the intriguing (though redundant) ‘hidden hideaway of the Florida Keys,’ this place is on 6 blissful acres of private sugar sand beach.
Charming
Lighthouse Hotel - Key West Historic Inns
93%
|
–
Old Town Key West
per night
Includes all fees
Prime central spot next to the Lighthouse Museum and across the street from the Ernest Hemingway Home.
1 Room Left
Luxe
Reefhouse Resort and Marina
89%
|
–
Florida Keys
per night
Includes all fees
Primping, preening, and pampering to the max with onsite spa services.
Solid
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort
91%
|
–
Islamorada
per night
Includes all fees
Relaxingly retro for a good ol' beachy days vibe.
1 Room Left
Solid
Silver Palms Inn & Historic Homes
–
Florida Keys
per night
Includes all fees
Leave your car behind (free parking!) and rent one of the house bikes to truly get a lay of the land (and burn off some of that free breakfast).
1 Room Left
Basic
DEAL
Sunset Cove Beach Resort
–
Florida Keys
per night
Includes all fees
Relax, early riser. Light continental breakfast included.
Basic
Best Western Hibiscus Motel
–
Key West
per night
Includes all fees
Courtyard pool confirms you have indeed arrived in Key West, lined with palms and loungers.
1 Room Left
Luxe
Santa Maria Suites
95%
|
–
Key West
per night
Includes all fees
Classic Key West digs boasting contemporary-tropical decor in the rooms juxtaposed with the original, historic facade just a block off Duval.
Solid
Even Hotel Sweetwater Doral
75%
|
–
Florida Keys
per night
Includes all fees
Solid
Holiday Inn Key Largo
88%
|
–
Key Largo
per night
Includes all fees
Don't go chasing waterfalls (unless they're in one of the two onsite pools — you should chase those).
1 Room Left
Solid
Parrot Key Hotel & Villas
94%
|
–
Key West
per night
Includes all fees
5 acres of tropical and sculpture gardens (might wanna LoJack your shades just in case…).
Charming
Fitch Lodge- Key West Historic Inns
88%
|
–
Old Town Key West
per night
Includes all fees
Situated in five conch-style buildings that just scream classic Key West, rooms are comfy and cozy.
Luxe
Pier House Resort & Spa
91%
|
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Key West
per night
Includes all fees
Jutting out into the water on a pier (surprise!), it has its very own slice of private beach.
1 Room Left
Luxe
DEAL
Casa Morada
96%
|
–
Islamorada
per night
Includes all fees
The hotel has its own private island, complete with a pool, secluded cabana, bar and, of course, stunning views.
1 Room Left
Charming
The Gardens Hotel
99%
|
–
Key West
per night
Includes all fees
Former private mansion lets you live like a millionaire without footing the whole bill.
1 Room Left
Charming
Largo Resort
100%
|
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Key Largo
per night
Includes all fees
Hotel pool hits the spot when you need to cool off or swim it out.