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Unavailable
3 Rooms Left
Luxe
DEAL
Cheeca Lodge & Spa
$319
93%
|
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Islamorada
Borrowable bikes, sea kayaks & paddleboats make the most of this scenic + explorable locale.
Unavailable
1 Room Left
Solid
Islander Bayside Resort
$279
97%
|
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Islamorada
was on HT
$485
Max the vacay vibes in your very own vintage-cool villa (bedecked with musts like a kitchen, tons of space & tropical ‘tude).
Unavailable
1 Room Left
Solid
DEAL
Islander Resort
$288
94%
|
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islamorada
was on HT
$339
Unbeatable location on the gorgeous beach – fitting that this spot is owned by an artist.
Unavailable
Charming
DEAL
Winslow's Bungalows
$293
92%
|
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Old Town Key West
was on HT
$415
Smack dab in the middle of historic Old Town, two blocks from Duval Street and half a mile from the beach.
Unavailable
Solid
Skipjack Resort Suites & Marina
$275
85%
|
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Florida Keys
was on HT
$305
All-suite escape complete with galley kitchens for whipping up whatever it is you like to whip up on vaycay.
Unavailable
Solid
DEAL
Banana Bay Resort & Marina
$225
91%
|
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Marathon
Rooms’ chilled-out, classically Floribbean ‘tude maxes the vaycay vibes.
Unavailable
Solid
DEAL
Faro Blanco Resort & Yacht Club
$244
90%
|
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Florida Keys
was on HT
$335
In the mood for a leisurely lunch? Look no further than the hotel’s own eatery.
Unavailable
2 Rooms Left
Charming
Ridley House
$335
94%
|
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Old Town Key West
was on HT
$401
One block from Duval Street, walking (or stumbling) distance to plenty of restaurants and nightlife.
Unavailable
2 Rooms Left
Solid
DEAL
Parrot Key Hotel & Villas
$399
94%
|
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Key West
was on HT
$474
5 acres of tropical and sculpture gardens (might wanna LoJack your shades just in case…).
Unavailable
1 Room Left
Charming
The Inn on Fleming
$289
100%
|
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Florida Keys
Serene, lush green setting on a quiet street strollable to the action on Duval, and 2 blocks from the big sunset viewing spot.
Unavailable
2 Rooms Left
Solid
DEAL
Oceans Edge Key West Resort & Marina
$327
92%
|
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Key West
was on HT
$503
Ocean views from every rooms’ floor-to-ceiling windows & private balconies.
Unavailable
1 Room Left
Charming
The Duval House - Adults Only
$308
97%
|
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Florida Keys
was on HT
$539
7 classic Caribbean-style houses behind a li’l front gate, complete with gazebo and 100-year-old Banyan tree, steps from the Duval Street action.
Unavailable
3 Rooms Left
Solid
DEAL
Creekside Inn Islamorada
$189
81%
|
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Tavernier
was on HT
$256
Maxin’ & relaxin’ by the canal (right outside!) is how we love to end our day.
Unavailable
1 Room Left
Charming
Ella's Cottages
$365
93%
|
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Old Town Key West
was on HT
$565
Close proximity to sweet sites like Ernest Hemingway's home, as well as Jimmy Buffet's (Margaritaville).
Unavailable
Luxe
Isla Bella Beach Resort & Spa Florida Keys
$629
96%
|
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Florida Keys
was on HT
$959
Sleek, lavishly-appointed oceanview escape, just steps from the iconic 7 Mile Bridge. Explore by land on bikes, or by sea in kayaks.
Unavailable
1 Room Left
Charming
Island City House Hotel
$376
98%
|
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Key West
was on HT
$450
Eclectic style covers it all from Caribbean to Victorian, with plenty of space to enjoy it.
Unavailable
1 Room Left
Charming
Eden House Key West
$469
92%
|
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Key West
In the heart of Key West, walkable to the beach, downtown and lively Duval Street.
Unavailable
Luxe
Ocean Key Resort & Spa
$929
93%
|
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Key West
Ace location sandwiches you between the Gulf and the buzz of Duval St. (So many umbrella drinks are just a stroll away.)
Unavailable
Solid
Casa Marina Resort - A Waldorf Astoria Resort
$800
86%
|
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Key West
was on HT
$950
Set on over 1000 feet of postcard-worthy private beach (with cocktail service, natch) & within stumbling distance of hopping' Duval Street.
Unavailable
Basic
Hampton Inn Marathon-Florida Keys, FL
$319
100%
|
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Florida Keys
Hot breakfast spread every day, free – plus weekday grab & go brekkie for when you've gotta jet.
Unavailable
Luxe
Baker's Cay Resort Key Largo, Curio Collection by Hilton
$810
91%
|
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Key Largo
was on HT
$1,200
Two words: private beach. Snorkel, paddleboard, kayak, fish or just kick back and relax.
Unavailable
Basic
Fairfield Inn & Suites Homestead Florida City
$119
100%
|
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Florida City
Unavailable
Basic
Holiday Inn Express Hotel & Suites Florida City
$109
86%
|
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Florida City
Shopping, golfing, Everglades alligator spotting, Key Largo beaches – all nearby.
Unavailable
Basic
Home2 Suites by Hilton Florida City, FL
$144
80%
|
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Florida City
was on HT
$179
Suites are modern and have plenty of space.
Unavailable
HighRoller
The Marker Key West Highroller
$1,073
–
Florida Keys
was on HT
$1,567
Over 1000 sq ft of stylish space to relax in, featuring chic decor, soothing hues and a plush, king-sized bed.
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