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Unavailable
Charming
DAILY DROP
The Guesthouses at Southernmost Beach Resort - Adults only
$210
80%
|
–
Florida Keys
was on HT
$299
The outdoor pool takes vacay vibes to new heights.
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Unavailable
Hip
DEAL
Amara Cay Resort
$295
93%
|
–
Islamorada
We’ll be in a hammock on the private beach all day (right after we Instagram it).
Unavailable
2 Rooms Left
Solid
DEAL
Banana Bay Resort & Marina
$189
90%
|
–
Marathon
was on HT
$309
Rooms’ chilled-out, classically Floribbean ‘tude maxes the vaycay vibes.
Unavailable
1 Room Left
Basic
Breezy Palms Resort
$179
100%
|
–
Florida Keys
It’s not often you find a resort that exceeds your expectations, Breezy Palms Resort takes everything you’ve ever wanted in a seaside vacation and places it in one scenic, majestic location.
Unavailable
1 Room Left
Charming
The Mermaid & The Alligator - Adults Only
$310
99%
|
–
Key West
was on HT
$340
Oozing with captivating character, from lush gardens to the uniquely decorated guestrooms.
Unavailable
1 Room Left
Luxe
DEAL
Reefhouse Resort and Marina
$357
91%
|
–
Florida Keys
was on HT
$419
Primping, preening, and pampering to the max with onsite spa services.
Unavailable
1 Room Left
Charming
The Duval House - Adults Only
$269
97%
|
–
Florida Keys
was on HT
$369
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
2 Rooms Left
Hip
The Perry Hotel Key West at The Stock Island Marina
$329
94%
|
–
Florida Keys
was on HT
$419
Some rooms rock outdoor showers – others, poolside access.
Unavailable
Basic
DEAL
Hadley House
$157
88%
|
–
Florida Keys
was on HT
$174
Indoor/outdoor lobby lounge, plus an outdoor oceanfront(!) tiki bar. Get out of your beverage rut and order something bright blue or umbrella’d.
Unavailable
2 Rooms Left
Basic
DEAL
Creekside Inn Islamorada
$153
82%
|
–
Tavernier
was on HT
$171
Maxin’ & relaxin’ by the canal (right outside!) is how we love to end our day.
Unavailable
Charming
The Guesthouses at Southernmost Beach Resort - Adults only
$299
80%
|
–
Florida Keys
The outdoor pool takes vacay vibes to new heights.
Unavailable
Basic
DEAL
Looe Key Resort
$214
–
Florida Keys
Non-smoking rooms are a breath of fresh air.
Unavailable
Solid
Holiday Inn Key Largo
$269
88%
|
–
Key Largo
Don't go chasing waterfalls (unless they're in one of the two onsite pools — you should chase those).
Unavailable
1 Room Left
Charming
Coco Plum Inn
$250
96%
|
–
Florida Keys
was on HT
$359
Gorgeous 19th century homes in the heart of Key West, steps from Duval Street.
Unavailable
Solid
Margaritaville Beach House Key West
$369
91%
|
–
Key West
was on HT
$387
Yup, all rooms are spacious with Sweet Sleeper beds as deliciously comfortable as they sound.
Unavailable
Basic
Fisher Inn Resort & Marina
$180
88%
|
–
Florida Keys
was on HT
$199
Got a boat in tow? Fisher Inn is Islamorada’s only hotel with boat parking and a ramp. Brag accordingly.
Unavailable
1 Room Left
Charming
Island City House Hotel
$359
98%
|
–
Key West
was on HT
$373
Eclectic style covers it all from Caribbean to Victorian, with plenty of space to enjoy it.
Unavailable
3 Rooms Left
Luxe
DEAL
Ocean Key Resort & Spa
$450
93%
|
–
Key West
was on HT
$649
Ace location sandwiches you between the Gulf and the buzz of Duval St. (So many umbrella drinks are just a stroll away.)
Unavailable
2 Rooms Left
Solid
Skipjack Resort Suites & Marina
$285
87%
|
–
Florida Keys
was on HT
$313
All-suite escape complete with galley kitchens for whipping up whatever it is you like to whip up on vaycay.
Unavailable
1 Room Left
Solid
DEAL
Islander Resort
$414
95%
|
–
islamorada
was on HT
$459
Unbeatable location on the gorgeous beach – fitting that this spot is owned by an artist.
Unavailable
1 Room Left
Solid
DEAL
Parrot Key Hotel & Villas
$299
93%
|
–
Key West
was on HT
$529
5 acres of tropical and sculpture gardens (might wanna LoJack your shades just in case…).
Unavailable
1 Room Left
Basic
Knight's Key Suites
$149
–
Florida Keys
was on HT
$229
Gorgeous little getaway in Marathon with easy access to the bay and the ocean.
Unavailable
Luxe
Baker's Cay Resort Key Largo, Curio Collection by Hilton
$470
92%
|
–
Key Largo
was on HT
$486
Two words: private beach. Snorkel, paddleboard, kayak, fish or just kick back and relax.
Unavailable
1 Room Left
Charming
The Gardens Hotel
$574
98%
|
–
Key West
was on HT
$804
Former private mansion lets you live like a millionaire without footing the whole bill.
Unavailable
1 Room Left
Charming
The Inn on Fleming
$329
95%
|
–
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
Islander Bayside Villas & Boatslips
$359
95%
|
–
Islamorada
Max the vacay vibes in your very own vintage-cool villa (bedecked with musts like a kitchen, tons of space & tropical ‘tude).
Unavailable
Basic
Hampton Inn Marathon - Florida Keys
$309
97%
|
–
Florida Keys
was on HT
$321
Hot breakfast spread every day, free – plus weekday grab & go brekkie for when you've gotta jet.
Unavailable
Solid
Hilton Garden Inn Homestead
$139
100%
|
–
Florida City
We're off Florida's Turnpike, walking distance of Homestead Pavilion shops and restaurants.
Unavailable
Basic
DEAL
Fairfield Inn & Suites Homestead Florida City
$126
91%
|
–
Florida City
was on HT
$179
Unavailable
Basic
Holiday Inn Express Hotel & Suites Florida City
$259
84%
|
–
Florida City
Shopping, golfing, Everglades alligator spotting, Key Largo beaches – all nearby.
Unavailable
1 Room Left
HighRoller
DEAL
Southernmost Beach Resort - Simonton Suite
$1,892
–
Key West- Upper Duval
was on HT
$2,167
Magnificent, beautifully appointed room. At two stories and over 2,000 sq ft, the Simonton Suite has all the grace and style you expect from Key West.
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