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Hotels (41)

B&Bs / Inns (97)

Specialty Lodging (22)

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Travelers' Choice® 2014 Winner Romance | Small Hotels
 
Orchid Key Inn (Key West, FL) 3.5 of 5
1004 Duval Street, Key West, FL 33040
Orchid Key Inn Slideshow
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$252 - $507 Avg. price/night*
Ollie #1 of 41 hotels in Key West
  •  Wonderful Experience! 
  • This place was fabulous from the day before we arrived throughout our... more
  • September 16, 2014
Professional photos | Traveler photos (743)
Special Offer $20 TripAdvisor Discount
Almond Tree Inn (Key West, FL) 3.5 of 5
512 Truman Avenue, Key West, FL 33040
Almond Tree Inn Slideshow
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$234 - $550 Avg. price/night*
Ollie #2 of 41 hotels in Key West
  •  Loved it 
  • Loved our stay at The Almond Tree. Tropical landscaping, a staff that is... more
  • September 16, 2014
Professional photos | Traveler photos (559)
Special Offer $20 Tripadvisor Discount
Travelers' Choice® 2014 Winner Small Hotels | Romance
 
Marquesa Hotel (Key West, FL)
600 Fleming St, Key West, FL 33040
Marquesa Hotel Slideshow
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$209 - $402 Avg. price/night*
Ollie #3 of 41 hotels in Key West
Professional photos | Traveler photos (492)
Special Rate Lowest Rate, Guarantee
Santa Maria Suites (Key West, FL) 4.0 of 5
1401 Simonton Street, Key West, FL 33040
Santa Maria Suites Slideshow
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$331 - $854 Avg. price/night*
Ollie #4 of 41 hotels in Key West
  •  Next to perfect! 
  • Although it was the off season and the weather in Key West was terrible... more
  • September 14, 2014
Professional photos | Traveler photos (885)
Special Offer 10% Trip Advisor...
508 South Street, Key West, FL 33040
Southernmost on the Beach Slideshow
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$295 - $737 Avg. price/night*
Ollie #5 of 41 hotels in Key West
  •  Wonderful vacation 
  • Complimentary upgrade upon check in...to the most beautiful room. the... more
  • September 15, 2014
Professional photos | Traveler photos (1725)
Offers & Announcements Save up to 15%
Eden House (Key West, FL) 3.0 of 5
1015 Fleming Street, Key West, FL 33040
Eden House Slideshow
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$185 - $412 Avg. price/night*
Ollie #6 of 41 hotels in Key West
Professional photos | Traveler photos (718)
Special Price DIRECT BOOKING SPECIAL
Ocean Key Resort & Spa (Key West, FL) 4.0 of 5
Zero Duval Street, Key West, FL 33040
Ocean Key Resort & Spa Slideshow
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$294 - $793 Avg. price/night*
Ollie #7 of 41 hotels in Key West
Professional photos | Traveler photos (1392)
Offers & Announcements $100 resort credit
Southernmost Hotel (Key West, FL) 3.5 of 5
1319 Duval St, Key West, FL 33040
Southernmost Hotel Slideshow
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$212 - $636 Avg. price/night*
Ollie #8 of 41 hotels in Key West
  •  Awesome location 
  • This was the hotel where I proposed to my now wife. It is beautiful and... more
  • September 16, 2014
Professional photos | Traveler photos (665)
Offers & Announcements Save up to 15%
1 Duval St, Key West, FL 33040
Pier House Resort and Spa Slideshow
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$268 - $613 Avg. price/night*
Ollie #9 of 41 hotels in Key West
Professional photos | Traveler photos (684)
Hyatt Windward Pointe (Key West, FL) 3.5 of 5
3675 S Roosevelt Blvd, Key West, FL 33040
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$313 - $628 Avg. price/night*
Ollie #10 of 41 hotels in Key West
Professional photos | Traveler photos (234)
Cypress House Key West (Key West, FL) 2.5 of 5
601 Caroline Street, Key West, FL 33040
Cypress House Key West Slideshow
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$210 - $459 Avg. price/night*
Ollie #11 of 41 hotels in Key West
  •  Hidden GEM 
  • 2 couples,2days Really don't want to review....THIS IS A HIDDEN GEM Just... more
  • September 12, 2014
Professional photos | Traveler photos (98)
Special Offer Key West 3 Nights $50...
2801 N Roosevelt Blvd, Key West, FL 33040
Parrot Key Hotel and Resort Slideshow
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$220 - $695 Avg. price/night*
Ollie #12 of 41 hotels in Key West
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Offers & Announcements SALE: $250 For Dining
601 Front Street, Key West, FL 33040
Hyatt Key West Resort and Spa Slideshow
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$313 - $744 Avg. price/night*
Ollie #13 of 41 hotels in Key West
Professional photos | Traveler photos (702)
Offers & Announcements Adv Purchase $20/NT Off
3841 North Roosevelt Boulevard, Key West, FL 33040
Key West Marriott Beachside Hotel Slideshow
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$205 - $779 Avg. price/night*
Ollie #14 of 41 hotels in Key West
Professional photos | Traveler photos (1231)
Special Offer Earn Rewards Points
1313 Simonton Street, Key West, FL 33040
BEST WESTERN Hibiscus Motel Slideshow
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$159 - $355 Avg. price/night*
Ollie #15 of 41 hotels in Key West
  •  family wedding 
  • front desk staff (Yvonne & Roman) very helpful, courteous and... more
  • September 16, 2014
Professional photos | Traveler photos (595)
Offers & Announcements Save up to 20%
Silver Palms Inn (Key West, FL) 3.5 of 5
830 Truman Avenue, Key West, FL 33040
Silver Palms Inn Slideshow
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$209 - $536 Avg. price/night*
Ollie #16 of 41 hotels in Key West
  •  Great Hotel 
  • We stayed here at the tail end of our Holiday Sep 2014. The Hotel I found... more
  • September 16, 2014
Professional photos | Traveler photos (289)
Offers & Announcements Click for Summer Special
Key Lime Inn (Key West, FL) 3.0 of 5
725 Truman Ave, Key West, FL 33040
Key Lime Inn Slideshow
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$177 - $434 Avg. price/night*
Ollie #17 of 41 hotels in Key West
  •  Quick weekend 
  • Love key lime inn...king room was wonderful and very spacious . Staff... more
  • September 15, 2014
Professional photos | Traveler photos (725)
Special Offer Key West 3 Nights $50...
245 Front St, Key West, FL 33040
Sunset Key Guest Cottages, A Westin Resort Slideshow
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$653 - $1,352 Avg. price/night*
Ollie #18 of 41 hotels in Key West
Professional photos | Traveler photos (525)
Special Offer 5th Night Free & Credit
3990 S Roosevelt Blvd, Key West, FL 33040
DoubleTree by Hilton Hotel Grand Key Resort - Key West Slideshow
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$188 - $426 Avg. price/night*
Ollie #19 of 41 hotels in Key West
  •  Wonderful! 
  • From the time arrived until the time I left the property I felt like a new... more
  • September 11, 2014
Professional photos | Traveler photos (481)
Special Offer Book now and save 20%
La Te Da Hotel (Key West, FL)
1125 Duval St, Key West, FL 33040
$90 - $285 Avg. price/night*
Ollie #20 of 41 hotels in Key West
  •  New Years Eve Get a Way 
  • This past New Years Eve we decided to do something a little different and... more
  • September 2, 2014
Traveler photos (183)

Additional Square One Information

4.5 of 5 stars | 391 Reviews