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Best of Both Worlds

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Map of Best of Both Worlds

Hotels (20)

B&Bs / Inns (13)

Specialty Lodging (7)

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Ocean House (Islamorada, FL)
82885 Old Highway, Islamorada, FL 33036
Ocean House Slideshow
Ollie #1 of 20 hotels in Islamorada
Traveler photos (210)
Announcement Elope With Ocean House
123 Beach Rd, Islamorada, FL 33036
The Moorings Village and Spa Slideshow
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$560 - $1,337 Avg. price/night*
Ollie #2 of 20 hotels in Islamorada
  •  Amazingly quiet! 
  • If you want quiet and romantic this is it. We came for a 4 day weekend for... more
  • October 6, 2014
Professional photos | Traveler photos (157)
Special Offer $499 2BR Cottages
Casa Morada (Islamorada, FL)
136 Madeira Road, Islamorada, FL 33036
Casa Morada Slideshow
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$293 - $668 Avg. price/night*
Ollie #3 of 20 hotels in Islamorada
Professional photos | Traveler photos (764)
Coral Bay Resort (Islamorada, FL)
75690 Overseas Hwy, MM 75.5 Bayside, Islamorada, FL 33036
$119 - $305 Avg. price/night*
Ollie #4 of 20 hotels in Islamorada
  •  Laid back get away 
  • We just returned from a great weekend stay as my sister and her husband... more
  • October 19, 2014
Traveler photos (142)
Drop Anchor Resort (Islamorada, FL) 3.0 of 5
84959 Overseas Hwy, Islamorada, FL 33036
Drop Anchor Resort Slideshow
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$140 - $303 Avg. price/night*
Ollie #5 of 20 hotels in Islamorada
  •  Excellent! Clean! 
  • We just got back from a weekend at Drop Anchor. We were celebrating our... more
  • October 19, 2014
Professional photos | Traveler photos (225)
Special Offer Resort Room Special!
117 South Carroll Street, Mile Marker 82, Islamorada, FL 33036
The Caribbean Resort at Sea Isle Slideshow
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$392 - $1,685 Avg. price/night*
Ollie #6 of 20 hotels in Islamorada
Professional photos | Traveler photos (55)
Announcement Free Boat Dockage.
The Islamorada Resort (Islamorada, FL) 2.5 of 5
80001 Overseas Highway, Islamorada, FL 33036
The Islamorada Resort Slideshow
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$193 - $296 Avg. price/night*
Ollie #7 of 20 hotels in Islamorada
Professional photos | Traveler photos (536)
Special Price 15% off room rate
Cheeca Lodge & Spa (Islamorada, FL) 4.0 of 5
81801 Overseas Highway, Mile Marker 82, Islamorada, FL 33036
Cheeca Lodge & Spa Slideshow
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$225 - $900 Avg. price/night*
Ollie #8 of 20 hotels in Islamorada
Professional photos | Traveler photos (915)
Special Offer Up To 25% Off Suites
Islander Resort (Islamorada, FL) 3.0 of 5
Mile Marker 82.1 Oceanfront, P.O. BOX 766, Islamorada, FL 33036
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$129 - $312 Avg. price/night*
Ollie #9 of 20 hotels in Islamorada
  •  Beautiful and Relaxing 
  • My husband and I spent 4 nights at this wonderful resort last week. It was... more
  • October 20, 2014
Professional photos | Traveler photos (362)
84801 Overseas Hwy, Islamorada, FL 33036
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$124 - $196 Avg. price/night*
Ollie #10 of 20 hotels in Islamorada
  •  A trip to paradise! 
  • Always a great experience and it is our favorite place. The family and... more
  • October 11, 2014
Professional photos | Traveler photos (139)
84500 Overseas Highway, Islamorada, FL 33036
Ollie #11 of 20 hotels in Islamorada
  •  Good Times! 
  • Wow, what a great place. Went for Sunday football after our scuba diving... more
  • September 16, 2014
Traveler photos (69)
Top Value! $187 less than similar hotels in Best of Both Worlds
 
Sands of Islamorada (Islamorada, FL)
80051 Overseas Highway, Mile Marker 80, Islamorada, FL 33036
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$167 - $172 Avg. price/night*
Ollie #12 of 20 hotels in Islamorada
  •  Best Experience!!! 
  • We fell in the love with the Sands of Islamorada. Stay away from the... more
  • October 13, 2014
Professional photos | Traveler photos (131)
Chesapeake Beach Resort (Islamorada, FL) 2.5 of 5
83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
Chesapeake Beach Resort Slideshow
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$200 - $281 Avg. price/night*
Ollie #13 of 20 hotels in Islamorada
Professional photos | Traveler photos (252)
Special Price 15% off room rate
Kon-Tiki Resort (Islamorada, FL)
81200 Overseas Highway, Islamorada, FL 33036
$88 - $350 Avg. price/night*
Ollie #14 of 20 hotels in Islamorada
  •  Wonderful 
  • My husband and I stayed at Kon Tiki Resort for the first time for our... more
  • October 7, 2014
Traveler photos (59)
Special Rate Fall Specials
84001 Overseas Hwy, Islamorada, FL 33036
Postcard Inn Beach Resort & Marina at Holiday Isle Slideshow
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$144 - $707 Avg. price/night*
Ollie #15 of 20 hotels in Islamorada
  •  Dive vacation 
  • We had a great time here, but the hotel is in need of repairs. Our room... more
  • October 18, 2014
Professional photos | Traveler photos (1145)
Special Offer 20% ENDLESS SUMMER SALE
La Siesta Resort & Marina (Islamorada, FL) 3.0 of 5
80241 Overseas Highway, Mile Marker 80.5 Oceanside, Islamorada, FL 33036
La Siesta Resort & Marina Slideshow
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$144 - $385 Avg. price/night*
Ollie #16 of 20 hotels in Islamorada
  •  The perfect getaway 
  • My fiancé and I have been taking two day trips down to the keys and... more
  • October 18, 2014
Professional photos | Traveler photos (568)
84457 Old Overseas Highway, Islamorada, FL 33036
Pelican Cove Resort Marina Hotel Islamorada Slideshow
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$177 - $430 Avg. price/night*
Ollie #17 of 20 hotels in Islamorada
  •  Great location 
  • This is my hideaway in the keys. It's not the best or most popular but it... more
  • October 3, 2014
Professional photos | Traveler photos (179)
83409 Overseas Highway Islamorada Keys, Islamorada, FL 33036
Ollie #18 of 20 hotels in Islamorada
  •  Terrible 
  • Bottom line: terrible service! The manager and owner were extremely rude... more
  • February 17, 2013
82749 Overseas Highway, Islamorada, FL 33036
Show Prices
$187 - $295 Avg. price/night*
Ollie #19 of 20 hotels in Islamorada
  •  Relaxing and FUN 
  • We planned on staying one night and then head down to key west. We never... more
  • September 21, 2014
Professional photos | Traveler photos (92)
Harbor Lights Motel (Islamorada, FL) 2.0 of 5
84951 Overseas Highway, Islamorada, FL
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$85 - $196 Avg. price/night*
Ollie #20 of 20 hotels in Islamorada
  •  Best location  
  • We stayed for 4 days here and loved every minute. Charter fishing right... more
  • October 16, 2014
Professional photos | Traveler photos (166)

Additional Best of Both Worlds Information

5.0 of 5 stars | 24 Reviews
Price range (per night): $85 - $196