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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 (8)

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Ocean House (Islamorada, FL) 2.0 of 5
82885 Old Highway, Islamorada, FL 33036
Ocean House Slideshow
Ollie #1 of 20 hotels in Islamorada
Traveler photos (232)
123 Beach Rd, Islamorada, FL 33036
The Moorings Village and Spa Slideshow
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$577 - $1,232 Avg. price/night*
Ollie #2 of 20 hotels in Islamorada
Professional photos | Traveler photos (168)
Special Offer Summer Savings!
Casa Morada (Islamorada, FL) 3.0 of 5
136 Madeira Road, Islamorada, FL 33036
Casa Morada Slideshow
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$257 - $486 Avg. price/night*
Ollie #3 of 20 hotels in Islamorada
Traveler photos (801)
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
  •  Boaters Paradise 
  • This place is Boaters Paradise! The rooms are spacious and clean with a... more
  • May 22, 2015
Traveler photos (158)
117 South Carroll Street, Mile Marker 82, Islamorada, FL 33036
The Caribbean Resort at Sea Isle Slideshow
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$387 - $1,685 Avg. price/night*
Ollie #5 of 20 hotels in Islamorada
Professional photos | Traveler photos (65)
Special Offer Free boat dockage
Drop Anchor Resort (Islamorada, FL) 3.0 of 5
84959 Overseas Hwy, Islamorada, FL 33036
Drop Anchor Resort Slideshow
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$163 - $312 Avg. price/night*
Ollie #6 of 20 hotels in Islamorada
  •  Great place! 
  • It was a while ago we stayed at this lovely place and I have just not come... more
  • May 22, 2015
Professional photos | Traveler photos (276)
Mile Marker 82.1 Oceanfront, 82100 Overseas Highway, Islamorada, FL 33036
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$168 - $367 Avg. price/night*
Ollie #7 of 20 hotels in Islamorada
  •  Birthday trip 
  • We flew in on Thursday morning and spent a long weekend, flying out on... more
  • May 25, 2015
Professional photos | Traveler photos (475)
Amara Cay Resort (Islamorada, FL) 3.5 of 5
80001 Overseas Highway, Islamorada, FL 33036
Amara Cay Resort Slideshow
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$234 - $528 Avg. price/night*
Ollie #8 of 20 hotels in Islamorada
Professional photos | Traveler photos (563)
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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$229 - $715 Avg. price/night*
Ollie #9 of 20 hotels in Islamorada
Professional photos | Traveler photos (1028)
Special Offer Celebrate Mom this May
Kon-Tiki Resort (Islamorada, FL)
81200 Overseas Highway, Islamorada, FL 33036
$88 - $350 Avg. price/night*
Ollie #10 of 20 hotels in Islamorada
  •  Love Kon-Tiki! 
  • My husband has been staying here for 40 years, me for the last 20, and... more
  • May 23, 2015
Traveler photos (74)
Top Value! $184 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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$145 - $191 Avg. price/night*
Ollie #11 of 20 hotels in Islamorada
  •  An Islamorada Gem 
  • I really have to hesitate to write this. I don't want it to end up being... more
  • May 19, 2015
Professional photos | Traveler photos (142)
84500 Overseas Highway, Islamorada, FL 33036
Ollie #12 of 20 hotels in Islamorada
  •  GREAT PLACE TO STAY 
  • The staff at the Ocean View Inn & Pub are awesome! Made us feel welcome... more
  • May 13, 2015
Traveler photos (89)
84801 Overseas Hwy, Islamorada, FL 33036
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$128 - $196 Avg. price/night*
Ollie #13 of 20 hotels in Islamorada
  •  Lovely Stay 
  • We came in late...just a last minute drop in..... and it was beautiful... more
  • May 18, 2015
Professional photos | Traveler photos (164)
84457 Old Overseas Highway, Islamorada, FL 33036
Pelican Cove Resort Marina Hotel Islamorada Slideshow
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$193 - $498 Avg. price/night*
Ollie #14 of 20 hotels in Islamorada
  •  Poolside bar and staff 
  • I have stayed at pelican cove several times and the hospitality is through... more
  • May 25, 2015
Professional photos | Traveler photos (75)
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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$207 - $315 Avg. price/night*
Ollie #15 of 20 hotels in Islamorada
  •  Cozy and Picturesque 
  • My family and I choose this resort because it was affordable and ideal for... more
  • May 23, 2015
Professional photos | Traveler photos (538)
Special Price 15% off room rate
84001 Overseas Hwy, Islamorada, FL 33036
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$201 - $455 Avg. price/night*
Ollie #16 of 20 hotels in Islamorada
Professional photos | Traveler photos (1262)
La Siesta Resort & Marina (Islamorada, FL) 3.0 of 5
80241 Overseas Highway, Mile Marker 80.5 Oceanside, Islamorada, FL 33036
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$163 - $447 Avg. price/night*
Ollie #17 of 20 hotels in Islamorada
  •  DO NOT STAY HERE 
  • I come ot Islamorada 20-30 days a year working with local charities... more
  • May 25, 2015
Professional photos | Traveler photos (617)
Harbor Lights Motel (Islamorada, FL) 2.0 of 5
84951 Overseas Highway, Islamorada, FL
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$84 - $177 Avg. price/night*
Ollie #18 of 20 hotels in Islamorada
Professional photos | Traveler photos (165)
83409 Overseas Highway Islamorada Keys, Islamorada, FL 33036
Ollie #19 of 20 hotels in Islamorada
  •  Birthday weekend 
  • We love going to the Keys and this was for my husbands birthday. We had... more
  • April 26, 2015
Traveler photos (1)
82749 Overseas Highway, Islamorada, FL 33036
Days Inn & Suites Islamorada Slideshow
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$217 - $274 Avg. price/night*
Ollie #20 of 20 hotels in Islamorada
  •  Question the Value 
  • I was called the day of my check in by this motel to see if I was still... more
  • May 25, 2015
Professional photos | Traveler photos (106)
Special Offer Plan Ahead and Save 15%

Additional Best of Both Worlds Information

5.0 of 5 stars | 31 Reviews
Price range (per night): $217 - $274