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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 (228)
123 Beach Rd, Islamorada, FL 33036
The Moorings Village and Spa Slideshow
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$571 - $1,390 Avg. price/night*
Ollie #2 of 20 hotels in Islamorada
  •  Paradise found 
  • The Moorings is paradise found. We couldn't imagine a better place to... more
  • May 3, 2015
Professional photos | Traveler photos (166)
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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$260 - $471 Avg. price/night*
Ollie #3 of 20 hotels in Islamorada
  •  Girls weekend getaway 
  • Where do I even start with this slice of paradise? From the moment you... more
  • April 27, 2015
Traveler photos (800)
Special Price $10 off room rate
117 South Carroll Street, Mile Marker 82, Islamorada, FL 33036
The Caribbean Resort at Sea Isle Slideshow
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$386 - $1,684 Avg. price/night*
Ollie #4 of 20 hotels in Islamorada
  •  ABSOLUTELY A PARADISE 
  • My fiance has been staying to this place for quite some time. He told me... more
  • April 30, 2015
Professional photos | Traveler photos (65)
Special Offer Free boat dockage
Coral Bay Resort (Islamorada, FL)
75690 Overseas Hwy, MM 75.5 Bayside, Islamorada, FL 33036
$119 - $305 Avg. price/night*
Ollie #5 of 20 hotels in Islamorada
Traveler photos (155)
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
Professional photos | Traveler photos (272)
Mile Marker 82.1 Oceanfront, 82100 Overseas Highway, Islamorada, FL 33036
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$178 - $360 Avg. price/night*
Ollie #7 of 20 hotels in Islamorada
Professional photos | Traveler photos (455)
Amara Cay Resort (Islamorada, FL) 3.5 of 5
80001 Overseas Highway, Islamorada, FL 33036
Amara Cay Resort Slideshow
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$233 - $517 Avg. price/night*
Ollie #8 of 20 hotels in Islamorada
  •  Paradise!! 
  • We went to Islamorada as a get-a-way with another couple. The hotel was... more
  • May 2, 2015
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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$235 - $677 Avg. price/night*
Ollie #9 of 20 hotels in Islamorada
Professional photos | Traveler photos (1004)
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
  •  Another great stay 
  • Been staying here for yrs upon yrs. This time we used rooms 1&2. They... more
  • April 23, 2015
Traveler photos (74)
Sands of Islamorada (Islamorada, FL)
80051 Overseas Highway, Mile Marker 80, Islamorada, FL 33036
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$187 - $191 Avg. price/night*
Ollie #11 of 20 hotels in Islamorada
  •  Great stay 
  • Spent a fun weekend here with my cousin. The resort is made up of vintage... more
  • April 3, 2015
Professional photos | Traveler photos (141)
84500 Overseas Highway, Islamorada, FL 33036
Ollie #12 of 20 hotels in Islamorada
Traveler photos (89)
84801 Overseas Hwy, Islamorada, FL 33036
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$129 - $196 Avg. price/night*
Ollie #13 of 20 hotels in Islamorada
Professional photos | Traveler photos (164)
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 - $331 Avg. price/night*
Ollie #14 of 20 hotels in Islamorada
Professional photos | Traveler photos (529)
Special Price 15% off room rate
84457 Old Overseas Highway, Islamorada, FL 33036
Pelican Cove Resort Marina Hotel Islamorada Slideshow
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$221 - $493 Avg. price/night*
Ollie #15 of 20 hotels in Islamorada
  •  NOT FOR FAMILIES 
  • FAMILIES- STAY AWAY! We stayed at the Pelican Grove Resort on April 24th... more
  • May 2, 2015
Professional photos | Traveler photos (56)
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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$179 - $449 Avg. price/night*
Ollie #16 of 20 hotels in Islamorada
  •  Gross 
  • Extremely dirty hotel. Front desk does not answer phones. Has a great... more
  • May 3, 2015
Professional photos | Traveler photos (603)
84001 Overseas Hwy, Islamorada, FL 33036
Postcard Inn Beach Resort & Marina at Holiday Isle Slideshow
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$218 - $456 Avg. price/night*
Ollie #17 of 20 hotels in Islamorada
Professional photos | Traveler photos (1255)
Harbor Lights Motel (Islamorada, FL) 2.0 of 5
84951 Overseas Highway, Islamorada, FL
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$84 - $186 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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$187 - $281 Avg. price/night*
Ollie #20 of 20 hotels in Islamorada
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): $187 - $281