Islamorada Vacations
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Where to stay in Islamorada
Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada
Matecumbe
6 out of top 10 points of interest in this area
If you're spending some time in Matecumbe, Bud n' Mary's Dive Center and Anne's Beach are top sights worth seeing.
Find the Best Islamorada Vacation Packages
Islamorada Hotel Deals
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is SAR 987 per night from May 26 to May 27
SAR 987
SAR 1,363 total
26 May - 27 May
includes taxes & fees
9/10 Wonderful! (1,068 reviews)
"Cheeca is very nice , laid back resort, great pools, most employees were friendly. Pier is cool, golf course short but fun. Lagoon view rooms are needing some updating and they should cut down the number of tiki torches at night, gets kind of smoky if wind not blowing. Great beach, activities ..."
Reviewed on 8 May 2025
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is SAR 638 per night from May 26 to May 27
SAR 638
SAR 929 total
26 May - 27 May
includes taxes & fees
9/10 Wonderful! (1,445 reviews)
"Great location and very clean safe property."
Reviewed on 11 May 2025
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy, Islamorada, FL
The price is SAR 953 per night from Jun 1 to Jun 2
SAR 953
SAR 1,321 total
1 Jun - 2 Jun
includes taxes & fees
9/10 Wonderful! (20 reviews)
"Nice, clean, beautiful… unfortunately is too expensive"
Reviewed on 9 May 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Islamorada
Anne's Beach
3.5/5(139 reviews)
If a restful vacation is part of your travel plans, Anne's Beach might be the perfect place to seek out during your trip to Islamorada.
Founders Park
4.5/5(137 reviews)
Enjoy the beautiful sunsets and explore Founders Park, a lovely green space in Islamorada. Wander the seaside and beautiful beaches in this family-friendly area.
Florida Keys Brewing Co.
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.