Book Exclusive Islamorada Vacation Packages
Islamorada flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Eden Roc Miami Beach
Mid Beach
Save 100% on your flight
per person
Jun. 27 - Jul. 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
Book a stay at this luxury resort in Miami Beach. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions Miami Beach Boardwalk and Collins Avenue Shopping Area are located nearby.
Casablanca Miami Beach
North Beach
Save 100% on your flight
per person
Jul. 29 - Aug. 5
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
Stay at this 3-star beach aparthotel in Miami Beach. Enjoy a beach locale, valet parking (surcharge), and laundry facilities. Popular attractions Miami Beach Boardwalk and Collins Avenue Shopping Area are located nearby.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Save 100% on your flight
per person
Jun. 12 - Jun. 16
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Miami (MIA)
Stay at this 5-star luxury condo in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and 2 restaurants. Popular attractions Collins Avenue Shopping Area and Miami Beach Boardwalk are located nearby.
1 Hotel South Beach
South Beach
Save 100% on your flight
per person
Jun. 25 - Jun. 30
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
Stay at this 5-star luxury hotel in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Miami Beach Boardwalk are located nearby.
Fitch Lodge - Key West Historic Inns
Key West Historic District
Save 100% on your flight
per person
Jun. 21 - Jun. 28
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
Stay at this 3.5-star hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Top Islamorada hotels deals
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $310 per night
CA $310
CA $443 total
Jun 9 - Jun 10
includes taxes & fees
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Matecumbe United Methodist Church and Florida Keys Brewing Co. are located nearby.
On private beach
Pool
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $235 per night
CA $235
CA $343 total
May 26 - May 27
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy 2 outdoor pools, a private beach, and a 24-hour front desk. Our guests praise the breakfast and the pool in our reviews. Popular attractions History of Diving Museum and Windley Key Fossil Reef Geological State Park are located nearby.
On private beach
Pool
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $352 per night
CA $352
CA $488 total
Jun 5 - Jun 6
includes taxes & fees
Stay at this 3.5-star beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Windley Key Fossil Reef Geological State Park and History of Diving Museum are located nearby.
On private beach
Pool
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $296 per night
CA $296
CA $426 total
Jun 9 - Jun 10
includes taxes & fees
Stay at this 4-star beach resort in Islamorada. Enjoy free parking, 2 restaurants, and a private beach. Our guests praise the pool and the bar in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby.
On private beach
Pool
La Siesta Resort & Villas
80241 Overseas Highway, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $279 per night
CA $279
CA $406 total
May 21 - May 22
includes taxes & fees
Stay at this 4-star beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious rooms in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby.
On private beach
Pool
Islander Resort
82100 Overseas Highway, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $404 per night
CA $404
CA $542 total
May 19 - May 20
includes taxes & fees
Stay at this 4-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Keys History & Discovery Center and Islamorada Brewery & Distillery are located nearby.
On private beach
Pool
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.
Popular places to visit
Theater of the Sea
4/5(6 reviews)
Take the kids to visit the sea life you'll find at Theater of the Sea during your trip to Islamorada. Take in the entertainment choices and beautiful sunsets in this family-friendly area.
Anne's Beach
4/5(14 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
3.5/5(2 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.
Islamorada Vacations
If you're going to Islamorada and you don't really know much about it, you don't need to worry — we'll let you in on the basics!
Islamorada is located 170 miles (274 kilometers) to the northeast of Havana, a significant city.
At last count, the population of this area of Florida Keys was 7,000.
Places to visit in Islamorada
If you've got an inquiring mind, stop by History of Diving Museum. You never know what you'll find out here! Need some more ideas? We all dote on our fuzzy and feathery friends, but how about getting familiar with those who are a tad more scaly and slippery? Meet some of the most magnificent occupants of the marine world at Theater of the Sea. And that's not all. Hurricane Monument offers a space for reflection and solitude. Learn about the importance of this memorial and find out more about how, when and why it was erected.Where do you fly into for Islamorada?
While you're arranging your upcoming Islamorada escape, keep in mind that the closest terminal, Homestead Air Reserve Base Airport (HST), is about 40 miles (64 kilometers) north of the city center. Book your flight, fill up your luggage and get set for some exciting new adventures!Photos of local treasures
Browse Islamorada vacation photos for more inspiration
Book a vacation to Islamorada
Most popular
Hotels
Flights
Activities