Deals on vacations and trips to Islamorada, FL

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Islamorada flight + hotel vacation packages

Marenas Beach Resort

Marenas Beach Resort

4 out of 5
Save 100% on your flightPrice was $1,002, price is now $669 per person
per person
Mar 27 - Mar 30
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the 24-hour gym, poolside bar, and convenience store.
The Diane Oceanfront Suites

The Diane Oceanfront Suites

2.5 out of 5
Hollywood Beach
Save 100% on your flightPrice was $1,624, price is now $1,090 per person
per person
Apr 9 - Apr 16
Roundtrip flight included
Newark (EWR) to Miami (MIA)
This motel features self parking and free WiFi in public areas. A terrace and a safe deposit box are also provided.
The Gates Hotel South Beach - a DoubleTree by Hilton

The Gates Hotel South Beach - a DoubleTree by Hilton

4 out of 5
South Beach
Save 100% on your flightPrice was $950, price is now $647 per person
per person
Mar 27 - Mar 30
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the 24-hour gym, poolside bar, and laundry facilities.
Residence Inn by Marriott Miami Aventura Mall

Residence Inn by Marriott Miami Aventura Mall

3 out of 5
Save 100% on your flightPrice was $941, price is now $645 per person
per person
Mar 9 - Mar 13
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 4 conference rooms, as well as the 24-hour business center and free WiFi in public areas. Enjoy the free full breakfast each morning.
W South Beach

W South Beach

5 out of 5
Miami Beach City Center
Save 100% on your flightPrice was $2,122, price is now $1,462 per person
per person
Apr 11 - Apr 15
Roundtrip flight included
Boston (BOS) to Miami (MIA)
A full-service spa, 2 outdoor pools, and a 24-hour gym are all featured at this luxury hotel. Relax with beach cabanas, sun loungers, and beach umbrellas. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.

Top Islamorada hotels deals

Postcard Inn Beach Resort & Marina

Postcard Inn Beach Resort & Marina

3 out of 5
84001 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $287 per night
This Art Deco resort features a private beach, a marina, and 3 restaurants. Dine at the beachfront restaurant and relax with sun loungers. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.
Amara Cay Resort

Amara Cay Resort

3.5 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is $299 per night
A private beach, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and visit the 2 bars/lounges and poolside bar for drinks.
Chesapeake Beach Resort

Chesapeake Beach Resort

2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $239 per night
This smoke-free resort's private beach and 2 outdoor pools are some of the highlights. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the spa tub and free perks like continental breakfast and WiFi in public areas.
Islander Resort

Islander Resort

3 out of 5
82100 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $509 per night
This resort features a private beach, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Enjoy the spa tub and perks like free self parking and free WiFi.
La Siesta Resort & Marina

La Siesta Resort & Marina

3 out of 5
80241 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $264 per night
This smoke-free resort features a private beach, a marina, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. There's a bar/lounge on site, and a 24-hour front desk and wedding services are also provided.
Pelican Cove Resort & Marina

Pelican Cove Resort & Marina

3 out of 5
84457 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
The price is $265 per night
This Art Deco hotel features a private beach, a marina, and a restaurant. Dine at the beachfront restaurant and relax with sun loungers. Enjoy the outdoor pool and perks like free WiFi.
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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 in Islamorada

Image for Theater of the Sea

Theater of the Sea

4.5/5(215 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.

Theater of the Sea
Image for Anne's Beach

Anne's Beach

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. Wander the seaside or discover the beautiful sunsets in this relaxing area.

Anne's Beach
Image for Florida Keys Brewing Co.

Florida Keys Brewing Co.

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada. Amble around this relaxing area's seaside or experience its entertainment choices.

Florida Keys Brewing Co.

Frequently asked questions