Islamorada Vacations from $200

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Your Islamorada Vacation

The laid-back lifestyle and spectacular views are just the beginning of the things Islamorada has to offer. Enjoy the sights and sounds of this captivating city the way you want with a customized Islamorada vacation package. You'll want to do some exploring during your trip to Islamorada. Make time for popular attractions like Theater of the Sea, Bud n Marys Dive Center and Founders Park. Check out Expedia's wide range of travel options and start organizing your dream vacation to Islamorada today.

The Latest Islamorada vacation packages

Price found within the past 48 hours. Click for updated prices.
Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8.4/10 Very Good! (795 reviews)
Good location and friendly staff, Lois recently remodeled. My room door had plenty of sand in the floor.

Reviewed on Jun 28, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8/10 Very Good! (1 review)
Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8.6/10 Excellent! (1,119 reviews)
Lazy river was great along with the pool and great beach access. GG the lady server that brings you food and drinks at the pool was one of the nicest and kindest people I’ve ever met at a hotel. She truly deserves a big raise. If GG isn’t making a little less than the manager then the management doesn’t know how to manage. GG literally went out of her way to try to make your pool day unforgettable. The only place I would ever be staying at when I return to Fort Lauderdale would be Pelican and reason being is the staff.

Reviewed on Jul 12, 2025

iCoconutGrove Vacation Rentals

iCoconutGrove Vacation Rentals

4 out of 5
Coconut Grove
Save 100% on your flight
per person
Sep 12 - Sep 16
found 19 hours ago
Roundtrip flight included
Philadelphia (PHL) to Miami (MIA)
9.2/10 Wonderful! (1,003 reviews)
The property was in a very populated area with lots of shops, restaurants and nightlife (if that’s your thing). The studio was very clean and there were no issues at all. Unlike hotel rooms, I could not hear what was happening right next door, so it was quiet as well. I would stay here again.

Reviewed on Jul 12, 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Miami (MIA)
9.4/10 Exceptional! (1,212 reviews)
The property was beautiful. The overall esthetics of the One Hotel was intoxicating and welcoming at the same time. My only complaint was with the hotel service in terms of house cleaning; they could use some improvement.

Reviewed on Jul 9, 2025

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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
Islamorada showing a beach bar

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 hotels in Matecumbe

Discover the most popular places to visit in Islamorada

Anne\'s Beach featuring a bridge

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.

Anne's Beach
Founders Park featuring theater scenes, a garden and modern architecture

Founders Park

4.5/5(137 reviews)

Play soccer, baseball and volleyball just meters from the Atlantic Ocean before you dive into the water at this family-friendly beach park.

Founders Park
Florida Keys Brewing Co. showing signage

Florida Keys Brewing Co.

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

Florida Keys Brewing Co.

What to do in Islamorada

Original Snorkel and Sandbar Combo in Islamorada

Original Snorkel and Sandbar Combo in Islamorada

$149
per adult
90% of travellers recommend
Original Snorkel and Sandbar Combo in Islamorada
Ft. Lauderdale to Key West Bus Tour w/ 6 hours of free time in KW

Ft. Lauderdale to Key West Day Trip Quality Day Tours

$225
per adult
Ft. Lauderdale to Key West Day Trip Quality Day Tours
Explore the Mangrove Creeks with an All Day Kayak Rental

Explore Mangrove Creeks with an All Day SUP/single kayak Rental

$47
per adult
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
See all activities in Islamorada

Islamorada Hotel Deals

Cheeca Lodge & Spa
Cheeca Lodge & Spa
5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
$233 nightly
The price is $263 total per night from Aug 13 to Aug 14
$263 total
Aug 13 - Aug 14
Total includes taxes and fees
9/10 Wonderful! (1,128 reviews)
"Resort has a lot of rentals and plenty to do there. Staff is awesome."

Reviewed on Jul 10, 2025

Cheeca Lodge & Spa
Chesapeake Beach Resort
Chesapeake Beach Resort
3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$192 nightly
The price is $217 total per night from Aug 11 to Aug 12
$217 total
Aug 11 - Aug 12
Total includes taxes and fees
9/10 Wonderful! (1,484 reviews)
"Amenities were great"

Reviewed on Jul 9, 2025

Chesapeake Beach Resort
Islander Resort
Islander Resort
4 out of 5
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
$268 nightly
The price is $302 total per night from Aug 4 to Aug 5
$302 total
Aug 4 - Aug 5
Total includes taxes and fees
9/10 Wonderful! (1,012 reviews)
"Fabulous vacation experience! Beautiful facilites with phenomenal ocean views!!!"

Reviewed on Jul 10, 2025

Islander Resort
See all 2,184 properties in Islamorada
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.

Find the Best Islamorada Vacation Packages

Islamorada Beach Vacation

Relax along the shoreline and feel the wind through your hair during your Islamorada vacation. If it's your first time, why not collect some unique seashells as a souvenir of your trip to Islamorada? Spend your nights near Anne's Beach, a popular stretch of coast just 9 miles from the town center. We also offer fantastic Islamorada packages closer to Sunset Drive Beach, another great nearby option.

Things You Should Know About Islamorada

  • Escape the daily grind at one of our Islamorada beach hotels. The sound of the waves and seagulls cawing high in the sky are just a few clicks away.
  • If you're searching for lots of room to spread out and relax, Islamorada private vacation homes are a great choice. After a much-needed family getaway or a few nights escape with your best friends? Treasure Harbor and Bud N' Mary's Fishing Marina will fit the bill.
  • Roughly 7,100 people reside in Islamorada. If you're after a few helpful tips on what to see and do during your stay, have a chat to some of the friendly locals or have a look at our Islamorada things to do page.

Islamorada Essential Information

Language
English
Currency
U.S dollars
Population
7,100
Max Temp Winter
75ºF
Max Temp Summer
85ºF
Top Sights
Theater of the Sea, Annes Beach and Windley Key Fossil Reef Geological State Park

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Frequently asked questions

How much does an Islamorada vacation package cost?
You can snap up a vacation package to this destination from $200 on Expedia. However, how much your vacation to Islamorada costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Islamorada?
April, September and October are great times to look for cheap Islamorada vacation packages. Traveling in quieter periods means you can generally find reduced prices on accommodations and flights.
How many days is enough for Islamorada?
Allow around 3 days for your Islamorada vacation if you're hoping to immerse yourself in everything that makes this place unique. Wander around key neighborhoods, including Plantation Key and Matecumbe. Then check out top sights like Windley Key Fossil Reef Geological State Park and Indian Key Historic State Park. With a good itinerary, you can keep busy with room for some rest and relaxation too. Want to venture outside of Islamorada? Consider fitting in an excursion or two.
Is it worth booking a vacation package to Islamorada?
Whether you're looking to visit top attractions like Theater of the Sea and Bud n' Mary's Dive Center on your Islamorada vacation, or coming for its great family-friendly attractions, underwater activities and walking trails, there's something for everyone here. With so many things to do, you'll quickly learn why so many families think Islamorada is a good vacation destination.
How to find the best Islamorada package deals?
Use Expedia's filter tool to help you find some tempting Islamorada package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Islamorada package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book an Islamorada vacation as a package?
You can enjoy significant savings on your Islamorada escape by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to browse the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Islamorada?
If you're considering a spur-of-the-moment Islamorada getaway, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Islamorada?

  1. Choose when to travel: Check your schedule and pack your bags. Your preferred time of year and the type of activities on offer will also help you decide when to escape to Islamorada.
  2. Set your budget: Factor in expenses such as transportation, flights and meals when calculating how much to save for your trip to Islamorada. Then, choose a property that works with your budget, whether that's an economical stay or a swankier getaway.
  3. Explore Islamorada using Expedia's trip planning tool: Gain insights into the most popular attractions and best properties for your trip to Islamorada. You can also save your must-visit places, collaborate with friends and family and organize your plans in one place.
  4. Decide your trip length: Think about how long you'd like to spend discovering Islamorada. Plan your days so you can get to all the activities and attractions you're interested in at a leisurely pace.
  5. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find an Islamorada vacation package that brings all your bookings together.
  6. Book any activities or excursions: Now to the fun part --- locking in everything you want to do and see. Browse some of the top things to do in Islamorada and reserve your tickets early to save time (and maybe some spending money too!).

Does Expedia offer Book Now, Pay Later Islamorada vacation packages?
Set off on your perfect trip to Islamorada with Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait for your next paycheck --- we've joined forces with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to stick to your budget and snap up cheap deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.