Islamorada Vacations from $553

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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.
Creekside Inn

Creekside Inn

2.5 out of 5
Price was $1,230, price is now $553 per person
$553
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,004 reviews)
Staff good Room with problems: toilet, safe vault, tv, no closet, no chair, too small

Reviewed on Jan 6, 2026

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was $1,311, price is now $569 per person
$569
per person
Apr 4 - Apr 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Main road in front of hotel was closed. When we arrived, the concierge had no idea where to tell us to park. If they were transparent about it, ok. I would be ok. Then they said they are out of the 'free' wine, but could charge me $8 for a Heineken. Then couldn't get the elevator to work (we were on the 2nd floor thank God) The room was in good shape. The parking is what set off the chain for me. It's not hard to update a website. Or at least tell your staff what to say. Ended up parking in the City parking garage. I'd give it like a 75/100.

Reviewed on Jan 6, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was $1,374, price is now $619 per person
$619
per person
Mar 17 - Mar 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.8/10 (311 reviews)
I stood in the multiple bed 1 bedroom everything was good beach right there pool and security where very friendly

Reviewed on Nov 12, 2025

1818 Meridian House Apartments and Suites by Eskape Collection

1818 Meridian House Apartments and Suites by Eskape Collection

3 out of 5
South Beach
Price was $1,277, price is now $584 per person
$584
per person
Mar 17 - Mar 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (664 reviews)
The location was great and walkable to the beach and shopping/dinning. The apartment was overall clean but looked old and had a smell. The kitchen has everything needed for cooking but the pots were in poor condition. After we have arrived and during the check-in, we have learned that all parking spots are reserved. This was not communicated to us. The person at the reception was rude, non-apologetic, and said that we signed the registration card which contained that information regarding potential unavailability of the parking. He also said that if we choose to cancel the reservation, there will be no refund.

Reviewed on Dec 31, 2025

Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Ocean Four
Price was $1,518, price is now $722 per person
$722
per person
Mar 22 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,935 reviews)
We always have a wonderful experience at the Sole’

Reviewed on Jan 10, 2026

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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

5 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 Florida Keys Brewing Co. 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

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
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.
Founders Park featuring theater scenes, a garden and modern architecture

Founders Park

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

What to do in Islamorada

Explore the Mangrove Creeks with an All Day Kayak Rental

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

$49
per adult
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
Fun for the whole family!

Explore the Mangrove Creeks with an ALL Day Tandem Kayak Rental

$67
per adult
Explore the Mangrove Creeks with an ALL Day Tandem Kayak Rental
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
See all activities in Islamorada

Islamorada Hotel Deals

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$249 nightly
The price is $280 total per night from Jan 28 to Jan 29
$280 total
Jan 28 - Jan 29
Total with taxes and fees
9.2/10 Wonderful! (1,625 reviews)
The resort is a great family friendly atmosphere. The staff was extremely hospitable. The beach is clean and lots of fun activities to do. Only wish we had more time!

Reviewed on Jan 6, 2026

Chesapeake Beach Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$356 nightly
The price is $400 total per night from Jan 21 to Jan 22
$400 total
Jan 21 - Jan 22
Total with taxes and fees
8.8/10 Excellent! (124 reviews)
Amazing place - so much variety

Reviewed on Jan 6, 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$320 nightly
The price is $361 total per night from Jan 29 to Jan 30
$361 total
Jan 29 - Jan 30
Total with taxes and fees
9.2/10 Wonderful! (1,284 reviews)
Fantastic resort, will definitely be heading back!

Reviewed on Jan 4, 2026

Cheeca Lodge & Spa
See all 2,207 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

Things to do in and around Islamorada

Islamorada is the perfect destination for a family-friendly beach vacation, offering a variety of outdoor activities. Enjoy a well-planned itinerary featuring exciting scuba excursions and fishing getaways. Explore local shopping centers and vibrant areas, along with friendly attractions that cater to all ages. With a host of activities available, Islamorada ensures a memorable experience for every visitor.

Shopping

In Islamorada, visit Rain Barrel Village, a charming spot known for its unique gifts and local art. If you're up for a drive, head to nearby malls like the Mall of the Americas, which offers a variety of shops and dining options for a more extensive shopping experience.

Recreation

Jacob's Aquatic Center is a family-friendly venue located 17 miles from Islamorada. Here, you can enjoy a variety of aquatic activities, including swimming and water aerobics, making it a perfect spot for relaxation and fun in the sun with loved ones.

Adventure

Experience the thrill of diving at Florida Keys Dive Center, located 8 miles from Islamorada, where you can explore vibrant coral reefs. For an adrenaline rush, visit Keys Cable Park, situated 22 miles away, offering wakeboarding and more. Hike the scenic Pa-hay-okee Trail, 24 miles from Islamorada, for stunning views.

Nightlife

For a vibrant nightlife in Islamorada, visit Jimmy Johnson's Big Chill, 17 miles away, where you can enjoy a lively atmosphere and romantic vibes. Alternatively, check out the Caribbean Club Bar, located 21 miles away, for a relaxed setting filled with entertainment and cozy charm.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Islamorada

Islamorada, Florida, is an ideal destination for family-friendly beach vacations, offering an array of outdoor activities and cultural experiences. Visitors can explore popular attractions such as marinas, beautiful beaches, and the nearby national parks. A must-visit is the Islamorada County Park, perfect for enjoying the area's natural beauty and recreational opportunities. Whether you're looking for adventure or relaxation, Islamorada caters to all types of travelers seeking a memorable getaway.

  • Anne's Beach: Experience the serene beauty of Anne's Beach, known for its soft sands and tranquil waters. This picturesque beach offers a perfect spot for sunbathing, swimming, or enjoying a relaxing picnic while soaking in the laid-back beach vibes.
  • Bud n' Mary's Dive Center: For adventure seekers, Bud n' Mary's Dive Center is a must-visit. This marina offers thrilling dive and snorkeling tours, allowing you to explore the vibrant underwater world of the Florida Keys, surrounded by stunning marine life.
  • Islamorada County Park: Ideal for families, Islamorada County Park features recreational facilities and scenic walking paths. Enjoy an outdoor day filled with picnics, playgrounds, and sports, all while being immersed in the charming atmosphere of the local community.

Best time to go to Islamorada

The best time to visit Islamorada can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Islamorada falls in August, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Islamorada falls in January, visitor numbers are average and weather is mostly sunny with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January70.0°F (21.1°C)No RainMostly SunnyAverageAverage
February71.8°F (22.1°C)No RainMostly SunnyAverageSlightly High
March72.9°F (22.7°C)No RainMostly SunnyModerately HighSlightly High
April76.6°F (24.8°C)No RainMostly SunnyModerately HighSlightly High
May79.3°F (26.3°C)Light RainMostly SunnyAverageAverage
June82.4°F (28.0°C)Light RainMostly SunnyAverageAverage
July83.8°F (28.8°C)Light RainMostly SunnyModerately HighAverage
August84.4°F (29.1°C)Light RainMostly SunnyAverageAverage
September83.3°F (28.5°C)Light RainMostly SunnyAverageSlightly Low
October80.2°F (26.8°C)Light RainMostly SunnyModerately LowSlightly Low
November75.9°F (24.4°C)Light RainMostly SunnyModerately LowSlightly Low
December72.9°F (22.7°C)No RainMostly SunnyModerately LowAverage

Tips to save on your trip to Islamorada

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Islamorada during the low season (September to November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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 $553 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.