Islamorada Vacation Packages 2026 from $565

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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.

President Hotel Villa

South Beach

Save 100% on your flight

$565

per person

Nov 4 - Nov 10

found 21 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,004 reviews)

Pelican Hotel

South Beach

Save 100% on your flight

$929

per person

Nov 4 - Nov 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (499 reviews)

The Pelican Hotel is an amazing boutique hotel with an outstanding restaurant! It has 33 individually themed rooms owned by Renzo Rosso, the Italian fashion mogul and founder of the Diesel clothing brand. There is a lot of attention to detail put into this hotel and the location is prime. The hand stamped copper elevator takes you to your room and speak easy rooftop. We had Rm 202, an oversized very large vintage themed king suite overlooking the main blvd. It had a view of muscle beach, the ocean and the sidewalk for some great people watching. It had windows wrapped around both sides of the room which was awesome. It had a little noise at night since it's on the main blvd, but they all do being in the epicenter. It didn't hinder us from a good nights sleep in the plush California King bed with crisp sheets and a duvet topper:) The service has been outstanding!! The staff really care about the guests, evident on many levels, and went above and beyond. It has been a long time since I feel like I had really great service, outstanding food, and a couple of generous offerings thrown in. If you're a guest at the hotel, you get a few options for an oversized, complimentary jumbo cocktail every evening. The 1st night we opted for the spicy, scratch made margarita and night 2 we got the Aperol Spritz with approval from the mgr. They also have a generous happy hour. The room offers complementary snacks (veggie chips & kind bars) as well as water. Your stay also includes complementary

Reviewed on Aug 30, 2026

President Hotel

South Beach

Save 100% on your flight

$572

per person

Nov 11 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (2,718 reviews)

Staff was helpful with everything we needed for our stay, well recommended place to stay

Reviewed on Aug 31, 2026

The Penguin Hotel

South Beach

Save 100% on your flight

$637

per person

Nov 4 - Nov 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,951 reviews)

I really nice little boutique hotel right on Miami Beach across the street from the water. The breakfast is really nice and then not very expensive. Reef State here at number of times and would go back again.

Reviewed on Aug 31, 2026

Lexington by Hotel RL Miami Beach

Mid Beach

Save 100% on your flight

$719

per person

Nov 7 - Nov 14

found 20 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.4/10 Good! (1,328 reviews)

Just finished our 5 night visit, overall this hotel is fine. Before travelling I read a lot of reviews regarding ongoing maintenance work which I hadn't realised when booking so this made me anxious. There clearly is alot of work that still needs to be done here but it was cheap and comfortable for the time we were there. We did have an issue with the room door not closing but this was sorted asap. The water did take a while to warm up but once it did it was boiling. The location of this hotel was just perfect for us, the beach being right outside was everything we wanted and I miss it already. If you're not going to be in the hotel too much and on a budget then this is fine please ignore the bad reviews. I really hope the renovations bring this hotel back to life purely for the location. Staff were all really friendly and welcoming

Reviewed on Aug 31, 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

A pier extending into calm waters with a covered seating area and a sandy beach.

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 Robbie’s of Islamorada are top sights worth seeing.

A sunset over a palm tree-lined pier extending into calm waters.

Venetian Shores

Venetian Shores might not have many top sights, but Islamorada County Park and Founders Park are two attractions nearby that you can check out.

A clear blue sea with a sandy beach and a distant horizon.

Lower Matecumbe Beach

Though Lower Matecumbe Beach might not have many top sights, you can venture to the surrounding area to see attractions like Anne's Beach and Sunset Drive Beach.

A beach with palm trees, lounge chairs, and a building with balconies.

Seabreeze Trailer Park

If you're looking for some top things to see and do in Seabreeze Trailer Park and surrounding area, you can visit Founders Park and Islamorada County Park.

Stay near popular Islamorada attractions

A sandy beach with green vegetation and a calm sea.

Anne's Beach

7.8/10 (597 reviews)

Anne's Beach offers shallow, calm waters and a scenic boardwalk winding through mangroves. Enjoy the covered pavilions for picnicking or launch your paddleboard into the crystal-clear waters of the Florida Keys.

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Florida Keys Brewing Co.

9.2/10 (520 reviews)

The Upper Keys' first microbrewery infuses local flavors like Key lime and honey into its craft beers. Sip seasonal brews in the vibrant taproom or lush beer garden while enjoying local art and live music.

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A small green leaf growing on a rough, textured surface.

Windley Key Fossil Reef Geological State Park

8.8/10 (184 reviews)

Walk through ancient coral walls rising eight feet high in this former limestone quarry turned state park. Ranger-guided tours reveal the fascinating geological history preserved in the fossilized reef.

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A building with a blue facade, a large mural of a diving scene, and a statue of a diver.

History of Diving Museum

9.0/10 (177 reviews)

Discover 4,000 years of underwater exploration at this unique museum featuring diving helmets from around the world. Explore exhibits showcasing the evolution of diving technology from ancient to modern times.

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Robbie’s of Islamorada

8.4/10 (15 reviews)

Explore the waterfront in Islamorada with a trip to Robbie’s of Islamorada.

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Islamorada County Park

8.8/10 (198 reviews)

This 40-acre waterfront retreat offers a bayfront beach, marina, and scenic trails for active relaxation. Enjoy a refreshing swim in the pool or bring your four-legged friend to the specialized dog parks.

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Islamorada Brewery & Distillery

9.4/10 (8 reviews)

The Florida Keys' first distillery crafts award-winning spirits and beers capturing the island's essence. Enjoy tastings in their relaxed taproom or pet-friendly garden with pub-style food available.

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Sunset Drive Beach

9.0/10 (91 reviews)

This secluded stretch of Islamorada shoreline offers a peaceful retreat from Florida's busier beaches. Watch the sky transform into a canvas of colors as the sun sinks into the Atlantic Ocean.

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What to do in Islamorada

Tavernier, FL: Mangrove and Manatees Guided Kayak Eco Tour

$69

per adult

100% of travellers recommend

Snorkel and Sandbar Combo Adventure in Islamorada

$139

per adult

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

$49

per adult

80% of travellers recommend

See all activities in Islamorada

Islamorada Hotel Deals

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

$214 nightly

$241 total

Sep 7 - Sep 8

Total with taxes and fees

9.2/10 Wonderful! (1,418 reviews)

"Excellent stay."

Reviewed on Aug 30, 2026

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$187 nightly

$210 total

Oct 1 - Oct 2

Total with taxes and fees

9.2/10 Wonderful! (1,771 reviews)

"Excellent location, nice breakfast."

Reviewed on Aug 30, 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$211 nightly

$237 total

Sep 23 - Sep 24

Total with taxes and fees

8.8/10 Excellent! (1,302 reviews)

"Muy buena atención desde Que llegamos ala recepción todo ordenado y limpio"

Reviewed on Aug 30, 2026

See all 2,155 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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	70.0°F (21.1°C)	No Rain	Mostly Sunny	Average	Average
February	71.8°F (22.1°C)	No Rain	Mostly Sunny	Average	Slightly High
March	72.9°F (22.7°C)	No Rain	Mostly Sunny	Moderately High	Slightly High
April	76.6°F (24.8°C)	No Rain	Mostly Sunny	Moderately High	Slightly High
May	79.3°F (26.3°C)	Light Rain	Mostly Sunny	Average	Average
June	82.4°F (28.0°C)	Light Rain	Mostly Sunny	Average	Average
July	83.8°F (28.8°C)	Light Rain	Mostly Sunny	Moderately High	Average
August	84.4°F (29.1°C)	Light Rain	Mostly Sunny	Average	Average
September	83.3°F (28.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
October	80.2°F (26.8°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
November	75.9°F (24.4°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
December	72.9°F (22.7°C)	No Rain	Mostly Sunny	Moderately Low	Average

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 $565 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?

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.
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.
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.
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.
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.
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.

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

Islamorada Vacations from $565

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Islamorada Vacation

The Latest Islamorada vacation packages

President Hotel Villa

Pelican Hotel

President Hotel

The Penguin Hotel

Lexington by Hotel RL Miami Beach

Where to stay in Islamorada

Matecumbe

Venetian Shores

Lower Matecumbe Beach

Seabreeze Trailer Park

Stay near popular Islamorada attractions

Anne's Beach

Florida Keys Brewing Co.

Windley Key Fossil Reef Geological State Park

History of Diving Museum

Robbie’s of Islamorada

Islamorada County Park

Islamorada Brewery & Distillery

Sunset Drive Beach

What to do in Islamorada

Tavernier, FL: Mangrove and Manatees Guided Kayak Eco Tour

Snorkel and Sandbar Combo Adventure in Islamorada

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

Islamorada Hotel Deals

Cheeca Lodge & Spa

Chesapeake Beach Resort

Amara Cay Resort

Find the Best Islamorada Vacation Packages

Things to do in and around Islamorada

Find the best attractions in Islamorada

Best time to go to Islamorada

Tips to save on your trip to Islamorada

Islamorada Beach Vacation

Things You Should Know About Islamorada

Islamorada Essential Information

More vacations you might like

Frequently asked questions

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