The Florida Keys on a Budget: How a $45 Southwest Fare Changed Everything (And Why We Cried at Sombrero Reef)

Where we stayed: Sunset Inn, Islamorada, Florida Keys Address: 82200 Overseas Hwy, Islamorada, FL 33036 | sunsetinnkeys.com Hotel cost: $130-$140 per night (everything else is $400+, so yes, book this immediately) Booked through: Southwest Airlines hotel portal (earned 15,000-20,000 Rapid Rewards points) Best for: Budget travelers, snorkelers, wildlife lovers, anyone who has ever wanted to see the Keys without going broke Rating: ⭐⭐⭐⭐⭐ (for the destination) / ⭐⭐⭐⭐⭐ (for Sunset Inn) / ⭐ (for my kayaking ability, and I am being generous)

It started in a parking lot.

Jude and I were sitting in the car waiting for a grocery pickup – and we had the Southwest Airlines app open because that is just what we do. We are always looking. Always watching. Budget travel is a mindset and the mindset never fully turns off. I was not even looking at what destination I was choosing. I just hit a destination, looked at a price, it was high since we were thinking of going someplace for a few days the week of Thanksgiving. Sigh at another high price, blindly clicked another destination. and continued….. 

And there it was. Miami. $45.

We looked at each other. We said about two words. We booked it.

That is how the Florida Keys trip started – impulsively, in a grocery store parking lot, on a Southwest Airlines fare that cost less than a nice dinner. And it turned into one of the most meaningful trips we have ever taken, including the moment I put my face in the water at Sombrero Reef for the first time in my life and almost cried because it looked like the whole ocean had been waiting for me to find it.

The Budget Booking Strategy (Pay Attention, This Is the Good Stuff)

The $45 Southwest fare each way got us to Miami. From there we decided to drive down to the Keys, which I knew basically nothing about except that people loved them and they were supposed to be beautiful and there was something called the Seven Mile Bridge that sounded dramatic.

The hotel situation in the Keys is the first thing that will humble you. I started searching and my eyes went wide. Four hundred dollars a night. Three hundred and fifty. Everywhere I looked, the Keys were telling me this was not my kind of destination price-wise, and I was not ready to hear that.

But I kept looking. And I found the Sunset Inn in Islamorada.

One hundred and thirty to one hundred and forty dollars a night. In the Florida Keys. I booked it so fast.

I also booked it through the Southwest Airlines hotel portal, which gave us somewhere between 15,000 and 20,000 Rapid Rewards points just for making the reservation. This is the move – Southwest’s hotel portal pays you in points for booking hotels you were going to book anyway. It is essentially a partial future trip, handed to you for doing nothing extra. Always check the Southwest portal before booking anything directly.

Sunset Inn Islamorada: The Budget Gem You Need to Know About

Let me tell you about Sunset Inn because it deserves its own moment.

The Sunset Inn has been established since 1955 and offers fully renovated contemporary design with a dash of Floridian flair – large, clean, comfortable rooms with kitchenettes available, a perfectly heated pool, and a quiet, peaceful location within walking distance to a marina on the bayside. It is not a waterfront hotel and it does not pretend to be. You are not waking up to ocean views. What you are waking up to is a clean, well-kept room, a great pool, Starbucks coffee in the room, and the knowledge that you just saved two hundred and fifty dollars a night compared to basically every other option in Islamorada.

We did not care about the ocean view because we were never in the room. We were out every single day from morning until we got back at night to sleep, and for that purpose Sunset Inn was absolutely perfect. It is right in the middle of everything – Robbie’s Marina is about a five minute drive away, the Islamorada Brewery is within walking distance, and the location makes it easy to get to water-based activities quickly.

The staff are friendly and helpful. The rooms are genuinely clean and well maintained. If you are not looking for upscale and are looking for a comfortable stay at a reasonable price, Sunset Inn is a good option – and in the context of the Florida Keys, a good option at this price point is genuinely remarkable. If you are going to the Keys on a budget, start here.

“Where Is the Ocean?” – The Drive Down That Surprised Me

We flew into Miami, stayed one night, and then drove down the next day. I had certain expectations about what driving into the Florida Keys would feel like. Dramatic ocean on both sides, crystal water everywhere, immediate tropical paradise vibes. You know, the postcard.

What actually happens, especially in the Upper Keys, is that you are driving down a highway and there is road stuff around you and the ocean is there but it is… not immediately obvious in the way I expected. You are like “we are in the Keys but I see no ocean” for a solid stretch of time. You catch glimpses of water and then you are back to driving past businesses and signs and it feels surprisingly normal.

It gets more beautiful as you go further south. By the time you hit Islamorada and the Middle Keys the water starts asserting itself more. And once you hit the Seven Mile Bridge area heading toward Key West, it delivers completely – water on both sides, the old bridge running parallel to the new one, the sky enormous above you. That part looks exactly like the postcards.

But the Upper Keys surprised me and I want to tell you so they do not surprise you. Watch some videos before you go. The Keys reveal themselves gradually and the payoff is absolutely worth the build.

Oh – and we got in late and the convertible I had reserved was gone. So we got a huge Lexus SUV instead and I felt extremely bougie driving that during our trip. Sometimes the upgrade finds you.

Sombrero Reef: The Day I Became a Snorkeler

This is the part of the post where I have to stop and just tell you what happened at Sombrero Reef, because it changed something in me and I want you to understand that going in.

We had never really snorkeled before. I had the idea that we would go snorkeling in the Keys because that is what you do in the Keys and it seemed fun and I had no real frame of reference for what it was actually going to be like. We booked a snorkel tour through Captain Pip’s and drove out to Sombrero Reef, which is part of the Florida Keys National Marine Sanctuary in the Middle Keys.

We got on the boat. We got to the reef. And I was in my head a little – “I have never really done this, am I going to be okay, is this going to be weird” – and then I put my face in the water.

I almost cried.

I am not exaggerating. I put my face in the water with a mask and snorkel for the first time and looked down and the whole ocean was just there. Fish everywhere and the water so clear it felt like flying. It was like someone had been keeping this entire world from me my whole life and I had finally been let in on the secret.

Jude, who is the kind of person who picks things up immediately and then acts like he has always known them, was pointing out fish before I had fully processed that I was breathing through a tube. “There’s a barracuda.” How do you know that is a barracuda? “I don’t know, I just know.” 16 years old and already an expert. I had absolutely no idea what any of the fish were and it did not matter even a little because I was too busy being overwhelmed by the fact that this world existed and I was in it.

It is like Ariel from The Little Mermaid. Exactly like that. You look up, you look down, you turn in circles, you cannot decide where to point your face because everything is worth looking at. I fully understand now why people become snorkelers and divers and spend their whole lives chasing reefs. I get it. I am one of those people now. Sombrero Reef did that to me.

Everything Else We Did (The Quick Version – Most Have Their Own Posts)

The Turtle Hospital – Sea turtles receiving medical care, being rehabbed, being prepared for release. We will have a full post on this.

Robbie’s Marina – you have to feed the tarpon at Robbie’s. You just have to. Giant prehistoric-looking fish leaping out of the water for food while you shriek. Also kayak and boat tours available right from the dock. 

Theater of the Sea – our Alligator Reef snorkel tour got cancelled due to November winds so we ended up here instead. Marine life encounters, shows, beautiful lagoon setting. Literally my favorite place in the keys. Plus you can snorkel and hang with parrot fish (and now I LOVE parrot fish).

Dolphin Research Center – not a performance attraction, a genuine research facility. A completely different experience from other dolphin encounters because the educational component is front and center. 

Atlantic’s Edge restaurant – we had dinner here and waited for manatees, which we had heard come to the area. Just sat there watching the water. That is a kind of patience that a beautiful waterfront restaurant makes very easy.

Sombrero Beach – free public beach in Marathon, gorgeous and not crowded. Perfect for a lazy afternoon between activities.

Key West – we drove there most evenings from Islamorada, which I will be honest was probably not the most practical plan. It is a long drive each way at night and the Keys highway is not something you want to do exhausted after a full day. Key West absolutely deserves its own full post – and it will get one – but next time I would stay in Key West for a couple of nights rather than driving back and forth.

John Pennekamp Coral Reef State Park, Key Largo – we kayaked here and I have to be honest about what happened. I am not a good kayaker. I kept accidentally pushing us sideways. We kept drifting into the mangroves on the side because I could not figure out how to steer, and Jude was not happy about this in a way that he was trying very hard to be polite about and mostly failing. We went in circles. We got stuck. It was hilarious to everyone except possibly Jude in the moment. I would kayak there again because it was beautiful and because I feel like I could do better now that I understand what I did wrong (I redeemed myself later at Xenotes in Mexico). Key Largo deserves at least one full day on a Keys itinerary – we did not give it enough time.

The Key Deer – driving through the Lower Keys we spotted Key Deer, which are the tiny white-tailed deer species that are native to the Keys and are genuinely the most adorable thing. They are much smaller than regular deer and they just exist on the side of the road casually and it is wonderful.

How I Would Do the Keys Differently Next Time

This trip taught me a lot about how to structure a Keys itinerary and I want to share that because we learned it the slightly hard way.

One day Key Largo – do the kayaking at John Pennekamp properly, explore the upper keys.

Two days Islamorada/Middle Keys – this is the snorkeling sweet spot, stay at Sunset Inn, do Robbie’s, Turtle Hospital, Dolphin Research Center.

Two days Key West – actually stay there instead of driving back and forth every night. Key West is its own complete world and it deserves real time, not just evening drives.

Add Bahia Honda somewhere in the Middle Keys to Lower Keys stretch if you can.

That is five days minimum and honestly you could do seven comfortably. The Keys reward slow travel. There is no rush.

About November in the Keys

We went in November and it was overall wonderful – less crowded, good weather, not brutally hot. The one downside: November can be windy, which affects snorkeling conditions. Our Alligator Reef tour got cancelled due to weather and we had to pivot to a different plan. If snorkeling is your primary goal, late spring or early fall might give you more reliable conditions. That said, November in the Keys is still beautiful and very much worth it – just build in some flexibility for weather-dependent activities.

The JB Roams Way: Our Final Take

The Florida Keys are one of those places that lives up to its reputation completely and then exceeds it in ways you did not expect. The snorkeling at Sombrero Reef. The turtles at the Turtle Hospital. The tarpon at Robbie’s. The impossibly clear water everywhere you look. The Key Deer appearing out of nowhere on the side of the road. The bougie Lexus SUV we ended up in by accident.

Book the Sunset Inn. Use the Southwest portal for the points. Get to Sombrero Reef as fast as you can. Put your face in the water.

That is the JB Roams way.

FAQ: Budget Florida Keys Trip from Miami

What is a budget (er cheap) hotel in Islamorada Florida Keys? Sunset Inn at 82200 Overseas Hwy is one of the best budget options in Islamorada at around $130-$140 per night – significantly cheaper than most Keys hotels which run $300-$400+. It is clean, well-located, has a heated pool, and is close to Robbie’s Marina and other attractions.

Should I book Florida Keys hotels through Southwest Airlines portal? Yes, if you fly Southwest. Booking hotels through the Southwest Rapid Rewards portal earns you significant points – we earned 15,000-20,000 points on our Islamorada stay. It is free money toward future flights.

Is November a good time to visit the Florida Keys? Generally yes – less crowded and cooler temperatures. The downside is that November can be windy which may affect snorkeling conditions and cause tour cancellations. Build flexibility into your itinerary for weather-dependent activities.

What is the best snorkeling in the Florida Keys? The Middle Keys around Islamorada and Marathon have some of the best reef snorkeling including Sombrero Reef and Alligator Reef, both part of the Florida Keys National Marine Sanctuary. Key Largo’s John Pennekamp Coral Reef State Park is excellent for snorkeling and kayaking.

How many days do you need in the Florida Keys? Five days minimum to cover Key Largo, the Middle Keys/Islamorada area, and Key West with any depth. Seven days is better. The Keys reward slow travel and there is more to do than most people expect.

Is it worth staying in Islamorada vs Key West? Both are worth staying in. Islamorada is central, budget-friendlier, and the best base for Middle Keys snorkeling. Key West is its own complete world and deserves at least two nights of its own rather than evening day trips from Islamorada – the drive each way is long and tiring at night.

What are Key Deer and where do you see them? Key Deer are a tiny subspecies of white-tailed deer native to the Florida Keys – much smaller than regular deer. They are concentrated in the Lower Keys around Big Pine Key and No Name Key. You can spot them from the road driving through the area.

Sunset Inn Islamorada | 82200 Overseas Hwy, Islamorada, FL 33036 | sunsetinnkeys.com | (305) 664-3454

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