How We Ended Up in a $2700/Night Oceanfront Suite… With a Baby in Tow

When we booked our stay at Casa Marina Key West, Curio Collection by Hilton, I had two competing thoughts:

I cannot wait for this beach getaway.
Are we completely unhinged for attempting our first trip with a baby?

Spoiler: it ended up being one of the best trips we’ve ever taken.

Thanks to incredible service, thoughtful upgrades, and a little bit of travel hacking magic, we found ourselves spending three nights in an oceanfront lanai suite that was retailing for over $2700 per night during our stay. And yes, we brought our baby with us.

If you’ve ever wondered whether a beach trip with a baby could actually feel like a vacation (and not just parenting somewhere with more sand), I’m here to tell you… it’s possible. Casa Marina made it possible.

View of the iconic and historic Casa Marina

The Experience Started Before We Even Arrived

The service impressed us before we even got there. A few weeks before the trip, I posted in the Hilton Honors Facebook group asking whether people preferred Casa Marina or their sister property, The Reach. To my surprise the hotel manager, personally replied to my post offering to help me decide.

She took the time to walk me through the differences between the properties, what each offered, and what might work better for traveling with a baby. That alone convinced me to choose Casa. But the best part? She didn’t just help me make the decision. She also upgraded us into the most incredible suite over a week before we even arrived.

The Upgrade of My Dreams, Confirmed Before We Even Arrived

There was no waiting to see what was available at check-in, no hoping for an upgrade. The manager proactively upgraded us to a massive oceanfront lanai suite with direct beach access. It was confirmed and ready before we even stepped on the plane.

This wasn’t just a minor bump. It was a huge upgrade. The suite was retailing for over $2700 per night during our dates.

She also arranged transportation for us to and from the airport in a black SUV with a car seat already installed. Any parent knows that alone is a game changer. We didn’t have to worry about lugging a car seat through the airport or dealing with a last-minute scramble for transportation. It was stress-free and seamless from the moment we landed.

Having this suite genuinely transformed our trip with a baby.

Nap time: we lounged on the daybed with coffee (or frose) while the baby slept just steps away inside
Mornings: we walked straight from the lanai to the beach
Evenings: we watched the sunset from our private patio with the baby sleeping and wine in hand

It wasn’t just luxury. It was flexibility, comfort, and peace of mind.

View from the bed of the oceanfront lanai suite

Our little one enjoying the huge oceanfront lanai with beach access.

What It’s Really Like Traveling to Casa Marina with a Baby

Here’s why Casa Marina worked so well for us as new parents:

Room layout: Beach access from our room meant no packing up a day bag or hauling gear. Everything we needed was within reach
Thoughtful touches: Housekeeping texted to check on us even when the Do Not Disturb sign was up during naps
Beachside service: Full food and drink service came right to our beach loungers. Frose and conch fritters while baby napped? Yes please
Stroller friendly: The entire property was easy to navigate, and the Old Town Trolley stop out front made exploring Key West simple
Pool options: One pool was family friendly and the other was adult only, which gave us options and balance

This trip proved that travel with a baby can be peaceful, enjoyable, and even restorative when the environment supports it.

The yummiest peach frose delivered straight to your oceanfront lounger.

How We Booked This Stay Using Points, Perks, and Perfect Timing

Here’s exactly how we booked it:

1 Free Night Certificate from my Hilton Amex Aspire card
210000 Hilton Honors Points, which covered the other two nights (105000 per night)
Resort fees waived since Hilton waives them on all point or free night stays

And the timing worked out perfectly:

The Hilton Aspire card includes a $200 Resort Credit twice per year, but only at select Hilton resort properties. We were already dreaming of Casa Marina, and seeing it on the eligible resort list helped finalize our decision. My credit was set to expire in July, so the timing aligned beautifully
As Hilton Diamond members (thanks to the Aspire card), we also received a $36 daily resort credit to use toward food and drinks

View from the oceanfront restaurant Dorada, where we used our dining credit

What That Looked Like in Practice:

Zero dollars out of pocket for the room
No resort fees
$200 Hilton resort credit applied
$36 per day Diamond credit (a total of $108 over three days)

A stay that could have easily cost over $8000 ended up being a nearly free luxury trip.

What We Ate (Because Food Matters)

Poolside favorite: Carne asada quesadilla — so good we ordered it twice
Snack MVP: Conch fritters and peach frose by the beach
Dinner at Dorada: Oceanfront views, fresh seafood, and top-notch service at sunset

Conch fritters delivered to your beachfront daybed… just steps from your oceanfront lanai.

Post-Renovation Vibes

If you’ve seen older reviews of the hotel, let me reassure you. Casa Marina has been fully renovated and it shows.

The rooms and property feel fresh and clean while still maintaining the historic charm
The space is thoughtfully designed with hammocks, fire pits, open lawns, and breezy walkways that make it feel relaxing and upscale

Would We Go Back?

Absolutely. We’re already talking about when we can return.

This trip reminded me why I love travel hacking. But more importantly, it reminded me that parents deserve relaxing, beautiful vacations too.

A huge thank you to the incredible hotel management team for helping make our stay so special. From the pre-arrival support to the day-to-day hospitality, everything was seamless.

Quick Tips for Parents Considering Casa Marina

Book an oceanfront lanai suite if you can. The space and beach access are worth it
Use the hotel’s car service and request a car seat in advance
Bring a baby monitor so you can enjoy the lanai during naps
Ride the Old Town Trolley from right outside the hotel to explore Key West
Don’t skip Dorada at sunset
No need to overpack snacks. The beachside service has you covered

Want to Travel Like This Too?

I love helping other families learn how to use points, perks, and smart planning to turn dream trips into real ones. If you want more travel hacks, hotel reviews, or family travel tips, follow along here at Rooted & Roaming.

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