If you’ve ever dreamed of a luxurious vacation where you can relax in style without breaking the bank, I’m about to show you how you can make it a reality. What if I told you that staying in beautiful resorts and enjoying unforgettable experiences in the Florida Keys could be yours—all by using points and miles?

Let me walk you through how my husband and I did just that, and how you can easily replicate our success! Plus, I’ve included an itinerary with some extra options for you to consider if you have more time or want to explore more of the Keys.

The Power of Points: Flights, Rental Cars, and Hotels

You don’t need to be a travel expert to leverage points and miles. With just a bit of planning, we were able to cover all of our major expenses—flights, rental car, and hotel stays—without spending a single penny on the actual cost. Here’s how we did it:

Flight from Kansas City to Fort Lauderdale

• 1 ticket with points: $11.20
• 1 Companion Pass ticket (no points needed): $11.20
  Total for both flights: $22.40

Yes, you read that right—just $22.40 for two tickets to the Florida Keys, thanks to the Southwest Companion Pass. This perk is a game-changer for travelers who want to stretch their miles even further.

A Car for the Road: Zero Cost with Points
When we landed in Fort Lauderdale, we used points from my favorite travel rewards credit card to book our rental car through the bank’s travel portal—for $0 out of pocket.

What’s more, we used Chase Sapphire Preferred, which offered primary rental car coverage, saving us from any extra insurance fees. Bonus: I backed into a pillar in Key West (oops!)—and Chase covered the entire bill. Travel should feel this stress-free, right?

Luxury Stays in the Florida Keys for FREE with Points

Here’s where the magic happened: we used points to book two incredible resorts that made our trip unforgettable.

Key West: Hyatt Residence Club—25,000 Points per Night
For our first stop, we stayed at the Hyatt Residence Club Key West, just a short walk from the lively Duval Street. I used 25,000 Hyatt points per night to secure a cozy room, perfect for unwinding after a day of exploring.

Want to know how I book these stays over and over again without spending a dime? Check out my guide on booking Hyatt Stays on Points: The Best Cards to Use and How to Book .

Key Largo: Hilton’s Baker’s Cay Resort—70,000 Points per Night
Next, we headed to Baker’s Cay Resort Key Largo, a stunning Hilton property right on the beach. This resort is perfect for anyone who wants the high-life experience—pristine beaches, lush gardens, and endless amenities. I used 70,000 Hilton Honors points per night for our king room.

If you want to learn how to maximize Hilton stays, including using Hilton Free Night Certificates, don’t miss my complete guide Maximizing Hilton Stays: A Complete Guide to Booking with Points & Free Night Certificates .

Our 4-Day Florida Keys Itinerary

Here’s a breakdown of our trip, and if you have more time or want to add extra activities, I’ve got some bonus options for you too!

Day 1: Arrival & Key West

Morning:
Arrive in Fort Lauderdale and drive down the Overseas Highway (approx. 3.5 hours) to Key West. Don’t forget to stop along the way for scenic views!

Afternoon:

• Check-in at Hyatt Residence Club Key West
• Lunch at Blue Heaven, known for fresh seafood and free-roaming roosters
• Explore Duval Street, filled with quirky shops and art galleries
• Grab a slice of Key Lime Pie at Kermit’s Key West Key Lime Shoppe YUM!

Evening:

• Watch the sunset at Mallory Square (get there early for a good spot!)
• Dinner at Conch Republic Seafood Company
• Nightcap at Sloppy Joe’s or The Green Parrot Bar (my favorite spot for Key West vibes)

Day 2: Key West Exploration & Relaxation

Morning:

• Breakfast at Sarabeth’s (delicious pastries & famous jam!)
• Discover the beauty of the coral reefs on this highly rated half-day adventure! Kayak through the pristine waters of the Keys and snorkel among vibrant marine life. Spots fill up fast—secure your experience today!

Afternoon:

• Lunch at Cuban Coffee Queen (delicious Cuban sandwiches!)
• Visit the Ernest Hemingway Home and Museum
• Relax at Higgs Beach

Evening:

• Set sail on a relaxing sunset cruise along the coastline, where you’ll enjoy stunning ocean views, a delicious dinner, refreshing drinks, and live music. An unforgettable evening awaits—reserve your spot now!

Day 3: Key West to Key Largo

Morning:

• Breakfast at Banana Cafe I had the inside out French Benedict and it was so good!
• Head to Key Largo (approx. 2.5 hours drive), stopping at Robbie’s of Islamorada to feed the tarpon fish

Afternoon:

• Check-in at Baker’s Cay Resort Key Largo
• Lunch at Harriette’s Restaurant is a great choice.
• Explore the breathtaking underwater world of John Pennekamp Coral Reef State Park on an eco-friendly snorkel tour! Swim among vibrant marine life, discover stunning coral reefs, and experience Florida’s only living coral barrier reef. Book your snorkel adventure today—you won’t regret it!

Evening:

• Dinner at The Fish House
• Relax at the resort or grab a nightcap at the Tiki Bar

Day 4: Key Largo & Departure

Morning:

• Breakfast at Baker’s Cay Resort
• Kayaking through the mangroves in Key Largo is an unforgettable experience you won’t want to miss! Glide through serene waterways, soak in the breathtaking scenery, and get up close with nature. Book your adventure now—you’ll be so grateful you did!

Afternoon:

• Lunch at Mrs. Mac’s Kitchen
• Depending on your flight time, take a sunset stroll or head back to Fort Lauderdale

Connecting with Your Partner: More Than Just a Vacation

While staying at luxury resorts and enjoying great activities is amazing, what makes a trip truly unforgettable is the time spent with loved ones. Whether kayaking through the mangroves or watching a sunset together, it’s those special moments that are priceless. And the best part? You don’t have to break the bank to make it happen.

How You Can Make This Happen

Ready to plan your own Florida Keys getaway? Here’s how:

1. Sign up for a credit card that offers travel rewards (like Southwest, Chase Sapphire Preferred, or Hilton Honors).
2. Earn points by booking flights, hotels, and rental cars with the right card.
3. Book your stay at top resorts like Hyatt and Hilton, all for $0 out of pocket using your points.

It’s that simple! If you want to learn more about how I manage my points and miles strategy to create these unforgettable trips, sign up through my affiliate links and start earning your own rewards today.

Don’t wait—luxury travel is closer than you think. Start planning your Florida Keys vacation today!

Thank you!

As you plan your incredible Yellowstone adventure, remember that using my affiliate links when booking activities I recommend or opening credit cards helps support Points and Miles Teachers at no extra cost to you. Ready to open you next card? Send me a DM on IG or visit my best offers page located at the top of my site.

This simple step allows me to continue providing the insider tips and resources you need to embark on big adventures without breaking the bank.

Your support means the world and keeps this valuable information coming your way, so thank you for helping me keep the dream of affordable travel alive!