If you have read my blog, you know how much I love planning extravagant vacations for a minimal cost. I’m all about saving money on the big stuff without sacrificing the Wow Factor! Saving money on our travel costs means we can spend more on dining and activities.
Planning ahead is one of the key ways to get the best rates and availability. The pricing model at some hotels is set to increase room rates as availability decreases. Booking early also gives you time to earn or manipulate your points and take advantage of special promotions or transfer bonuses. When I get started, the first thing I do is take stock of the tools I have available, like Hotel Free Night Certificates, Airline Companion Fares, or Special Credits that can help reduce travel costs.
The Trip
We live in Michigan, and by February, we are tired of the snow and dreaming about spring. That’s why we love to get away to a sunny destination each year in February. This year, we spent 2 wonderful weeks in Hawaii. For our 2026 trip, we are heading back to the Florida Keys. It’s a great place to relax and soak up some vitamin D.
We usually fly into Miami and enjoy the scenic drive to Key Largo. After spending a few days in Key Largo, we head further south for a day or two in Key West. Then we fly home from there. It’s a pretty sweet one-week itinerary.
Special Requests
For this trip, my husband requested that we fly directly into Key West instead of driving down from Miami. The need for hotels in Key West at both the beginning and end of our trip made planning more challenging. Also, because EYW is a smaller airport, it offers fewer flight options, which can also result in more expensive flights.
The most important component of the trip for me is spending several days at Baker’s Cay Resort in Key Largo. It’s a lovely waterfront Hilton Canopy property, offering numerous activities and amenities that we enjoy. Like a sunset champagne cart! So Bougie!
The Assignment
Budget for Car Rental/Hotel/Flights: $1000. I do love a good challenge!
Here are the components that needed to be booked for this trip.
- Round-trip airfare from DTW (Detroit) to EYW (Key West)
- 2 Hotel Nights in Key West on arrival
- 4 Hotel Nights at Baker’s Cay Resort in Key Largo
- 1 additional Hotel Night in Key West for the night before we fly home
- Car Rental for Key Largo
Starting With Flights
We have flown out of Key West on Delta for a few of our past trips. My Delta Platinum credit card has an annual Companion Flight Certificate. Of course, the certificate comes with some rules.
- Must book Round-Trip flights
- Must book Fare Class L, U, T, X, or V
- Must pay for my fare, plus the taxes and fees on the companion fare
I was excited because I immediately found a perfect flight from DTW to EYW. However, finding a return flight in an eligible fare class was like finding a needle in a haystack. Ideally, we would like to depart on Saturday in the mid-to-late afternoon. I looked at flights for Friday, Saturday, and Sunday, but there was only one in the required fare group. It was an ugly 7:00 a.m. flight on Saturday. Boo!
I am happy with $528.38 for round-trip flights directly into Key West for two passengers during high season. I booked the flights for now, but I will be checking regularly to see if any eligible flights with better times are added.
I had a variety of Airline Fee Credits that made it possible to upgrade all the segments of our flights to Comfort Plus for just $85.
Booking the Big Hotel
Booking our four nights at Baker’s Cay Resort was next in importance for me. Sometimes, the availability at this property is tricky in February. February means Super Bowl, Valentine’s Day, and the Presidents’ Day winter school break. This year, I planned our trip after those dates to get the best rates and availability.
I strive to maximize the value of our uncapped Hilton Free Night Certificates. They can be used to book any available standard room at any rate. Baker’s Cay is a great place to use them. The room rate for the best standard room for our dates was $753.45 per night plus taxes and fees for a total of $902.76 per night.
My husband and I each have separate Hilton accounts, with a Free Night Certificate available to use for this trip. We have also been busy refilling our points banks since draining them for our trip to Hawaii in February. One of the best parts of booking a Hilton award stay is that the Taxes and Resort Fees are included. I was able to apply both of our certificates and 200,000 points from my account to book our stay. That meant we got $900 in value from each of our certificates and saved $3,611.04 for our 4-night stay.
Four nights at a luxury resort – Zero Dollars! Previously, we were upgraded to gorgeous waterfront suites thanks to my Hilton Diamond Status. Maybe we will get lucky again this trip. Either way, they have just done a remodel, and I am excited to see how the rooms turned out.
When we arrive at the resort, we will receive a Hilton Food & Beverage Credit of $18 per person per day. I also have a $200 Resort Credit on my Hilton Aspire credit card. Together, that will give us $272 to spend on cocktails at the beach, fancy dinners, snacks at the pool, or spa treatments. I call these credits my “monopoly money,” and never waste any of it.
Wow! Good thing I booked the hotels when I did. Hilton increased the number of points needed for the award nights just days after I secured our reservation.
Filling In the Rest of the Nights
There are several good hotel options in Key West that all run about the same price, but we liked staying at the DoubleTree Resort during our past visits. An important feature for us is their Complimentary Shuttle. The shuttle picks guests up on demand from the airport and also runs hourly routes from the hotel to Duval Street and back. That means when we stay there, we don’t have to rent a car for those days, which is a huge savings.
I like to make the reservations through my Hilton account because I have a higher status than my husband. My top-tier status gets us better perks and upgrades at the hotel. Two nights at the DoubleTree Key West were coming in at $804.13 plus taxes and fees, or we could pay 85,000 points per night. After wiping out most of my Hilton stash on the Baker’s Cay reservation, I had to reach into my bag of tricks to find a way to make that happen.
American Express was running a 25% transfer bonus to Hilton at the time of booking. It is usually a 2:1 ratio, but by taking advantage of this promotion, I transferred 12,000 points from my Amex account, and 30,000 points were deposited into my Hilton Honors account.
Next, I initiated a Hilton Points Pool with my husband and moved 130,000 points from his account to mine. Combining our points gave us enough to book a 2-night award stay at the DoubleTree Resort in Key West for our first two nights.
By using my tools, we saved $972.15 per night at the DoubleTree. Once I book the final night, we will have saved over $6,000 for 7 hotel nights with zero dollars out of pocket.
The DoubleTree also issues a Hilton Food & Beverage Credit of $18 per person per day. My husband has a Hilton Surpass card, which has a $50 quarterly Hilton credit. That means if we use his card for incidentals at the DoubleTree, we will have $122 in “monopoly money” credits to use during our 2 nights. Using our credits to offset breakfast or lunch costs means no guilt for big-ticket dinners.
Hunting For a Car Rental Deal
The car rental reservation is next. We had to shift our hotel nights due to availability for our last trip to the Keys, so I wanted to see how the hotel reservations worked out for this trip before determining the dates and how many days I would need the rental for.
One of the biggest ways I save money when we travel is by not booking a car rental for more days than we actually need. I don’t want to waste money by paying the daily rate, rental insurance, and a hotel parking fee if we will be at the beach all the time, or if there is some other cheap or free transportation we can use?
When we arrive in Key West, the hotel shuttle will pick us up at the airport. We will continue to use the hotel shuttle until we check out. Then the shuttle will drop us off at the airport, where we will pick up the rental car and drive to Key Largo. If we need to get somewhere outside of the hotel’s free shuttle route, we will just grab a cheap Uber or Taxi.
Using the shuttle saves us 2 car rental days. When we check out in Key Largo and return to Key West, we will drop off the car on the way in and use the hotel shuttle again. This will shave off another day of car rental. Returning the car the day before we depart will also make it easier for us in the morning, since we have a 7 a.m. flight and the rental center won’t be open yet.
This plan will save us 3 rental days at $70 per day, totalling $210.
Once I know how long I want to rent a car for, I start searching for the best deal. I am very picky about the companies I use for car rentals. Many companies play games, are untrustworthy, or have huge operational issues (I’m talking about you Hertz).
I prefer to book pay-at-the-counter and fully cancellable reservations in case something comes up and we need to change or cancel the reservation.
I wish I could say method X works every time or company Z always has the best price, but it’s just not that simple. I start my searches by getting a baseline price for my trip dates. I like to price it first through two actual car rental companies and try the different corporate rates, coupons, and discount codes (AARP, AAA, Costco, etc.) that I have. Next, I check the rates through Autoslash. Autoslash is a car rental aggregator that often finds the best rates. I also watch my e-mail for any rental company promotions.
Did you know it is usually more expensive to book a car at the airport than it is anywhere else? Airports charge the rental companies a fee that they pass on to customers. Some airports, like SFO, have notoriously high fees. If your rental seems high, you may be able to save some money by taking an Uber or public transportation to an off-site car rental location.
After booking a car rental, I put an Autoslash Rate Tracker on the reservation. It doesn’t matter if you book through them or directly with the rental company. They will still track the rate and alert you if the price drops. They have even improved the tool so that you can add preferences to the tracker. Now you can set it to only alert you when there is a lower rate from one of your preferred companies.
I NEVER SET IT AND FORGET IT when I make reservations in advance of a trip. That goes for hotels, car rentals, and flights. I lock in the bookings when I find a good rate, then set trackers or check prices occasionally (especially if I see a sale) to try to save even more money.
Packing it All Up
Booking this trip was easy because we didn’t have any specific plans other than enjoying the beautiful weather and relaxing on the beach. This flexibility allowed us to make reservations without much hassle. I’m still hoping to find a later return flight so we can maximize every last moment of our vacation.
Planning ahead to use the hotel shuttle reduced the number of car rental days we needed and saved us 42% on our rental cost. I booked our car rental with Avis through Autoslash for $270. Then I added a Rate Tracker because I would love to get the car rental cost under $250. No need to keep checking rates, now I just wait for a price drop alert. (see 11/12/25 Update Below)
Using my tools, points, and credits really paid off for this bougie budget vacation. By saving on our car rental, booking seven award nights at Hilton hotels, and utilizing a Delta Companion Certificate, we will save over $7,000 on our total travel costs. We will also save an additional $394 by using credits for on-site dining and entertainment.
That is a significant savings! Keeping our travel costs low means we can travel more frequently and spend more on awesome activities, delicious stone crab claws, and yummy key lime pie. I hope sharing tips on how I save money on my travel costs helps you discover new ways to save money on yours.
Dream, Plan, Save, and have money left in your budget for Adventures!
11/12/25 Update
The World According to Dev 