Hotel Booking
Guide
How we use cash, points, and credit card perks to score family-friendly hotels for less
Finding Hotels — Start Here
Like everything else in travel — book early and track the rates. The earlier you start watching, the better sense you get of what a “good price” actually looks like for your destination.
Google Hotels — Get the Lay of the Land
Start at hotels.google.com to get a general idea of hotels and Airbnbs in your area. The map view shows you which neighborhoods cluster well, and you can quickly compare price ranges across properties. Our first stop before we commit to anywhere.
✓ Free · Best Starting PointAlways book direct when prices are the same or close. You earn loyalty benefits, hotel points, and the property is far more likely to upgrade you. If anything goes wrong — overbooked rooms, late check-in, room issues — you’re the hotel’s direct customer instead of someone they consider Booking.com’s problem.
Cash Bookings — Stack Cashback
When you’re paying cash on Booking.com, Priceline, Expedia, or Hotels.com — always check Rakuten first. It’s free money and most people skip it.
Rakuten — 5–20% Back on Most OTAs
Rakuten almost always has an offer of 5–20% cashback on Booking.com, Priceline, Expedia, and Hotels.com. Click through Rakuten before you book, then your cashback shows up as a check or PayPal deposit. Takes about 10 seconds, adds up to hundreds across a year of family travel.
★ Free Money
Booking with Points
Searching directly on Hyatt, Hilton, Marriott, and IHG works fine — but finding a whole week of award availability across all of them is tedious. One tool does it better than anything else we’ve used.
MaxMyPoint
maxmypoint.com makes it incredibly easy to find multi-night availability across all major chains. We’ve used it to lock in 4 nights at Kimpton Seafire in Cayman and 6 nights at Grand Hyatt Kauai, among many others. If you book hotels on points, this is the tool.
★ Best for Families
💎 Sweet Spots to Know
🏨 Real Hotel Redemptions We’ve Done
Grand Hyatt Kauai
6 nights for 150K Hyatt points. A resort that would have run thousands in cash during peak season. Chase Ultimate Rewards transfer to Hyatt is hands down our favorite trick.
150K Hyatt · 6 nightsKimpton Seafire, Cayman Islands
4 nights for 210K IHG points. With the IHG 4th-night-free perk built into points bookings, we got an oceanfront resort for a fraction of cash pricing.
210K IHG · 4 nightsITC Goa
2 nights for 96K Marriott points. A category sweet spot during a family trip back home — great value at a luxury Indian property.
96K Marriott · 2 nightsWaldorf Astoria Costa Rica
5 nights for 560K Hilton points (booked for an upcoming trip). Cash pricing on this property is brutal — points make it accessible. Hilton’s 5th-night-free did the heavy lifting.
560K Hilton · 5 nights · FuturePark Hyatt Tokyo
4 nights for 160K Hyatt points (booked for our October 2026 trip). Cash rates run $1,000+/night. This redemption alone is why we hoard Hyatt points.
160K Hyatt · 4 nights · FutureMost of our hotel points don’t come from hotel stays. They come from transferable credit card currencies (Chase, Amex, Bilt) and hotel co-branded card welcome bonuses. Earning enough points from stays alone is painfully slow — credit cards do the heavy lifting.
Hotel Status — It Pays to Have It
Status isn’t just a vanity thing. It genuinely changes how hotels treat you — upgrades, breakfast, lounge access, late checkout. The good news: most of it comes free with credit cards we already hold.
Travel Portals & Amex FHR
Card portals can be a surprisingly good deal — sometimes better than transferring points to airline or hotel partners. The trick is knowing when.
Chase, Capital One, Citi & Amex Travel
Chase Travel often runs “boosted value” promos where points stretch further. Sapphire Reserve effectively gets you up to 1.5 cents per point through the portal. Amex Travel lets you link your loyalty accounts — so you stack Amex perks (FHR/Hotel Collection) with hotel loyalty benefits on the same stay.
✓ Often 1.5+ cppAmex Fine Hotels + Resorts (FHR)
If you have Amex Platinum, FHR is incredible. You get $100 in food/spa credit, free breakfast, room upgrades, and on many properties a $300 statement credit toward the stay. Loews Portofino Bay is our favorite — you also get Universal Express Passes for two days. Use maxfhr.com to search FHR options easily.
★ Best Platinum PerkMistakes to Avoid
Which cards earn these points? Our full credit card strategy
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