Points/Miles Accommodations for 11 People-Advice/Ideas Needed

[James from BNA]

Every year we take a summer beach trip with my wife's extended family. 6 adults, 5 kids under age 12. I usually tell all the adults to get x, y, and z credit cards, add me as an AU, and then I complete all the min spends and make the bookings.

In 2015, we stayed at the Westin in Grand Cayman and found 11 AA award seats BNA->MIA->GCM. Everyone got an AA card and the SPG cards. We were a little cramped in only 3 standard hotel rooms but it worked out.

This past summer, we earned Southwest Companion Pass x 6, signed up for the Hyatt card, and strung together 3 rooms x 7 free nights at the Hyatt Ziva Puerta Vallarta. Fantastic.

Although both of these trips have been fabulous, I'm out of ideas for cards to sign up for going in 2017. The churning rules have become more restrictive.

Does anyone have ideas for house-style beach accommodations that can be booked with points in the Southeastern US, CA, Hawaii, or the Caribbean? Extra brownie points for locations bookable from BNA on Southwest. All-inclusive hotels would be ok too to save money on food. We just don't want to drop 5 large on a beach-front house with 5 bedrooms.

 

[nicnac]

Assuming you have the comp passes still.
There are other hotel credit cards, citi hhonors 2 free weekend nights, fairmont 2 free nights, ritz 3 free nights (tier 1-4), even the IHG at 75k x10 would work. Theres also a marriott, but meh on that one.

awardmapper.com is useful to find out where to stay

If you're paying cash the citi prestige 4th night free benefit could lessen the impact.

 

[Coldmode]

10 Chase Ritz cards could provide you with a damn fine vacation. You'd also wind up with $150x10 in extra travel credits next year ($300/yr travel credit - $450 AF). You might be able to use those credits to buy SW gift cards to pay for the cash portions of your companion pass flights. Getting everyone approved for the Ritz will probably be harder, but if everyone has a decent credit profile from your past escapades and decent income, you should be fine. The Ritz also is not under 5/24.

 

[MickiSue]

A slew of A+ cards could get enough "miles" at a 2x rate (on top of the sign up bonus) to book a beautiful beach house for all the families, and pay with the miles.

AirBnB could be your starting spot to check for whole houses available, and the cost per night.

Even if it's 1K/night, divided by 3 or 4 bonused spends, and filled in with the rest at 2x, you should be good for at least a few nights.