Each provider has her own donation for something like that, and if she'd prefer her own room or not. Your best bet is to contact the woman (or women) you're considering and discuss it with them. Let them know you're interested and just want to see what their donation / rules would be for something like that.

Enjoy Cabo

Hopefully you've built up some positive rapport and trust with her. Put together the itinerary and sell it like a travel agent. Have them give you a price. Be straight up with what you expect...you may find she would love a great vacation with you for little (like $1-2K) or nothing. These can be great - often more engaged in planning a shared fun experience. Offer a separate room but likely it's not needed. Be suspect if she wants full payment up front.  

If she's a professional, plan on doubling your vacation cost just on escort fees: 8-10k+. Expect a deposit (risky gambling) but no separate room. This maybe an awesome experience or you could be stuck with someone "along for the ride". That great hourly session provider may not be your dream travel date. With this type, you're paying for her time and lost market opportunity for 4 days regardless if you're in Cabo or locked in the Hilton for 4 days. It's just business.  

Good Luck! PM me if you want more tips on avoiding disappointment.

I have vacationed in Cabo a few years back...there are so many gorgeous escorts there from 1 hour to a night to full day or multiple days.  

Go ahead and explore the variety available there instead of taking someone from here, my two cents. I once took my GF to Costa Rica on vacation and wished a couple of times that I was single on my vacation. Cabo, though not as popular as Costa Rica or other European countries - have some amazing Latin women for your satisfaction.

Cabo is definitely on my repeat destination - go single and have fun, just my 2 cents for your consideration.

I may be off base here but it sounds like you might be starting out a relationship with this trip.   I'd definitely only take someone I new well and would enjoy extended time with.   There are some people that are lovely in small doses and wear thin.   Others are wonderful and fun and four days will fly by.   Best success with a trip like this is with a known quantity.

I've done several vacations with clients before. I always significantly discounted my rate as A) the client was already spending a good amount of money for me to come with them and B) we wouldn't be BCD pretty much until night time (and occasionally would be too tired from the events of the day to do more than cuddle). The clients I went on vacation with would pay me when we were heading home...but then they were very good clients that I had great trust in and knew would pay at the end of the trip. I never requested a separate room (though one of the clients chose to sleep in the adjoining living room...probably because of the light from my Kindle haha). A separate room (or at least a suite) would give both of you some time to be alone from each other which could be beneficial if either of you need some grounding time to yourself.

In my opinion this is one of the times when you want to have a good discussion with the provider you are thinking of taking. I would ask her if she will want a deposit to reserve that time with you, will want a deposit to book her own plane ticket (some providers may not be comfortable giving you their real name), if she expects a separate room, if she would prefer to be paid before or after the trip and discuss expectations during the trip as well.

Traveler8912 pay what is fair to both parties!

I agree communication is key with the provider and knowing what is required for travel.

Just make sure you also feel comfortable with her terms and pricing

going to Costa Rica BY YOURSELF and enjoy the country and plenty of women there. CR is much nicer than cabo. Cabo is way over rated, ugly country side and prices that rival LA (another shit hole). For what you'll waste bringing a potential "trip killer" you can spend on some of the talent in San Jose, some real beauties from South and Central America. US Air had a non stop flight from PHX 4 hours and your there.

Or, if you really want to treat YOURSELF to a once in a lifetime experience go to Thailand, you'll need much more time than 4 days.