Man, let me tell ya about our Dr Holidays disaster last month. Total dumpster fire. See, my sister got this wild idea for our family reunion – all 14 of us from grandparents down to screaming toddlers. She kept shoving Dr Holidays ads in our group chat saying “look how cheap this Caribbean deal is!” Like a dumbass, I didn’t research first.

The Booking Nightmare
Soon as I clicked “Book Now”, everything went downhill. Their family package page showed this gorgeous 4-bedroom villa. Called customer service to confirm it sleeps 14 people. Agent goes “oh yeah plenty space!” Took three freaking hours to input all our passports and birthdays. Payment finally went through after my credit card got declined twice. Got the confirmation email and… it says TWO-BEDROOM unit. Immediately called back. New agent says “whoops system glitch” and offers a cot for the toddler. A COT. For fourteen people.
Reality Check at the “Resort”
We show up exhausted after two layovers. Place looks decent from far away. Get closer and realize:
- “Private pool” is actually a murky puddle shared with four other units
- The “complimentary breakfast” is stale croissants dumped in the lobby at 7am sharp – gone by 7:05
- No laundry machines even though ad said “full amenities”
- That “kids club”? Literally one broken Xbox in a storage closet
Group Meltdown by Day Two
Little things exploded FAST. Grandma couldn’t walk to the restaurant (15 min uphill on gravel). Teen cousins complained about sharing rooms – started stealing each other’s chargers. We tried switching rooms but receptionist kept shrugging “sorry full”. Tried cooking one meal ourselves – rental kitchen had ONE pot. Cold sandwiches for fourteen people costs $200 there. Absurd.
What Actually Matters For Groups
Learned the hard way:

- ACTUAL room dimensions (demand floor plans!)
- Verify sleeping arrangements bed-by-bed not “sleeps X”
- Transportation logistics from airport AND between facilities
- No “shared amenities” unless explicitly listed (assume NOTHING included)
- Emergency contacts besides generic 1-800 numbers
Ended up splitting into three separate Airbnbs halfway through. Cost triple what Dr Holidays charged. Moral of the story? That cheap family package price is bait. Dr Holidays works maybe for two backpackers – not humans with different needs crammed together. Still paying off my therapy bills.