Owning a vacation rental sounds fun. Think of it as a business, not fun.
I own a vacation rental, near Kissimmee, FL. Disney World, Sea World, Universal Studios, Discover Cove, Busch Gardens, etc. are all there. One of the busiest vacation places in the USA. It is busy all year round.
I need several business licenses, and must collect and pay sales tax of 13.5%. Every month I have to fill out a sales tax report for both Florida and Osceola county, and if I do not fill it out, I get rewarded with a penalty. Even if I am vacant for the entire month.
From a tax perspective, if I stay in it over 14-days, I cannot take a loss. I never meet that 14-day threshold, so I get any tax write-offs available. I do maintenance when I am there, that doesn’t count towards the 14-days. This trip I am replacing a kitchen sink, replace washer and dryer, replace door handle, touch up paint, inspect the new floors I paid $8K for, and clean, clean, clean. I get 5-star reviews and want to keep it that way.
You will likely be there more than 14-days. You will lose on the property from a tax perspective if you run it correctly and you will not be allowed the loss. Depreciation, travel to it, maintenance, etc. all take their toll. When I do a round trip. It’s over 4,000 miles at $0.58 a mile deduction. Plus, hotels and meals for the entire trip. That’s about a $3K deduction. Then, add in all the repairs items that you have to buy, a sink and new drains, area rug, door knob, paint, etc.
I get an average of ~$112 a night. YTD I am booked 190 days across 37 bookings. The low is $95 (so far) and the high is $190. The place cost me ~$175K in a 1031 Exchange, plus furniture, etc. Far less than you are spending. It is a deeded townhome, and I own that unit exclusively. The ground is owned by the Condo Association.
You will likely not get 100% occupancy, ever. Shoot for ~60%. It is near impossible to get 100%, unless you have a long-term stay. Put in four guests stays of 5 or 6 days each, and it's hard to fill in the gaps. You wind up with ~60% occupancy. I sometimes get people for a month, and that helps. Know what occupancy is where you are planning on buying. If you want to stay in it during the busy and most expensive time, plan on even less.
You need a marketing company to handle the rentals, or do it yourself. There are fees for AirBnB, HomeAway, VRBO, FlipKey and Evolve. They handle payments and credit card processing (for a fee). I use Evolve Vacation Rental. They charge 10%, plus 3% for credit card processing. Plus, the Guest pays a few fees, like TicketMaster. The Guest pays for insurance, cleaning ($95), and I think a booking fee.
You need someone on the ground to handle maintenance and cleaning between tenants. Especially when you have back-to-back tenants, like I do a few times each month. They charge a fee as well. Even if you are vacant, or you are staying there. I pay $120 a month.
My costs are $420 for Association fees; Property taxes $200; Electricity $75; insurance $50; water $50; pest control $25. I pay that no matter if I am vacant or full.
Depending on where you buy, a resort may require you to use their rental office. And the resort will upgrade your unit when they want, as they want the resort to be top notch. They may have a higher priority on the rental that they own, not yours. They may charge 30%+, and add in more fees for anticipated maintenance, towel service, etc. The list is endless. You may not even get to stay in your unit when you get there.
Whatever you decide is good, just be aware there is a lot more to a vacation rental than just buying a place.