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Being a landlord in Hollywood sounded like a great idea at first. Steady rental income, property appreciation in a hot South Florida market, maybe even a little nest egg for retirement. But somewhere between the midnight maintenance calls, the tenant who stopped paying, and the property taxes that keep climbing, things changed. If you’re staring at your rental property right now wondering how to just be done with it, you’re not alone — and you have more options than you might think.

Whether your rental is sitting near Hollywood Lakes, tucked into the Emerald Hills neighborhood, or closer to the action in Downtown Hollywood, selling fast doesn’t have to mean settling for less than your property is worth. Let’s walk through what your options really look like.

Signs It’s Time to Stop Being a Landlord

Tired landlord syndrome is real. It usually doesn’t hit all at once — it builds up over months or years until one day you realize you dread checking your phone because it might be another tenant issue. If any of these sound familiar, it might be time to consider selling:

• You’re dealing with non-paying or problem tenants and feel stuck in the eviction process
• The property needs major repairs you don’t want to pay for — roof, AC, plumbing, hurricane shutters
• You’ve inherited the rental and never wanted to be a landlord in the first place
• Insurance premiums in Florida have made the cash flow disappear
• You live out of state and managing a Hollywood property remotely has become a nightmare
• You want to free up capital for something else — retirement, another investment, paying off debt

Whatever your reason, you don’t owe anyone an explanation. Your rental property should be working for you, not against you.

Selling With Tenants in Place — What Florida Landlords Need to Know

Here’s something a lot of Hollywood landlords don’t realize: you can absolutely sell a property with tenants still living in it. In Florida, leases transfer with the property under Florida Statute 83.561 and related landlord-tenant law, which means a new buyer steps into your shoes as the landlord until the lease ends. For a traditional buyer looking for a primary residence, that’s often a deal-breaker. For a cash investor, it can actually be a selling point.

A few things to keep in mind when selling occupied rental property in Florida:

• You must honor existing lease terms — you can’t kick tenants out just because you’re selling
• Security deposits transfer to the new owner, and you’ll need to account for them at closing
• Month-to-month tenants typically require 15 days’ notice for termination in Florida
• You should give tenants proper notice before showings, even if your lease allows access

Selling vacant gives you more buyer options and often a higher price, but selling occupied means you don’t have to wait out the lease or deal with vacancy loss. Both paths work — it just depends on your timeline.

The Tax Side: Capital Gains and 1031 Exchanges

Good news for Hollywood property owners: Florida has no state capital gains tax. But the IRS still wants its cut. When you sell a rental property you’ve owned for more than a year, you’ll typically owe federal long-term capital gains tax (0%, 15%, or 20% depending on your income), plus depreciation recapture at up to 25% on the depreciation you claimed during ownership.

If you’re not ready to write a check to Uncle Sam, a 1031 exchange lets you defer those taxes by rolling your sale proceeds into another investment property. A few rules to know:

• You have 45 days from closing to identify replacement properties
• You must close on the new property within 180 days
• The funds have to be held by a qualified intermediary — you can’t touch them
• The replacement property must be of equal or greater value to fully defer taxes

If you’ve owned a rental in Hallandale-adjacent areas or elsewhere in Hollywood for a long time, a 1031 can save you tens of thousands. Talk to a CPA before you list — timing matters.

Selling Fast Without the Headaches

A cash sale skips the financing contingencies, the repair requests, the appraisal hurdles, and the 60-day closing waits. For a rental property that needs work or has tenant complications, this can be the cleanest exit. You pick the closing date, you sell as-is, and you walk away with cash in hand — often in under two weeks.

If you’re ready to talk through your situation, get a no-pressure cash offer, or just ask questions about what your Hollywood rental might be worth in its current condition, give our team a call at (619) 480-0195. We’ll listen, lay out your options honestly, and help you figure out the right next step — whether that’s selling to us or not.

Frequently Asked Questions

Can I sell my rental property in Hollywood, FL if my tenant won’t cooperate with showings?

Yes, you can still sell — and a cash buyer is often the easiest route in this situation. Cash investors typically don’t need multiple showings or formal inspections and can make an offer based on a single walkthrough or even photos. This avoids the conflict of repeatedly asking an uncooperative tenant to accommodate buyers, and you can close without disturbing them further.

How much will I owe in taxes when I sell my Hollywood rental?

Florida has no state income tax, so you won’t owe state capital gains tax. Federally, you’ll likely owe long-term capital gains tax (0–20%) plus depreciation recapture up to 25% on the depreciation you’ve claimed. The exact amount depends on your income bracket, how long you’ve owned the property, and how much you’ve depreciated — a CPA can give you a precise estimate before you sell.

How fast can I actually close on a cash sale in Hollywood?

Most cash sales in Hollywood close in 7 to 21 days, depending on title work and your preferred timeline. There’s no waiting on bank approvals, appraisals, or buyer financing. If you need to close even faster for a 1031 exchange deadline or personal reasons, many cash buyers can accommodate that with a clear title.

Do I have to make repairs before selling my rental?

Not if you sell to a cash buyer. Investors purchase properties as-is, meaning you don’t need to fix the roof, replace the AC, paint, or even clean out tenant belongings in some cases. This is one of the biggest advantages for tired landlords — you skip the time, cost, and stress of preparing a property for the traditional market.