You signed the purchase agreement. You're "under contract." And if you're like most first-time short-term rental buyers, you're probably thinking the hard part is over.
It's not. Not even close.
Going under contract on an Airbnb rental is really just the starting gun for a sprint that involves inspections, financing, insurance, permits, title work, and a dozen STR-specific tasks that normal homebuyers never deal with. Miss one deadline or skip one verification step, and you can lose your earnest money, blow your closing date, or end up owning a property you can't legally rent out.
This guide walks you through everything that happens between contract day and closing day (and a bit beyond) so you can close with confidence, protect your investment, and get to your first guest as fast as possible. Whether you're buying your first STR or rolling a 1031 exchange into a vacation rental, this is the playbook.
What "Under Contract" Actually Means for STR Buyers
Once you and the seller sign the purchase agreement, you enter escrow. That's a neutral arrangement where a third party (usually a title company or escrow officer) holds your earnest money and key documents until every contract condition is satisfied. The National Association of Realtors describes escrow as a way to protect both buyer and seller during the transaction, with earnest money held in a separate account until closing.
So you have a signed deal. But you don't have a closed deal.
The difference between a regular homebuyer and an STR investor during this phase is real and significant. A typical buyer worries about three things: the condition of the property, the title, and the financing. You're worrying about all of that plus whether you can legally operate a short-term rental at this address, whether your HOA allows it, whether the existing bookings transfer (they usually don't), and whether your lender will actually underwrite based on STR income.
You're not just buying a property. You're buying a business location with rules. That mindset shift changes how you spend every single day between contract and closing. If you're new to the process, our complete guide to investing in your first Airbnb rental walks through each step before you even get to contract.
The Three Deadlines That Control Every STR Deal
Every under-contract deal runs on deadlines. Miss one and you lose negotiating power, money, or both. There are three separate "clocks" ticking simultaneously, and keeping them synchronized is half the job.
Clock 1: Contract Contingencies
These are your built-in escape hatches. Depending on your state and contract, they usually include:
Inspection or due diligence window (often 7–15 days)
Financing contingency (typically 21–30 days)
Appraisal contingency
Seller disclosure review
HOA/condo document review (if applicable)
The exact names and timelines vary by state. Some states have an attorney review period. Texas uses an "option period." Your contract is always the source of truth, so read it carefully and mark every single deadline on your calendar.
Clock 2: Lender Deadlines
Even if your contract gives you 30 days, your lender has their own workflow and federal requirements to meet. Two timing rules matter in most U.S. mortgage closings:
Loan Estimate: Lenders must provide this within 3 business days of receiving your application (CFPB, updated Aug 14, 2024).
Closing Disclosure: Lenders must deliver this 3 business days before closing (CFPB closing disclosure explainer).
If your lender falls behind on either of these, your closing date slips. And if your contract doesn't have a built-in extension mechanism, a delayed closing can become a breached contract.
Clock 3: STR Readiness Lead Times
Some STR tasks have long lead times that will blow up your launch timeline if you ignore them during escrow:
City permit applications and inspections
Fire safety requirements
Noise ordinance compliance
Insurance underwriting
Furnishings delivery and setup
Utility and internet installation
If you want to be taking guests shortly after closing, you need to start these processes during escrow, not after.
What to Do in the First 48 Hours After Going Under Contract
This is where most first-time investors quietly lose a week without realizing it. The decisions you make (or don't make) in the first 48 hours set the pace for the entire transaction.
1) Set Up a Deal Folder From Day One
Set up a folder (cloud-based, so your agent and lender can access it) with these subfolders:
Contract + addenda
Disclosures
Title/escrow
Lender documents
Insurance
Inspections
STR regulations + permits
HOA/COA
Rehab + bids
Furnishing + design
Ops setup (PM, cleaner, locks, etc.)
This isn't busywork. By the time you close, you'll have 50+ documents across these categories, and investors who don't organize from day one spend closing week scrambling to find things.
2) Confirm Your Earnest Money Was Received
Your contract specifies how much earnest money is due and when. Get written confirmation from your escrow or title company that the funds were received. Don't assume the wire went through. Follow up the same day.
3) Schedule Your Home Inspection Immediately
Inspection windows are often the tightest deadline in your contract, and the best inspectors book out fast, even in slower markets. Call your inspector before you do almost anything else.
Typical U.S. inspection costs: about $296 to $424, with an average around $343 (Rocket Mortgage, Feb 2026, citing HomeAdvisor data from Oct 2025).
4) Start Your Lender File the Same Day
Even if you're using a DSCR lender for your short-term rental, underwriting is a document chase. Your goal is to get to "appraisal ordered" as quickly as possible, because appraisals can become the longest single task in the entire process.
5) Request STR Insurance Quotes Before Your Contingency Closes
This is no longer something you handle in the final week. The NAIC warns that most homeowners policies are not designed for short-term rentals, and coverage can be denied even if an exclusion isn't obvious in the policy language.
If insurance turns out to be difficult or prohibitively expensive for your target property, you want to know before your contingency window closes.
Here's a quick reference for your first 48 hours:
| Action | Who's Responsible | Deadline |
|---|---|---|
| Deliver earnest money | You (wire or check) | Per contract (often 1-3 days) |
| Set up deal folder | You | Day 0 |
| Schedule home inspection | You or your agent | Day 0-1 |
| Submit lender docs / order appraisal | You + lender | Day 0-2 |
| Request STR insurance quotes | You | Day 0-2 |
| Pull local STR regulations | You | Day 0-2 |
| Request HOA docs (if applicable) | Your agent | Day 0-3 |
Pro tip: If you're buying in an unfamiliar market, Chalet's STR regulation guide lets you check local STR rules before you burn precious contingency time guessing.
STR Due Diligence: Inspections, Title, and Disclosures
Think of your due diligence period as answering three big questions: Is the property physically okay? Is the ownership clean? Is the seller hiding anything?
What STR Buyers Should Focus on During the Home Inspection
You still want the standard inspection items: roof, foundation, HVAC, electrical, plumbing. But STR buyers should also look at everything through a "guest abuse" lens. Guests treat properties differently than long-term tenants, and issues that a homeowner might tolerate can turn into bad reviews, refund requests, or liability.
Pay extra attention to:
Safety hazards: railings, stairs, decks, and anything a guest unfamiliar with the property might trip over or fall from
Water intrusion and mold risk: guests won't report a slow leak the way a homeowner would
High-use amenities: hot tub, pool, fireplace, septic, and well systems that get heavier use from short-stay guests
HVAC capacity: guest comfort directly drives your review scores
Parking and access issues: confusing parking or difficult access is one of the fastest routes to refund requests
If something fails inspection, you typically have three options: request the seller make repairs, request a credit toward closing costs, or walk away (assuming your contract allows it).
What Title Insurance Covers and Why STR Investors Need It
"Title" is the legal record of property ownership. Title problems include things like unpaid property taxes, contractor liens, or disputes about prior ownership. During escrow, a title company will run a search to uncover any issues.
There are two types of title insurance worth understanding:
Owner's title insurance protects you if someone later claims a right against the property from before you bought it (CFPB, Oct 19, 2023).
Lender's title insurance protects your lender, not you (CFPB, Sept 13, 2024).
Lender's title insurance is usually required. Owner's title insurance is optional but strongly recommended, especially for investors. It's the one that protects your equity.
STR-Specific Due Diligence Steps That Can Make or Break Your Deal
This is where STR deals get won or lost. Most generic homebuyer guides skip this section entirely, and that's exactly why investors who rely on general advice end up with properties they can't legally rent. For a deeper look at how to navigate local regulations and STR licensing, Chalet's blog covers the entire process.
How to Verify You Can Legally Operate a Short-Term Rental
Before you get excited about projected revenue, you need clear answers to these questions:
Is STR allowed in this zoning district or neighborhood?
Is a permit required? If so, is one available?
Are permits capped or waitlisted?
Is an existing permit transferable to a new owner?
Are there occupancy caps, parking rules, or inspection requirements?
Are there special taxes or registration requirements?
One common misconception: "Airbnb handles the taxes." Not always. Airbnb says it automatically collects and remits certain taxes in some jurisdictions, but hosts may still need to handle other taxes and compliance requirements manually. Don't assume the platform has you covered.
Practical move: Get a written or screenshot-able confirmation from the city or county. Don't rely on your agent saying "everyone Airbnbs here." Zoning enforcement can change overnight, and verbal assurances won't protect you.
You can start your research with Chalet's guide to navigating STR regulations, which covers rules for major markets across the U.S.
Why HOA and Condo Rules Can Override Your STR Plans
Even if the city allows short-term rentals, your HOA can ban or restrict them. This catches more buyers off guard than almost any other issue. We've written extensively about the specific risks of running an Airbnb in an HOA community. It's required reading before you sign anything.
Request these documents from the HOA or condo association:
CC&Rs (Covenants, Conditions, and Restrictions)
Rules and regulations
Rental policy (specifically short-term rental language)
Fine schedule for violations
Board meeting minutes from the last 12 months
Current rental cap status and waitlist policy
Read the meeting minutes carefully. They'll tell you whether the board has been discussing STR restrictions, which is a leading indicator of future rule changes.
The Turnkey STR Trap: What Buyers Need to Know About Existing Bookings
This is a big blind spot for first-time buyers. When a seller advertises a "turnkey Airbnb with active bookings," many buyers assume they're purchasing the Airbnb account, the review history, and the future reservations.
They're not.
Airbnb is clear that you cannot transfer account ownership to another host. Vrbo is equally explicit that listings cannot be transferred to another party and a new owner must create a new listing.
What you're actually buying is the real estate (and maybe the furniture). The reviews stay with the original host profile, and future bookings can get messy without a clear contract addendum. Before you pursue a turnkey deal, read our full breakdown of buying an Airbnb from another host, including the pros, cons, and what to watch for.
Here are three safer approaches investors use to handle this:
→ The seller continues to host and fulfill existing bookings for a defined period after closing, with transparent accounting.
→ A holdback amount is kept in escrow, tied to reservation performance during the transition.
→ The buyer launches a fresh listing and the seller stops accepting new bookings before close.
This is contract territory. Involve your attorney.
Why Your STR Income May Not Help You Qualify for a Loan
Even if your own spreadsheet shows great STR revenue, your lender might not care. Many conventional lenders qualify investment properties using long-term market rent, not short-term rental income.
Fannie Mae's selling guide explains that when lenders use market rents (Form 1007/1025), they calculate qualifying rental income by taking gross rent and multiplying by 75%. That 25% haircut accounts for vacancy and maintenance.
Some DSCR and non-QM programs do allow short-term rental income, but the proof requirements can be strict. Example lender guideline matrices show requirements like:
12-month rental history statements from a platform or manager
Appraiser-supported market rent (sometimes including STR-specific analysis)
Vacancy or expense factors of 20% or more applied to STR rents
The one question to ask your lender during escrow: "What exact income source will you use to qualify this deal?"
If the answer is long-term rent only, run the numbers both ways. It prevents a last-minute DSCR failure that blows up the deal. And you can sanity-check those numbers using Chalet's free Airbnb calculator. For more on securing the right short-term rental loan, our 2025 guide walks through every loan type and what qualifies.
What Lenders Actually Check When Financing an STR Property
Even for DSCR loans, underwriting comes down to three buckets:
Bucket 1: Property Value. That's what the appraisal determines.
Bucket 2: Property Income. For conventional loans, this often means the rent schedule with a 75% haircut (Fannie Mae selling guide). For DSCR programs, it depends on the lender. Some programs look for a minimum DSCR around 1.1. Others describe typical minimums in the 1.2 to 1.5 range, depending on program and risk level.
Bucket 3: Borrower Risk. Even DSCR lenders care about your credit score, liquidity and reserves, and the property's condition and insurance status.
Understanding the difference between loan types matters here. Our guide to DSCR financing for short-term rentals explains how lenders calculate coverage ratios and what documentation they require. If you're comparing STR loan options for 2025, Chalet's loan directory connects you with STR-specialist lenders.
How Long Does It Take to Close on an STR Property?
Most mainstream sources cite a closing timeline of around 30 to 45 days for financed deals. PNC (Aug 2025), Chase (Jan 2026), and Zillow (Jun 2025) all put the average somewhere around 44 days. Cash deals can close faster, sometimes in two weeks.
What to Do When Your Appraisal Comes in Below Contract Price
A low appraisal means your lender may not approve the loan amount you expected, because the loan is based on the appraised value, not your contract price. Your options are usually:
Renegotiate the purchase price with the seller based on the appraisal
Bring additional cash to cover the gap between appraised value and contract price
Challenge the appraisal (called a reconsideration of value) by providing better comparable sales
Switch loan programs if another program has more favorable terms
Walk away if you have an appraisal contingency in your contract
Why STR Insurance Has Become a Deal-Breaker in Some Markets
Two things can both be true at the same time: you need STR-specific insurance coverage, and property insurance availability has gotten meaningfully harder in climate-exposed areas.
How STR Insurance Differs from Standard Homeowners Coverage
Standard homeowners policies usually won't cover short-term rental activity. The NAIC warns that claims can be denied even when an exclusion isn't obvious in the policy language. You need either an STR endorsement added to a standard policy or a standalone short-term rental policy. Bankrate's STR insurance guide breaks down the difference between endorsements and standalone policies.
When you're ready to find coverage, Chalet's vendor directory includes vetted insurance providers who specialize in short-term rental properties. It's a faster route than searching carrier by carrier.
How Climate Risk Is Affecting STR Insurance Costs
Insurance isn't just about STR-specific coverage anymore. The U.S. Treasury's Federal Insurance Office released a major report in January 2025 on homeowners insurance cost and availability problems tied to climate risk. Reuters reported that premiums in the most climate-exposed areas have climbed materially.
If you're buying in a wildfire, hurricane, or flood-prone area, insurance availability and cost should be part of your due diligence before you waive contingencies.
STR Insurance Checklist for the Under-Contract Period
Get an insurance quote early (don't wait until closing week)
Ask the carrier specifically whether they're okay with short-term rental use
Ask about wind, wildfire, and flood exclusions
If you're in a high-risk area, check state residual markets (like FAIR plans), but understand that coverage may be limited and more expensive
What to Expect During Closing Week on Your STR Purchase
Closing week is when everything converges. If you've managed your deadlines well, this should feel like a controlled process, not a scramble.
How to Review Your Closing Disclosure
The CFPB requires lenders to deliver your Closing Disclosure three business days before closing. Use those three days to compare the numbers against your Loan Estimate. If something looks wrong or unexpected, resolve it before closing day.
What to Check During the Final Walkthrough
This is your last chance to verify the property before you take ownership:
Agreed-upon repairs have been completed
No new damage has occurred since inspection
All included items are still present (appliances, furniture if negotiated)
The property is in the condition specified in the contract
How Signing and Wire Transfers Work at Closing
Depending on your state, you'll sign at a title company, attorney's office, or escrow office. Your title/escrow officer will coordinate the wire transfer of funds. Make sure you verify wiring instructions directly with your title company (wire fraud in real estate transactions is a real and growing problem).
Typical Pre-Close Costs When Buying an STR Property
These are typical ranges for costs you'll pay between contract and closing. Numbers change by market and property type, so use these as starting points, not guarantees.
| Cost Item | Typical Range | Source |
|---|---|---|
| Home inspection | $296 to $424 (avg ~$343) | Rocket Mortgage (Feb 2026) citing HomeAdvisor Oct 2025 data |
| Appraisal | $314 to $423 (avg ~$357) | Bankrate (Mar 2025) citing 2025 Angi data |
| Closing costs | ~3% to 6% of loan amount | Rocket Mortgage closing costs guide (Dec 2025) |
| Closing costs (national avg) | ~$4,661 including recording/taxes | Bankrate (Sept 2025) citing LodeStar analysis |
How to Get Your First STR Guest Quickly After Closing
The keys are yours. Now the real work starts. Think in two parallel tracks.
Track 1: Legal and Compliance Tasks After Closing
Submit your permit application or transfer (if your market requires one)
Register for a business license (if required locally)
Complete tax registration (if required)
Confirm your insurance policy is active with the correct occupancy and use designation
Track 2: Operations and Guest Experience Setup
Get internet installed and tested (this is your most critical utility for guests)
Install smart locks and test them
Write your house rules and check-in instructions
Schedule and stock your cleaning crew
Schedule professional photos (or reshoot if the existing ones don't match your listing quality standards)
Create your listing on a new host account
The faster you complete both tracks, the sooner you're generating revenue. Many investors who plan ahead during escrow can be live within one to two weeks after closing.
One of the first decisions you'll make after closing: self-manage or hire a property manager? The right answer depends on your proximity, time availability, and scale goals. If you're leaning toward professional management, Chalet's property management directory connects you with vetted STR property managers in your target market.
You can also line up your operations vendors (property managers, cleaners, insurance providers, furnishing companies) through Chalet's STR vendor directory.
And don't overlook furnishing. Our guide to Airbnb furnishing budgets by bedroom count helps you plan setup costs before closing day, so you're not scrambling for cash the moment you get the keys.
How a 1031 Exchange Changes Your Under-Contract Timeline
If you're doing a 1031 exchange, every task described above still applies. But you have an additional layer of stress: IRS deadlines that cannot be extended for any reason.
The hard guardrails from IRS instructions for Form 8824 (updated Dec 8, 2025):
45-day identification rule: You must identify your replacement property within 45 days after transferring the relinquished property.
180-day closing rule: You must close on the replacement property within 180 days after the transfer.
What IRS Deadlines Mean for Your Under-Contract Tasks
→ Get your qualified intermediary aligned immediately if you haven't already. The QI needs to be in place before you close on the relinquished property.
→ Treat inspection and permit verification as "do it today" tasks, not "we'll get to it" tasks. You have zero room for delays.
→ Build a backup identification list early. STR-specific legality surprises (like discovering permits are capped or the HOA bans rentals) are common, and you need alternative properties identified before your 45-day window closes.
For more on the 1031 exchange timeline and how it interacts with STR purchases, see our 2025 guide to using a 1031 exchange for short-term rental investing. If you're worried about a contract falling through and losing your identification window, read about 1031 exchange inspection contingency issues. It's one of the most common problems 1031 investors face. And if you're comparing top investment property options for your 1031 exchange, our analysis covers which markets and property types have historically performed best.
You can explore Chalet's 1031 exchange hub for market-specific guidance on exchange-friendly destinations.
Why STR Deals Fall Apart After Going Under Contract (and How to Avoid It)
These are the patterns that kill STR purchases, and they're avoidable if you catch them early:
| Pitfall | How to Prevent It |
|---|---|
| Permit not available or not transferable | Verify with the city in writing during the first week |
| HOA bans STRs or rental cap waitlist is years long | Request and read HOA docs within 48 hours |
| Insurance quote shock or carrier refuses STR use | Get quotes in the first 48 hours, not closing week |
| Lender qualifies on long-term rent and the deal no longer pencils | Ask your lender what income source they'll use on Day 1 |
| "Turnkey" bookings aren't transferable, revenue drops after closing | Verify platform transfer policies and use contract addenda |
| Inspection reveals major deferred maintenance | Schedule inspection ASAP and budget for surprises |
| Appraisal comes in low | Have a backup plan (more cash, renegotiation, or walk) |
If you catch these in the first two weeks, you can renegotiate or walk before you've invested significant time and money. These pitfalls are also why working with an investor-friendly STR real estate agent matters so much. They've seen these problems before and know which flags to raise during due diligence.
Email Templates for Your STR Under-Contract Due Diligence
These templates are designed to get you clear answers fast. Copy, customize, and send.
Email to City or County STR Office
Subject: Short-term rental eligibility check for [address]
Hi [Name/Department],
I'm under contract to purchase [address] and want to confirm STR rules before closing.
Can you please confirm:
Whether STRs are allowed at this address or zoning district
Whether a permit/license is required
Whether permits are currently available (or capped/waitlisted)
Whether a permit is transferable to a new owner
Any required inspections, occupancy caps, or parking requirements
If there's a link to the applicable ordinance or application page, please share it.
Thank you,
[Your name]
[Phone]
Email to HOA or Condo Manager
Subject: Rental rules request for [community name] unit at [address]
Hi [Name],
I'm under contract to purchase a unit in [community]. Before closing, I need the current rental rules.
Please send:
Current CC&Rs and rules/regulations
Any short-term rental policy
Rental cap status and waitlist process
Fine schedule and enforcement policy
Last 12 months of meeting minutes (if available)
Thank you,
[Your name]
Seller Document Request for an Existing STR
Subject: STR operating docs request for [address]
Hi [Agent/Seller],
To complete due diligence, please share:
STR permit/license info (and whether transferable)
Last 12 months of platform statements and payout summaries
A list of included furnishings and equipment
Utility averages and any service contracts (cleaning, pest, pool/hot tub)
Any known neighbor/HOA complaints or notices related to STR use
Thanks,
[Your name]
How Chalet Helps You Navigate the Under-Contract Period
Going from contract to closing on an STR involves a lot of moving parts, and most of the tools and people you need are scattered across different websites, spreadsheets, and referrals from friends of friends. That's exactly the problem Chalet was built to solve.
Chalet is a free, one-stop platform for short-term rental investors. We pair market analytics with a vetted vendor network so you can research, buy, and operate without juggling a dozen disconnected resources. Here's how our tools map to what you're dealing with during the under-contract period:
Sanity-check your deal numbers. Our free Airbnb calculator lets you run ROI and DSCR projections for any address. Before your lender tells you the deal doesn't pencil, run it yourself.
Verify local STR regulations. Our guide to navigating STR regulations and licensing covers what you need to know about permits, zoning, and local rules before you spend a week emailing city offices.
Connect with an STR-savvy agent. Not every real estate agent understands STR due diligence. Meet an Airbnb-friendly agent through our vetted network who's closed deals like yours before. Our blog also explains the benefits of working with an investor-friendly STR realtor if you're still deciding whether a specialist agent is worth it.
Explore market analytics. If you're still comparing markets or need data to support your appraisal challenge, our free analytics dashboards show ADR, occupancy, and revenue trends.
Browse Airbnb rentals for sale. Looking for your next deal (or a backup property for your 1031 identification)? See Airbnb rentals for sale across top STR markets.
Line up your ops team. From property managers and cleaners to insurance and furnishing companies, our vendor directory helps you build your operations stack before closing day.
Frequently Asked Questions
How Long Does the Under-Contract Period Last for an STR Purchase?
Most financed STR deals close in 30 to 45 days from contract signing. Cash deals can close in as few as 10 to 14 days. The timeline depends on your contract terms, lender speed, and how quickly you complete due diligence. STR-specific tasks like permit verification and insurance quotes can add complexity, so starting everything on Day 0 is critical.
What Is Earnest Money and How Much Should I Put Down for an STR?
Earnest money is a deposit that shows the seller you're serious about the purchase. It's held in escrow and applied toward your down payment or closing costs at closing. The amount varies, but it's typically 1% to 3% of the purchase price in most markets. If you back out for reasons not covered by your contingencies, you risk losing it.
Can I Transfer the Existing Airbnb Listing and Reviews to My Name?
No. Airbnb does not allow account or listing transfers between hosts. Vrbo has the same policy. You'll need to create a new host account and build reviews from scratch. If the property has active future bookings, work with your attorney to include a transition plan in your purchase contract.
What Happens If the Property Can't Be Used as an STR After Going Under Contract?
If you have an inspection or due diligence contingency in your contract (and most contracts do), you can typically walk away and get your earnest money back. This is one reason why STR regulatory verification should be one of your first tasks after going under contract, not something you check at the end. Chalet's how-to guide on navigating local STR licensing can help you understand permit requirements quickly without spending days emailing local offices.
Do I Need Special Insurance for a Short-Term Rental?
Yes. Standard homeowners insurance policies typically don't cover short-term rental activity. You need either an STR endorsement on an existing policy or a standalone short-term rental insurance policy. Get quotes early in the escrow process, because some carriers refuse to cover STR properties entirely, and finding an alternative takes time.
DSCR Loan vs. Conventional Loan: Which Is Better for STR Investors?
A conventional investment property loan typically qualifies you based on your personal income, credit, and debt-to-income ratio. It usually counts rental income at only 75% of market rent. A DSCR (Debt Service Coverage Ratio) loan focuses on whether the property's income covers the debt payments. DSCR minimums vary by lender, generally ranging from 1.1 to 1.5. DSCR loans are popular with STR investors because they don't require W-2 income verification, but they often come with slightly higher interest rates. Our complete guide to DSCR financing for short-term rentals covers the full qualification process.
What Should I Do If the Appraisal Comes in Lower Than My Contract Price?
You have several options: renegotiate the price with the seller, bring extra cash to closing to cover the difference, challenge the appraisal by submitting better comparable sales (called a reconsideration of value), explore a different loan program, or walk away if your contract includes an appraisal contingency. The best approach depends on how strong your deal still looks after the lower valuation.
How Does a 1031 Exchange Change the Under-Contract Timeline?
A 1031 exchange adds strict IRS deadlines on top of your normal closing process. You must identify replacement property within 45 days and close within 180 days after transferring the relinquished property. These deadlines can't be extended, so every under-contract task (inspections, permits, financing) needs to happen faster. Build a backup identification list early in case STR-specific issues force you to switch properties. Chalet's 1031 exchange hub can help you identify exchange-friendly markets and connect with 1031-savvy agents.
What Are the Biggest Reasons STR Deals Fall Apart After Going Under Contract?
The most common deal killers: discovering that STR permits aren't available or aren't transferable, finding out the HOA bans short-term rentals, insurance being unavailable or prohibitively expensive, the lender qualifying on long-term rent instead of STR income (making the DSCR fail), learning that Airbnb bookings and reviews don't transfer, major deferred maintenance discovered during inspection, and appraisals coming in low.
Should I Start Setting Up My STR Operations Before Closing?
Yes. Start lining up your property manager, cleaning crew, furnishing plan, and listing photos during escrow. You can't sign contracts or make purchases for the property until you own it, but you can get quotes, interview vendors, and have everything ready to execute on closing day. Investors who prepare during escrow often go live within one to two weeks after closing. Chalet's STR vendor directory is a good starting point for vetting your operations team while you're still in escrow.
Costs, timelines, and regulatory references in this guide are based on publicly available U.S. sources published or updated in 2024 through early 2026 (accessed March 2, 2026). Prices and rules change fast, especially insurance availability and city STR ordinances. Always verify locally before you waive any contingency.
