Vacation Rental Events Calendar 2026: 30+ Demand Spikes

Property managers who treat every month the same leave money on the table. A PM in Austin who doesn't plan for SXSW in March and Formula 1 in October misses two of the three biggest revenue windows of the year. A PM in Miami who ignores Art Basel in December and the Grand Prix in May operates at 60% of their revenue potential. And a PM in Palm Desert who doesn't prepare for Coachella in April is sitting 15 minutes from one of the highest-demand weekends in the country without a plan.

Events are the heartbeat of vacation rental demand. They spike nightly rates, compress booking windows, and create operational pressure that breaks teams without systems in place. Yet most property managers run event season the same way they run a random Tuesday in November. No calendar. No prep timeline. No revenue capture strategy beyond raising the nightly rate.

This is the calendar you should have had at the start of the year. Month-by-month, event-by-event, with revenue estimates, preparation timelines, and links to deep-dive guides for the biggest events on the list. Print it. Bookmark it. Build your year around it.

Why Event Revenue Matters More Than You Think

The obvious revenue play during events is the nightly rate increase. Properties within 20 miles of major events see 2-5x their normal rates during event windows. That's well-documented. Every PM knows to raise prices for Coachella weekend or Super Bowl weekend.

But the nightly rate is only the base layer. On top of it sits the operational revenue stack: early check-in fees, late checkout fees, gap night fills between event weekends, extended stay conversions, and turnaround premium services. This is the revenue most PMs never capture because they don't have systems to identify and offer it at scale.

Desert Sol Real Estate manages 130+ properties in Palm Desert, California — 15 minutes from the Coachella Valley Music and Arts Festival. During event cycles, their automated systems capture $8,000-$12,000 in operational revenue on top of premium nightly rates. That's not from raising prices. That's from gap night offers between Coachella's two weekends, early check-in for Thursday arrivals, late checkout for Monday departures, and extended stay conversions for guests who want to stay through both weekends.

Across 210+ total properties on the Dimora platform, the pattern holds in every market. Events that spike demand also spike operational revenue — if you have systems to capture it. 1,800+ guest calls handled by Voice AI. 6,300+ inbox drafts generated by Inbox AI. 470+ early/late checkout and gap night offers sent by the Revenue Engine. The infrastructure works the same whether the event is a music festival in California or an F1 race in Texas.

The question isn't whether events create revenue opportunities. It's whether you're capturing all of them or just the obvious one.

Q1: January - March

The year starts slow and accelerates fast. January is recovery from holiday season. February is when the first major events land. March picks up with conference season and spring break overlap.

Super Bowl (February)

Single city. One weekend. The highest per-night rates of any US sporting event.

The Super Bowl rotates cities annually, which means one market gets a massive windfall while the rest of the country watches on TV. If you manage properties within 30 miles of the host city, this is your single highest-revenue weekend of the year. If you don't, skip this event and focus on the next one.

The math for a PM in the host city: 20 properties at $700/night average, 3-night minimum stay (Friday to Monday), that's $42,000 in gross booking revenue for one weekend. Add early check-in for Thursday arrivals ($50 each x 12 properties = $600) and late checkout for Monday departures ($50 each x 15 properties = $750), and you've added $1,350 in operational revenue without changing a single nightly rate.

The operational challenge is turnaround compression. Every property turns over on the same day. Your cleaning crew is maxed out. This is where Voice AI earns its cost — handling the flood of guest calls about parking, directions, noise policies, and check-in instructions without a single call going to voicemail.

Read the full Super Bowl operations guide for turnaround scheduling, guest communication scripts, and pricing strategy.

Mardi Gras, New Orleans (February - March)

Twelve days of parades, parties, and packed French Quarter streets. STR demand spreads across three weekends, with mid-week dips between parade schedules.

The hidden revenue stream here isn't the weekend rates. It's the gap nights between parade days. Tuesday through Thursday occupancy drops 30-40% compared to Friday through Sunday, creating one-night and two-night gaps that most PMs leave empty. Automated gap night scanning during Mardi Gras can fill 5-10 nights per portfolio that would otherwise sit vacant.

Guest communication during Mardi Gras is different from other events. Noise complaints are common. Parking is nonexistent. Public transit schedules change daily. Your Inbox AI and Voice AI need event-specific knowledge base updates at least two weeks before the first parade.

SXSW, Austin (March)

Ten days of conferences, film screenings, and live music. SXSW is unusual because it attracts two completely different guest profiles at the same time.

Monday through Friday: corporate travelers attending tech panels and pitch events. They want quiet, reliable Wi-Fi, and proximity to the convention center. They book for 3-5 nights. Communication style is professional and brief.

Friday through Sunday: festival-goers attending live music showcases. They want proximity to bars, late checkout, and flexible noise policies. They book for 2-3 nights. Communication style is casual and enthusiastic.

If you manage properties in Austin, you're running two parallel operations during SXSW. Your Voice AI needs to handle "Where's the nearest Starbucks with good Wi-Fi?" on Tuesday and "What's the noise curfew?" on Saturday. Different guests, different needs, same property.

The revenue opportunity: SXSW's mid-week corporate travelers often check out Thursday or Friday, and the weekend festival crowd checks in Friday or Saturday. That creates a one-night gap Thursday night that's prime for a gap night offer to the departing corporate guest. "Enjoying Austin? Stay one more night at 10% off and catch some live music before you fly home."

Spring Training, Arizona and Florida (February - March)

Six weeks of baseball preseason games across the Cactus League (Arizona) and Grapefruit League (Florida). Lower nightly rates than the big-ticket events — $150-$250/night — but high occupancy and long stays.

Spring Training guests are different from festival guests. They're older. They're repeat visitors (same team, same city, every year). They book 5-10 nights. They don't need event-specific communication because they've been coming to this market longer than you've been managing properties.

The revenue play here is extended stay conversion. A guest books 7 nights for the first week of Spring Training. Their team plays the next week too. Offer an extension at 10% off. The marginal cost is near zero and the guest was probably considering it anyway.

Q1 Revenue Tip

Super Bowl and Mardi Gras overlap in February. If you manage properties in both markets, your operations team gets tested early. Treat January as prep month: update Voice AI knowledge bases, test gap night automation, confirm cleaning crew capacity. By February 1, every system should be running clean.

Q2: April - June

The densest event quarter of the year. If you manage properties in Southern California, South Florida, or Central Texas, you could be running continuous event operations from April through early July.

Coachella, Indio CA (April)

Two weekends plus a gap week. Desert Sol's backyard. 130+ properties within 15 minutes of the Empire Polo Club.

Coachella is the event that best illustrates why operational revenue matters as much as nightly rates. Weekend 1 rates spike 3-5x. Weekend 2 rates spike 2-4x. But between those two weekends sits a Monday-through-Thursday gap that most PMs treat as dead space.

It's not dead space. It's the biggest overlooked revenue opportunity in the Coachella cycle.

Guests who attend Weekend 1 and Weekend 2 need somewhere to stay between them. PMs who offer gap week packages capture 4 nights at 80-90% of weekend rates. PMs who let those nights sit empty because "the festival isn't happening" miss $800-$1,200 per property in gap week revenue.

Desert Sol's automated Revenue Engine scans for these gaps and sends offers to departing Weekend 1 guests and arriving Weekend 2 guests. The system also handles early check-in for Thursday arrivals (the day before Weekend 1 and Weekend 2 start) and late checkout for Monday departures.

Read the full Coachella operations guide for gap week strategy, turnaround scheduling for 130+ properties, and guest communication templates.

Kentucky Derby, Louisville (May)

Two days of racing, seven days of demand. Derby Week — the Wednesday through Sunday leading up to the race — fills Louisville's STR inventory completely. Horse country mansions go for $1,000+/night. Even modest downtown condos hit $400-$600.

Early check-in demand is extremely high during Derby Week. Guests fly in Thursday for Saturday's race. Standard 4pm check-in means they lose half a day of Derby festivities. Offering 1pm check-in at $50 is nearly an automatic yes for a guest who paid $900/night.

The operational challenge: Derby weekend has a single mass checkout on Sunday. Every property turns over simultaneously. If you manage 20+ properties in Louisville, your cleaning team needs backup crews booked six weeks in advance.

Miami Grand Prix (May)

Formula 1 premium pricing in a market that already runs hot. $400-$900/night depending on proximity to the circuit. Three-night minimum stays are standard.

The Miami GP is part of a broader F1 strategy for US-based PMs. Three Formula 1 races happen on US soil in 2026: Miami in May, Austin in October, and Las Vegas in November. Each has different market dynamics, different guest profiles, and different revenue ceilings.

Read the full F1 US races guide for city-by-city breakdown, pricing strategy, and the 8-week prep timeline.

FIFA World Cup 2026 (June - July)

Eleven US host cities. Thirty-nine days of matches. The single largest event in this entire calendar.

The World Cup is different from every other event on this list in one critical way: multilingual guest communication. Fans from 48 qualifying nations will travel to 11 US cities. Your Voice AI and Inbox AI need to handle inquiries in Spanish, Portuguese, French, German, and Japanese — at minimum.

PMs in host cities (New York/New Jersey, Los Angeles, Dallas, Houston, Atlanta, Philadelphia, Miami, Seattle, San Francisco, Kansas City, Boston) face 4-6 weeks of sustained elevated demand. This isn't a weekend spike. It's a marathon. Your operational systems need to run consistently for over a month without burning out your team.

The revenue opportunity extends beyond the match days themselves. Group stage matches happen across multiple cities, which means fans travel between cities over the tournament's duration. A fan who watches their team play in Dallas on June 15 might need a property in Houston on June 22. PMs who offer multi-city referral partnerships can capture demand that flows between markets.

Read the full World Cup 2026 guide for host city analysis, multilingual operations strategy, and demand projections.

CMA Fest, Nashville (June)

Country music's biggest annual festival. 80,000+ attendees over four days in downtown Nashville. STR rates spike 2-3x.

Nashville's STR market is saturated — over 6,000 active listings in Davidson County alone. During CMA Fest, every listing fills. But after CMA Fest, the PMs who captured great reviews and repeat guest data outperform for the rest of the year.

The revenue play during CMA Fest isn't just the event weekend itself. It's the guest relationship. A guest who has a great experience during CMA Fest becomes a direct booking customer for their next Nashville trip. That's worth $500-$1,000 in saved channel fees over the next two years.

Fast response times matter here more than pricing. In a market with 6,000 options, the PM who responds to a booking inquiry in under 10 seconds beats the PM who responds in 2 hours — even if the slower PM offers a lower rate. Dimora's Inbox AI generates draft responses in under 10 seconds across 6,300+ drafts and counting.

Q2 Revenue Tip

If you're in Southern California or Florida, Q2 is a continuous event season. Coachella in April, Kentucky Derby in May (if you have Louisville properties in your network), Miami GP in May, World Cup starting in June, CMA Fest in June. You could be running event operations for three consecutive months. Build stamina into your systems. Rotate cleaning crews. Pre-load Voice AI knowledge bases for all events by March 31.

Q3: July - September

Summer is less about single marquee events and more about sustained high demand punctuated by two bookend holidays. Every beach, mountain, and lake market runs hot from Memorial Day through Labor Day. The event overlays add spikes to an already elevated baseline.

July 4th (Nationwide)

Not one event — hundreds of local events happening simultaneously in every market in the country. Beach towns, mountain towns, lake towns, desert towns. Everyone travels for the 4th.

July 4th is the number one gap night opportunity of the year. Here's why: the holiday falls on a single day, but guests book around it in inconsistent patterns. Some book Wednesday through Sunday. Others book Thursday through Saturday. Others book just Friday and Saturday. The result is a patchwork of bookings with July 3 and July 5 gaps scattered across every portfolio.

If you manage 50 properties and your automated gap night scanning isn't running by June 15, you're leaving $2,000-$4,000 in fillable gap nights on the table over the July 4th week alone.

The operational challenge: July 4th is the loudest holiday. Noise complaints spike. Fireworks damage happens. Pool party violations happen. Your Voice AI needs to handle "my neighbor is setting off fireworks at 2am" calls without routing every complaint to the PM's personal phone.

Lollapalooza, Chicago (August)

Four-day festival in Grant Park. 100,000+ daily attendance. Chicago STR rates in the Loop and Near South Side jump 2-3x during Lolla weekend.

The revenue pattern mirrors Coachella's on a smaller scale. Thursday through Sunday demand is extreme. Monday is a ghost town. If you manage properties in downtown Chicago, offer late checkout on Monday to Lolla guests who are too exhausted to pack by 10am. $50 for a 1pm checkout is easy money.

US Open Tennis, New York (August - September)

Two weeks of matches at the USTA Billie Jean King National Tennis Center in Flushing, Queens. Demand for Queens and Flushing-adjacent properties is massive. Manhattan overflow drives Brooklyn and Long Island STR rates up 40-60%.

The US Open is a longer event than most festivals, which changes the operational dynamics. Guests book 5-7 night stays (for one week of the tournament) or 12-14 night stays (for the full tournament). Extended stay management matters more here than gap night scanning.

Mid-tournament checkout is common — guests who book through the quarterfinals leave if their favorite player loses. That creates unexpected availability that can be filled with short-notice bookings at premium rates. The PM who can relist a property within hours of an unexpected checkout captures revenue that slower operators miss.

Burning Man, Black Rock City NV (August - September)

The event happens in the desert, but the STR demand hits Reno and the Lake Tahoe area. Burners book rentals for pre-Burn prep (packing, testing art installations, acclimatizing) and post-Burn recovery (showers, real beds, decompression).

Average stay: 7-10 days. Guest communication style: unlike any other event on this list. Burning Man attendees have specific expectations about sustainability, community, and self-reliance. Generic welcome messages feel tone-deaf. Event-specific templates that reference "playa prep" and "decompression" convert better.

This is a niche market, but if you manage properties in Reno or Tahoe, it's a reliable annual revenue bump. 80,000 participants need somewhere to sleep before and after the Burn.

Labor Day (Nationwide)

Last summer hurrah. Beach and mountain markets peak one final time before fall. Three-night minimums are standard (Friday through Monday).

Labor Day is operationally simpler than July 4th because the booking patterns are more predictable. Friday arrivals, Monday departures, everyone on the same schedule. The revenue play is late checkout — Monday is travel day, and every guest wants an extra hour or two to pack without rushing.

Every PM should have automated early check-in and late checkout offers active for Labor Day weekend. At $50 per offer with a 15% acceptance rate across 50 properties, that's $375 for doing nothing except letting the system run.

Q3 Revenue Tip

July 4th and Labor Day bookend the summer. Treat them as operational dress rehearsals for your fall event season. If your gap night automation, early/late checkout offers, and Voice AI knowledge bases all perform cleanly on July 4th, you're ready for the Q4 premium event gauntlet. If they don't, you have August to fix them.

Q4: October - December

The premium event quarter. F1 races, Art Basel, New Year's Eve, and bowl season stack on top of each other from October through January 1. If you manage properties in Austin, Miami, or Las Vegas, Q4 is your Super Bowl season — not the actual Super Bowl, but the stretch where you make 30-40% of your annual operational revenue.

US Grand Prix, Austin (October)

Formula 1 race number two of the year. The Circuit of the Americas (COTA) draws 400,000+ fans over the race weekend. Austin STR rates hit $300-$600/night within a 15-mile radius of the track.

If you ran event operations during the Miami GP in May, apply everything you learned here. Same guest profile (international, affluent, F1-obsessed), same operational challenges (turnaround compression, noise policies, early check-in demand), same revenue playbook.

The difference: Austin also has Austin City Limits Music Festival in October, often the week before or after F1. Two back-to-back premium events in the same city in the same month. If you manage Austin properties, October is your highest-revenue month — but only if your systems can handle two event cycles without crashing.

Read the full F1 guide for Austin-specific pricing data and prep timelines.

Las Vegas F1 Grand Prix (November)

The biggest F1 event in America. Night race on the Las Vegas Strip. $600-$1,500/night depending on proximity to the circuit. Three-night minimums.

Vegas F1 is the event where operational revenue per property hits its ceiling. Premium nightly rates plus early check-in (Thursday arrivals for Saturday night race) plus late checkout (Sunday morning departures) plus gap night fills (Monday night between F1 departures and regular Vegas weekend arrivals). A single property can generate $200-$400 in operational revenue on top of $2,000-$4,500 in nightly rate revenue.

The guest profile is the highest-spending of any US event. Corporate hospitality packages, VIP track access, afterparties at nightclubs. Service expectations match Five-Star hotels. Your Voice AI needs to handle concierge-level requests: restaurant reservations, car service, event tickets. If it can't, guests call the PM directly at midnight.

Read the full F1 guide for Vegas-specific operational challenges.

Art Basel Miami (December)

Ultra-premium art fair in Miami Beach. Art collectors, gallery owners, and celebrities descend on Wynwood, Design District, and South Beach. $800-$2,000/night for luxury properties. $300-$600 for standard units.

Art Basel guests are different from sports fans. They don't care about proximity to a venue. They care about aesthetics, neighborhood vibe, and Instagram-worthiness of the property listing. Your listing photos and description matter more during Art Basel week than any other event of the year.

The operational challenge: Art Basel overlaps with Miami's general December tourism season, so your cleaning and operations team is already stretched. Adding event-premium turnover on top of normal holiday season turnover requires backup crews booked by October.

The revenue play: extended stays. Art Basel officially runs Wednesday through Sunday, but satellite fairs and private events run the full week. Guests who book for the official dates often want to extend through the weekend. An automated "Would you like to stay through Sunday?" message on Thursday captures 15-20% acceptance rates at these price points.

New Year's Eve (Major Cities)

New York, Las Vegas, Miami, Nashville, and Los Angeles all surge. Two-night to three-night minimum stays are standard (December 30 through January 1 or 2).

Mass checkout on January 1-2 creates the single biggest scheduling challenge of the year. Every property in your portfolio turns over on the same day. If you manage 50 properties in a major city, you need 50 clean-and-flip completions between 10am and 4pm on New Year's Day — when your cleaning crew is hungover and half your backup crew didn't show up.

This is the event where automation isn't just about revenue. It's about survival. Voice AI handling the flood of "where do I leave the keys?" calls. Inbox AI drafting checkout reminders at scale. Revenue Engine capturing late checkout offers from guests who don't want to leave their warm bed at 10am on January 1.

Automated late checkout offers on NYE: $50 per offer, 25% acceptance rate (higher than normal because no one wants to leave at 10am on New Year's Day), 50 properties = $625 in revenue plus the operational benefit of staggered checkouts that reduce the turnaround crunch.

College Football Playoff and Bowl Season (December - January)

Rotating cities. The locations are announced weeks or months before the games, which means demand spikes suddenly rather than building gradually.

This is the event category where PMs who can pivot pricing fast win. When your city gets announced as a semifinal or championship host, you have 2-4 weeks to adjust pricing, update minimum stays, activate event-specific Voice AI knowledge bases, and confirm cleaning crew capacity. PMs who wait a week to react find their competitors already booked at 3x rates.

The revenue pattern: short stays (2-3 nights), high turnover, intense checkout compression (everyone leaves the morning after the game). Early check-in demand is massive — fans fly in the day before the game and don't want to wait until 4pm to drop their bags.

Q4 Revenue Tip

October through December has four major premium events in three cities. If you manage properties in Austin, you have F1 in October. If you manage in Vegas, you have F1 in November and NYE in December — back-to-back premium weekends with a Thanksgiving dip in between. If you manage in Miami, you have Art Basel in December and NYE one week later. Plan your cleaning crew rotation in September. You won't have time to scramble once the season starts.

The Universal 8-Week Event Prep Checklist

This checklist works for every event on this calendar. Coachella, Super Bowl, a local wine festival — the event changes, but the operational preparation doesn't.

Week 8: Pricing and Calendar Strategy Set your event pricing. Adjust minimum stays (increase to 3-night minimum for premium events). Scan the calendar for gap nights in the event window and flag them for monitoring.

Week 7: Guest Communication Templates Update your message templates with event-specific information: driving directions from the airport, parking options near the venue, local restaurant recommendations, noise policy reminders. Load these into your Inbox AI and Voice AI systems.

Week 6: Cleaning Crew Capacity Confirm your primary cleaning crew availability for every turnaround day during the event window. Book backup crews for peak turnover days. If you manage 50+ properties, you need a crew schedule, not a hope-and-prayer.

Week 5: Voice AI Knowledge Base Update Load event FAQs into your Voice AI: transit schedules, venue location, noise curfews, parking passes, nearby grocery stores, emergency contacts. The Voice AI should be able to answer "How do I get to the venue from my rental?" without routing to a human.

Week 4: Gap Night Automation Activation Activate gap night scanning for the event window. Set the system to identify gaps between event-adjacent bookings and queue offers for PM review. Pre-set discount levels (10% standard, 15% for 48-hour escalation).

Week 3: Early Check-In and Late Checkout Setup Configure turnaround availability calculations for the event window. Set pricing for early check-in and late checkout ($35-$50 depending on property tier). Activate automated offer generation.

Week 2: Full System Test Run end-to-end tests on every automated system: Voice AI handles a sample call with event questions. Inbox AI drafts a response to an event-specific inquiry. Revenue Engine identifies a test gap night and generates an offer. Everything works. Nothing is broken.

Week 1: Execution Systems are live. Monitor dashboards, don't micromanage. Let the automation run. Your job shifts from "do everything manually" to "review and approve what the AI drafted." That's the difference between working 14-hour days during event season and working 8-hour days.

This checklist is the same whether you're prepping for Coachella or the Super Bowl. The event changes. The operations don't.

Building an Event Revenue Strategy

Not every PM operates at the same level. Here's where you might be now and where you need to go.

Level 1: Reactive

You notice events when bookings spike. You raise prices when Airbnb suggests it. You don't prepare in advance. You don't offer operational upsells. You answer guest calls yourself because you don't have Voice AI.

Revenue captured: base nightly rate increase only. You leave $3,000-$6,000 per property per year in operational revenue untouched.

Level 2: Planned

You have this calendar. You know which events affect your market. You plan pricing and staffing 8 weeks out. You might manually send a few gap night offers or early checkout messages during peak events.

Revenue captured: base nightly rate increase plus some manual operational revenue. You capture 70-80% of available revenue. The 20-30% you miss is from opportunities you identified but couldn't execute — the gap night you saw but didn't have time to message about, the late checkout request you couldn't process because you were on the phone with a cleaning crew.

Level 3: Automated

Voice AI handles all guest calls — 1,800+ and counting across the Dimora platform. Inbox AI drafts responses in under 10 seconds — 6,300+ drafts and counting. Revenue Engine scans calendars, identifies opportunities, and queues offers for your review — 470+ early/late and gap night offers sent. AI Learning improves draft quality every day based on your edits.

Revenue captured: base nightly rate increase plus full operational revenue stack. Early check-in, late checkout, gap nights, extended stays, payment recovery. This is where the 2-5x revenue multiplier lives.

The difference between Level 2 and Level 3 isn't knowledge. Level 2 PMs know about gap nights and early checkout offers. The difference is execution capacity. You can only manually send 5-10 offers per day. Automation can send 50-100. Scale is the gap.

Read how AI operations deliver ROI in 90 days for the full implementation timeline.

What to Do Next

Save this calendar. Print it if you have to. Identify which events affect your market — not just the obvious ones in your city, but the secondary events that drive overflow demand into your market (a Super Bowl in Houston sends overflow to Austin and San Antonio; a World Cup match in Dallas sends overflow to Fort Worth and Denton).

Start the 8-week prep checklist for your next event. If your next event is less than 8 weeks away, start from wherever you are and compress the remaining weeks. Something is better than nothing.

Then go deep on the events that matter most to your portfolio:

• Coachella Property Management Guide — Two weekends, one gap week, 130+ properties
• World Cup 2026 Vacation Rental Guide — 11 cities, 39 days, multilingual operations
• LA Olympics 2028 Property Management Prep — The mega-event that will redefine LA's STR market
• F1 US Races Revenue Guide — Miami, Austin, Vegas: three races, three strategies
• Super Bowl Operations Guide — One city, one weekend, maximum revenue per night

And if you want the complete framework for capturing operational revenue beyond event windows:

• Revenue Optimization Guide — The five revenue streams beyond nightly rates
• Gap Night Automation Guide — Turn empty calendar nights into revenue
• Platform Overview — How Voice AI, Inbox AI, and Revenue Engine work together

Events don't wait for you to be ready. The calendar is set. The question is whether you'll treat each event as a revenue opportunity or an operational emergency.