October brings the kind of travel moments that are easy to look forward to: fairground lights in Arizona, desert design in California, crisp mountain weekends in Washington, and live music and Halloween magic in Florida.
Across the Good Life Vacations collection, you can stay in professionally managed homes designed for comfort, flexibility, and time well spent. Choose your event, find the destination that suits your plans, and make room for the moments in between.
October Events in Arizona
Arizona State Fair
Oct 1–Nov 1, 2026 Phoenix, AZ
The Arizona State Fair returns to Phoenix with classic fair favorites, including rides, food, entertainment, and attractions for the whole family. The 2026 fair runs Thursdays through Sundays from October 1 through November 1. Stay in a Phoenix vacation rental and make the fair part of a longer desert escape. Spend the day enjoying the midway, then return to a comfortable home with space to prepare a late dinner, relax, and plan the next day at your own pace.
Breaking Benjamin
Oct 5, 2026 Phoenix, AZ
Rock fans can catch Breaking Benjamin at Talking Stick Resort Amphitheatre on October 5. The Phoenix stop is part of the band’s 2026 North American tour. A home-style stay in Phoenix gives concertgoers a comfortable place to recharge before the show and unwind afterward. Add a day for local dining, desert scenery, or a relaxed morning by the pool.
Rocktoberfest
Oct 9–11, 2026 Tempe, AZ
Rocktoberfest brings live music, food, and an energetic fall atmosphere to Tempe Beach Park. The three-day event is a fun choice for travelers who want music and outdoor entertainment in the same weekend. Choose a Tempe vacation rental or stay nearby in the Phoenix area. With a vacation home as your base, you can enjoy the festival without giving up the space and privacy that make a weekend away feel easy.
October Events in California
Epson Tour Championship
Oct 1–4, 2026 Indian Wells, CA
Golf enthusiasts can watch rising professionals compete at the Epson Tour Championship at Indian Wells Golf Resort. The tournament runs through October 4 on the Players Course and offers a close look at the next generation of women’s professional golf. Stay or explore our Palm Desert rentals for easy access to the course, restaurants, spas, and desert views. Between rounds, leave time for a scenic drive through the Coachella Valley.
Modernism Week, October
Oct 16–19, 2026 Palm Springs, CA
Modernism Week October invites visitors to explore Palm Springs through architecture, design, art, and midcentury culture. Expect tours, talks, parties, and experiences that showcase the city’s distinctive style. A Palm Springs vacation rental puts you close to the action while giving you a private place to relax between events. Look for a home with a pool or outdoor space and extend the design-focused weekend with a little desert downtime.
Jerry Seinfeld
Oct 3, 2026 Rancho Mirage, CA
Spend an evening laughing with Jerry Seinfeld at The Show at Agua Caliente Casino in Rancho Mirage. His stand-up performance makes a memorable addition to a Palm Springs-area getaway. Stay in a Rancho Mirage vacation rental or choose a Palm Springs home for easy access to entertainment, dining, and desert attractions. Make it a weekend for two, or gather friends for a relaxed comedy-and-desert escape.
October Events in Washington
Leavenworth Oktoberfest
Oct 2-17, 2026 Leavenworth, WA
Leavenworth’s Bavarian-style Oktoberfest takes over the village for three weekends with live music, dancing, beer, food, and festive mountain-town energy. A Leavenworth vacation rental lets you enjoy the celebration while staying close to the surrounding Cascade scenery. Spend the day in the village, then return to a private home for a quieter evening and crisp autumn views.
Cashmere Apple Days
Oct 3, 2026 Cashmere, WA
Celebrate harvest season at Cashmere Apple Days, a local fall event filled with apple-themed traditions, community activities, and the flavors of central Washington. The nearby Pioneer Village Festival takes place on October 3, with an Apple Pie Contest scheduled for October 2. Stay in a nearby vacation rental, pick up local treats, explore the valley, and enjoy the slower pace of a fall weekend in Washington.
Frosty Pumpkin 4-Player Scramble
Oct 31, 2026 Malaga, WA
Golfers can add a seasonal twist to their trip with the Frost Pumpkin 4-Player Scramble. The event combines a day on the course with the crisp atmosphere of an October getaway. Choose a Washington vacation rental with room for your foursome, or look for a home near the course. After the final hole, gather around the table, share a meal, and make the most of having your own space.
October Events in Florida
Moon Crush: Odie’s Beach Vacation
Oct 1–3, 2026 Miramar Beach, FL
Moon Crush: Odie’s Beach Vacation brings live music, beach activities, and performances hosted by Old Dominion to Miramar Beach. The festival runs each evening from 5 to 10 p.m. Stay at Good Life Vacations Resort rentals and keep the Gulf close throughout your trip. Spend the day on the sand, head to the festival in the evening, and return to a resort home with pools, private beach access, and space to unwind.
Mickey’s Not-So-Scary Halloween Party
Select nights in October Orlando, FL
Mickey’s Not-So-Scary Halloween Party brings costumes, special entertainment, treats, and after-hours fun to Magic Kingdom. Disney lists select October dates through Halloween, but tickets are limited, and availability can change quickly. A vacation home can make a theme-park trip feel more comfortable, especially for families who want a kitchen, separate bedrooms, and a little breathing room.
Chayanne
Oct 24, 30, 31, 2026 Across FL Cities
Fans of Latin pop can look forward to Chayanne in Florida this October. His concert adds a high-energy music night to a month already filled with beach days, theme-park adventures, and warm-weather escapes. Browse Florida vacation rentals and choose the destination that fits your plans. Whether you are pairing the concert with time at the parks or adding a few quiet days near the coast, a private home gives you flexibility beyond the event itself.
October Is Waiting
October gives you plenty of ways to travel well. Follow the music to Phoenix or Miramar Beach, explore Palm Springs through its architecture and design, celebrate harvest season in Washington, or turn a Florida theme-park trip into a more comfortable stay.
Explore the Good Life Vacations collection and find a home that makes the event only the beginning of your trip. Book direct for official rates, thoughtful design, professional management, and a stay built around comfort.
Event dates, ticket availability, and schedules may change. Check each event’s official website before making final plans.
Featured Vacation Homes
*Prices shown may not be accurate. Please search with dates to view accurate nightly prices
