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Best Things to Do in October

September 25, 2026

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

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Miramar Beach, FL

TOPS'L Tides 0803

2
2
6

$434/night (incl. all fees)

Nov 12 – Nov 13
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Miramar Beach, FL

TOPS'L Summit 1114

2
2
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Davenport, FL

Bahama Bay Resort 33516

3
2
8

$170/night (incl. all fees)

Nov 20 – Nov 23
A private oasis where you can unwind poolside under bright desert skies, surrounded by lush greenery and mountain views. Lounge in the sun, dine alfresco under the umbrellas, or simply soak in the peaceful ambiance.

Palm Springs, CA

Hokona House

3
2.5
6

$686/night (incl. all fees)

Nov 11 – Nov 14
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Davenport, FL

Bahama Bay Resort 27902

3
2
6

$169/night (incl. all fees)

Nov 11 – Nov 14
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Davenport, FL

Bahama Bay Resort 09102

3
2
8

$181/night (incl. all fees)

Nov 11 – Nov 14
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Miramar Beach, Florida

Bayou Beach House

4
4
10

$741/night (incl. all fees)

Nov 11 – Nov 13
Step into your bright, open living space with soaring ceilings and warm wood floors. The modern ceiling fan keeps you comfortable while you relax on the plush sectional or gather around the dining table for meals together.

Palm Desert, CA

Palm Valley Desert Chic

2
2
4

$384/night (incl. all fees)

Nov 11 – Nov 13
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Miramar Beach, FL

TOPS'L Summit 104

2
2
6

$389/night (incl. all fees)

Nov 11 – Nov 12
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Davenport, FL

Bahama Bay Resort 18713

3
2
8

$227/night (incl. all fees)

Nov 11 – Nov 14
Inviting single-story vacation home with private pool, shaded lawn, and sunny patio. Perfect for outdoor living and relaxation under swaying palm trees.

Palm Springs, CA

Sapphire Hideaway

4
3
8

$587/night (incl. all fees)

Nov 11 – Nov 14
Sink into plush seating by your private fireplace and enjoy views of the sunny backyard through glass doors—a cozy retreat for unwinding after a day of adventure.

Palm Desert, CA

White Bright Drive

2
2
4

$297/night (incl. all fees)

Nov 11 – Nov 14
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Davenport, FL

Bahama Bay Resort 32607

2
2
6

$208/night (incl. all fees)

Nov 14 – Nov 16
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Davenport, FL

Bahama Bay Resort 06201

2
2
6

$224/night (incl. all fees)

Nov 11 – Nov 13
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Miramar Beach, FL

TOPS'L Tides 0404

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Miramar Beach, Florida

TOPS'L Beach Manor 1206

2
2
6

$444/night (incl. all fees)

Mar 11 – Mar 14
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Miramar Beach, FL

TOPS'L Summit 307

2
2
Palm trees sway over sparkling pools framed by white pergolas and loungers—a sun-soaked oasis where your desert getaway comes to life.

Palm Desert, CA

Costa Circle

1
1
2

$275/night (incl. all fees)

Nov 11 – Nov 14
Settle into this welcoming living space where high vaulted ceilings and plush leather seating create your perfect retreat. Sliding glass doors open to your private patio with palm-lined views and warm desert sunshine.

Palm Desert, CA

Dahlia's Delight

3
3
6

$272/night (incl. all fees)

Dec 06 – Dec 11
Sink into the plush sectional and let natural light stream through plantation shutters opening to your private patio—your perfect retreat for unwinding after a day of exploring.

Palm Desert, CA

Cottonwood Gem

3
2
6

$361/night (incl. all fees)

Nov 11 – Nov 14
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Miramar Beach, FL

TOPS'L Tides 0109

Relax in your bright, open living space with mountain views framed by sliding glass doors. Sink into the plush sofa, gather at the dining table, or step outside to enjoy the fresh air and lush greenery.

Palm Desert, CA

Lake Fairway

2
2
4

$310/night (incl. all fees)

Nov 11 – Nov 14
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Davenport, FL

Bahama Bay Resort 20901

2
2
4

$197/night (incl. all fees)

Nov 18 – Nov 20
This inviting backyard combines relaxation and resort-style comfort with a sparkling pool, lush lawn, thatched palapa, and covered patio—your private retreat awaits.

Indio, CA

Antigua Villa

5
2
10

$824/night (incl. all fees)

Nov 11 – Nov 14
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Davenport, FL

Bahama Bay Resort 29610

3
2
8

$198/night (incl. all fees)

Nov 26 – Nov 29
A sparkling pool awaits, framed by swaying palms and abundant sunshine. Your perfect spot to relax is ready—just choose your lounger and soak in the warm desert vibes.

Palm Desert, CA

Morning Fairway

2
2
4

$297/night (incl. all fees)

Nov 11 – Nov 14
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Miramar Beach, FL

TOPS'L Tides 1010

2
2
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Davenport, FL

Bahama Bay Resort 22101

2
2
6

$166/night (incl. all fees)

Nov 30 – Dec 03
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Davenport, FL

Bahama Bay Resort 34405

2
2
6

$192/night (incl. all fees)

Dec 08 – Dec 10
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Miramar Beach, FL

TOPS'L Beach Manor 401

2
2
6

$365/night (incl. all fees)

Nov 11 – Nov 13
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$268/night (incl. all fees)

Nov 15 – Nov 17
2
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$499/night (incl. all fees)

Nov 11 – Nov 14
6

$362/night (incl. all fees)

Nov 11 – Nov 12
2
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$424/night (incl. all fees)

Feb 28 – Mar 03
6

$312/night (incl. all fees)

Nov 11 – Nov 14