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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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Sink into plush seating and let sunlight stream through expansive glass doors that open to your private patio and lush green views beyond.

Rancho Mirage, CA

Sunny Rancho

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2
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$260/night (incl. all fees)

Nov 11 – Dec 11
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Miramar Beach, FL

TOPS'L Beach Manor 312

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Sink into plush leather seating with plantation shutters framing lush greenery beyond. Your living room balances comfort and style, complete with a cozy fireplace for cooler evenings.

Palm Desert, CA

Bahama Breeze

2
2
4

$226/night (incl. all fees)

Nov 11 – Dec 09
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Miramar Beach, FL

TOPS'L Tides 0111

Sink into plush seating by your private fireplace, where natural light pours through shuttered doors and warmth meets modern comfort in your inviting retreat.

Palm Desert, CA

Lobelia Luxe

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3
4

$290/night (incl. all fees)

Nov 11 – Nov 18
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Miramar Beach, FL

TOPS'L Summit 811

2
2
6

$297/night (incl. all fees)

Nov 11 – Nov 14
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Davenport, Florida

Bahama Bay Resort 02608

3
2
6

$235/night (incl. all fees)

Nov 11 – Nov 13
Settle into your bright, open living space where floor-to-ceiling windows frame swaying palm trees and sunshine spills across plush seating—your perfect spot to unwind after exploring the area.

Palm Desert, CA

Palm Beauty

2
2
4

$282/night (incl. all fees)

Nov 11 – Nov 16
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Miramar Beach, FL

TOPS'L Tides 0409

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Davenport, FL

Bahama Bay Resort 02606

2
2
6

$140/night (incl. all fees)

Nov 11 – Nov 13
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Miramar Beach, FL

TOPS'L Summit 603

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Davenport, FL

Bahama Bay Resort 17606

2
2
6

$197/night (incl. all fees)

Nov 11 – Nov 13
Challenge your travel companions to a friendly game at the elegant billiards table, perfectly set and ready for your next shot.

Palm Desert, CA

Bay Hill Star

2
2
4

$349/night (incl. all fees)

Nov 11 – Nov 13
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Miramar Beach, FL

TOPS'L Tides 1203

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Davenport, FL

Bahama Bay Resort 27904

2
2
6

$210/night (incl. all fees)

Nov 25 – Nov 28
Step into your bright open-concept living area where contemporary style meets comfort. Natural light pours through large windows, illuminating sleek furnishings and a fully-equipped kitchen—your perfect home base for relaxation and memorable moments.

Palm Desert, CA

Desert Escape

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2.5
6

$347/night (incl. all fees)

Nov 11 – Nov 16
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Davenport, Florida

Bahama Bay Resort 04411

3
2
6

$197/night (incl. all fees)

Nov 15 – Nov 17
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Miramar Beach, FL

TOPS'L Summit 108 Combo

3
3
6

$300/night (incl. all fees)

Nov 11 – Nov 14
Your private oasis awaits under the desert sky—dive into the sparkling pool, lounge poolside, or gather at the built-in bar for sunset cocktails and grilled favorites.

Palm Springs, CA

Miralon Maison

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3.5
6

$370/night (incl. all fees)

Nov 24 – Nov 30
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Miramar Beach, FL

TOPS'L Tides 1107

2
2
4

$491/night (incl. all fees)

Dec 08 – Dec 09
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Davenport, FL

Bahama Bay Resort 33514

3
2
8

$169/night (incl. all fees)

Nov 11 – Nov 14
Settle into this bright, airy living space where soaring ceilings and warm touches create your perfect retreat. Cozy up by the fireplace with a good book, or gather around the coffee table for game night.

Palm Desert, CA

Palm Getaway

2
2
4

$348/night (incl. all fees)

Dec 03 – Dec 06
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Davenport, FL

Bahama Bay Resort 20903

3
2
8

$166/night (incl. all fees)

Nov 11 – Nov 14
Sink into plush sofas and unwind in this serene living space, where soft textures, warm wood accents, and abundant natural light create the perfect retreat for your downtime.
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Miramar Beach, FL

TOPS'L Beach Manor 314

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Davenport, FL

Bahama Bay Resort 23101

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2
6

$192/night (incl. all fees)

Nov 30 – Dec 02
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Davenport, Florida

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Davenport, FL

Bahama Bay Resort 32602

Sink into plush leather seating in your spacious living room, where sunlight streams through sliding glass doors leading to your private patio. Perfect for unwinding after desert adventures.
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$340/night (incl. all fees)

Nov 14 – Nov 17
5
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12

$565/night (incl. all fees)

Nov 21 – Nov 24
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$282/night (incl. all fees)

Nov 11 – Nov 13
6

$308/night (incl. all fees)

Nov 11 – Nov 13
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$874/night (incl. all fees)

Nov 11 – Nov 13

Palm Springs, CA

Palm Canyon Modern Bungalow

2
2
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$264/night (incl. all fees)

Nov 14 – Nov 19
2
2
6

$375/night (incl. all fees)

Nov 11 – Nov 13

Bahama Bay Resort 09105

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2
6

$258/night (incl. all fees)

Nov 23 – Nov 25
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$169/night (incl. all fees)

Nov 11 – Nov 14
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Miramar Beach, FL

TOPS'L Tennis Village 23

2
2
4

$424/night (incl. all fees)

Nov 11 – Nov 12

Palm Desert, CA

Lite Hideaway

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2
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$283/night (incl. all fees)

Nov 11 – Nov 14
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