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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 sofas with vibrant pillows, gather around the elegant dining table, and enjoy an open layout that flows seamlessly from living to kitchen—your perfect home away from home.

Palm Desert, CA

Jupiter View

2
2
4

$297/night (incl. all fees)

Nov 11 – Nov 14
Relax in your spacious living area with comfortable seating, a dining nook, and sliding glass doors that open to stunning views of lush golf greens and open sky.

Palm Desert, CA

Green Fairway

2
2
4

$314/night (incl. all fees)

Nov 11 – Nov 13
Step into your bright, modern retreat where clean lines and artistic touches create the perfect escape. Relax on plush seating as natural light pours through plantation shutters, framing your private outdoor space just beyond.

Palm Desert, CA

Palm Glamour

2
2
4

$391/night (incl. all fees)

Nov 11 – Nov 13
Pool

Phoenix, Arizona

Happy Haus

Step onto your shaded poolside loungers and sink into resort-style relaxation. The sparkling pool, lush lawn, and mountain-framed backyard create your perfect desert oasis for sun-soaked days.

Palm Springs, CA

Mag's Mountain View

4
4
8

$749/night (incl. all fees)

Nov 11 – Nov 14
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Davenport, FL

Bahama Bay Resort 13510

3
2
8

$169/night (incl. all fees)

Nov 11 – Nov 14
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Kissimmee, FL

Caribe Cove Condominiums 40102

2
2
6

$193/night (incl. all fees)

Nov 24 – Nov 26
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Davenport, FL

Bahama Bay Resort 25101

2
2
4

$228/night (incl. all fees)

Nov 11 – Nov 13
The Seaside Bohemian - Backyard Pool

Chandler, Arizona

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Miramar Beach, FL

TOPS'L Beach Manor 612

3
3
7

$602/night (incl. all fees)

May 04 – May 08
Sink into plush sofas and enjoy your favorite shows or unwind by the fireplace in this inviting living room, with sunny views and touches of greenery throughout.

Palm Desert, CA

Palm Deluxe

3
3.5
6

$376/night (incl. all fees)

Nov 11 – Nov 14
The property features multiple outdoor pools illuminated for evening relaxation, surrounded by comfortable loungers and lush greenery—ideal for unwinding after a day of desert exploration.
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Miramar Beach, FL

TOPS'L Summit 708

2
2
5

$416/night (incl. all fees)

Nov 11 – Nov 12
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Davenport, FL

Bahama Bay Resort 33502

3
2
8

$169/night (incl. all fees)

Nov 11 – Nov 14
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Davenport, FL

Bahama Bay Resort 35310

3
2
6

$188/night (incl. all fees)

Nov 21 – Nov 24
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Miramar Beach, FL

TOPS'L Summit 807A

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Davenport, FL

Bahama Bay Resort 01714

3
2
8

$166/night (incl. all fees)

Nov 12 – Nov 15
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Davenport, FL

Bahama Bay Resort 26108

The property's outdoor pool area offers lounge seating surrounded by mature landscaping, with mountain ranges visible in the background.
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Your private balcony offers a stunning mountain backdrop, lush garden views, and a cozy spot to sip morning coffee or unwind with evening drinks under the palms.
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Living Room
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3
2
8

$327/night (incl. all fees)

Nov 11 – Nov 13

The Seaside Bohemian

6
2.5
15

$435/night (incl. all fees)

Nov 11 – Nov 13

Palm Springs, CA

Deja Blue

4
4.5
8

$674/night (incl. all fees)

Nov 11 – Nov 13
2

$248/night (incl. all fees)

Nov 11 – Nov 12

Miramar Beach, Florida

TOPS'L Tides 0106

3
3
7

$705/night (incl. all fees)

Nov 11 – Nov 14
Exterior

Mesa, Arizona

Desert Sunset

3
2
6

$233/night (incl. all fees)

Dec 15 – Dec 20

Kissimmee, FL

Caribe Cove Condominiums 10206

3
2
6

$156/night (incl. all fees)

Nov 11 – Nov 14
2
2
6

$165/night (incl. all fees)

Dec 01 – Dec 04

Palm Springs, CA

Sonora Charmer

4
2.5
8

$666/night (incl. all fees)

Nov 11 – Nov 13

Miramar Beach, Florida

TOPS'L Beach Manor 108

2
2
6

$322/night (incl. all fees)

Nov 11 – Nov 13

Palm Springs, CA

Mascarpones Mojo Dojo

2
2
4

$312/night (incl. all fees)

Jan 07 – Jan 14
OUTDOOR POOL

Gold Canyon, Arizona

Primrose Paradise

4
3.5
10

$220/night (incl. all fees)

Nov 15 – Nov 17
Yard

Payson, Arizona

Timberland Hideaway

5
2
16

$402/night (incl. all fees)

Nov 11 – Nov 13
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Miramar Beach, FL

TOPS'L Tides 0406

3
3
8

$584/night (incl. all fees)

Nov 11 – Nov 14

Davenport, FL

Bahama Bay Resort 19810

3
2
8

$169/night (incl. all fees)

Nov 11 – Nov 14

Miramar Beach, FL

Casa Paradiso at TOPS'L

4
4.5
10

$837/night (incl. all fees)

Nov 11 – Nov 14

Phoenix, Arizona

Desert Gem

2
1
5

$123/night (incl. all fees)

Nov 11 – Dec 12
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