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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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230050911

Palm Desert, California

5.0 (3)

VV818 - Wada Way

2
2.5
4

$324/night (incl. all fees)

Oct 01 – Oct 03
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Miramar Beach, FL

TOPS'L Tides 0410

2
2
6

$452/night (incl. all fees)

Sep 27 – Sep 28
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Davenport, FL

Bahama Bay Resort 18711

3
2
6

$166/night (incl. all fees)

Sep 26 – Sep 29
Pool

Phoenix, Arizona

Happy Haus

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Pensacola, Florida

Spanish Key 708

3
3
8

$375/night (incl. all fees)

Oct 30 – Nov 01
Living

Palm Desert, California

V3998 - Dozen Palms

2
3
4

$311/night (incl. all fees)

Sep 26 – Sep 28
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Davenport, FL

Bahama Bay Resort 32602

3
2
8

$169/night (incl. all fees)

Sep 26 – Sep 29
Outdoor Fire Pit and Pool

Scottsdale, Arizona

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Miramar Beach, FL

TOPS'L Summit 1006 Combo

3
3
8

$456/night (incl. all fees)

Oct 12 – Oct 14
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Pensacola, Florida

Perdido Towers 102E

3
3.5
8

$343/night (incl. all fees)

Sep 26 – Sep 28
Image

Davenport, FL

Bahama Bay Resort 32607

2
2
6

$208/night (incl. all fees)

Sep 26 – Sep 28
POOL TABLE

Palm Desert, California

PS627 -Bay Hill Star

2
2
4

$352/night (incl. all fees)

Sep 26 – Sep 28
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Miramar Beach, Florida

TOPS'L Summit 409 B

2
2
6

$291/night (incl. all fees)

Sep 27 – Sep 30
Living Room

Flagstaff, Arizona

NEW
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Pensacola, Florida

Perdido Cottage

3
2
9

$518/night (incl. all fees)

Sep 26 – Sep 27
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Davenport, FL

Bahama Bay Resort 15207

3
2
8

$166/night (incl. all fees)

Sep 26 – Sep 29
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Miramar Beach, FL

TOPS'L Tennis Village 10

2
2
6

$288/night (incl. all fees)

Sep 26 – Sep 29
LIVING ROOM

Palm Desert, California

VB887 - Desert Vacay

2
2
4

$170/night (incl. all fees)

Sep 27 – Sep 29
OUTDOOR POOL

Gold Canyon, Arizona

Gorgeous Custom Lodge Cabin

Leavenworth, Washington

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Pensacola, Florida

Windemere 406

2
2
6

$358/night (incl. all fees)

Sep 26 – Sep 28
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Kissimmee, FL

Caribe Cove Condominiums 50202

3
2
8

$190/night (incl. all fees)

Jan 30 – Feb 02
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Miramar Beach, FL

TOPS'L Beach Manor 311

2
2
6
Living Area with comfortable seating

Palm Desert, California

V3625 - Cottonwood Hole

3
2
6

$340/night (incl. all fees)

Sep 26 – Sep 29
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Scottsdale, Arizona

The Talon House

4
3.5
8

$446/night (incl. all fees)

Sep 26 – Sep 29
Aerial View

Manson, Washington

Three Lakes Haven

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Pensacola, Florida

Lost Key 6522

4
4
10

$439/night (incl. all fees)

Sep 26 – Sep 28
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Davenport, FL

Bahama Bay Resort 09113

3
2
6

$184/night (incl. all fees)

Sep 26 – Sep 29
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Miramar Beach, Florida

TOPS'L Summit 409 A

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1
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$259/night (incl. all fees)

Sep 27 – Sep 29
LIVING SPACE TIGHT

Palm Desert, California

4.6 (33)
4.9 (107)
5.0 (2)
5.0 (110)
4.7 (6)
5.0 (30)
4.8 (31)
5.0 (4)
5.0 (46)
5.0 (52)
4.5 (54)
5.0 (7)
5.0 (12)
4.8 (16)
5.0 (8)
3
2
8

$327/night (incl. all fees)

Oct 02 – Oct 04

AZSC21-Andora

3
2
6

$319/night (incl. all fees)

Sep 27 – Sep 29

High country retreat

5
4
18

$444/night (incl. all fees)

Sep 26 – Sep 28

Primrose Paradise

4
3.5
10

$204/night (incl. all fees)

Oct 06 – Oct 08

Big Jim Mountain Lodge

3
2
6

$581/night (incl. all fees)

Oct 04 – Oct 07

$508/night (incl. all fees)

Sep 27 – Sep 28
5
3.5
8

$719/night (incl. all fees)

Sep 26 – Sep 28

V3820 - Palm Golf

3
2
6

$326/night (incl. all fees)

Sep 26 – Sep 29