10 Best Places to Visit in Florida in October

October is quietly one of the best places to visit in Florida in October – not just because the weather begins to mellow, but because the entire state shifts into a calmer, more spacious rhythm. The summer humidity eases, beaches feel less crowded, and outdoor dining, coastal walks, and theme park days become far more comfortable.

If you’re wondering about the best Florida vacation spots in October or where to visit in Florida in October for warm days without peak-season intensity, this is your window. From Gulf Coast beaches to the Florida Keys and relaxed Panhandle towns, October offers warm water, golden sunsets, and space to truly unwind.

In this Wander guide, we’ve gathered the Sunshine State’s standout destinations and some of key luxury vacation rentals in Florida to help you plan the trip of a lifetime, no matter what sort of stay you’re after.

1. Siesta Key

October on Siesta Key feels like a well-kept secret. The summer crowds fade, but the Gulf remains warm enough for swimming. The light softens, sunsets stretch longer, and the powder-white quartz sand feels blissfully uncrowded.

Things to do in October

• Swim and paddleboard at Siesta Beach

• Catch golden-hour views along Crescent Beach

• Explore Siesta Village’s boutiques and restaurants

• Kayak through mangrove tunnels at nearby Turtle Beach

Travel tips for October

• Midweek stays offer the most peaceful beach time

• Evenings cool slightly – pack a light layer

• Reserve sunset dining early; fall skies are spectacular

Where to stay

Wander Siesta Key Breeze – 12 guests, 4 bedrooms
Spacious and effortlessly coastal, this four-bedroom retreat sleeps up to twelve guests and is designed for laid-back Gulf living. Open-plan interiors flow to outdoor gathering spaces, making it ideal for multigenerational trips or groups traveling together. After a beach day, evenings here feel relaxed and expansive – exactly what October in Siesta Key is meant to be.

2. St. George Island

October transforms St. George Island into a serene coastal haven. The heat recedes, fishing improves, and the barrier island returns to its quiet, natural rhythm.

Things to do in October

• Surf fish along uncrowded stretches of beach

• Bike the island’s scenic paved path

• Climb the Cape St. George Lighthouse

• Watch migrating shorebirds along the dunes

Travel tips

• Bring binoculars for fall bird migrations

• Grocery shop before crossing the bridge – options are limited

• Book fishing charters in advance; fall is prime season

Where to stay

Wander St. George Tides – 8 guests, 4 bedrooms
Sleeping eight across four bedrooms, this refined coastal home blends elevated design with relaxed Gulf charm. October mornings begin quietly on the deck, and evenings stretch out with sea breezes and uninterrupted star views. It’s a polished base for travelers seeking nature-forward luxury.

3. Kissimmee (Orlando Area)

October in Kissimmee means comfortable theme park days without peak summer heat. Crowds ease slightly, and Halloween events begin across Orlando’s major parks.

Things to do in October

• Experience Halloween events at Universal and Disney

• Explore Celebration’s fall festivals

• Golf at nearby championship courses

• Visit airboat tours in the headwaters of the Everglades

Travel tips

• Plan park visits midweek for lighter crowds

• October evenings can be breezy – pack layers

• Purchase event tickets in advance for seasonal attractions

Where to stay

Wander Orlando Sky – 20 guests, 10 bedrooms
A ten-bedroom estate designed for large groups, this home accommodates up to twenty guests with room to truly spread out. Resort-style amenities, expansive entertaining spaces, and entertainment-focused interiors make it ideal for multi-family October getaways. After theme park days, returning here feels like entering a private retreat.

4. Sarasota

Cultural, coastal, and quietly refined, Sarasota shines in October. The beaches are warm, the humidity drops, and the arts scene returns in full swing.

Things to do in October

• Explore The Ringling Museum and gardens

• Walk Siesta Key Beach at sunset

• Attend early-season performances and gallery openings

• Paddleboard Sarasota Bay

Travel tips

• Reserve waterfront dining ahead of the weekends

• Plan beach mornings – afternoons stay warm

• October is ideal for kayaking before peak winter visitors arrive

Where to stay

Wander Sarasota Bay Breeze – 10 guests, 6 bedrooms
With six bedrooms accommodating up to ten guests, this coastal retreat offers generous living spaces and breezy bay views. Designed for seamless indoor-outdoor flow, it’s perfectly suited to October’s milder evenings and long, golden afternoons.

5. Destin

Destin’s emerald waters remain swimmable in October, but the atmosphere softens. It’s one of the best Florida vacation spots in October for beach lovers who want warmth without peak-season bustle.

Things to do in October

• Snorkel in clear Gulf waters

• Charter a fishing excursion

• Walk Henderson Beach State Park

• Visit HarborWalk Village for fall events

Travel tips

• Morning beach time offers the calmest conditions

• Bring reef-safe sunscreen; UV levels remain strong

• October is prime fishing season

Where to stay

Wander Destin Escape – 16 guests, 8 bedrooms
Spanning eight bedrooms and sleeping sixteen guests, this expansive coastal estate is built for gathering. Large common areas, refined finishes, and outdoor entertaining space make it ideal for family reunions or celebratory October trips.

6. Captiva

Captiva in October feels intimate and restorative. The shelling improves, sunsets deepen in color, and island life slows beautifully.

Things to do in October

• Collect seashells along Bowman’s Beach

• Paddle through mangroves

• Dine waterfront at sunset

• Explore nearby wildlife refuges

Travel tips

• October sunsets are especially vivid – plan for golden hour

• Rent bikes to explore the island quietly

• Book spa appointments ahead of weekends

Where to stay

Wander Captiva Eden – 18 guests, 6 bedrooms
This six-bedroom coastal estate welcomes up to eighteen guests in elevated island style. Expansive interiors open to private outdoor space, creating the kind of effortless luxury that defines fall in Captiva – warm days, cool evenings, and room for everyone to unwind.

7. Eastpoint

Often overlooked, Eastpoint offers raw Gulf Coast beauty in October. Fishing improves, beaches quiet down, and sunsets feel cinematic.

Things to do in October

• Charter a fishing trip in Apalachicola Bay

• Explore quiet barrier beaches

• Kayak calm coastal waters

• Visit nearby historic Apalachicola

Travel tips

• Stock up on supplies before heading to quieter stretches

• Evenings are cooler than summer – bring light layers

• Plan sunset dinners outdoors

Where to stay

Wander St. George Island Drift – 10 guests, 5 bedrooms
With five bedrooms sleeping ten guests, this elevated coastal home balances comfort and design-forward detail. October breezes move through expansive living spaces, making it ideal for a peaceful Gulf Coast retreat.

8. Port St. Joe

October is one of the best times to experience Port St. Joe’s understated charm. Beaches are wide open, temperatures are mild, and the small-town atmosphere shines.

Things to do in October

• Walk Cape San Blas trails

• Enjoy Gulf-front dining

• Fish along St. Joseph Bay

• Bike coastal paths

Travel tips

• Book boat rentals in advance

• October mornings are perfect for paddleboarding

• Pack for warm days and cooler evenings

Where to stay

Wander Port St. Joe Beach – 20 guests, 6 bedrooms
This six-bedroom beachfront property accommodates up to twenty guests, making it ideal for extended family gatherings. Expansive living areas and direct beach access create an immersive October coastal experience.

9. Bradenton Beach

Located on Anna Maria Island, Bradenton Beach is vibrant yet relaxed in October. The water stays warm, but the pace feels unhurried.

Things to do in October

• Stroll Bridge Street’s boutiques

• Paddleboard calm Gulf waters

• Enjoy sunset cruises

• Explore nearby nature preserves

Travel tips

• Early fall offers ideal swimming conditions

• Book weekend dining reservations early

• Rent bikes to explore the island

Where to stay

Wander Bradenton Beach – 14 guests, 7 bedrooms
Seven bedrooms host up to fourteen guests in this polished island retreat. Thoughtful design and generous gathering spaces make it perfect for fall family escapes.

10. Hollywood

Hollywood blends beachfront energy with refined South Florida style. October brings warm water, fewer crowds, and ideal outdoor evenings.

Things to do in October

• Walk the Hollywood Beach Broadwalk

• Explore waterfront dining

• Kayak through calm Intracoastal waters

• Visit nearby art and cultural events

Travel tips

• Early mornings are ideal for beach walks

• Evenings are perfect for waterfront dining

• October sees lower humidity than peak summer

Where to stay

Wander Hollywood Beach – 10 guests, 5 bedrooms
Sleeping ten across five bedrooms, this waterfront retreat pairs modern design with South Florida ease. Outdoor living areas make the most of October’s milder evenings.

What to Expect from Florida in October

• Daytime temperatures typically hover in the low-to-mid 80s°F

• Humidity drops compared to summer

• Gulf and Atlantic waters remain swimmable

• Beaches and attractions feel noticeably calmer

October sits at the edge of hurricane season, but it also marks a return to outdoor comfort and clearer skies. It’s one of the smartest months for travelers who want warmth without intensity.

Why October Is Ideal for Families, Couples & Long Stays

October blends summer’s warmth with fall’s calm. It’s ideal for:

• Multigenerational family gatherings

• Couples seeking quieter beachfront escapes

• Remote workers planning extended stays

• Travelers who value space and shoulder-season pricing

Plan Your October Escape with Wander

There isn’t just one of the best places to visit in Florida in October – there are many. From the serene Gulf Coast to vibrant South Florida shores, October reshapes the entire state into something more spacious and refined.

Choosing the right destination defines the tone of your trip. Choosing the right place to stay defines everything else.

Wander’s luxury vacation homes across Florida offer elevated design, seamless comfort, and the kind of thoughtful amenities that turn a warm October getaway into something exceptional. Wherever you decide to go, you’ll have a beautiful place to land.