October 21, 2026There’s still time to make Halloween a beach weekend.
Oversee has homes showing availability for Friday, October 30, through Sunday, November 1, including a stay in Seaside itself. And with Halloween falling on Saturday, you can arrive, unpack, and wake up at the beach before anyone needs help getting into a costume.
We’ve narrowed the choices to five homes, each with a different reason to go: Seaside’s Halloween celebration, a private pool for the whole family, room for the dog, or a couple of days enjoying your favorite 30A neighborhood.
Start with the one that sounds like your kind of weekend.
Availability checked October 21, 2026, for October 30–November 1. Homes remain subject to booking availability. Enter your full guest count and any pets to confirm the current total and booking requirements.
Ingle’s Nest: Spend Halloween in Seaside
Seaside | Sleeps 8 | 3 bedrooms | 2.5 bathrooms
For a trip built around Halloween in Seaside, this is our first pick.
Ingle’s Nest puts you in the neighborhood where you want to spend Saturday evening. The home sits on Forest Street, surrounded by greenery, with screened and covered porches that make a two-night trip feel worth slowing down for.
There’s a proper kitchen for breakfast before heading out, a comfortable living room, and three included bikes for exploring. The listing also includes access to Seaside’s swimming, tennis, and fitness amenities, with West Ruskin Beach Access approximately 0.2 miles away.
We’d choose it for a family who wants to enjoy Seaside throughout the weekend: coffee, a little shopping, beach time, then back to the house to get everyone into costume. The Halloween outing becomes part of your stay in town, rather than a separate trip to another neighborhood.
Seaside’s Halloween celebration is scheduled for Saturday, October 31, from 4–7 p.m. in Central Square.
Check Ingle’s Nest for Halloween weekend →
Sapphire Bay: Bring the Cousins, Too
Seagrove | Sleeps 15 | 5 bedrooms | 5.5 bathrooms
If one family’s beach idea tends to become everyone’s beach idea, take a look at Sapphire Bay.
Five bedrooms and five-and-a-half bathrooms give a larger group room to settle in. The sleeping arrangements include king and queen suites alongside bunk accommodations, making this a tempting option for an extended-family weekend.
The private pool gives Saturday afternoon a plan of its own. Five bikes and a six-seat golf cart are included, while the kitchen’s large island offers a natural gathering spot for breakfast, snacks, and the post-trick-or-treat candy inspection.
We’d pick Sapphire Bay for families who want as much time together at the house as they do out exploring. Head to your chosen Halloween event, then come back to a place with room for everyone.
Seasonal pool heating is available for an additional charge; arrange it with Oversee before your stay.
Good Times and Tan Lines: A Pool Weekend With the Dog
Seagrove | Sleeps 12 | 5 bedrooms | 4.5 bathrooms
The dog doesn’t have to be the reason a last-minute trip falls apart.
Good Times and Tan Lines considers up to two dogs under 50 pounds, with a nonrefundable fee per dog. It also brings a private pool, four included bikes, and plenty of outdoor space for enjoying the hours between Halloween outings.
Inside, the kitchen has an oversized island, and sliding doors open onto a deck overlooking the pool. Bedrooms are spread across three floors, with a bunkroom giving younger guests a space to claim.
This would be our pick for a larger family looking for a pet-friendly stay with a private pool. Pack something easy to cook on Friday night, settle everyone in, and leave Saturday open for the beach and costumes.
Confirm pet approval and fees when booking. Pool heating is optional and costs extra.
See Good Times and Tan Lines →
Salt and Pine: Keep the Weekend Small and Easy
Dune Allen | Sleeps 6 | 3 bedrooms | 2.5 bathrooms
Not every Halloween getaway needs a crowd.
Salt and Pine is a single-level home in Cypress Dunes with two king bedrooms and a third bedroom with twin beds. The kitchen, dining area, and living room connect, so making breakfast doesn’t mean missing the conversation.
Four bikes and a six-seat golf cart are included, along with access to the community infinity pool and fitness center. There are also board games and puzzles for an evening back at the house.
We’d choose Salt and Pine for a family or a small group who wants to stay on the western end of 30A. You can make a Halloween outing part of the weekend and still leave plenty of time for porch coffee and a quiet dinner.
For beach plans, the listing places Dune Allen Beach Access approximately 1.6 miles away.
Take a look at Salt and Pine →
Gulf and Green Main: Make Rosemary Beach Your Weekend Address
Rosemary Beach | Sleeps 8 | 3 bedrooms | 3.5 bathrooms
A rooftop pool is a pretty persuasive answer to “Should we go?”
Gulf and Green Main sits across from Eastern Green in Rosemary Beach, with private beach access, a courtyard, and Gulf views from the rooftop. The three bedrooms include a king room, a queen room, and a bunkroom, each with its own bathroom.
We’d pick this home for guests who already love Rosemary’s restaurants, shops, and neighborhood walks—and want a reason to return before the holidays. Spend part of the day out, then leave time to enjoy the house itself.
Seasonal pool heating carries an additional charge. This listing is for the main home; review its access details, including the owner lockout covering most of the third floor and its balcony.
One date to know: Rosemary Beach’s organized Halloween Bash takes place October 24, the weekend before this stay. Choose this home for a Rosemary Beach getaway, with Halloween-weekend events elsewhere along the coast.
Pick Your Halloween Outing
Once you’ve chosen the house, the weekend doesn’t need much more planning.
On Friday, October 30, The Big Chill’s Halloween party runs from 5–9:30 p.m., with trick-or-treating during the first hour, crafts, and a DJ dance party. Allow time to arrive and check in before heading over.
On Saturday, October 31, choose Seaside’s celebration from 4–7 p.m., or head toward Miramar Beach for Grand Boulevard’s trick-or-treating from 4–6 p.m. Baytowne Wharf’s Trick or Treat Street follows from 6–8 p.m., with fireworks scheduled for 8 p.m. Pick the outing that suits your location and your children’s energy levels.
You’ll find more details and organizer links in our Halloween on 30A guide. Check the latest event updates before leaving the house.
Your Last-Minute Plan Starts With a House
Choose your favorite, check October 30–November 1, and enter everyone who’s coming to see the current availability and total price.
If you’d like help comparing the homes, our Oversee team is available at 888-290-3489 or booknow@oversee.us. We can help with the details that matter for a short stay, from sleeping arrangements to optional pool heating.
Two nights, a day at the beach, and Halloween somewhere a little different. There’s still time to put it on the calendar.
