Ole Ole 5K – Orlando 2027 — Orlando, FL
The Ole Ole 5K takes place on May 2, 2026, in Orlando, Florida at 5165 Metrowest Boulevard. Despite its name, the event offers a 1-mile distance rather than the traditional 5K length. The race starts at 7:00 PM, making it an evening event for local runners and visiting athletes. Entry fees range from $37 to $55 depending on registration timing and options. This shorter distance format works well for those looking to test fitness or participate in a low-key weeknight race while traveling to the Orlando area.
Hotels Near This Race
Find accommodation close to the start line in Orlando, FL. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.
Ole Ole 5K – Orlando 2027 — Orlando, FL
Race day is approaching. Hotels fill up fast.
Race weekend dates pre-loaded on Booking.com. RaceHotelFinder may earn a commission at no extra cost to you.
Race Travel Insurance
Don't forget travel insurance for May 1.
You've trained for months and booked a trip to Orlando, FL. A pre-race injury, a delayed flight, or a family emergency can derail the whole thing. Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it, and may cover medical costs if something goes wrong on the course. Plans typically only run 5-7% of your total trip cost — and running events are covered under standard plans with no additional coverage needed.
- Trip cancellation up to 100% of prepaid costs
- Running events covered under standard plans — no add-ons needed
- Trip interruption up to 150% of non-refundable costs
- Emergency medical up to $250,000
- Cancel For Any Reason add-on available
- 24/7 real-time support
Affiliate links — we may earn a commission at no cost to you. Coverage terms vary by state and plan. Review policy details before purchase.
Frequently Asked Questions
When is Ole Ole 5K – Orlando 2027 — Orlando, FL?
Ole Ole 5K – Orlando 2027 — Orlando, FL takes place on May 1, 2027. The race is held in Orlando, Florida.
Where is Ole Ole 5K – Orlando 2027 — Orlando, FL held?
Ole Ole 5K – Orlando 2027 — Orlando, FL is held at 5165 Metrowest Boulevard in Orlando, Florida.
Where can I find hotels near Ole Ole 5K – Orlando 2027 — Orlando, FL?
RaceHotelFinder shows hotels sorted by distance from the race venue in Orlando. Use the map or list view on this page to compare options and book race weekend accommodation.