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Hotels and vacation rentals in Middleburg serve a specific kind of trip, so start by deciding whether you want to walk to the historic district, sit on the beach, or have room for a family group. In Middleburg that choice narrows the list fast. Ask about parking, minimum night stays, and whether the posted rate includes resort, cleaning and tourist taxes, which can add 20 to 30 percent to the number you first saw. Hurricane season refund terms matter from June through November.
Pick the location before the property
Downtown means walking and higher rates. The beaches mean a car for everything but the sand. World Golf Village and CR 210 mean cheaper rooms and 20 to 30 minutes of driving. Decide what your trip is about and the right properties sort themselves out.
Add up the real nightly cost
Compare the all-in number: room rate plus county tourist tax, state sales tax, resort or amenity fees, cleaning fees on rentals, and parking. A $180 downtown room with $25 garage parking and fees can cost more than a $230 inn that includes a spot.
Check that a vacation rental is licensed
Florida requires most short term rentals to hold a DBPR transient lodging license, and St. Johns County collects tourist development tax from them. Legitimate hosts will give you the license number. A rental that cannot may be operating against HOA or county rules and could cancel on you.
Read the storm and cancellation policy
Hurricane season runs June through November and A1A evacuation orders do happen. Hotels usually waive fees under a mandatory evacuation; rentals vary widely. If you book through a platform, know whose policy actually applies.
Look at the room count and age of the property
Many downtown inns are converted historic houses with stairs, no elevator and small bathrooms. That is charming for a couple and difficult with a stroller or a wheelchair. Beachside condos built before 2000 may lack working elevators or updated kitchens, so ask for recent photos.
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