Where to Stay in Florida

South Beach runs from 5th to 23rd Street between Ocean Drive and Alton Road. Stay between 8th and 17th Street to be in the middle of everything. Ocean Drive is loud and touristy, but Collins Avenue one block back has the nicer hotels and quieter rooms. Lincoln Road Mall is a pedestrian-only stretch of shops and cafes. Espanola Way feels like a small Spanish village tucked between Washington and Drexel. Skip anything south of 5th unless you want condos with no nightlife, and skip north of 23rd unless you booked Faena. Walking is easy. Driving and parking are not.

Best for

Couplesparty travelersdesign lovers

Walk times

Ocean Drive to Lincoln Road 12 min
8th Street to South Pointe Park 15 min
Collins at 16th to Faena District 10 min

Skip if: You want quiet, you have small kids, or you hate paying $40 for valet

Local tip: Take the free South Beach Trolley along Washington Avenue. It runs every 15 minutes and saves you the parking nightmare.

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$246per night

Old Town, Key West

The end of the road, in the best way

Luxury $280-$650/night

Old Town is the historic core, roughly bounded by Truman Avenue, White Street, and the water. Duval Street is the spine, but the real charm is one block off it on streets like Eaton, Caroline, and Fleming. Stay near Mallory Square if you want sunset celebrations at your doorstep, or near Bahama Village for quieter conch houses and Blue Heaven brunches. The Truman Annex area is leafy and residential. Avoid New Town near the airport unless you only need a cheap bed. Everything in Old Town is walkable or bikeable, and most hotels lend bikes for free.

Best for

Couplesfoodiesanyone over 30 who still wants a drink at 2am

Walk times

Mallory Square to Hemingway House 10 min
Duval and Caroline to Southernmost Point 18 min
Bahama Village to Higgs Beach 14 min

Skip if: You came for big resorts or all-inclusive pools

Local tip: Book a hotel with parking included. Public parking in Old Town runs $4 per hour and lots fill by 11am during high season.

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$314per night

Old Naples

Florida the way it used to be, with a serious wine list

Luxury $350-$900/night

Old Naples sits between 5th Avenue South and the Gulf, running roughly from Central Avenue down to 14th Avenue South. Fifth Avenue South is the dining and shopping spine. Third Street South is the older, leafier sister with courtyards and boutiques. The Naples Pier at 12th Avenue South is the postcard view at sunset. Stay west of US-41 to keep the beach walkable. Skip North Naples and Pelican Bay if you want to walk to dinner, since those are car-dependent gated zones. The Bayfront and Tin City areas are touristy but fun for one night.

Best for

Couplesretireesanyone wanting calm Gulf water

Walk times

5th Avenue South to Naples Pier 12 min
3rd Street South to the beach 8 min
Pier to Lowdermilk Park 22 min

Skip if: You are on a budget or traveling with teenagers who need action

Local tip: Tuesday and Thursday are the best dinner reservation nights on 5th Avenue. Weekends book out two weeks ahead in season, which runs January through April.

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$392per night

Lake Buena Vista, Orlando

Closest to Disney without paying Disney resort prices

Mid-range $160-$420/night

Lake Buena Vista is the strip of hotels just outside Walt Disney World, mostly along Hotel Plaza Boulevard and around Disney Springs. Staying here gets you 30 minute extra theme park hours at Disney parks and free shuttle buses, without the official resort price tag. The Disney Springs area has free parking, dozens of restaurants, and is walkable from several hotels. Skip International Drive if Disney is your priority, since traffic on I-4 can add 45 minutes. Skip Kissimmee Highway 192 unless you booked a vacation home, since the strip is dated and walking is unpleasant.

Best for

Familiesfirst-time Disney visitorstheme park weeks

Walk times

Hotel Plaza Boulevard to Disney Springs 10 min
Disney Springs to Saratoga Springs Resort 20 min
Buena Vista Drive bus stop to Magic Kingdom 25 min

Skip if: You came for beaches or Universal Studios

Local tip: Book a Disney Springs area hotel with a Disney shuttle and skip the rental car. Disney parking is $30 per day and the buses run every 20 minutes from 6am to midnight.

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$179per night