Where to stay near downtown Winter Park, Florida: boutique hotels on and near Park Avenue, nearby options, drive times and local tips from Orlando.
Winter Park is the part of Orlando locals take out-of-town friends to when they want to show off. Downtown is a few walkable blocks of brick streets around Central Park, where Park Avenue's cafes, galleries and boutiques look out over live oaks and the old train depot.
There are only a handful of hotels right downtown, which is part of the charm, and they book up on festival weekends and Rollins College events. This guide covers the boutique stays within walking distance of Park Avenue, where else to look, and how to spend a slow Winter Park weekend.
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Each area has trade-offs. Here is how they compare.
Walk to everything
Staying downtown means walking to dinner, the Saturday farmers market, the Morse Museum and the Scenic Boat Tour dock.
About 10 minutes
Just north along I-4, Maitland and Altamonte have more mainstream hotels and easy access to Winter Park.
About 15 minutes, or a short SunRail ride
Downtown Orlando hotels pair Winter Park days with Lake Eola, sports and nightlife, and SunRail connects the two.
Compare live rates for your dates on each hotel before you book.
| To | Approx. drive |
|---|---|
| Park Avenue (from downtown hotels) | 2–5 min walk |
| Downtown Orlando | 15 min |
| Orlando International Airport (MCO) | 30 min |
| Universal Orlando Resort | 25 min |
| Walt Disney World | 35–40 min |
Times are without traffic. Allow extra time on weekday rush hours and event days.
The Scenic Boat Tour has been running since 1938. The pontoon glides through narrow canals between three lakes, past lakefront estates and Rollins College, and it leaves from the dock at the end of Morse Boulevard.
The Winter Park Farmers' Market fills the old train depot on Saturday mornings. Get there early for pastries and coffee, then walk Park Avenue.
The Charles Hosmer Morse Museum of American Art on Park Avenue holds a world-famous Tiffany collection, including a chapel interior Louis Comfort Tiffany designed.
SunRail's Winter Park station sits beside Central Park, so you can visit from downtown Orlando without looking for parking.
Real, bookable experiences with live prices and traveler reviews.
Free cancellation
Free cancellation
Free cancellationYes, a few. The Park Plaza Hotel sits right on Park Avenue, and The Alfond Inn is a short walk away. Rooms are limited, so book early for weekends.
Yes, for couples, repeat visitors and anyone who prefers restaurants and walkable streets to theme park crowds. It is about 35 to 40 minutes from Disney, so it is less ideal for park-heavy trips.
About 15 minutes by car, or a short SunRail train ride.
