Title: Book the Best BOUTIQUE Hotels in Winter Park in 2026 | Expedia.ca

[Hotels in Winter Park](https://expedia.ca/Winter-Park-Hotels.d7902.Travel-Guide-Hotels)[Vacation Rentals in Winter Park](https://expedia.ca/Winter-Park-Vacation-Rentals.d7902.Travel-Guide-VacationRentals)[Flights to Winter Park](https://expedia.ca/Cheap-Flights-To-Winter-Park.d7902.Travel-Guide-Flights)[Winter Park Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Park.d7902.Car-Rental-Guide)[Winter Park Vacation Packages](https://expedia.ca/Winter-Park.d7902.Destination-Travel-Guides)

![Kraft Azalea Gardens showing a fountain, a park and a pond](https://images.trvl-media.com/place/553248621532654339/aef9d03a-cd86-4dcc-8e9d-049aef598da5.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find Boutique Hotels in Winter Park, FL 

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## Check availability on Winter Park Boutique Hotels

Tonight

[Dec 24 - Dec 25](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-12-24&endDate=2025-12-25&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 25 - Dec 26](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-12-25&endDate=2025-12-26&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-12-26&endDate=2025-12-28&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2026-01-02&endDate=2026-01-04&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winter Park boutique hotels

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/51fdc461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/93bcae58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, dinner, brunch served; southern cuisine ](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/104a8bc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 outdoor pools, open 10:00 AM to 5:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/2186e4f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Alfond Inn

[](https://www.expedia.ca/Orlando-Hotels-The-Alfond-Inn.h19791.Hotel-Information)

Winter Park

9.6/10

Exceptional

(1000)

"Great very clean staff wonderful "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lisa

[](https://www.expedia.ca/Orlando-Hotels-The-Alfond-Inn.h19791.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-07&endDate=2026-01-08&regionId=7902&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true)

## Top Winter Park Hotel Reviews

![Caribe Royale Orlando](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/033f2fa5_y.jpg)

### Caribe Royale Orlando

10/10 Excellent

"Yes"

[](https://expedia.ca/Orlando-Hotels-Caribe-Royale-Orlando.h40865.Hotel-Information)

![Waldorf Astoria Orlando - An Official Walt Disney World® Hotel](https://images.trvl-media.com/lodging/3000000/2440000/2432800/2432727/0589fd64_y.jpg)

### Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

10/10 Excellent

"Great stay "

[](https://expedia.ca/Orlando-Hotels-Waldorf-Astoria-Orlando.h2432727.Hotel-Information)

![Hyatt Regency Orlando](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/1bb0a2ac_y.jpg)

### Hyatt Regency Orlando

10/10 Excellent

"Staff was great. Great location for an event at the convention center. "

[](https://expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.Hotel-Information)

## Frequently asked questions

### What's the best boutique-style hotel in Winter Park?

### What's there to see and do in Winter Park?

### What kind of weather should I plan for when I travel to Winter Park?

### What's the best way to get to my boutique hotel in Winter Park?

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