Extended Stay Hotels in Winter Park | Flexible Booking Options

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Top Winter Park Extended Stay Hotels | Reserve now, pay later

Winter Park Gem, 2BR Near Parks, 3MI to Downtown

College Park

Danielle H.

$253 nightly

Dec 10 - Dec 11

Total with taxes and fees

Quiet and safe neighborhood come to this great place with lots of room for relax

Orlando

Geri Lamborn M.

$244 nightly

Dec 21 - Dec 22

Total with taxes and fees

Funky Remodeled Otown Bungalow Sleeps 8

Fairview Shores

$213 nightly

Dec 14 - Dec 15

Total with taxes and fees

Stylish Boutique Guest house in Winter Park

Winter Park

Colin W.

$313 nightly

Dec 15 - Dec 16

Total with taxes and fees

1-bedroom vacation room just 12 minutes from University of Central Florida

Orlando

Marek K.

$148 nightly

Dec 21 - Dec 22

Total with taxes and fees

Magic Studio

Orlando

Nan D.

$204 nightly

Dec 31 - Jan 1, 2026

Total with taxes and fees

Charming home @wp. Patio +Gazebo. close to highwys

Fairview Shores

$204 nightly

Dec 10 - Dec 11

Total with taxes and fees

Sleek, Spacious & Central – Your Ideal Getaway

Fairview Shores

$174 nightly

Dec 26 - Dec 27

Total with taxes and fees

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Find out more about Winter Park

Discover top Winter Park attractions

Winter Park, Florida, offers a delightful mix of cultural attractions and outdoor activities that cater to travelers seeking quality experiences. Start your journey at the Charles Hosmer Morse Museum of American Art, home to the world's most comprehensive collection of works by Louis Comfort Tiffany, including stunning stained glass and ceramics. For a taste of the outdoors, take a leisurely stroll through the beautiful Mead Botanical Garden, where you can explore scenic trails, butterfly gardens, and serene waterways – perfect for a family outing. Families will love the interactive exhibits at the Orlando Science Center, which is just a short drive away, providing an engaging and educational experience for children of all ages. After a day of exploration, unwind at the picturesque Lake Virginia, where you can rent a kayak or take a scenic boat tour to soak in the stunning views. Finally, the quaint Park Avenue offers a charming shopping and dining experience, with upscale boutiques and gourmet eateries that will satisfy any culinary craving. Consider staying in the heart of Winter Park, where boutique hotels like the Alfond Inn provide luxurious accommodations with exceptional service. This area allows you to easily explore local attractions, enjoy fine dining, and retreat to your comfortable stay after a day of adventures, ensuring every moment of your trip is memorable.

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Most booked related extended stays in Winter Park in 2026

Winter Park vacation homes with a kitchen

Frequently asked questions

What are the best long-term hotels in Winter Park?

The best long-term hotels in Winter Park feature lots of conveniences that let you unwind and enjoy your downtime. For example, Casa Aloma. In addition to a kitchen, you'll have access to a sofa bed and a barbecue grill. Another great pick where you can put your feet up is Cute Bungalow Minutes Walk From Park Avenue. Amenities like a queen bed, an oven and kitchen facilities will help make your extended stay in Winter Park even more comfortable.

What are the top pet-friendly extended stay hotels in Winter Park?

You don't have to leave your best chum with a pet sitter during your extended stay in Winter Park. One place that'll welcome your doggy — and you — with open arms is Beautiful Peaceful Fenced Yard Home. It comes with amenities designed for both humans and furry guests, including pet-friendly services and a garden. Your pup can also join in the good times at Mid Century Luxury, 1 Block From Park Ave - #3. Plan a long-term stay in a pet-friendly room and make use of this hotel's many conveniences, such as pet-friendly services and a water park.

What are the best extended stay hotels in Winter Park near Winter Park Memorial Hospital?

Cozy Comfort In The Heart Of Winter Park is popular for its convenient location. This long-term stay is around 2 mi from Winter Park Memorial Hospital and features on-site parking options and a patio. We also recommend Mid Century Luxury, 1 Block From Park Ave - #3. Just 1 mi away, guests have access to towels and internet services.

What's the best extended stay hotel in downtown Winter Park?

Soak up the culture and energy of Winter Park from Cute Bungalow Minutes Walk From Park Avenue. With conveniences like an oven and a queen bed, you'll be kicking it with the locals while staying in the center of this fantastic destination. Also take a look at Casa Winter Park. Another extended stay hotel that'll place you in the downtown area, it offers a washing machine and a sofa bed. When you're ready to enjoy some of the best attractions in town, Full Sail University and Rollins College should be on your must-see list.

What are the best extended stay hotels with kitchens in Winter Park?

Do some sightseeing and then return and whip up a delicious homestyle meal at Summer Special. Offering a kitchen, free WiFi and a firepit, it has conveniences that are well suited to a long-term stay with the family. Cottage On Cornell - Quaint And Cozy W is another popular property with a kitchen. Make the most of a barbecue grill, a firepit and more during your visit to Winter Park.

Can I find extended stay hotels with pools in Winter Park?

Nothing screams good times like a pool does. Pack your bikini or board shorts and spend your days splashing around at Casa Aloma. A kitchen, a barbecue grill and a swimming pool are among the amenities here. Another top pick for your extended stay in Winter Park is Just Like Home. . . With A Pool. The kids (and you!) will love the pool at this getaway, which also comes with a queen bed, a swimming pool and a kitchen where you can cook up a storm.Anytime is a perfect time to vacation in Winter Park, which has a humid subtropical climate. But if you'd prefer to spend your escape frolicking about in the water, head there in the summer months when temperatures range between 77 ºF and 91 ºF.

Why book an extended stay hotel in Winter Park through Expedia?

From our exclusive deals to our rewards programs, you can expect to save big when you reserve your extended stay in Winter Park through Expedia. Enter your travel dates to discover our range of long-term rentals, then narrow down your search using our filters to find your perfect accommodations. Our extended stay hotels in Winter Park come with conveniences like kitchens, laundries and refrigerators to help make your long-term stay feel homey. Whether you're seeking a hotel for a quick stay or a property with cheaper weekly rates, Expedia will help you find the right match.

What can I expect from an extended stay hotel?

Book an extended stay hotel in Winter Park and take all the time you need exploring this top destination. In addition to being able to stay a few weeks or more, these types of properties include conveniences that'll make your journey an easy one. Kitchens and laundry areas are just the start. To help you find the perfect extended stay hotel, use Expedia's filters to fine-tune your search based on amenities, price range, area and more. Often with competitive weekly rates, extended stay hotels can be more affordable than standard accommodations.

Top Winter Park Hotel Reviews

Universal's Cabana Bay Beach Resort

10/10 Excellent

"The wait to check in was over 30 minutes. The desk agent I had DJ was marvelous. She was very personable and helpful. It was worth the wait to have someone so wonderful "