History and Culture

In the tapestry of time, Winter Park’s rich history unfurls with the arrival of the South Florida Railroad in 1880, marking the genesis of a city destined for refinement. As the locomotives rolled in, the charm of Winter Park began to carve its identity, and this narrative gained depth with the establishment of Rollins College, Florida’s inaugural four-year university. The inception of Rollins College not only transformed Winter Park into an educational epicenter but also solidified its status as an intellectual and cultural hub.
At the heart of this flourishing city, Park Avenue emerged as a testament to Winter Park’s commitment to elegance and sophistication. This tree-lined cobblestone street, weaving through the cityscape, became the pulsating core of the charm of Winter Park. Adorned with acclaimed eateries, museums, and high-end shopping establishments, Park Avenue captivates visitors with its alluring blend of cultural vibrancy and refined tastes.
Delve into the cultural narrative as you traverse Park Avenue, where every step reveals a piece of Winter Park’s story. Acclaimed eateries dot the landscape, offering gastronomic delights that mirror the city’s commitment to culinary excellence. Museums stand as guardians of history and art, beckoning patrons to explore the diverse cultural tapestry that defines Winter Park.
Accommodations at Casiola vacation homes
Culinary Delights
Winter Park’s culinary landscape unfolds as a haven for discerning food enthusiasts, where the exquisite charm of Winter Park is artfully translated onto every plate. Renowned chefs, notably the visionary Brandon McGlamery, grace the city with their culinary prowess, pushing the boundaries of gastronomic excellence. At the heart of this culinary renaissance lies Prato, a distinguished restaurant that has earned its place in the MICHELIN Guide as a Recommended establishment. Here, indulge in the mastery of innovative Italian cuisine, where each dish is a symphony of flavors curated to perfection.
Venturing beyond, just a short distance away in Maitland, Luke’s Kitchen emerges as a culinary gem specializing in classic American dishes. The blend of traditional flavors with a modern twist creates an unparalleled dining experience that resonates with the unique charm that defines Winter Park.
The culinary adventure continues with The Ravenous Pig, a seasonal gastropub that adds a delightful dimension to Winter Park’s diverse gastronomic tapestry. Embracing a farm-to-table philosophy, The Ravenous Pig crafts a menu that mirrors the seasonal abundance of Central Florida. This commitment to freshness and innovation has earned the gastropub prestigious recognition in the form of a MICHELIN Bib Gourmand.
Diverse Dining Options
Shopping Paradise

Indulge in a delightful shopping escapade along the enchanting Park Avenue, where the irresistible charm of Winter Park extends to every boutique and store. For those with a penchant for fashion, Winter Park’s local boutiques on Park Avenue are a treasure trove of style. Tuni Trendy + Chic and John Craig Clothier cater to adults, offering sophisticated and on-trend fashion choices that reflect the city’s commitment to elegance. Meanwhile, Tugboat & The Bird and Bebe’s and Liz’s ensure that even the youngest fashion enthusiasts are adorned in the latest and most fashionable attire.
National retailers like Lilly Pulitzer and J. McLaughlin seamlessly weave into the fabric of Park Avenue, contributing to the diverse shopping experience that Winter Park offers. Here, every storefront tells a story, and every boutique adds a layer to the vibrant tapestry of the city’s unique charm. As you explore the charming streets, specialty merchants like The Ancient Olive Gourmet and Writer’s Block Bookstore beckon, promising unique finds that transcend the ordinary. Immerse yourself in a shopping experience that mirrors the eclectic and sophisticated essence that defines the charm of Winter Park.
Winter Park’s Park Avenue is not just a shopping district, it is a celebration of style, uniqueness, and the vibrant charm of Winter Park. From local boutiques catering to adults and children alike to national retailers and specialty merchants, each storefront contributes to the diverse and enchanting shopping experience that makes Winter Park a haven for those seeking to explore the city’s unique charm through the lens of fashion and discovery.
Art and Culture
Immerse yourself in the artistic tapestry that defines the unmistakable charm of Winter Park, where the city’s unwavering commitment to the arts comes to life in its galleries and museums. Discover the treasures housed within the Rollins Museum of Art, where a vast collection spanning ancient to modern periods captivates art enthusiasts and provides a glimpse into the city’s cultural evolution. Delve into the artistic legacy of Winter Park at The Charles Hosmer Morse Museum of American Art, home to the world’s most comprehensive collection of Louis Comfort Tiffany’s creations. Wander through the museum’s halls, where the delicate beauty of Tiffany’s masterpieces unfolds, adding a layer of enchantment to Winter Park’s cultural narrative.
The city’s celebration of the arts extends beyond museum walls to the vibrant streets, evident in the annual Winter Park Sidewalk Art Festival and Winter Park Autumn Art Festival. These outdoor extravaganzas showcase the creativity of both local and international artists, transforming the city into a living canvas. As you stroll through the festivals, the charm of Winter Park becomes palpable, interwoven with the strokes of paint, the intricacies of sculptures, and the vibrant energy that emanates from each artistic creation. Winter Park’s commitment to fostering a thriving arts community is not merely seen, it is experienced, making every visit an immersive journey into the heart of the city’s cultural identity.
Cultural Heritage and Outdoor Adventures
Discover the immersive cultural heritage of Winter Park at the Hannibal Square Heritage Center, an invaluable repository of history where the narrative of the Hannibal Square district unfolds. This cultural haven unravels the origins of Winter Park, tracing its evolution into a prestigious neighborhood and shedding light on its pivotal role in Civil Rights history. Gain insights into the city’s transformative journey, from its humble beginnings to becoming a cultural epicenter, with the Heritage Center serving as a poignant reminder of Winter Park’s enduring legacy.
For outdoor enthusiasts, Winter Park extends an invitation to explore its natural wonders, adding an adventurous layer to the city’s diverse offerings. The Winter Park Chain of Lakes, with its 12 pristine lakes spanning 2,781 acres, provides a serene backdrop for water-based activities. Immerse yourself in the picturesque surroundings on the Winter Park Scenic Boat Tour, gliding past multimillion-dollar mansions, Rollins College, and the scenic Kraft Azalea Gardens. As you navigate the city’s waterways, the charm of Winter Park becomes palpable, harmoniously blending nature with urban sophistication. Beyond the water, Winter Park boasts an array of parks and gardens, from the beautifully curated Mead Botanical Garden to the historic Winter Park Golf Course, each contributing to the city’s allure. In every outdoor haven, the multifaceted charm of Winter Park prevails, inviting visitors to explore the city’s rich tapestry of history and nature.
Discovering the Enchanting Charm of Winter Park with Casiola vacation homes
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6 Bedroom W/Private Pool! Spa! Near Disney!
House - Solterra Resort - Orlando
Welcome to your luxurious vacation retreat at Solterra Resort! Nestled within this prestigious community, this stunning vacation pool home offers the perfect blend of comfort, convenience, and entertainment for your family getaway. Step into elegance and modernity as you enter this meticulously designed property. The formal living area sets the stage for relaxation and sophistication, while the spacious living area provides ample space for gatherings and quality time with loved ones. Enjoy culinary delights in the dining area, prepared in the fully equipped kitchen featuring top-of-the-line appliances and granite countertops. With six uniquely designed bedrooms spread across the home, there's plenty of space for everyone to unwind and rest after a day of adventures. Bedroom 1, is a haven of luxury, featuring a plush king-size bed adorned with premium linens. Unwind in front of the smart TV or bask in the gentle breeze from the ceiling fan. Bedroom , indulge in comfort in this spacious bedroom, featuring another king-size bed and a smart TV for entertainment. The ceiling fan provides a gentle breeze, while the private bathroom offers both a walk-in shower and bathtub for ultimate relaxation. Bedroom 3, retreat to tranquility in this serene bedroom, featuring a queen-size bed draped in luxurious linens. Enjoy entertainment on the smart TV or unwind under the gentle breeze of the ceiling fan. The private bathroom includes a bathtub for a soothing soak. Bedroom 4, perfect for guests or children, this cozy bedroom features two charming twin beds. The room is equipped with a smart TV for entertainment and a ceiling fan for added comfort. The private bathroom includes a bathtub for a relaxing bath. Bedroom 5, step into luxury in this spacious bedroom, featuring a queen-size bed adorned with premium linens. Relax in front of the smart TV or enjoy the gentle breeze from the ceiling fan. The private bathroom includes a bathtub for a rejuvenating soak. Bedroom 6, ideal for guests or children, this charming bedroom boasts two cozy twin beds. The room features a smart TV for entertainment and a ceiling fan for added comfort. The private bathroom includes a bathtub for a soothing bath. Entertainment abounds in this vacation home, with a private game room equipped with a pool table and foosball table for hours of fun. Step outside to your private pool and spa, where you can soak up the Florida sun or enjoy a refreshing dip. **Optional pool heat is available for $35/day + tax. - We recommend adding this option to your reservation between the months of November and April.** The outdoor dining area and BBQ grill provide the perfect setting for al fresco meals and gatherings with friends and family. Indulge in the resort's unparalleled amenities, including a spectacular pool with a lazy river and slide, perfect for endless hours of fun in the sun. Stay active at the on-site gym, unwind at the bars, or let the little ones explore the playground. Located just a short drive from the magic of Disney and a plethora of restaurants and shops, this vacation pool home at Solterra Resort offers the ultimate in convenience and luxury. And with free WiFi and a washer and dryer included, you'll have everything you need for a seamless and memorable stay. Book your getaway today and create unforgettable memories at this exquisite vacation retreat!- 12
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- 5.5
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$146/night -
Arcade games * Smart TV's * Close to Parks
Condo - Vista Cay Resort - Orlando
Beautifully remodeled ocean-themed condo with a brand new look and feel. This recently renovated unit features exquisite tile flooring throughout, ensuring a clean and comfortable environment for all guests. Say goodbye to carpets and hello to a fresh, modern space. Step into a world of comfort with brand new furniture and a vibrant coat of paint that brings a breath of fresh air to the entire space. Each room is equipped with a Roku smart TV, and the living room boosts an arcade with over 100 classic arcade games, providing endless entertainment options for everyone. The kitchen is stocked with basic essentials, allowing you to whip up a quick meal whenever you'd like. And for added convenience, a dedicated laundry room is equipped with a full-size washer and dryer. Located in the heart of Vista Cay resort in Orlando, this condo offers access to a host of fantastic amenities. Take a dip in one of the two large heated resort pools or unwind in the two spacious hot tubs. Stay active in the modern fitness center, or let the little ones splash around in the kiddie pool. The game room, playground, and sport courts provide additional opportunities for fun and recreation. BBQ enthusiasts will love the designated area, while the lakeside walking/jogging trail offers a scenic route for exercise. With so much to do within the resort, you might find it hard to leave. Conveniently within walking distance, you'll find grocery stores and restaurants for all your needs. For evening entertainment, venture just a mile or two away to discover attractions like Top Golf, Andretti Racing, Icon Park, and a plethora of restaurants and activities along International Drive. Orlando's major theme parks like Universal, Disney and SeaWorld are all less than 15 minutes away. Bedroom 1 features a luxurious king bed, while Bedroom 2 offers another spacious king bed for a restful night's sleep. Bedroom 3 provides two cozy queen beds. The large closet has been converted into a sleeping area with two standard size twin beds, ideal for the kids. Experience the perfect blend of comfort, convenience, and coastal charm at our ocean-themed condo. Book now and make your Orlando getaway one to remember!- 10
- 3
- 2
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$123/night -
Free Water Park * Themed Rooms * Pool + BBQ * Near Disney!
Townhome - The Cove East - Orlando
Welcome to our enchanting townhome in The Cove East at the newest phase of Storey Lake Resort! This vacation home is a hidden gem nestled within the resort, offering a truly magical experience for your stay. Prepare to embark on an exciting adventure as you uncover the 20 hidden Mickeys scattered throughout the house, adding an element of delight and surprise to your vacation. As you step inside, you'll be greeted by a wonderfull private splash pool, perfect for those warm Florida days. Imagine lounging on the comfortable lounge chairs, sipping your favorite beverage while the enticing aroma of a barbecue fills the air from the adjacent grill. The outdoor dining table invites you to savor delicious meals under the clear blue skies, creating memorable moments with your loved ones. **Optional pool and spa heat is available for $35/day + tax. We would recommend adding this option to your reservation between the months of November and April.** Enter the townhome and discover the beautiful and impeccably decorated living room. Sink into the plush seating as you unwind after a day of exploration, and indulge in entertainment with the smart TV at your fingertips. The dining area, with its charming view of the pool area, provides a comfortable and inviting space for shared meals and laughter. The fully equipped kitchen boasts sleek stainless steel appliances, ensuring convenience and ease as you prepare your favorite dishes. This delightful abode features four bedrooms to accommodate your family and friends. The first bedroom, located on the first floor, boasts a comfortable queen-size bed adorned in beautiful, relaxing colors. It also offers a smart TV for your entertainment needs. The main bedroom on the second floor welcomes you with a king-size bed, a smart TV, and a ceiling fan to ensure a comfortable night's sleep. Unwind in the privacy of your own bathroom, complete with a combination shower and bathtub. The third bedroom, playfully decorated with Mickey Mouse themes, offers two single beds and a smart TV. It's perfect for younger guests or those who are young at heart. The fourth bedroom is a haven for Star Wars enthusiasts, featuring two bunk beds with a total of four single beds and a smart TV. The kids will delight in this imaginative space. The third bathroom features a walk-in shower, providing convenience for all guests. Beyond the comforts of this townhome, the Storylake Resort itself offers a wealth of amenities and attractions. Located in close proximity to the renowned theme parks of Orlando, including Walt Disney World Resort, Universal Orlando Resort, and SeaWorld Orlando, adventure awaits just moments from your doorstep. Immerse yourself in the magic and thrills of these world-class attractions, creating cherished memories that will last a lifetime. When it's time to refuel, the resort's convenient location ensures easy access to an array of restaurants, catering to every palate and preference. Whether you're craving delectable international cuisine, mouthwatering steaks, or indulgent desserts, you'll find a culinary delight to suit your taste. Additionally, nearby shopping areas offer a plethora of options for those seeking retail therapy, with an abundance of stores and boutiques to explore. Experience the best of both worlds – the serenity of your own private oasis within the townhome and the excitement of the Storylake Resort and its surrounding attractions. Book your stay now and unlock the magic of this captivating vacation home, where hidden Mickeys await and unforgettable adventures are just a step away.- 10
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- 3
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$135/night -
New
Luxurious Unique 8-Bedroom Vacation Home at Solara Resort
House - Solara Resort - Orlando
Luxurious Unique 8-Bedroom Vacation Home at Solara Resort Welcome to this absolutely stunning 8-bedroom, 7-bathroom vacation home located in Solara Resort. This brand-new property is designed with exceptional taste and offers luxurious amenities for an unforgettable stay. All rooms are decorated with beautiful furniture, luxury bedding, and stylish décor, ensuring that you feel comfortable and pampered. Whether you are planning a family vacation or a group getaway, this home provides the perfect combination of comfort, entertainment, and privacy. The spacious home offers 8 beautifully designed bedrooms and 7 full bathrooms, providing plenty of space for large groups and multi-family stays. Each bedroom is thoughtfully furnished to ensure a comfortable and relaxing experience. The huge Harry Potter Themed Bedroom offers an immersive wizarding world experience, making bedtime an adventure for young fans sleeping in the Hogwarts Express train. The Under the Sea Themed Bedroom is designed for little explorers. This room brings the wonders of the ocean to life with playful and cozy décor. Guests will enjoy the private theater room, a huge entertainment space where you can watch your favorite movies in style. The upstairs game room is equipped with arcade games, Air Hockey and other exciting games, perfect for both kids and adults to enjoy. On the main level, there is a luxurious pool billiard space that leads to the private pool and covered outdoor dining space. This outdoor area is ideal for relaxing, dining, and entertaining, and you could also enjoy a game of table tennis! With no rear neighbors, you can enjoy your stay in complete privacy. The fully equipped open kitchen has everything ready for you to prepare a lovely meal and to enjoy food and drinks at the bar or in the formal dining room. This home is designed to provide entertainment for all ages while offering quiet retreats for rest and relaxation. Whether you want to challenge your friends to a game of pool, enjoy a movie marathon in the private theater, or unwind by the pool, there is something for everyone. When staying at this exquisite home, you will have access to Solara Resort’s world-class amenities. Enjoy the Resort-Style Pool & Splash Pad – Perfect for cooling off and having fun under the sun. The Surf Simulator is a unique feature for those looking to catch a wave (for a fee). Enjoy free use of the Fitness Center – Fully equipped with modern equipment for your workout needs. There are also Sports Courts, On-Site Dining and a Bar. Our luxurious 8-bedroom home at Solara Resort is the perfect destination for your next vacation. With plenty of space, exciting entertainment areas, and access to incredible resort amenities, this property offers an unmatched vacation experience.- 20
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- 6.5
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$292/night
4 of 258 properties