Vacation Rentals By Owner In Winter Park, FL

Your cozy getaway awaits in Winter Park at this enchanting house. With four bedrooms featuring three queen beds, one king bed, and a twin bed, guests have plenty of space to relax. Two bathrooms offer refreshing showers and convenient hair dryers. The house stays comfortable year-round with heating and air conditioning. Whether you’re unwinding after a day of adventure or enjoying a quiet morning, this delightful home provides a marvelous setting for your stay. We’ll be available to answer any questions while you stay at our place.

Spacious 5-bedroom house in gorgeous Winter Park

Winter Park, Florida, United States

Bed

Bath

Sleeps

$186.77

Location, location, location - this immaculate Olde Winter Park home is ready for you to relax and enjoy Winter Park and the fabulous Orlando area. brOur home features an entertainment bar, a well-appointed kitchen and an open dining area for eight; a relaxing living room with two new couches and a 65 tv; and three bedrooms with each having a full bath. The bedroom and full bath areas offer both privacy and comfort with the spacious master featuring a large screen tv and reading area with a luxurious jacuzzi tub and separate shower.ok

GREAT LOCATION

Winter Park, Florida, United States

Bed

Bath

Sleeps

$133.12

This duplex unit is cozy and comfortable. It's updated with all new appliances, is tastefully decorated and has very comfortable mattresses. brbrLocated just 3 blocks from PARK AVE to the east and 2 blocks from THE WINTER PARK VILLAGE to the west. Vast amounts of restaurants and shops within walking distance. Parks and museums within easy walking distance as well. We have bikes available on property for your use as well, free, of course. Cheesecake Factory and PF Chang's two blocks away. Publix Grocery two blocks, Whole Foods 1/2 mile and Trader Joes 3/4 mile away. And many fantastic local restaurants and shops within a pleasant walking distance.brbrThe Charles Hosmer Morse Museum of American Art is just three blocks away and the Scenic Boat Tour offers a boat tour through the canals to three of the five lakes on the Winter Park Chain of Lakes. The Winter Park Country Club nine hole golf course is just a few blocks away and open to the public.brbrThe property is professionally managed in a mom and pop fashion. Your privacy is respected and protected. The amenities are very nice with a lovely pool area that has a massive bouganvillea trellis hedge running atop a wall. The pool area also offers outside dining, a grill station for cooking outside and a hot tub. The pool is heated in winter. Everything is kept very clean. There are seven bikes, including one child's bike and two other relatively small ones available for guests in the fourteen unit complex.

LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!

Winter Park, Florida, United States

Bed

Bath

Sleeps

$119.62

This duplex unit is cozy and comfortable. It's updated with all new appliances, is tastefully decorated and has very comfortable mattresses. brbrLocated just 3 blocks from PARK AVE to the east and 2 blocks from THE WINTER PARK VILLAGE to the west. Vast amounts of restaurants and shops within walking distance. Parks and museums within easy walking distance as well. We have bikes available on property for your use as well, free, of course. Cheesecake Factory and PF Chang's two blocks away. Publix Grocery two blocks, Whole Foods 1/2 mile and Trader Joes 3/4 mile away. And many fantastic local restaurants and shops within a pleasant walking distance.brbrThe Charles Hosmer Morse Museum of American Art is just three blocks away and the Scenic Boat Tour offers a boat tour through the canals to three of the five lakes on the Winter Park Chain of Lakes. The Winter Park Country Club nine hole golf course is just a few blocks away and open to the public.brbrThe property is professionally managed in a mom and pop fashion. Your privacy is respected and protected. The amenities are very nice with a lovely pool area that has a massive bouganvillea trellis hedge running atop a wall. The pool area also offers outside dining, a grill station for cooking outside and a hot tub. The pool is heated in winter. Everything is kept very clean. There are seven bikes, including one child's bike and two other relatively small ones available for guests in the fourteen unit complex.

Cozy Comfort Just 2 Blocks From Park Ave!

Winter Park, Florida, United States

Bed

Bath

Sleeps

$187.48

Come and stay awhile at the Killarney Retreat, built in the 50s, tucked away from the hub of city, yet just a short drive from the Winter Park Village, Rollins College, grabbing dinner and taking a walk down Park Avenue. brbrConveniently located just 10 minutes from Downtown Orlando, 20 minutes from Disney World and Universal, 25 minutes from the Orlando Int'l Airport, less than an hour from world famous Daytona Beach and an hour from Kennedy Space Center and Cocoa Beach.brbrA private older 50s charming remodeled bungalow with two bedrooms and 2 bathrooms sharing the same authentic shower/tub combo with a spacious eat in kitchen, dining room and comfortable living room including a coffee table/work desk and a laundry space in the garage. brThe fenced backyard let's you enjoy the Florida sunshine.brThis home has everything you need for a short getaway or to stay awhile for a work contract.brbrNOTE: The two full baths do share the same shower with a deep step down. The house does not have a dishwasher. The washer/dryer are located in the connected garage off the kitchen. brbrDO NOT instant book if you are traveling with a pet. Pre-Approval and Pet deposit is required.

CHARMING - Cozy Retreat Near Lake Killarney in Winter Park

Winter Park, Florida, United States

Bed

Bath

Sleeps

$234.5

Escape to our charming 3BD/1BA home in Winter Park, FL—modern, cozy, and pet-friendly! Perfect for families, couples, and travel professionals, with a fenced-in backyard for relaxing.brbr Prime Location:br2 min – AdventHealth Winter Parkbr8 min – Rollins College & Park Avebr10 min – Winter Park Villagebr15 min – AdventHealth Orlandobr20 min – UCFbr25 min – MCO Airportbr30 min – Universal StudiosbrbrEnjoy comfort, style & convenience—we can't wait to host you!brbrWe’re always available and strive to respond as quickly as possible! ⏳ If you message between 9 PM – 5 AM, our response time may be a bit slower, but we’ll get back to you as soon as we can. If you anticipate needing assistance during these hours, just let us know in advance—we’re happy to accommodate however we can!brbrNestled in a quiet, friendly neighborhood, our home is just minutes from Park Avenue, Winter Park Village, Rollins College, and popular wedding venues. Enjoy the charm of Winter Park while being only 20 minutes from Downtown Orlando and UCF—the perfect balance of convenience and relaxation!brbrGuests have full access to the entire property. Entry is easy and secure with a smart lock on the front door—no keys required!brbrStep inside and feel at home in our spacious, thoughtfully designed retreat, where modern amenities meet cozy charm. The inviting living room features plush seating and a flat-screen TV, perfect for movie nights or unwinding after a day of exploring Winter Park.brbrOur home offers three beautifully decorated bedrooms, each designed for ultimate comfort and relaxation. Sink into plush beds and enjoy a restful night’s sleep. The third bedroom doubles as a dedicated workspace and vanity, making it ideal for work trips or getting ready for a night out.brbrThe fully equipped kitchen boasts stainless steel appliances, ample counter space, and all essential cookware—perfect for preparing home-cooked meals. Gather around the dining table for intimate dinners or lively breakfasts.brbr☕ Coffee lovers, rejoice! Our fully stocked coffee bar includes coffee, creamers, syrups, and sweeteners so you can start your morning just the way you like it.brbrWe recommend having a car for the easiest access to nearby attractions, but Uber and Lyft are typically readily available for convenient transportation around Winter Park and Orlando.brbrConveniently located in Winter Park, our home offers easy access to the best of the area! Stroll along Park Avenue to enjoy charming boutiques, art galleries, and cafés, or relax in scenic Central Park. Visit Rollins College, the Morse Museum, and Winter Park Village, all just minutes away. This is the perfect location for those wanting to be near Orlando's attractions while staying in a peaceful, friendly neighborhood.brbr✨ Additional Highlights:br✔ Pet-Friendly! (Max 2 pets, please keep them off furniture)br✔ Fenced-in backyard – Private & great for unwindingbr✔ Modern & cozy – Thoughtfully designed for comfortbrbrWhether you're here for work, leisure, or a weekend getaway, we can't wait to host you!

Modern, Charming Home in the heart of Winter Park- Perfect for a couples retreat or small group!

Winter Park, Florida, United States

Bed

Bath

Sleeps

$250.43

Welcome to Your Stylish Winter Park Retreat brbrSpacious 3BR/3BA Townhome in the Heart of Winter Park, FL Perfect for families, remote workers, or extended stays. Each bedroom features its own bathroom for added privacy brbrEnjoy a modern open-concept layout, fully equipped kitchen , and in-unit washer/dryer . Located minutes from Rollins College, downtown Winter Park, top dining spots, boutique shopping, and a short drive to Orlando’s theme parks brbrStylish, comfortable, and centrally located — your ideal Winter Park retreat!brbr Sleeping Arrangementsbr✔ Master Bedroom – King Bed (Sleeps 2)br✔ Second Bedroom – Queen Bed (Sleeps 2)br✔ Third Bedroom – Queen Bed (Sleeps 2)brbr Key Featuresbr✅ Spacious living areas with contemporary decor and open floor plan ️br✅ Fully equipped kitchen with stainless steel appliances br✅ In-unit washer & dryer — perfect for longer stays br✅ Fast Wi-Fi & Smart TVs for work and entertainment br✅ Private bathrooms for each bedroom br✅ Central location near dining, shopping, and parks brbr Explore the Neighborhoodbr✔ Park Avenue District – Upscale shopping, sidewalk cafés, and art galleriesbr✔ Charles Hosmer Morse Museum – World’s largest collection of Tiffany glassbr✔ Albin Polasek Museum & Sculpture Gardens – Art meets nature on the lakesidebr✔ Lake Baldwin Park – Dog-friendly trails and waterfront viewsbr✔ Winter Park Farmers’ Market – Local produce, flowers, and artisan goods every Saturdaybrbr ️ Guest-Favorite Restaurants NearbybrBriarpatch – Beloved brunch spot with waffles and ice creambrHillstone – Upscale lakeside dining with steaks and seafoodbrSixty Vines – Stylish wine bar with seasonal New American farebrThe Wine Room – Self-serve wine tastings and gourmet bitesbrGarp & Fuss – Cozy gastropub with creative comfort foodbrbr Local Events & ExperiencesbrWinter Park hosts year-round events like art festivals, wine walks, outdoor concerts, and food truck nights. In December, enjoy holiday boat parades, festive markets, and seasonal celebrations around Park Avenue and nearby lakes.brbrWhether you`re here for work, family, or fun, this inviting townhome offers everything you need for a relaxing and memorable stay. brbrBook now to secure your dates and experience Winter Park like a local!brbrDuring your stay, you will have complete and exclusive access to the entire home.brbrIt features a keyless code lock, offering flexible, secure access at any time—no need to worry about keys. Check-in is simple, flexible, and designed to fit your schedule.brbr- The home is professionally cleaned and sanitized between each guest. We ensure that our cleaners are committed to the highest standards of cleanliness.brbr- All bedrooms are located on the second floor of the homebrbr- This is a gated community. Guests are required to share a copy of their ID with us via messenger for home access.brbr Our Smart TVs include all major streaming apps —feel free to log in with your own accounts and enjoy your favorite shows! Don’t forget to log out before checkout br Florida Weather & NaturebrPlease note that in sunny Florida, with beautiful weather and greenery, come humidity and BUGS. (Yes, dare I say it...) These elements are a natural & very common occurrence! We have our property professionally sprayed for pests, but please remember to pack sunscreen and bug spray! brbrbr Guest Requirementsbr- Guests must carefully review the full listing details before booking. Failure to read disclosures or comply with house rules does not qualify for a refund.brbr- If you choose to cancel, our standard cancellation policy will apply.brbr- The primary guest listed on the reservation must provide a photo of their government-issued ID via messenger once the booking is confirmed.brbr- The individual making the reservation must be at least 21 years old and must be one of the guests staying at the property.brbr- If the person who booked the reservation is under the age of 21, a $100 security deposit is required and will be returned after 14 days if no damages are found. There are no exceptions to this rule.brbr- No third-party bookings allowed unless agreed upon in writing.brbr- Only the number of guests listed in the reservation may stay overnight, unless approved in writing.brbr- We can accommodate a maximum of 6 guests. With prior approval, up to 2 additional guests are allowed at $15/night per guest. This helps ensure your comfort and supports our cleaning team.brbrbr No Pets AllowedbrPets are not permitted. Unauthorized pets will incur a $300 fee.brbrbr⏰ Check-In / Check-Outbr- Early check-in is available upon request for $30 (subject to availability, not guaranteed).br- Late check-out is available upon request for $50 and extends your stay until 12 noon. Please make the request before your scheduled check-out time so we can notify our cleaners in advance.br- Standard check-out is by 10 AM. Unauthorized late check-out will incur a $100 fee. Please respect this time so our cleaners can prepare the home for the next guests.brbrbr ParkingbrYou will be assigned a designated parking area, and all vehicles must park in the assigned space. brbrbr Reservation ChangesbrWe kindly ask all guests to review their travel plans carefully before booking.brbr- We do not accept any reservation changes within 30 days of the check-in date, except for stay extensions (if available).br- This means we are unable to approve requests to:br❌ Shorten your staybr❌ Move your reservation to a later datebr❌ Adjust your existing dates once you are within the 30-day windowbrbr✅ If you’re unable to keep your reserved dates, please cancel your reservation through Airbnb at your earliest convenience so the calendar can open for other guests.brbrbr Stay Guidelinesbr- All trash must be placed inside the bins provided. Leaving trash outside will result in a $100 fine.br- No smoking or drugs allowed inside or outside the home. A fee starting at $500 will apply if there are signs or smells of smoking.br- Please wipe your shoes at the door. It’s preferred that shoes be removed indoors when possible, so we can keep the space clean for you and the next guests!br- No food or drinks on the bed.br- Decorative items are not for use. Damage or removal will result in a fine.br- Follow any posted guidelines inside the home. Before you leave, please take out the trash as instructed and report any damages right away.brbrbr Respect for Neighbors & Propertybr- Quiet hours are from 10 PM to 8 AM. Please be considerate while socializing outdoors during this time.br- Keep noise to a minimum to respect our neighbors.br- No parties or events.br- No fireworks of any kind.br- No firearms on the property unless securely locked in a vehiclebrbrbr⚠️ Violations & EnforcementbrWe reserve the right to terminate a reservation without refund and/or pursue monetary fines if guests violate any of these rules.brbrbr⚠️ Unexpected Issues & AmenitiesbrIf any issue or amenity is found not working after a previous guest, we’ll notify you before check-in so expectations are clear. We’ll always offer a resolution or alternative to ensure your comfort, and guests are expected to agree with the proposed solution.brbrIf you choose to cancel instead, our standard cancellation policy will apply, as emergencies can arise unexpectedly and are beyond our control.brbrbr Need Help brIf you have any questions, concerns, or special requests, please don’t hesitate to message us—we’re happy to help and want your stay to be as comfortable as possible!

Villa

Stylish and Spacious Winter Park Retreat Close to Dining, Shopping and Rollins College

Winter Park, Florida, United States

Bed

Bath

Sleeps

$198.89

This charming bungalow in the heart of Winter Park's upscale Forest Hills neighborhood is the perfect retreat for your next stay! Million-dollar homes line the walkable brick streets, leading you to this beautiful property featuring two king sized beds, dedicated home office, spacious living area and a fully appointed kitchen that make you feel right at home. brbrStep out on the back patio to a secluded tropical paradise, complete with patio furniture and grill. Maintained landscaping surround the house to give it a true Winter Park feel!brbrMinutes from Park Avenue, Rollins College, Downtown Orlando, the Farmers Market, fine dining and the Winter Park Chain of Lakes have you in the middle of it all.

Winter Park Bungalow & Outdoor Oasis - Rollins College, Park Ave & Fenced Yard

Winter Park, Florida, United States

Bed

Bath

4

Sleeps

$426.57

Location, Location, Location!!! Greatest location! Well appointed condo -one block from Park Avenue! This is a Downstairs unit. It is two bedroom / two bath - living room, separate dining room , split floor plan, enclosed porch and an additional private patio. There is a washer and dryer in the unit. 2 parking spaces. Walking distance to all the wonderful shops and restaurants. Located Next to Lake Virginia which has a jogging trail. Come stay with us and take a stroll down the famous brick-lined Park Avenue!

Condo

Greatest location! Condo with private yard!

Winter Park, Florida, United States

Bed

Bath

Sleeps

$133.12

Welcome to beautiful Winter Park, Florida and your home away from home in your lakeside, super-convenient 1 bedroom /1 home office condo. Designed with the working traveler in mind, or locals needing a temporary space, we offer you an attention to detail not commonly found in most short term rentals. At Urban Oasis, you will enjoy the many amenities of the private lakefront park, an enclosed sunlit patio, a dedicated office, and fast access to all of the spoils of Winter Park, Orlando and the attractions.brbrA perfect day... Linger in your king size bed with luxury linens after a refreshing night of sleep. Slowly sip a cup of coffee on the sun room love seat, enjoying the relaxing views of the lake in one direction and the road that leads to exploration in the other. Plan your day, choosing from dozens of nearby options for entertainment, shopping, nature, and adventure. If you are traveling for business and working from the condo, enjoy the private dedicated office with laptop writing desk, wifi printer and convertible couch. In the evening, whip up a meal in the well-appointed kitchen or choose from a dozen acclaimed restaurants within a 5 minute walk. Close out the day admiring the sunset from a kayak on Lake Killarney, a residents-only 293-acre lake, or while enjoying the amenities at the neighborhood lakefront park. Choose from Adirondack chairs, gated swimming pool, shuffleboard, boat dock, charcoal grills, picnic tables and shady park benches.brbrLocation... Located in the epicenter of Winter Park, you will find anything you could possibly want either in walking distance or within a short drive. In less than a mile you will find retailers such as Nordstrom Rack, Homegoods, Michael's, and Ulta. Within the same distance you can acquire groceries at Whole Foods, Trader Joes and Publix. Or you can enjoy a delicious meal out at Hillstone, Ruth's Chris, Cheesecake Factory, Shake Shack, Bulla, P.F. Chang's and dozens of others. ABC Liquor is less than a block away and Regal Cinemas is across the street. Easily reach Olde Town Winter Park with a 5 minute drive, and downtown Orlando in only 20 minutes. Catch I-4 only 1.5 miles away for fast access to the parks (Universal - 30 minutes, Disney 50 minutes) and the beaches (Daytona or New Smyrna, just over one hour). Sunrail, the local light rail train, will pick you up at the charming Winter Park station just 5 minutes away. Uber and Lyft are fast alternatives as well.brbrAbout Winter Park... Winter Park was established in the late 1800's as a playground escape for wealthy Northerners. They built mansions and enjoyed the abundance of giant oaks, countless lakes and daily sunshine. While these are still some of the best attributes of Winter Park, contemporary visitors may also now choose from a wide variety of cultural activities, shopping, museums, and entertainment. Countless restaurants include international cuisine, mom and pop eateries, breweries, and well-loved chains. Don't miss famous Park Avenue, several blocks of quaint boutique shopping, some of the best restaurants in the area, and home to multiple museums and the oldest Central Florida attraction, the Winter Park Scenic Boat Tour.

Condo

Lakefront Condo w/ Sunroom, Office, & Lakeside Pool

Winter Park, Florida, United States

Bed

Bath

Sleeps

$83.06

Get ready to relax in this Inexpensive 1-bedroom apartment on the Winter Park / Orlando Border. Enjoy the over 113 Restaurants within 1 mile of this convenient efficient quiet private comfortable property.

Apartment

Virbo Host Website is not working for me. Do not book this property. Thank you

Winter Park, Florida, United States

Bed

Bath

Sleeps

$281.03

Entire Private Home - br2 bed 2 bath fully furnished unit located just one block from Park Ave in Winter Park. ***Several units are available in the same building so please inquire for accurate availability***

Condo

Amazing location- walk to everything

Winter Park, Florida, United States

Bed

Bath

Sleeps

$146.25

Enjoy our newly renovated home in Winter Park. We are centrally located and within minutes from Rollins College and Park Avenue. Downtown is only a short drive and the theme parks are a 30 minute drive. Our home comes fully stocked with everything you need to feel at home during your stay. The master bedroom comes equipped with a comfortable king size bed and a smart tv. Both t.v's in the house have firesticks so you can log into your streaming accounts. We allow pets(and charge a pet fee). This is a duplex and the back unit has a permanent tenant. We ask that you are respectful of them and our neighbors. You will have access to the garage. We provide smart TVs and a fire-stick which have a streaming service that allows you to watch over 12,000 channels.

Home Away from Home- Winter Park

Winter Park, Florida, United States

Bed

Bath

4

Sleeps

$214.11

Discover this 2-bedroom house in Winter Park. The bedrooms feature a queen bed and a king bed, offering plenty of comfort for guests. Two bathrooms include a bathtub and a bidet, adding a touch of luxury to your stay. The living room provides extra sleeping options with a sofa bed and a twin bed, perfect for families or friends Near Park Ave dining, shops, cafés, and scenic strolls.brbr• Minutes to Rollins College & Full Sail Universitybrbr• Easy access with free parking close to the entrancebrbr• Fast Wi-Fi plus a work-ready space for remote workbrbr• Fully equipped kitchen with complimentary breakfast items, snacks, bottled water, and light dinner essentialsbrbr• Ideal for visiting family, medical trips, college visits, or brlonger stays. br brWHY GUESTS LOVE ITbrbr• Clean, light, modern design with an open living, dining, and kitchen layoutbr• Easy self check-in with keypad (no key handoffs)br• Private fenced patio for coffee, fresh air, and relaxing eveningsbr• In-unit washer and dryer so you can pack lighterbr• Fully equipped kitchen plus a coffee setupbrbr• Complimentary starter groceries: breakfast items, snacks, bottled water, plus a few ready-to-use dinner essentials so you can settle in immediatelybr• Shower heads with built-in water filters for a cleaner, softer shower experience.brbrSLEEPING ARRANGEMENTS (SLEEPS UP TO 6)br• Bedroom 1: King bedbr• Bedroom 2: Queen bedbr• Living room: Single sleeper (great for one adult or a child)br• Pull Out Sleeper Sofa (great for one adult or a child)brbrTHE SPACEbrThis is a private side of a duplex with its own entrance and exclusive access to the full interior plus the fenced outdoor space. The layout is simple and comfortable:br• Living room with TV and comfortable seatingbr• Open kitchen and dining area (easy for meals and conversation)br• Two full bathroomsbr• Laundry in-unit for conveniencebrbrKITCHEN AND DININGbrCook a full meal or keep it simple.br• Fully equipped kitchen with cookware and essentialsbr• Coffee and tea setupbr• Grill available for easy outdoor mealsbrbrWORK-FRIENDLY SETUPbrPerfect for solo business travelers, traveling nurses, and small work trips.br• Fast WiFibr• Extra Monitor, Keyboard and Mousebr• Dedicated workspacebr• Quiet, residential feelbrbrPARKINGbrFree parking on site. Please follow the posted parking guidance and keep access areas clear so everyone has an easy stay.brbrLOCATION, WITHOUT THE TOURIST CHAOSbrYou get the convenience of being close to the best of Winter Park and Orlando while staying in a calm neighborhood:br• Park Ave area, dining, shopping, and scenic walks nearbybr• Full Sail University close bybr• Quick access to major roads for downtown Orlando, attractions, and the airportbrbrGOOD TO KNOW BEFORE YOU BOOKbr• Check-in: after 4:00 PMbr• Check-out: before 11:00 AMbr• No smoking anywhere on the property (inside or outside)br• No petsbr• No shoes inside the homebr• Please keep food and drinks off the bedsbr• For everyone’s safety, there is an exterior security camera on the propertybrbrWe host with a focus on cleanliness, clear communication, and a smooth stay from start to finish. If you have questions before booking, message us. We are happy to help.

Brizzy 2BR/2BA Near Park Ave and Rollins, Perfect for Families and Long Stays.

Winter Park, Florida, United States

Bed

Bath

6

Sleeps

$439.9

The Classic King with Balcony room measures 323 square feet and has the added feature of a balcony with French doors that open to the warm tropical breezes. The room is appointed with handsome contemporary furnishings, including an armoire, mini fridge, flat-screen TV and a spacious work area equipped with multiple outlets, docking station and USB connections. The King bed is fitted with a pillowtop mattress and luxury linens. The large marble bathroom features a walk-in shower, designer toiletries, a hair dryer and plush towels. In room amenities include a Juluis Meinl coffeemaker with complimentary coffee and tea pods. WiFi in the room and public areas is free.brbrJust outside of Orlando, The Alfond Inn is practically a cultural experience in itself. On every wall of this AAA Four Diamond hotel hangs work from the prestigious Alfond Collection of Contemporary Art, which showcases established and emerging international painters, sculptors, and photographers. Framed by award-winning luxury, your stay at The Alfond Inn promises impeccable service and pristine accommodations as well as gourmet culinary artistry at acclaimed Hamilton’s Kitchen. From the moment you arrive, you understand why Condé Nast Traveler's Readers’ Choice Awards voted it “Best Hotel in Florida.”brbrUnwind in one of 112 handsomely appointed guestrooms and suitesbrFeast on the freshest local cuisine with a glass of wine at historic Hamilton’s KitchenbrTake a dip in the serene heated pool atop the roof lined with palm treesbrExperience the fun and adventure of Orlando’s many theme parksbrBe charmed by Winter Park’s museums, galleries, and green spacesbrExplore the hotel’s exceptional 240-piece Alfond Collection of Contemporary ArtbrThe hotel’s award-winning accommodations put you within steps of the beloved Hamilton’s Kitchen eatery and only a short drive from downtown Orlando and the nearby amusement parks.

Private Balcony in Award Winning Hotel, Roof-top Pool, Close to Rollins College

Winter Park, Florida, United States

Bed

Bath

Sleeps

$393.72

Our 323 square foot King Room is appointed with handsome contemporary furnishings, including an armoire, mini fridge, flat-screen TV and a spacious work area equipped with multiple outlets, docking station and USB connections. The King bed is fitted with a pillowtop mattress and luxury linens. The large marble bathroom features a walk-in shower, designer toiletries, a hair dryer and plush towels. In room amenities include a Julius Meinl coffeemaker with complimentary coffee and tea pods. WiFi in the room and public areas is free.brbrJust outside of Orlando, The Alfond Inn is practically a cultural experience in itself. On every wall of this AAA Four Diamond hotel hangs work from the prestigious Alfond Collection of Contemporary Art, which showcases established and emerging international painters, sculptors, and photographers. Framed by award-winning luxury, your stay at The Alfond Inn promises impeccable service and pristine accommodations as well as gourmet culinary artistry at acclaimed Hamilton’s Kitchen. From the moment you arrive, you understand why Condé Nast Traveler's Readers’ Choice Awards voted it “Best Hotel in Florida.”brbrUnwind in one of 112 handsomely appointed guestrooms and suitesbrFeast on the freshest local cuisine with a glass of wine at historic Hamilton’s KitchenbrTake a dip in the serene heated pool atop the roof lined with palm treesbrExperience the fun and adventure of Orlando’s many theme parksbrBe charmed by Winter Park’s museums, galleries, and green spacesbrExplore the hotel’s exceptional 240-piece Alfond Collection of Contemporary ArtbrThe hotel’s award-winning accommodations put you within steps of the beloved Hamilton’s Kitchen eatery and only a short drive from downtown Orlando and the nearby amusement parks.

Contemporary Award Winning Hotel w/Rooftop Close to Parks & Rollins College

Winter Park, Florida, United States

Bed

Bath

Sleeps

$430.85

Our Premier ADA Queen is a larger room at 448 square feet and is wheelchair-accessible. The room features an additional seating area with a sleeper sofa and is appointed with handsome contemporary furnishings, including an armoire, mini fridge, flat-screen TV and a spacious work area equipped with multiple outlets, docking station and USB connections. The two Queen beds are fitted with pillowtop mattresses and luxury linens. The large marble bathroom features a tub/shower combination, designer toiletries, a hair dryer and plush towels. In room amenities include a Julius Meinl coffeemaker with complimentary coffee and tea pods. WiFi in the room and public areas is free.brbrJust outside of Orlando, The Alfond Inn is practically a cultural experience in itself. On every wall of this AAA Four Diamond hotel hangs work from the prestigious Alfond Collection of Contemporary Art, which showcases established and emerging international painters, sculptors, and photographers. Framed by award-winning luxury, your stay at The Alfond Inn promises impeccable service and pristine accommodations as well as gourmet culinary artistry at acclaimed Hamilton’s Kitchen. From the moment you arrive, you understand why Condé Nast Traveler's Readers’ Choice Awards voted it “Best Hotel in Florida.”brbrUnwind in one of 112 handsomely appointed guestrooms and suitesbrFeast on the freshest local cuisine with a glass of wine at historic Hamilton’s KitchenbrTake a dip in the serene heated pool atop the roof lined with palm treesbrExperience the fun and adventure of Orlando’s many theme parksbrBe charmed by Winter Park’s museums, galleries, and green spacesbrExplore the hotel’s exceptional 240-piece Alfond Collection of Contemporary ArtbrThe hotel’s award-winning accommodations put you within steps of the beloved Hamilton’s Kitchen eatery and only a short drive from downtown Orlando and the nearby amusement parks.

Rooftop Pool, Close to Parks & Rollins College - Award Winning Accommodations

Winter Park, Florida, United States

Bed

Bath

4

Sleeps

$488.26

Our Parlor King is a larger room at 435 square feet and features a separate Parlor seating area with a sleeper sofa and is appointed with handsome contemporary furnishings, including an armoire, mini fridge, flat-screen TV and a spacious work area equipped with multiple outlets, docking station and USB connections. The King bed is fitted with a pillowtop mattress and luxury linens. The large marble bathroom features a walk-in shower, designer toiletries, a hair dryer and plush towels. In room amenities include a Juluis Meinl coffeemaker with complimentary coffee and tea pods. WiFi in the room and public areas is free.brbrJust outside of Orlando, The Alfond Inn is practically a cultural experience in itself. On every wall of this AAA Four Diamond hotel hangs work from the prestigious Alfond Collection of Contemporary Art, which showcases established and emerging international painters, sculptors, and photographers. Framed by award-winning luxury, your stay at The Alfond Inn promises impeccable service and pristine accommodations as well as gourmet culinary artistry at acclaimed Hamilton’s Kitchen. From the moment you arrive, you understand why Condé Nast Traveler's Readers’ Choice Awards voted it “Best Hotel in Florida.”brbrUnwind in one of 112 handsomely appointed guestrooms and suitesbrFeast on the freshest local cuisine with a glass of wine at historic Hamilton’s KitchenbrTake a dip in the serene heated pool atop the roof lined with palm treesbrExperience the fun and adventure of Orlando’s many theme parksbrBe charmed by Winter Park’s museums, galleries, and green spacesbrExplore the hotel’s exceptional 240-piece Alfond Collection of Contemporary ArtbrThe hotel’s award-winning accommodations put you within steps of the beloved Hamilton’s Kitchen eatery and only a short drive from downtown Orlando and the nearby amusement parks.

Large Room Award Winning Hotel w/Rooftop Pool - Close to Parks & Rollins College

Winter Park, Florida, United States

Bed

Bath

Sleeps

$391.51

Our Classic King ADA is wheelchair-accessible. The room is appointed with handsome contemporary furnishings, including an armoire, mini fridge, flat-screen TV and a spacious work area equipped with multiple outlets, docking station and USB connections. The King bed is fitted with a pillowtop mattress and luxury linens. The large marble bathroom features a roll-in shower, designer toiletries, a hair dryer and plush towels. In room amenities include a Julius Meinl coffeemaker with complimentary coffee and tea pods. WiFi in the room and public areas is free.brbrJust outside of Orlando, The Alfond Inn is practically a cultural experience in itself. On every wall of this AAA Four Diamond hotel hangs work from the prestigious Alfond Collection of Contemporary Art, which showcases established and emerging international painters, sculptors, and photographers. Framed by award-winning luxury, your stay at The Alfond Inn promises impeccable service and pristine accommodations as well as gourmet culinary artistry at acclaimed Hamilton’s Kitchen. From the moment you arrive, you understand why Condé Nast Traveler's Readers’ Choice Awards voted it “Best Hotel in Florida.”brbrUnwind in one of 112 handsomely appointed guestrooms and suitesbrFeast on the freshest local cuisine with a glass of wine at historic Hamilton’s KitchenbrTake a dip in the serene heated pool atop the roof lined with palm treesbrExperience the fun and adventure of Orlando’s many theme parksbrBe charmed by Winter Park’s museums, galleries, and green spacesbrExplore the hotel’s exceptional 240-piece Alfond Collection of Contemporary ArtbrThe hotel’s award-winning accommodations put you within steps of the beloved Hamilton’s Kitchen eatery and only a short drive from downtown Orlando and the nearby amusement parks.

ADA Compliant Room - Contemporary Furnishings - Rooftop Pool - Close to Parks

Winter Park, Florida, United States

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