Vacation Rentals By Owner In Winter Park, FL

Enjoy our guest house and the new space we created in Oct 2015! The guest house has a kitchenette with two glass burners, refrigerator, coffee maker, toaster, convection microwave, AC wall unit, TV w/ HD antenna for over a dozen local channels (we've cut the cord, but the TV is a smart TV with Netflicks, HBO Go, Amazon Prime Video), wifi (50Mbps), utensils, plates / mugs. The guest house has a queen size CASPER bed (check it out online), great for couples or single travelers. Max we can take are 2 guests in this studio to fit comfortably. brbrYou will have a separate private entrance to the guest house on the site of the main home. The guest house sits in our back yard of the main home. You'll also have free parking in front of the main home during your stay.brbrTHE NEIGHBORHOODbrWinter Park has a variety of things to see and do, we love the neighborhood because of that. Tons of incredible eateries, also great shopping, and the famous park avenue is just a short DRIVE AWAY. Also you can easily jump on I-4 to take you all around the city and hit the world famous attractions, Outlet malls or I-Drive area.brbrHOUSE RULES are: br- No smoking inside the guest home, outside only br- Only registered renters are allowed in the studio, please no overnight guests.br- Parking is free, please park on our side of the street, not across the street.br- Lock the front door when leaving, simply press the Schlage Button and remember to turn off the AC wall unit.br- Please wash dishes before checkout.br- Renters will need to have a fully verified profile to book this guest house through the homeaway's verification system. br- The studio is on a septic tank, please only flush down toilet paper down the toilet. No Femine products, wipes, paper towels or condoms in the toilet. These items block the septic system and if you back up the system you will forfeit your security deposit. br- If you see any issues during your stay please bring it to our attention right away so we can address it during your stay and handle accordingly. br- No question is a silly question please always feel free to ask anything :)brbrGETTING AROUNDbrWe recommend you rent a car to maximize your limited time here in Winter Park / Orlando. We provide free parking in front of the home on our side of the street. The home is located near the following areas by car:brbr1 minute from Killarney Lakebr3 minutes from I-4 (main highway in the city) br5 minutes to Winter Park/Park Ave & Rollins College br8 minutes to Maitland br10 minutes to Altamonte Springs br12 minutes from Downtown Orlando / Amyway Arena / Church st / Lake Eola / Citrus Bowl / MEGABUS bus stop br15 minutes to Millenia Mall & 1st Prime Outlet Mall br19 minutes to Universal Studios/Island of Adventures / Halloween Horror Nights / Mardi Gras / Harry Potter / Transformer br21 minutes to Orlando Convention Center br24 minutes to Seaworld / Aquatica br26 minutes to 2nd Prime Outlet Mall br30 minutes to Orlando International Airport br33 minutes to Epcot / Downtown Disneybr34 minutes to Animal Kingdom/Magic Kingdom br1 hr to Port Canaveral (cruise port) / Coco Beach br1 hr to New Smyrna Beach br1 hr 15 minutes to Kennedy Space Center br1.5 hours to Clearwater Beach br1 hr 45mins to St. AugustinebrbrAs you can see we highly recommend a car with your visit to see what the city offers. You can park on the street in front of the house and yes parking is FREE!brbrIf you will not have a car during your stay you can use UBER as your taxi, for first time users we can give you a free credits, simply download the app (iOS, Android & Windows) and enter in promo code SFJYPbrbrOr you can use LYFT, for first time users download the app and use promo code javier424 for free credits.brbrAlso Super Shuttle is a great and easy way to reach the home if you're flying in without a car.br brOr if you're taking the bus into the city check out MEGABUS.

Apartment

Cute Guest House In Winter Park Minutes From Downtown in Car

Winter Park, Florida, United States

Bed

Bath

Sleeps

$95.63

Private 2 bedroom guest suite with its own entry and a separate sitting room. Tandem bedroom include 1 queen sized bed and bunk beds. Easily sleeping 4. We are located very close to downtown Winter Park and steps off Park Ave. Museums, restaurants, golf and shopping are all within walking distance. There is a dedicated desk/work area for corporate guest. Designed to feel like home away from home we want to make sure your stay with us is enjoyable.

Winter Park charm. Close to Park Ave

Winter Park, Florida, United States

Bed

Bath

Sleeps

$5582.86

Welcome to your perfect Orlando getaway! This stunning new home boasts 5 spacious bedrooms and 4 modern baths, comfortably accommodating over 20 guests. With its prime location near CP, WP and DT Orlando, you’ll have access to the best areas!brbrStep inside to tall ceilings and expansive living spaces, designed for ultimate comfort and style. Enjoy a movie night in the dedicated movie room with a state-of-the-art projector, or relax on the screened-in patio featuring a Jacuzzi tub that seats 6.brbrWelcome to your perfect Orlando getaway! This stunning new home boasts 5 spacious bedrooms and 4 modern baths, comfortably accommodating over 20 guests. With its prime location near College Park, Winter Park, and downtown Orlando, you’ll have easy access to the best dining, shopping, and entertainment in the area.brbrStep inside to tall ceilings and expansive living spaces, designed for ultimate comfort and style. Enjoy a movie night in the dedicated movie room with a state-of-the-art projector, or relax on the screened-in patio featuring a Jacuzzi tub that seats 6.brbrEach room is equipped with a TV and Roku, offering endless entertainment options. Whether you`re planning a family reunion, group vacation, or corporate retreat, this luxurious home offers ample space and modern amenities for everyone in your group.brbrBook now for an unforgettable stay in the heart of Orlando!brbrTHE SPACE:br1st FLOORbrMaster Bedroom:brbrLarge tall 12ft ceilings and a KING bed. En suite bathroom with separate tub and shower, double sink vanity and 2 walk in closets. Sliding glass door access to screened in patio and jacuzzi tub. Sleeps 2brbrOpen floorplan with large dinning table, open kitchen with island and bar stool seating, large sectional, separate breakfast table, lounge chairs and 80+ inch Roku enabled TV. Sleeps 2 small adults/kidsbrbrExtra Guest Bathroom Downstairs with large Shower.brbr2nd FLOOR:brbrBonus Area/Movie room area - equipped with 4k projector and Roku, large sectional sofa, Arcade game machine.brbrBedroom 2 - Equipped with 55` Roku smart TV, Queen bed and plenty of storage + closet space. Sleeps 2.brbrBedroom 3 - 55` roku smart tv, queen bed, storage space and large closet.brbrBedroom 4 - 55` roku smart tv, queen bed, storage space and large closet.brbrBedroom 5 - `The BLUEROOM` - Large bedroom setup with 4 full size bunk beds (x4). En suite bathroom with large shower and double closets sleeps 8.brbrLaundry area - has full size washer and dryer with overhead storage cabinetsbrbrPatio - Screened in patio, lots of outdoor seating and 6 person jacuzzi tub. Backyard, paver bbq area with overhead canopy cover to keep you shielded from the sun and elements. Large fenced in backyard.brbrGarage - 1-2 vehicles and also has workout space with bench and workout equipment.brbrGuest has access to the full home for the exception of the staff storage closets labeled accordingly.brbrInteraction from guests is as needed or upon request.brbrHot tub - temperature does not exceed 103F for safety reasons. See hot tub info and rules under house rules for more details.brbrPropane & Grill - please let us know in advance if you`ll be needing propane. Tank fee per stay is $10brbrAir Mattress - please notify host in advance if you`ll need onebrbr ✅ This property has special local compliance requirements which include a signed rental agreement, verification, and a security hold of (which is not a traditional security deposit, just a pending transaction). As an optional alternative to the security hold, you may opt in to purchase a damage waiver provided by a third-party insurance company. The optional damage waiver is for stays up to 10 nights, with an additional $2 per day for stays longer than 10 nights. Damage waiver purchases are optional.brbrTo make this process easy for you, we use a secure and very simple, app-free platform called Happy Guest. It is not an app, and you do not have to sign up for an account - it’s a safe and secure website. It also gives you a guest portal with all the info about the home and all of my favorite local spots.brbrYour guest portal includes advertisements with third-party upgrades that you may want to enhance your stay. These upgrades are optional for things like early check in (when available).brBy booking this property, Guest agree to follow house rules :brbr Please do not park inside the garage/Gameroombrbr- Do not move gameroom games outdoors as may be damaged if left outsidebrbr No parties, events or professional photographybrbr No Smoking or Vaping. Smoke-free property. $550 remediation fee applies.brbr No Pets. No Animals -- $350 animal remediation and cancellation of the reservation - non refundablebrbr - Parking for 3-4 vehicles - ONLY ON DRIVEWAYbrbr - For stays 10+ days we require a complimentary weekly tidy clean.brbr Yard is serviced once per week. Landscapers will need access to front and back yard to cut grass.brbr Hot tub is also serviced once per week, they will need access to the back patio for weekly cleanings and service. NO MORE THAN 6 PEOPLE max occupancy in the Hot tub at a time.br-Please shower before entering hot tubbr-no food or glass drink in hot tubbr-no children underage unattended br-please do not shut off the hot tub heater as it takes several days to heat and can affect other guest experience br-failure to follow care/instructions here or posted on site can lead to damaging the hot tub and or parts. Guest are responsible for remediation cost of hot tub repair/damages.brbr Follow all hot tub rules in house manual. brbr ✅ This property has special local compliance requirements which include a signed rental agreement, verification, and a security hold of (which is not a traditional security deposit, just a pending transaction). As an optional alternative to the security hold, you may opt in to purchase a damage waiver provided by a third-party insurance company. The optional damage waiver is for stays up to 10 nights, with an additional $2 per day for stays longer than 10 nights. Damage waiver purchases are optional.brbrTo make this process easy for you, we use a secure and very simple, app-free platform called Happy Guest. It is not an app, and you do not have to sign up for an account - it’s a safe and secure website. It also gives you a guest portal with all the info about the home and all of my favorite local spots.brbrYour guest portal includes advertisements with third-party upgrades that you may want to enhance your stay. These upgrades are optional for things like early check in (when available).brbrRunning business activity like Massage services, salon or any other kind of business services traffic at the property is strictly prohibited and can result in non refundable cancelation of your reservation

5/4 King bed LUX Arcade near WP/CP & DT Orlando ‼️

Winter Park, Florida, United States

Bed

Bath

Sleeps

$239.64

Enjoy a stylish experience at this centrally-located place. MillsHouse is conveniently located for a foodie adventure. The best of Winter Park and Mills 50 is just blocks away.brbrbr✅ minutes to Lake Eola, Park Ave, Mills 50, shopping, parks and highwaysbrbr✅ Covid-19 enhanced cleaningbrbr✅ Walk to many winter park restaurants brbr✅ 25min to theme parksbrbr✅ Free Parking ️brbr✅ Se Habla Españolbrbr❌ Strict No Pets Allowedbrbr❌ No Smokingbrbr⭐ Stylish and comfortable living room - wifi TV equipped with Roku so you can login/stream from your favorite services. The couch serves as an optional futon to sleep ️ an additional 2 guest.brbr ️ - Dinning Table and bar topbrbr ‍ - Kitchen fully stocked including coffee maker, coffee microwave, dishwasher, toaster and refrigeratorbrbr ‍♂️ ‍♀️ - Master bedroom: The tranquiltiy suite with queen bed, 55` roku tv, ensuite bathroom and washer dryer space brbr - Bedroom 2: The Black & Gold room with queen bed, vintage lighting, 55` roku tv and wall design.brbr - Bedroom 3: The Quad with 2 sets of bunk beds, sleeps 5 (3 twins, 1 full) also has a dedicated work space.brbr - Living room with 55`RokuTV and 2 sofa couches. PLEASE NOTE sleeping here is best suited for children and not full size adultsbrbr - Backyard: Large rock paved yard off the master suite with BBQ grill.brbr - Covered Porch entry way facing the rock paved driveway. there is parking for 4 vehicles. brbrGuest have full use of the property as well as fenced in backyard.brbr ️Parking can accommodate 3-4 vehicles and is located to the left of the home when looking at the front doorbrbrWe are available via messenger in the airbnb app and so are our cohost.brbrThe property is located just off the main mills area which is packed with restaurants, bars, gastropubs, and more. brbrYou`ll enjoy plenty of privacy as the home is nestled in the rear of a larger resort complex . Our guest say they enjoy the close proximity to both College Park, Winter Park, Downtown Orlando and the Mills50 zone. You`re also just a few minutes from I-4 and expressway.brbrThis area is growing quickly and has become the `Foodie Zone` of Orlando. There are restaurants of all types catering to sit down and also quick bites.brbrRecently a vibrant nightlife with over 10 pubs, bars and social lounges nearby.brbrBus stop is a few blocks away on MillsbrbrParking - please ensure to park in the designated parking to the left of the home. Parking in front of the entrance to the home is prohibited as it will block access to the neighbors home.brbrPlease ensure NOT to park in front of the entryway as this will block access to the neighbors parking area.brbrMASTER BEDROOM - PENDANT LIGHTS: Lights are always on, to turn off simply unplug from the wall connections at the nightstands. At departure We just ask you plug them back in.brbr✅ This property has special local compliance requirements which include a signed rental agreement, verification, and a security hold of (which is not a traditional security deposit, just a pending transaction). As an optional alternative to the security hold, you may opt in to purchase a damage waiver provided by a third-party insurance company. The optional damage waiver is for stays up to 10 nights, with an additional $2 per day for stays longer than 10 nights. Damage waiver purchases are optional.brbrTo make this process easy for you, we use a secure and very simple, app-free platform called Happy Guest. It is not an app, and you do not have to sign up for an account - it’s a safe and secure website. It also gives you a guest portal with all the info about the home and all of my favorite local spots.brbrYour guest portal includes advertisements with third-party upgrades that you may want to enhance your stay. These upgrades are optional for things like early check in (when available).br No parties, events or professional photographybrbr No Smoking or Vaping indoors. Smoke-free property - non refundable $300 smoke remediation fee and grounds for cancelation of the reservation brbr NO PETS - BE RESPECTFUL, please do not circumvent this rule. $500 fine applied for the cleaning mitigation of any animal.brbr - No parking vehicles in backyard. If you need additional parking, please contact us to make arrangements with host.brbrbrRunning business activity like Massage services, salon or any other kind of business services traffic at the property is strictly prohibited and can result in non refundable cancelation of your reservationbrbr - For stays 10+ days we require a complimentary weekly tidy clean.brbr ️ - Do not park inside the backyard as their is a drain fieldbrbr✅ This property has special local compliance requirements which include a signed rental agreement, verification, and a security hold of (which is not a traditional security deposit, just a pending transaction). As an optional alternative to the security hold, you may opt in to purchase a damage waiver provided by a third-party insurance company. The optional damage waiver is for stays up to 10 nights, with an additional $2 per day for stays longer than 10 nights. Damage waiver purchases are optional.brbrTo make this process easy for you, we use a secure and very simple, app-free platform called Happy Guest. It is not an app, and you do not have to sign up for an account - it’s a safe and secure website. It also gives you a guest portal with all the info about the home and all of my favorite local spots.brbrYour guest portal includes advertisements with third-party upgrades that you may want to enhance your stay. These upgrades are optional for things like early check in (when available).brbr Yard is serviced once per week. Landscapers will need access to front and back yard to cut grass.

Mills House @WP. Sleeps 11 Renovated. Queen beds

Winter Park, Florida, United States

Bed

Bath

Sleeps

$267.34

Our home is located in Winter Park and can serve as a central base to live like a local. You can enjoy all of the great shops and restaurants on Park Avenue within driving distance from the home. The location is great to hit all the sites in Winter Park or drive to the theme parks, Outlets and experience Winter Park or Orlando as a local. The home is away from the tourist traps and in a secure neighborhood, just recommend renting a car to move around. Come stay here with the family or if you're in town for business!brbrThe home sits on a double lot. The home is a 3 bedroom and 2 bathroom, full kitchen, living room, dining room, front porch area and large back yard (shared back yard). Total square footage is about 1530 Sq Ft or .092 m2. In the back of the home sits a guest house that we rent out as well to other renters (max 2 guests at a time). The driveway takes max 2 cars. brbrWe have made the home a smart home with an Alexa, Nest thermostat, Smart door locks, smart light switches and exterior security camera. We have put our personal touches in home and opening it up to share with travelers. We look forward to sharing our home with new guests coming into town. Any questions about the setup we encourage you to ask.brbrAlso in the garage we have a washer and dryer you can use. We have instructions on how to use and even provide detergent and dryer sheets for your use. brYou also have access to the backyard. Just note there is a separate guest house in the back yard detached from the main home. That is another rental please do not disturb them in the guest house.

Comfy Home in Winter Park, can accommodate up 6 guests!

Winter Park, Florida, United States

Bed

Bath

Sleeps

$151.88

Furnished Mid Century Modern Short/Long term rental located in charming Olde Winter Park. Two bedrooms and one and half baths. Steps from shopping and restaurants and less than a mile from Park Ave with it's famous museums, parks, shops and dining. This home is complete with authentic mid century modern furnishings, comfortable bedding, mid century couches and chairs, new linens, two televisions (includes cable tv), central heat and air, new landscaping, irrigation and yard maintenance provided, fenced back yard, dishwasher, disposal, washer, dryer, and a fully stocked kitchen, including appliances and dishes. Power, internet, water, sewer and trash pick up included.brQueen bed in Master, two twin beds in Guest room, sleeper sofa in Sun Room. Sleeps 5 comfortably.brRates vary with length of stay.brJust bring your toothbrush.brPets upon approval.brView Virtual Tour:

Cottage

Mid Century Modern Cottage in The Heart of Winter Park

Winter Park, Florida, United States

Bed

Bath

5

Sleeps

$222.0

Easy access to drive in and out, ample parking available. A good open yard space is available at the back of the house for sitting, especially during the second half of the day. It is located close to restaurants, groceries, and banks and Rolling College.brbrDiscover this charming and comfortable home nestled in the heart of Winter Park, with the added convenience of being only a 5-minute drive from Orlando. It offers an idyllic retreat for you and your loved ones, providing a tranquil escape from the hustle and bustle. Additionally, you'll find an array of entertainment options nearby, including excellent dining, shopping, vibrant nightlife, and countless other attractions to enhance your stay. brbrThe house provides a cozy living area featuring a stunningly designed Victorian-style living room. The ambiance is laid-back and comfortable, mirroring the overall atmosphere of the house. The entire space is bathed in natural light, creating a warm and natural feel. You can unwind and enjoy your favorite movies or shows on the smart TV while lounging on our comfortable white sofa.brbrOur kitchen is fully equipped with two refrigerators, a brand new washer and dryer located at the back of the kitchen for your convenience, and modern stainless-steel appliances that provide everything necessary to prepare your favorite homemade dishes.brbrThe Victorian dining area offers a panoramic view of the entire living space in the house. It provides a perfect setting for gathering around our rectangular table to enjoy meals, drinks, and discuss plans for tomorrow's adventures.brbrEnjoy a peaceful getaway in our calm and spacious three-bedroom accommodations. Each room is furnished with ceiling fans, clean linens, plenty of storage, and a private bathroom in the master suite. The master bedroom offers a luxurious King bed, a smart TV, and an attached bathroom with a shower, while the remaining two bedrooms feature cozy queen size beds. The additional bathroom includes a bathtub for a relaxing soak.brbrWe provide detergent by the washer laundry room during your stay in case you need to do a quick wash!brbrQuite HoursbrPlease be aware of quite hours between 10:00 pm and 8:00 am. This helps maintain a peaceful environment and our standing as courteous neighbors.brbrSmokingbrLet’s keep the property fresh and clean, smoking is not permitted inside.brbrPet:brWe charge $200 for pet fee per stay, dog only no cat. We prefer less than 20lbs dog onlybrbrOur goal is to ensure that your visit to our lovely house is an exciting and unforgettable one.br

Comfortable House in the lovely Winter Park, Olando Fl .

Winter Park, Florida, United States

3

Bed

Bath

6

Sleeps

$253.17

This special place is close to everything, making it easy to plan your visit. The MillsHouse property is a convenient place to stay during your visit to Orlando, Winter Park, shopping, restaurants, bars, mills 50 and so much more!brbr3Min to major highwaysbr20Min to Universal Studiosbr4Min to Winter Park Golf Couse and Park Avenuebr6Min to Downtown Orlandobr30Minuts to Disneybr30Minutes to AirportbrbrLiving area - sleeper sofa with 55` Roku TV and large fireplace.brbrBedroom - the Quad, has 4 beds (2 twin bunks) so sleeps 4 guests. Equipped with 55` roku TV.brbrHallway - Desk workstation dedicated for cpu or laptop device. Also found here is a high table bartop for dining at. Seats 3.brbrKitchen ‍ ‍ - Microwave dishwasher, range, refrigerator, full size washer and dryer, large island and seperate countertop bar with seating for meals. brbrLiving area 2 - shared along side the kitchen is a sleeper sofa, love seat and 55` Roku TV.brbrBathroom 1 - full size bath with shower.brbrBedroom - Master bedroom, the room with queen bed, 55` smart TV and full ensuite bath equipped with a shower.brbrPatio - located off the master suitebrbrGazebo is located outside the gated patio and is for your use. There is also a common space with seating and soon to be bbq grill area that is shared by 4 guest units. We just ask you be mindful and considerate of other guests utilizing the space.brbrThe property is just blocks away from a supermarket, many restaurants, bars and shopping.brbr ✅ This property has special local compliance requirements which include a signed rental agreement, verification, and a security hold of (which is not a traditional security deposit, just a pending transaction). As an optional alternative to the security hold, you may opt in to purchase a damage waiver provided by a third-party insurance company. The optional damage waiver is for stays up to 10 nights, with an additional $2 per day for stays longer than 10 nights. Damage waiver purchases are optional.brbrTo make this process easy for you, we use a secure and very simple, app-free platform called Happy Guest. It is not an app, and you do not have to sign up for an account - it’s a safe and secure website. It also gives you a guest portal with all the info about the home and all of my favorite local spots.brbrYour guest portal includes advertisements with third-party upgrades that you may want to enhance your stay. These upgrades are optional for things like early check in (when available).brNo AnimalsbrNo Smoking - $500 penaltybrbrNo Eventsbrbr ✅ This property has special local compliance requirements which include a signed rental agreement, verification, and a security hold of (which is not a traditional security deposit, just a pending transaction). As an optional alternative to the security hold, you may opt in to purchase a damage waiver provided by a third-party insurance company. The optional damage waiver is for stays up to 10 nights, with an additional $2 per day for stays longer than 10 nights. Damage waiver purchases are optional.brbrTo make this process easy for you, we use a secure and very simple, app-free platform called Happy Guest. It is not an app, and you do not have to sign up for an account - it’s a safe and secure website. It also gives you a guest portal with all the info about the home and all of my favorite local spots.brbrYour guest portal includes advertisements with third-party upgrades that you may want to enhance your stay. These upgrades are optional for things like early check in (when available).brbrRunning business activity like Massage services, salon or any other kind of business services traffic at the property is strictly prohibited and can result in non refundable cancelation of your reservation

Funky Remodeled Otown Bungalow Sleeps 8

Winter Park, Florida, United States

Bed

Bath

Sleeps

$225.81

Enjoy a peaceful stay in this comfortable, easy-access 2BR/2BA home in a quiet Winter Park neighborhood near Park Avenue, Rollins College, and Full Sail University.brbrExtended stays are welcome. This home is a great fit for visiting family, work trips, traveling nurses, and guests who want a calm, convenient place with everything needed for a smooth stay. The layout is simple and functional, offering privacy, comfort, and a relaxed residential feel.brbrWHY GUESTS LOVE ITbrClean, light, modern design with an open living, dining, and kitchen layoutbrEasy self check-in with keypad (no key handoffs)brbrPrivate fenced patio for coffee, fresh air, and relaxing eveningsbrbrIn-unit washer and dryer so you can pack lighterbrbrFully equipped kitchen plus a coffee setupbrbrComplimentary starter groceries: breakfast items, snacks, bottled water, plus a few ready-to-use dinner essentials so you can settle in immediatelybrbrShower heads with built-in water filters for a cleaner, softer shower experiencebrbrSmart backyard lighting that also works as a Bluetooth speaker, connect your phone and enjoy music while you unwind outsidebrbrSLEEPING ARRANGEMENTS (SLEEPS UP TO 6)brBedroom 1: Queen bedbrBedroom 2: Queen bedbrbrLiving room: Single sleeper (great for one adult or a child)brPull-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 home includes:brLiving room with TV and comfortable seatingbrOpen kitchen and dining area (easy for meals and conversation)brbrTwo full bathroomsbrbrLaundry in-unit for conveniencebrbrKITCHEN AND DININGbrCook a full meal or keep it simple.brFully equipped kitchen with cookware and essentialsbrCoffee and tea setupbrGrill available for easy outdoor mealsbrbrWORK-FRIENDLY SETUPbrIdeal for longer stays and business travel.brFast WiFibrExtra monitor, keyboard, and mousebrDedicated workspacebrQuiet, residential feelbrbrPARKINGbrFree parking on site. Up to 4 carsbrbrLOCATION, WITHOUT THE TOURIST CHAOSbrYou’ll be close to the best of Winter Park and Orlando while staying in a calm neighborhood:brPark Ave dining, shopping, and scenic walks nearbybrRollins College close bybrFull Sail University close bybrQuick access to major roads for downtown Orlando, attractions, and the airportbrbrGOOD TO KNOW BEFORE YOU BOOKbrCheck-in: after 4:00 PMbrCheck-out: before 11:00 AMbrNo smoking anywhere on the property (inside or outside)brNo petsbrNo shoes inside the homebrPlease keep food and drinks off the bedsbrbrFor everyone’s safety, there is an exterior security camera on the propertybrWe host with a focus on cleanliness, clear communication, and a smooth stay from start to finish. If you have any questions before booking, send a message. brbr We’re happy to help, extended stays are subject to long term lease polices

Comfortable & Quiet 2BR/2BA, Near Park Ave & Rollins, Extended Stays Welcome.

Winter Park, Florida, United States

Bed

Bath

Sleeps

$147.0

Beautiful and comfortable two-story cottage/detached guest house, centrally-located within an historic neighborhood. Located in the heart of Winter Park – close to I-4 for easy access to the theme parks. Includes a private entrance, efficiency kitchen, and access to a beautiful resort-style heated pool and grill.brbrFirst story features a comfortable living room with a cozy couch and flat-screen TV (with a Roku, including Netflix, Hulu, and a variety of other apps), a dining table and an efficiency kitchen with a small fridge and a two-burner stove (equipped with all the essentials - pots, pans, glasses/mugs, plates/bowls, microwave and coffee maker).brbrSecond story features a spacious bedroom, with direct entrance at the top of the wooden staircase. Bedroom includes a comfy queen-size bed, dresser and closet. A full bathroom is located right off the bedroom.brbrIncludes central AC/heating with a nest thermostat for easy controlling, push-button light switches throughout, access to a washer and dryer in the garage, and access to the outdoor backyard, including the pool and summer kitchen/grill.brbrAccess the guest home with a keypad/smart lock. For the utmost security, each guest receives a unique code that is only active through the period of the stay. You'll have access to the whole guest home, washer and dryer in the garage, and everything in the back yard (including the pool and summer kitchen).brbrAll backyard/common areas are shared with the main house, which is rented separately. Landscape and pool are maintained weekly.

Guest House

Private Poolside Guest House In Winter Park/Orlando

Winter Park, Florida, United States

Bed

Bath

Sleeps

$311.39

Located in Winter Park, this charming house with 3 queen beds is a dream. The adorable living room with a cozy sofa bed is perfect for relaxing after a day of exploring. With 2 bathrooms equipped with showers and hair dryers, guests will feel right at home. Enjoy the convenience of amenities like AC, WiFi, and a washing machine. On the second floor there is a comfortable space dedicated to office work. We're happy to assist with any questions while you stay at our house.

Charming 3-bedroom house with WiFi, AC in Winter Park

Winter Park, Florida, United States

Bed

Bath

Sleeps

$158.65

In the heart of Winter Park, this charming 2-bedroom apartment offers non-stop chances for unwinding and exploring. Unwind by the sparkling outdoor pool while enjoying the convenience of free WiFi and a smart TV with satellite/cable channels. Indulge in home-cooked meals prepared in the fully stocked kitchen, complete with a stove, oven, refrigerator, grill, and all the necessary appliances and utensils. Enjoy your meals at the dining table, or step outside and fire up the grill for an alfresco dining experience. When it's time to explore, you'll be just a short drive away from top attractions like the Kia Center, Universal Orlando Resort, and the Orlando International Premium Outlets. After a day of adventure, retreat to the comfort of your apartment, where you'll find essential amenities like a bathroom with towels and basic soaps, an iron and board, and air conditioning and heating to keep you comfortable. Whether you're seeking a relaxing getaway or an action-packed vacation, our 2-bedroom apartment in Winter Park has everything you need for an unforgettable stay.

Apartment

Stay near Winter Park action at our 2-bedroom apartment

Winter Park, Florida, United States

Bed

Bath

Sleeps

$239.67

The College Quarters in Winter Park is located in the charming city of Winter Park Historic District. Located within blocks. of SunRail stations, shopping, movie theatres, grocery, gas stations, banks, and golf courses, and Rollins College founded in1885 along the shores of Lake Virginia

Villa

Winter Park College quarters historic district

WINTER PARK, Florida, United States

Bed

Bath

4

Sleeps

$249.4

Welcome to your perfect getaway! This stylish 2-bedroom, 1-bath home is just 5 minutes from Park Avenue in Winter Park, where you’ll find top-rated restaurants, boutique shopping, and charming cafés. Plus, you’re less than 7 minutes from downtown Orlando!brbrUnwind in a spacious living area with vaulted ceilings and 50” Roku TVs, a dedicated office space and patio. With comfortable sleeping arrangements for up to 6 guests, this home is perfect for families, couples, or business travelers.brbrWe take guest security and safety seriously No fraud bookings, must complete an easy, online hotel-style check-in with a Rental Agreement, ID check, and a refundable hold. Or you can opt for a damage waiver for stays under 10 nights, whichever you prefer! Full details in the House Rules.brBy booking you agree to respect the house rules herein:brbrNo Smoking, Vaping or E cigarettes brbrNo Animals brbrNo parties or Events - Reservation can be cancelled and is non refundable brbrMail/Packages - we do not accept mail or packages. we are not responsible for any misplaced or lost packages. it`s recommended to mail to local post office or amazon locker if needed. brbrDo not tamper with security devices, cameras, fire or carbon monoxide sensors/alarms.brbr***This property has special local compliance requirements which include a signed rental agreement, verification, and a security hold of (which is not a traditional security deposit, just a pending transaction). As an optional alternative to the security hold, you may opt in to purchase a damage waiver provided by a third-party insurance company. The optional damage waiver is for stays up to 10 nights, with an additional $2 per day for stays longer than 10 nights. Damage waiver purchases are optional.brbrTo make this process easy for you, we use a secure and very simple, app-free platform called Happy Guest. It is not an app, and you do not have to sign up for an account - it’s a safe and secure website. It also gives you a guest portal with all the info about the home and all of my favorite local spots.brbrYour guest portal includes advertisements with third-party upgrades that you may want to enhance your stay. These upgrades are optional for things like early check in (when available).brbrLeft storage area is off limits and used only by staff or maintenance team between stays. The Ladder is only for decor purposes. DO NOT CLIMB

Cozy home 5min to Park Ave and Downtown Orlando. Dedicated office.

Winter Park, Florida, United States

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Bath

Sleeps

$178.12

This newly renovated mid century split level home has all the modern ammenities of today with the charm and craftsmanship of the 50s. Winter Park is home to some of the most elegant homes in Orange County, and this neighborhood is absolutely beautiful. If you're looking for a unique and cozy experience for your family that is an alternative to the hotels and resorts, you'll find it here.brbrLong term stays of 30 days+

Beautiful Mid Term Home in the Elegance of Winter Park!nn

Winter Park, Florida, United States

3

Bed

Bath

6

Sleeps

$135.93

Experience Winter Park like a local in this superb 1-bedroom bungalow. This enchanting property offers all the comforts you need, from AC to WiFi. We're happy to assist with any questions while you stay at our bungalow.

Quaint Key West Pool Bungalow

Winter Park, Florida, United States

Bed

Bath

Sleeps

$239.47

Stay comfortably in Winter Park at this 3-bedroom house. Guests will find two queen beds and one king bed, perfect for a restful night. The house features two bathrooms with refreshing showers to start your day right. Enjoy a serene atmosphere where you can relax and unwind after exploring. The welcoming space keeps you comfortable with air conditioning and heating throughout your stay. Whether you’re gathering with family or friends, this pleasant home offers a cozy retreat. Book now and enjoy everything this house has to offer.

3-bedroom house in charming Winter Park with cool AC

Winter Park, Florida, United States

Bed

Bath

Sleeps

$123.75

Looking for a peaceful getaway This is the ideal spot in Winter Park, FL.brbrThis beautifully updated entire downstairs unit offers a cozy living room, a remodeled modern kitchen, Smart TV, a clean bedroom with a comfortable queen-sized bed, and a full bathroom. brbrEnjoy free Wi-Fi, one dedicated parking spot per booking, and a convenient location close to everything and privacy in a quiet, upscale residential neighborhood. brbrLong-term stay available!brbrYOUR PROPERTY:brbr*Guests have the whole downstairs unit to themselves. This usually includes a bedroom, a bathroom, and a kitchen. Entire downstairs unit featuring a cozy living room, a remodeled modern kitchen, a clean bedroom with a comfortable queen-sized bed, and a full bathroom. brbr*Conveniently located just minutes from Winter Park Downtown, Orlando Downtown, Baldwin Lake, Rollins College, Full Sail University, shopping plazas, grocery stores, and a wide variety of restaurants. Whether you're visiting for leisure or here for work, this space offers the comfort and convenience you need.brbrGUEST ACCESS:brbr* Private downstairs unit with its own living room, kitchen, bathroom, and separate entrance. brbrShared Yard with the other tenants and guests.brbrADDITIONAL RULES:brbr* One pet is allowed per booking at no extra charge. Additional pets will incur a $50 fee each. Any damage caused by pets will result in additional fees.brbr* Your pets must be leashed and supervised by you at all times while in the yard, as it is a shared space with other tenants. brbr*Loud noises, smoking and heavy drinking is strictly prohibited in or around the property.brbr* Free yard parking in front of premises available for ONE car on each booking.brbr*We need picture ID to provide access to the property. Please take a picture of your valid ID and the person who is coming with you and send it to us one day prior your arrival.brbr*No outside visitors allowed. brbr*Smoking is strictly prohibited inside or around the premises.brbr*Any unapproved late checkouts may result in additional fees.brbr* Unable to receive packages or mail because it is a Domestic security issue. (but that long-term guests can ask permission first)brbr*$200 fee for each house rule broken.brbrThe property has outdoor and common areas security cameras for your safety and anyone caught breaking these rules will be escorted off the premises without refund and will forfeit their deposit.

Sleek, Spacious & Central – Your Ideal Getaway

Winter Park, Florida, United States

Bed

Bath

Sleeps

$128.62

Located in Winter Park, this apartment is a dream. With 2 nice bedrooms, AC, WiFi, a hair dryer, an iron, and a washing machine, guests will find everything they need for a comfortable stay. The bathroom is marvelous, adding a touch of luxury to the space. We hope you enjoy what our place and Winter Park has to offer.

Apartment

Charming 2-bedroom apartment with AC and WiFi in enchanting Winter Park

Winter Park, Florida, United States

Bed