Home Vacation Home Rentals By Owner In Winter Park, FL

Showing 65 Of 65 Vacation Rentals
Slider Thumb
Exceptional(1)

$161.76

/ Nightly
Private Vacation Home

Cheerful and stylish 2-bedroom with parking, centrally located

Winter Park, Florida, United States

Relax in this cheerful, sun-filled home, walking distance to restaurants, shopping, groceries and our favorite local coffee shop. Mid-century modern meets Scandinavian design to create an inviting and soothing home-base for exploring Winter Park, College Park or Rollins College. Minutes to downtown Winter Park and all of the shopping and dining of Park Avenue. Ten minutes to hospital complex and less than fifteen minutes to downtown Orlando.
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb
Exceptional(2)

$198.37

/ Nightly
Private Vacation Home

Charming Home Winter Park, Near Rollins College, Lake Baldwin Park, Orlando FL

Winter Park, Florida, United States

Discover the convenience of this exceptional locale strategically situated just 5-7 minutes away from the vibrant Park Avenue, Lake Baldwin Park, 5 minutes to Rollins college, adorned with charming cafes and boutiques stores, and immerse yourself in the warmth of my luminous 3 bedroom residence, thought fully furnished for your Winter Park visit.brbrThe non smoking unit boasts modern amenities such as AC, wIFI, and security cameras by the front door, ensuring a seamless and comfortable stay. Step into the living room, featuring a generous television and expansive windows that usher in natural light, crafting a luminous and open ambiance. Your ideal Winter Park visit begins here.brbrUpon entering, you are greeted by a spacious living room, with a big TV, and large windows allow natural light to flood the space, creating a bright and airy atmosphere.br brThe sunny kitchen with stainless steel frig, a place for you to enjoy your meal or morning coffee. Each bedroom has a double bed, with a big closet and lots of storage and fans. The master bedroom has a dresser, big closet and an updated bathroom with a walking shower. The other bathroom has modern fixtures, a big mirror and a soaking tub for your relaxation. The bedroom #3 has a dresser, desk with chair and a comfortable futon double bed.brbrThe sunny backroom welcomes the warmth of sunlight, creating a bright and uplifting atmosphere. With a view of the fenced backyard. It has a piano and desk with chair.brbrIt offers a perfect balance of tranquility and accessibility. A great location for you to discover winter park the best way. We look forward to hosting you!
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb

$222.0

/ Nightly
Private Vacation Home

Comfortable House in the lovely Winter Park, Olando Fl .

Winter Park, Florida, United States

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
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(2)

$170.45

/ Nightly
Private Vacation Home

Townhome w/ Fenced Yard in Orlando Suburbs!

Winter Park, Florida, United States

In-Unit Washer & Dryer | 5 Mi to Park Ave Shopping & Dining | 20 Mi to Orlando Theme ParksbrbrFind the best of both worlds at this pet-friendly vacation rental in Winter Park — a cozy 1-bed, 1-bath escape for quiet nights and a convenient base for exploring Orlando and nearby theme parks! Fuel up, then take a scenic boat tour at Central Park or chase thrills at Universal Studios. Back at the townhome, grab your popcorn and settle in for a relaxing movie night. Book your next getaway now!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom: 1 king bedbr- Living Room: 1 twin daybed w/ 1 twin trundlebrbrSHARED AMENITIESbr- Expansive fenced yardbrbrMAIN FEATURESbr- 2 Smart TVsbr- Dining tablebr- Sitting areabrbrKITCHENETTEbr- Refrigerator, microwavebr- Drip coffee maker (coffee provided), toasterbrbrGENERALbr- Free WiFibr- Central A/C & heat (thermostat control)br- Washer & dryerbr- Linens, towelsbrbrFAQbr- 2 exterior security cameras (facing out)br- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- Single-story townhome, step-free entrybr- 1 interior step for kitchenette/laundry areabr- Grab rail in showerbrbrPARKINGbr- Shared driveway (4 vehicles)br- Free street parking (first-come, first-served)brbrADDT’L ACCOMMODATIONSbr- An additional vacation rental is available in the same duplex on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbr- Quiet residential area near parks, lakes & conveniencesbr- 5 miles to Central Park & Scenic Boat Tourbr- 5 miles to Charles Hosmer Morse Museum of American Artbr- 6 miles to Mead Botanical Gardenbr- 7 miles to Orlando Science Centerbr- 20 miles to Universal Studios & 30 miles to Walt Disney Worldbr- 20 miles to Orlando Int’l Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking or vaping of any kindbr- Pet friendly w/ $125 fee (+ fees & taxes, 1 max)br- No events, parties, or large gatheringsbr- Must be at least 18 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- While this single-story townhome offers step-free entry, 1 interior step is required to access the kitchenette and laundry areabr- Your safety matters. This property features 2 exterior security cameras: 1 camera is in front of the house facing the front entrance, and 1 camera is in the back of the house facing the backyard. The cameras do not look into any interior spaces. The cameras record video and sound when activated by motionbr- There is another bookable vacation rental in the same duplex on-site that shares the backyard and driveway; other travelers may be present during your stay
Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb

$214.6

/ Nightly
Private Vacation Home

Gateway to Orlando Theme Parks! Home w/ Large Yard

Winter Park, Florida, United States

5 Mi to Park Ave Shopping | Spacious Sunroom | In-Unit LaundrybrbrWelcome to your peaceful Winter Park retreat! This 2-bedroom, 1-bath vacation rental offers a convenient home base for both city adventures and theme park thrills. Stroll through Mead Botanical Garden, explore the Orlando Science Center, and make memories park-hopping with the kids. Ready to relax at the townhome Make dinner your way and dive into your latest watchlist obsession. Secure your spot today!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Living Room: 1 twin daybed w/ 1 twin trundlebrbrSHARED AMENITIESbr- Expansive fenced yardbrbrMAIN FEATURESbr- 3 Smart TVsbr- Dining areabr- Large sunroombr- Shower/tub combobrbrKITCHENbr- Refrigerator, microwave, stove/oven, dishwasherbr- Drip coffee maker (coffee provided), toasterbrbrGENERALbr- Free WiFibr- Central A/C & heat (thermostat control)br- Washer & dryerbr- Linens, towelsbrbrFAQbr- 2 exterior security cameras (facing out)br- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- Single-story townhome, 3 steps to enterbrbrPARKINGbr- Shared driveway (4 vehicles)br- Free street parking (first-come, first-served)brbrADDT’L ACCOMMODATIONSbr- An additional vacation rental is available in the same duplex on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbr- Quiet residential area near parks, lakes & conveniencesbr- 5 miles to Central Park & Scenic Boat Tourbr- 5 miles to Charles Hosmer Morse Museum of American Artbr- 6 miles to Mead Botanical Gardenbr- 7 miles to Orlando Science Centerbr- 20 miles to Universal Studios & 30 miles to Walt Disney Worldbr- 20 miles to Orlando Int’l Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking or vaping of any kindbr- Pet friendly w/ $125 fee (+ fees & taxes, 1 max)br- No events, parties, or large gatheringsbr- Must be at least 18 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story townhome requires 3 steps to enterbr- Your safety matters. This property features 2 exterior security cameras: 1 camera is in front of the house facing the front entrance, and 1 camera is in the back of the house facing the backyard. The cameras do not look into any interior spaces. The cameras record video and sound when activated by motionbr- There is another bookable vacation rental in the same duplex on-site that shares the backyard and driveway; other travelers may be present during your stay
Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps

Home Rent a place that suits your needs

Private vacation home

Private vacation home

View 61 Private vacation home

Home Most popular vacation rentals in Winter Park

Slider Thumb

$138.57

/ Nightly
Apartment

Stay near Winter Park action at our 2-bedroom apartment

Winter Park, Florida, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb

$206.13

/ Nightly
Private vacation home

Great Family Home

Winter Park, Florida, United States

Bed 3

Bed

Bath 2

Bath

Sleep 5

Sleeps
Slider Thumb

$203.06

/ Nightly
Apartment

Just 3 Blocks to Park Ave Shops/ Restaurants, 2 From The Winter Park Village!

Winter Park, Florida, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb

$190.86

/ Nightly
Private vacation home

Funky Remodeled Otown Bungalow Sleeps 8

Winter Park, Florida, United States

Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps
Slider Thumb

$187.88

/ Nightly
Private vacation home

GREAT LOCATION ?

Winter Park, Florida, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
Slider Thumb

$178.12

/ Nightly
Private vacation home

Beautiful Mid Term Home in the Elegance of Winter Park!

Winter Park, Florida, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb

$161.75

/ Nightly
Private vacation home

Home away from home in the heart of charming Winter Park!

Winter Park, Florida, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
Slider Thumb

$146.47

/ Nightly
Apartment

LUXURY AND LOCATION!!!

WINTER PARK, Florida, United States

Bed 2

Bed

Bath 2

Bath

Sleep 5

Sleeps
Slider Thumb

$146.25

/ Nightly
Cottage

A curated stay in the Historic College Quarter

Winter Park, Florida, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb

$102.68

/ Nightly
Apartment

Little gem apartment

Winter Park, Florida, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

Most Popular Cities in Florida