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Results: 53 Rentals

  • Comfy Home in Winter Park, can accommodate up 6 guests!
    From $267 per night (USD)

    VRBO

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

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    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 ...

    From $267 per night (USD)

    VRBO

    Details
  • A curated stay in the Historic College Quarter
    From $146 per night (USD)

    Expedia

    A curated stay in the Historic College Quarter

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    You'll fall in love with this beautiful historic cottage located in the heart of Winter Park. Filled with charming vinta ...

    From $146 per night (USD)

    Expedia

    Details
  • Modern Mediterranean Oasis
    From $254 per night (USD)

    VRBO

    Modern Mediterranean Oasis

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Warm and stylish getaway. Very spacious bedrooms open dining and family room. Relax outside with beautifully lit paved p ...

    From $254 per night (USD)

    VRBO

    Details
  • Amazing College Park private walled in estate
    Click For Pricing

    Expedia

    Amazing College Park private walled in estate

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    7

    Amazing private Mediterranean walled estate located across from the historic DubsDread golf course! Centrally located in ...

    Click For Pricing

    Expedia

    Details
  • Amazing location- walk to everything
    From $281 per night (USD)

    VRBO

    Amazing location- walk to everything

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Entire Private Home - 2 bed 2 bath fully furnished unit located just one block from Park Ave in Winter Park. ***Several ...

    From $281 per night (USD)

    VRBO

    Details
  • Tiny Cottage - 3 MI to Downtown w\/Grill & Hammocks
    From $122 per night (USD)

    Expedia

    Tiny Cottage - 3 MI to Downtown w\/Grill & Hammocks

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Renovated guest suite using original reclaimed materials to create a modern vintage farmhouse vibe. Centrally l ...

    From $122 per night (USD)

    Expedia

    Details
  • Home away from home in the heart of charming Winter Park!
    From $162 per night (USD)

    VRBO

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

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    You'll fall in love with this beautifully curated historic home located in the heart of Winter Park. Filled with curated ...

    From $162 per night (USD)

    VRBO

    Details
  • Little gem apartment
    From $103 per night (USD)

    Expedia

    Little gem apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    You'll fall in love with this little gem located in the heart of Winter Park. Filled with charming vintage furniture and ...

    From $103 per night (USD)

    Expedia

    Details
  • Charming 3-bedroom townhome with AC and WiFi in Winter Park
    From $548 per night (USD)

    VRBO

    Charming 3-bedroom townhome with AC and WiFi in Winter Park

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    Stay comfortably in Winter Park at this 3-bedroom townhome. With 1 king bed and 2 queen beds, this adorable property is ...

    From $548 per night (USD)

    VRBO

    Details
  • College quater charming Winter Park Historic Dist Rollins College quarters
    From $77 per night (USD)

    Expedia

    College quater charming Winter Park Historic Dist Rollins College quarters

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    The College Quarters in Winter Park is located in the charming city of Winter Park Historic District. Located within blo ...

    From $77 per night (USD)

    Expedia

    Details
  • Bungalow Near Downtown Orlando, Winter Park, Major Hospitals, and Disney!
    From $142 per night (USD)

    VRBO

    Bungalow Near Downtown Orlando, Winter Park, Major Hospitals, and Disney!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Charming Renovated Studio in Downtown Orlando’s College Park Experience the best of urban and small-town living in this ...

    From $142 per night (USD)

    VRBO

    Details
  • King Room Near Fracture Care Center ORL
    From $229 per night (USD)

    VRBO

    King Room Near Fracture Care Center ORL

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This property is located opposite Florida Hospital, 700 metres from the Orlando Science Center. A complimentary hot brea ...

    From $229 per night (USD)

    VRBO

    Details
  • 2 Bed 1.5 Bath in Winter Park
    From $109 per night (USD)

    VRBO

    2 Bed 1.5 Bath in Winter Park

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Property Description Please reference other sites for more detailed ratings and reviews. Spacious 2 bedroom/ 1.5 bath d ...

    From $109 per night (USD)

    VRBO

    Details
  • Lakefront Condo w\/ Sunroom, Office, & Lakeside Pool
    From $133 per night (USD)

    VRBO

    Lakefront Condo w\/ Sunroom, Office, & Lakeside Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to beautiful Winter Park, Florida and your home away from home in your lakeside, super-convenient 1 bedroom /1 h ...

    From $133 per night (USD)

    VRBO

    Details
  • Charming home 3 blocks from historic Park Avenue & one block from Lake Virginia
    From $314 per night (USD)

    VRBO

    Charming home 3 blocks from historic Park Avenue & one block from Lake Virginia

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Open kitchen / family room with dining area to comfortable seat 4, dining room and living room, screened in porch for wa ...

    From $314 per night (USD)

    VRBO

    Details
  • Private Luxury Pool \/ Smart-home
    From $427 per night (USD)

    Expedia

    Private Luxury Pool \/ Smart-home

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Owners have freshly renovated September 2023 Investing over ($75,000) adding the following - Brand new single slope met ...

    From $427 per night (USD)

    Expedia

    Details
  • Stroll to Park Avenue from Vintage Lake-View House
    From $248 per night (USD)

    VRBO

    Stroll to Park Avenue from Vintage Lake-View House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This cozy, quaint Winter Park home was built in 1925. The house has updated appliances and plenty of space. There are tw ...

    From $248 per night (USD)

    VRBO

    Details
  • Quaint 3 BR Home in Winter Park\/Orlando with Large Yard
    From $208 per night (USD)

    Expedia

    Quaint 3 BR Home in Winter Park\/Orlando with Large Yard

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Lovely private home located just minutes from the quaint and historic Downtown Winter Park. There is a Large backyard wi ...

    From $208 per night (USD)

    Expedia

    Details
  • Cute Guest House In Winter Park Minutes From Downtown in Car
    From $139 per night (USD)

    VRBO

    Cute Guest House In Winter Park Minutes From Downtown in Car

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Enjoy our guest house and the new space we created in Oct 2015! The guest house has a kitchenette with two glass burners ...

    From $139 per night (USD)

    VRBO

    Details
  • Cottage Retreat in the City
    From $153 per night (USD)

    VRBO

    Cottage Retreat in the City

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    QUICK LOOK Newly Constructed, 1-Bedroom Cottage in College Park, a quaint downtown Orlando neighborhood Available Night ...

    From $153 per night (USD)

    VRBO

    Details
  • β˜€οΈ King Condo w\/ Sunroom, Lakeside Pool and Waterfront Park
    From $133 per night (USD)

    VRBO

    ☀️ King Condo w\/ Sunroom, Lakeside Pool and Waterfront Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to beautiful Winter Park, Florida and your home away from home in our trendy, super-convenient 1/1 King bed ...

    From $133 per night (USD)

    VRBO

    Details
  • Cabana style studio apt\/private garden near Rollins and Park Ave. 1 week minim<br><br>
    From $137 per night (USD)

    VRBO

    Cabana style studio apt\/private garden near Rollins and Park Ave. 1 week minim<br><br>

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    3

    About this space Cook in or don't in this private and luxurious yet serene studio, where fun mid century meets old flori ...

    From $137 per night (USD)

    VRBO

    Details
  • THE CLOUD 9 SUITE
    From $209 per night (USD)

    VRBO

    THE CLOUD 9 SUITE

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    PET FRIENDLY 🐾 Book the Cloud 9 Suite, located in the heart of downtown Winter Park FL and Orlando! Beautifully furnish ...

    From $209 per night (USD)

    VRBO

    Details
  • Home Away from Home- Winter Park
    From $146 per night (USD)

    Expedia

    Home Away from Home- Winter Park

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy our newly renovated home in Winter Park. We are centrally located and within minutes from Rollins College and Park ...

    From $146 per night (USD)

    Expedia

    Details
  • Total Serenity #2, 2 BDRM, 2 Bath
    From $287 per night (USD)

    VRBO

    Total Serenity #2, 2 BDRM, 2 Bath

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Enjoy your stay in this cozy, newly remodeled 2 Bedroom 2 bath, 1200 sq ft apartment! Centrally located in the heart of ...

    From $287 per night (USD)

    VRBO

    Details
  • Tranquil & Tiny house
    From $171 per night (USD)

    Expedia

    Tranquil & Tiny house

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    This recently restored Tiny house has everything you need in such a unique, tranquil and surreal setting in the heart of ...

    From $171 per night (USD)

    Expedia

    Details
  • Cute and Cozy Apartment-B     1 Bedroom Duplex
    From $170 per night (USD)

    VRBO

    Cute and Cozy Apartment-B 1 Bedroom Duplex

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    ENJOY YOUR STAY IN WINTER PARK IN THIS COZY, NEWLY RENOVATED APARTMENT CENTRALLY LOCATED IN A QUIET NEIGHBORHOOD WITHIN ...

    From $170 per night (USD)

    VRBO

    Details
  • Hidden Oasis #4  2 BDRM, 2 Bath
    From $309 per night (USD)

    Expedia

    Hidden Oasis #4 2 BDRM, 2 Bath

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy your stay in this cozy, newly remodeled 2 Bedroom 2 bath, 1200 sq ft apartment! Centrally located in the heart of ...

    From $309 per night (USD)

    Expedia

    Details
  • Peace and the Park #3  -2 BDRM, 2 Bath
    From $256 per night (USD)

    VRBO

    Peace and the Park #3 -2 BDRM, 2 Bath

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy your stay in this huge 1200 square foot newly remodeled 2 Bedroom 2 bath apartment! Centrally located in Winter Pa ...

    From $256 per night (USD)

    VRBO

    Details
  • LUXURY 5\/4 w Jacuzzi tub Winter Park\/CP Orlando Gem
    From $1406 per night (USD)

    Expedia

    LUXURY 5\/4 w Jacuzzi tub Winter Park\/CP Orlando Gem

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    22

    Welcome to your perfect Orlando getaway! This stunning new home boasts 5 spacious bedrooms and 4 modern baths, comfortab ...

    From $1406 per night (USD)

    Expedia

    Details
  • Charming 2-bedroom apartment with AC and WiFi in enchanting Winter Park
    Click For Pricing

    VRBO

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

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    Located in Winter Park, this apartment is a dream. With 2 nice bedrooms, AC, WiFi, a hair dryer, an iron, and a washing ...

    Click For Pricing

    VRBO

    Details
  • LUXURY π•„π•šπ•• β„‚π•–π•Ÿπ•₯𝕦𝕣π•ͺ π•„π• π••π•–π•£π•Ÿ α΄ α΄€α΄„α΄€α΄›Ιͺᴏɴ in 𝒲𝒾𝓃𝓉𝑒𝓇 𝒫𝒢𝓇𝓀
    From $286 per night (USD)

    VRBO

    LUXURY 𝕄𝕚𝕕 ℂ𝕖𝕟𝕥𝕦𝕣𝕪 𝕄𝕠𝕕𝕖𝕣𝕟 ᴠᴀᴄᴀᴛɪᴏɴ in 𝒲𝒾𝓃𝓉𝑒𝓇 𝒫𝒶𝓇𝓀

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    NEW CONSTRUCTION Luxury Home north of Downtown Orlando in the heart of Winter Park steps from Winter Park Village near t ...

    From $286 per night (USD)

    VRBO

    Details
  • 3-bedroom Bungalow in Welcoming Winter Park with WiFi, AC
    From $308 per night (USD)

    VRBO

    3-bedroom Bungalow in Welcoming Winter Park with WiFi, AC

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Discover this marvelous 3-bedroom gem in Orlando. This lovely bungalow features 1 king bed and 2 queen beds, perfect for ...

    From $308 per night (USD)

    VRBO

    Details
  • Winter Park College quarters historic district
    From $121 per night (USD)

    VRBO

    Winter Park College quarters historic district

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    The College Quarters in Winter Park is located in the charming city of Winter Park Historic District. Located within blo ...

    From $121 per night (USD)

    VRBO

    Details
  • Cheerful and stylish 2-bedroom with parking, centrally located
    From $162 per night (USD)

    VRBO

    Cheerful and stylish 2-bedroom with parking, centrally located

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Relax in this cheerful, sun-filled home, walking distance to restaurants, shopping, groceries and our favorite local cof ...

    From $162 per night (USD)

    VRBO

    Details
  • Modern, fabulous two-bedroom with parking in Winter Park
    From $156 per night (USD)

    Expedia

    Modern, fabulous two-bedroom with parking in Winter Park

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Our newly renovated duplex home is stylish and well-appointed with everything you need for a getaway or a longer visit. ...

    From $156 per night (USD)

    Expedia

    Details
  • Peaceful Retreat #1    -2B \/2B Apartment
    From $248 per night (USD)

    VRBO

    Peaceful Retreat #1 -2B \/2B Apartment

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Everything that a small to large group of 8 could ask for. Centrally located in the heart of Winter Park. A short walk o ...

    From $248 per night (USD)

    VRBO

    Details
  • Comfy and Charming -A 1 Bedroom Duplex Apartment
    From $169 per night (USD)

    Expedia

    Comfy and Charming -A 1 Bedroom Duplex Apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    ENJOY YOUR STAY IN WINTER PARK IN THIS COMFY, NEWLY RENOVATED APARTMENT CENTRALLY LOCATED IN A QUIET NEIGHBORHOOD WITHIN ...

    From $169 per night (USD)

    Expedia

    Details
  • Greatest location! Condo with private yard!
    From $427 per night (USD)

    VRBO

    Greatest location! Condo with private yard!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Location, Location, Location!!! Greatest location! Well appointed condo -one block from Park Avenue! This is a Downstair ...

    From $427 per night (USD)

    VRBO

    Details
  • Mills House @WP. Sleeps 11 Renovated. Queen beds
    Click For Pricing

    Expedia

    Mills House @WP. Sleeps 11 Renovated. Queen beds

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    11

    Enjoy a stylish experience at this centrally-located place. MillsHouse is conveniently located for a foodie adventure. T ...

    Click For Pricing

    Expedia

    Details
  • Advent health all white unit
    Click For Pricing

    VRBO

    Advent health all white unit

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to my charming 2 bedroom 2 bathroom home in the heart of Orlando FL located right of the I4 highway exit Princet ...

    Click For Pricing

    VRBO

    Details
  • LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!
    From $153 per night (USD)

    Expedia

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

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This duplex unit is cozy and comfortable. It's updated with all new appliances, is tastefully decorated and has very com ...

    From $153 per night (USD)

    Expedia

    Details
  • NEW! β˜€Bungalow+Patio+FirePit! Close to Everything!
    Click For Pricing

    VRBO

    NEW! ☀Bungalow+Patio+FirePit! Close to Everything!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    You will love it here! This trendy winter park home will feel like home! Well equipped with all your essentials (Soaps+ ...

    Click For Pricing

    VRBO

    Details
  • CHARMING - Cozy Retreat Near Lake Killarney in Winter Park
    From $213 per night (USD)

    Expedia

    CHARMING - Cozy Retreat Near Lake Killarney in Winter Park

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Come and stay awhile at the Killarney Retreat, built in the 50s, tucked away from the hub of city, yet just a short driv ...

    From $213 per night (USD)

    Expedia

    Details
  • Cottage on Cornell - Quaint & Cozy w\/Outdoor Kitchen
    Click For Pricing

    VRBO

    Cottage on Cornell - Quaint & Cozy w\/Outdoor Kitchen

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    0

    Newly renovated guest suite using original reclaimed materials to create a modern vintage farmhouse vibe. Centrally loca ...

    Click For Pricing

    VRBO

    Details
  • Fire Pit + Grill + 2MI to DT + Long Term Stays!
    From $238 per night (USD)

    Expedia

    Fire Pit + Grill + 2MI to DT + Long Term Stays!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Summary: Come and relax in our newly remodeled, stylish home. Moments away from craft beer bars, brewery, AdventHealth O ...

    From $238 per night (USD)

    Expedia

    Details
  • Elegant & Spacious Historic Winter Park Home with Pool + Spa
    From $289 per night (USD)

    VRBO

    Elegant & Spacious Historic Winter Park Home with Pool + Spa

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Historic Winter Park home, located within a beautiful neighborhood. The home is spacious, charming and elegantly-appoint ...

    From $289 per night (USD)

    VRBO

    Details
  • Winter Park Pool home close to Lake Virginia, Rollins College & Park Ave.
    From $375 per night (USD)

    VRBO

    Winter Park Pool home close to Lake Virginia, Rollins College & Park Ave.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    One month minimum to rent (30 nights). A hidden gem, this meticulous sun-filled 3 BR + Office/2.5 bath home offers ult ...

    From $375 per night (USD)

    VRBO

    Details
  • 3BR - 3BA : Location, Location, Location : Rose Isle\/Beverly Shores Neighborhood
    From $238 per night (USD)

    VRBO

    3BR - 3BA : Location, Location, Location : Rose Isle\/Beverly Shores Neighborhood

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    As you drive into the established and highly desirable neighborhood of Beverly Shores / Rose Isle, you will be embraced ...

    From $238 per night (USD)

    VRBO

    Details
  • Private Poolside Guest House In Winter Park\/Orlando
    From $147 per night (USD)

    Expedia

    Private Poolside Guest House In Winter Park\/Orlando

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Beautiful and comfortable two-story cottage/detached guest house, centrally-located within an historic neighborhood. Loc ...

    From $147 per night (USD)

    Expedia

    Details
  • Cheerful 4-bedroom with large and lush backyard
    From $321 per night (USD)

    VRBO

    Cheerful 4-bedroom with large and lush backyard

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Your family will be close to everything when you stay at this centrally-located place. Close to multiple interstate entr ...

    From $321 per night (USD)

    VRBO

    Details
  • Enjoy more space and relax in Downtown Orlando !!
    From $442 per night (USD)

    VRBO

    Enjoy more space and relax in Downtown Orlando !!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Take advantage of our fast and free WiFi, free hot breakfast, free coffee, free parking and free weekday newspapers thro ...

    From $442 per night (USD)

    VRBO

    Details
  • Tiny Home - 3 MI to Downtown & Winter Park
    From $228 per night (USD)

    VRBO

    Tiny Home - 3 MI to Downtown & Winter Park

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Summary: Welcome to our charming 2 bedroom house in the heart of Winter Park, Florida! This beautiful home is the perfec ...

    From $228 per night (USD)

    VRBO

    Details