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Winter Park Rentals

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Results: 202 Rentals

  • Modern Garden Suite!
    From $200 per night (USD)

    VRBO

    Modern Garden Suite!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    The space is a newly built 600+ sq ft Modern Chic style home, located in The Audubon Park Garden District! Enjoy the con ...

    From $200 per night (USD)

    VRBO

    Details
  • 2-bedroom vacation home on Lake, NON-SMOKERS only please
    From $235 per night (USD)

    VRBO

    2-bedroom vacation home on Lake, NON-SMOKERS only please

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    In our charming accommodations in exclusive Maitland neighborhood, you can easily reach all the popular spots in Orlando ...

    From $235 per night (USD)

    VRBO

    Details
  • Family Friendly home with Fenced in Backyard to enjoy with kids & pets
    From $261 per night (USD)

    VRBO

    Family Friendly home with Fenced in Backyard to enjoy with kids & pets

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    This beautiful 3 bedroom, 2 full bathrooms home is located in a lovely and quiet community. Close to shops, restaurants ...

    From $261 per night (USD)

    VRBO

    Details
  • The Bird House Spa Winter Park
    From $312 per night (USD)

    Expedia

    The Bird House Spa Winter Park

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Soar into The Birdhouse, a spa-like retreat for those who traveling to Central Florida for a little wow and a little rel ...

    From $312 per night (USD)

    Expedia

    Details
  • Lakefront Paradise Near Attractions
    From $613 per night (USD)

    VRBO

    Lakefront Paradise Near Attractions

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    Nestled in the heart of Winter Park, just five miles from downtown Orlando and twenty minutes from Disney/Universal, thi ...

    From $613 per night (USD)

    VRBO

    Details
  • Downtown Groovy Studio
    From $158 per night (USD)

    Expedia

    Downtown Groovy Studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This groovy place to stay is truly one of a kind! Just walking distance from a plethora of Orlando’s most popular eateri ...

    From $158 per night (USD)

    Expedia

    Details
  • Cozy 2BR\/2BA w\/ Modern Amenities
    From $200 per night (USD)

    VRBO

    Cozy 2BR\/2BA w\/ Modern Amenities

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Your Winter Park adventure begins at this 2-bedroom house. With AC, WiFi, and a washing machine, guests can enjoy a nice ...

    From $200 per night (USD)

    VRBO

    Details
  • Prvt Home w\/large pool\/4Beds\/3Baths
    From $312 per night (USD)

    Expedia

    Prvt Home w\/large pool\/4Beds\/3Baths

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    No matter the occasion—be it a family gathering, reunion, corporate retreat, wellness retreat, creative workshop, social ...

    From $312 per night (USD)

    Expedia

    Details
  • Beautifully Renovated Home in Winter Park, Florida
    From $151 per night (USD)

    VRBO

    Beautifully Renovated Home in Winter Park, Florida

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Just outside of Orlando is the enchanting suburb of Winter Park. Known for a quaint shopping area, great restaurants, b ...

    From $151 per night (USD)

    VRBO

    Details
  • Stunning Luxury Home in Artsy Winter Park featuring Nintendo-Themed Game Room!
    From $1252 per night (USD)

    Expedia

    Stunning Luxury Home in Artsy Winter Park featuring Nintendo-Themed Game Room!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    13

    Newly redesigned and just 40 minutes from the theme parks, Atlantic Oasis is an award-winning, custom-built resort-style ...

    From $1252 per night (USD)

    Expedia

    Details
  • 3BR Outdoor Kitchen w MIL suite - 3 MI to DT
    From $400 per night (USD)

    VRBO

    3BR Outdoor Kitchen w MIL suite - 3 MI to DT

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Summary: Looking for a tiny home with private space in the heart of Winter Park, Florida? This beautiful home is the per ...

    From $400 per night (USD)

    VRBO

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

    Expedia

    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)

    Expedia

    Details
  • Upscale 3\/2 Townhome | King Bed | Patio | Wifi
    From $349 per night (USD)

    VRBO

    Upscale 3\/2 Townhome | King Bed | Patio | Wifi

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Come experience luxury in Winter Park in our upscale two-story townhome! ✓ Private Entrance & Self-Check In ✓ Perfect f ...

    From $349 per night (USD)

    VRBO

    Details
  • Charming CozyLux 2-bedroom apartment
    From $194 per night (USD)

    Expedia

    Charming CozyLux 2-bedroom apartment

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Escape to this enchanting apartment in picturesque Winter Park. This cozy retreat features 2 bedrooms with a king bed, q ...

    From $194 per night (USD)

    Expedia

    Details
  • Long Term Stays! 2 MI to DT Orlando & Winter Park
    From $242 per night (USD)

    VRBO

    Long Term Stays! 2 MI to DT Orlando & Winter Park

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Looking for a stylish getaway home? Say no more, this is IT! in one of Orlando's best neighborhoods, College Pa ...

    From $242 per night (USD)

    VRBO

    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
  • King Room Near West Marine ORL
    From $174 per night (USD)

    VRBO

    King Room Near West Marine ORL

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    property offers the following amenities for all guests Free wireless high-speed Internet access, exercise room, and free ...

    From $174 per night (USD)

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    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
  • Pondside Retreat with Koi in Charming Winter Park, FL
    From $228 per night (USD)

    VRBO

    Pondside Retreat with Koi in Charming Winter Park, FL

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Welcome home to your pondside retreat, perfect for relaxing longer stays with access to all the best of Central Florida. ...

    From $228 per night (USD)

    VRBO

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

    VRBO

    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)

    VRBO

    Details
  • Ivanhoe Village Quiet Home, Walk to Restaurants, Shops, Hospital, Everything!
    From $90 per night (USD)

    VRBO

    Ivanhoe Village Quiet Home, Walk to Restaurants, Shops, Hospital, Everything!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Looking for a 2 bedroom or a shorter term rental near here? See my other rental on here Prop ID:3011707 Nestled on a ...

    From $90 per night (USD)

    VRBO

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

    VRBO

    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)

    VRBO

    Details
  • Lakefront Luxury Furnished  Split Floor Plan First Floor Condo
    From $76 per night (USD)

    VRBO

    Lakefront Luxury Furnished Split Floor Plan First Floor Condo

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    You will enjoy lake front living on Lake Howell, a 500 acre fishing, sailing and skiing lake. Large first floor 3 bedroo ...

    From $76 per night (USD)

    VRBO

    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
  • Very Special HGTV Type 2 bed 1 bath
    From $139 per night (USD)

    VRBO

    Very Special HGTV Type 2 bed 1 bath

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Beautiful 2 bed 1 Bath first floor, fenced in just completely remodeled Condo. Located on 500 Acre fish/ski Lake Howell. ...

    From $139 per night (USD)

    VRBO

    Details
  • Million Dollar View on the Lake!
    From $178 per night (USD)

    VRBO

    Million Dollar View on the Lake!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Peaceful and centrally-located in Winter Park, Fl.. A home within a home. You have your own living area, bathroom and be ...

    From $178 per night (USD)

    VRBO

    Details
  • 3Bdrm Home Near Downtown Orlando and Winter park
    From $352 per night (USD)

    Expedia

    3Bdrm Home Near Downtown Orlando and Winter park

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    This stylish place to stay is perfect for group trips! This is a 3 bedroom modern home that is conveniently located near ...

    From $352 per night (USD)

    Expedia

    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
  • Welcome to the Treetop Villa. An Orlando Victorian Getaway!
    From $316 per night (USD)

    Expedia

    Welcome to the Treetop Villa. An Orlando Victorian Getaway!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    Step into a fairytale at our Treetop Villa, nestled within a charming 1920 Victorian home on a lush half-acre lot in the ...

    From $316 per night (USD)

    Expedia

    Details
  • Modern Cuartito by Winter Park
    From $115 per night (USD)

    VRBO

    Modern Cuartito by Winter Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This Cuartito is located near all major attractions the Orlando area has to offer. Below is a list of the top attraction ...

    From $115 per night (USD)

    VRBO

    Details
  • This house is a 3 bedroom(s), 1 bathrooms, located in Winter Park, FL.
    From $283 per night (USD)

    Expedia

    This house is a 3 bedroom(s), 1 bathrooms, located in Winter Park, FL.

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Escape to our charming 3-bedroom, 1-bathroom retreat nestled in the heart of Winter Park, FL, where comfort meets conven ...

    From $283 per night (USD)

    Expedia

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

    VRBO

    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)

    VRBO

    Details
  • Lovely Spacious Guesthouse in Mills 50 District, Orlando
    From $87 per night (USD)

    Expedia

    Lovely Spacious Guesthouse in Mills 50 District, Orlando

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Renovated guesthouse on the same property behind our 1920s historic home in the Mills 50 District near Downtown Orlando. ...

    From $87 per night (USD)

    Expedia

    Details
  • Beautiful Mid Term Home in the Elegance of Winter Park!\n\n
    From $178 per night (USD)

    VRBO

    Beautiful Mid Term Home in the Elegance of Winter Park!\n\n

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This newly renovated mid century split level home has all the modern ammenities of today with the charm and craftsmanshi ...

    From $178 per night (USD)

    VRBO

    Details
  • Dog-friendly home with access to Lake Druid & downtown, firepit, deck, & 2 bikes
    From $227 per night (USD)

    Expedia

    Dog-friendly home with access to Lake Druid & downtown, firepit, deck, & 2 bikes

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Paradise on Lake Druid Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...

    From $227 per night (USD)

    Expedia

    Details
  • Safe and Quiet - 3bdrm house in charming Winter Park
    From $145 per night (USD)

    VRBO

    Safe and Quiet - 3bdrm house in charming Winter Park

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Safe, quiet neighborhood! Shopping and restaurants 3 mins, 417 & 408 expwys 5 mins. Yet, the 3/2 house is tucked away in ...

    From $145 per night (USD)

    VRBO

    Details
  • Eclectic 1 Bedroom Apt in Downtown Orlando. 15mins from Airport & UCF.
    From $197 per night (USD)

    Expedia

    Eclectic 1 Bedroom Apt in Downtown Orlando. 15mins from Airport & UCF.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Keep it simple at our peaceful and centrally-located 1 bedroom apartment situated in the quaint Mills/50 corridor. We a ...

    From $197 per night (USD)

    Expedia

    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
  • Peaceful Lakefront Oasis - Relax & Recharge
    From $137 per night (USD)

    Expedia

    Peaceful Lakefront Oasis - Relax & Recharge

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Escape to this inviting waterfront 1-bedroom, 1-bathroom vacation rental just 7 miles from Orlando! Designed for snowbir ...

    From $137 per night (USD)

    Expedia

    Details
  • Landing at Azul Baldwin Park Apartments - 1 Bedroom in Northeast Orlando
    From $129 per night (USD)

    VRBO

    Landing at Azul Baldwin Park Apartments - 1 Bedroom in Northeast Orlando

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Azul Baldwin Park Apartments is a popular property in the Northeast Orlando neighborhood of Orlando where Landing offers ...

    From $129 per night (USD)

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    Details
  • Landing at Azul Baldwin Park Apartments - 1 Bedroom in Northeast Orlando
    From $131 per night (USD)

    VRBO

    Landing at Azul Baldwin Park Apartments - 1 Bedroom in Northeast Orlando

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Azul Baldwin Park Apartments is a lively property in the Northeast Orlando neighborhood of Orlando where Landing offers ...

    From $131 per night (USD)

    VRBO

    Details
  • Beautiful Direct Fish & Ski Lakefront Town home In N. Orlando with Pool &  WiFi
    From $126 per night (USD)

    VRBO

    Beautiful Direct Fish & Ski Lakefront Town home In N. Orlando with Pool & WiFi

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    5

    Direct lake front condo 2 bed 2 ½ bath townhouse w/private boat dock. Includes Electric with Password Protected Spectrum ...

    From $126 per night (USD)

    VRBO

    Details
  • Deck Condo
    From $190 per night (USD)

    Expedia

    Deck Condo

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Your family will be close to everything when you stay at this centrally-located place. Nestled along the SHORELINE of be ...

    From $190 per night (USD)

    Expedia

    Details
  • Beautiful 2 Story Winter Park Villa
    From $167 per night (USD)

    VRBO

    Beautiful 2 Story Winter Park Villa

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    *POOL IS CURRENTLY CLOSED *PERFECT LOCATION! 5 min from Baldwin Park, 10 min ride to the airport, 10 min from Park Ave, ...

    From $167 per night (USD)

    VRBO

    Details
  • Spacious Home w\/Pool & Hot Tub near Downtown Orlando!
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    Expedia

    Spacious Home w\/Pool & Hot Tub near Downtown Orlando!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Nestled in one of the best neighborhoods near Downtown Orlando (Ivanhoe Village), you'll be within a 5 min walk to tons ...

    Click For Pricing

    Expedia

    Details
  • Luxury Tiny Home -2 MI to DT Orlando & Winter Park
    From $187 per night (USD)

    VRBO

    Luxury Tiny Home -2 MI to DT Orlando & Winter Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Summary: Enjoy your stay in a stylish, new construction tiny home in one of Orlando's best neighborhoods, College Park. ...

    From $187 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
  • NEW! ☀Bungalow+Patio+FirePit! Close to Everything!
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    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
  • Yuki's City Pool Home!
    From $288 per night (USD)

    Expedia

    Yuki's City Pool Home!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy living in a stylish city charm at this centrally-located pool home! Minutes drive to park Ave, restaurants, shoppi ...

    From $288 per night (USD)

    Expedia

    Details
  • By the Sea Style Condo
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    VRBO

    By the Sea Style Condo

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    4

    Welcome to your home away from home. This rental unit is located just 10 minutes from Downtown Orlando and is a 25-30 mt ...

    Click For Pricing

    VRBO

    Details
  • 1 bed, 1 bath college park gem
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    Expedia

    1 bed, 1 bath college park gem

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    28

    My home is on a quiet street nestled in the Dubsdread Golf Course, less than 10 minutes from downtown Orlando and Winter ...

    Click For Pricing

    Expedia

    Details
  • Luxury Ranch 2 Master Kg Bed w\/ heated Salted Pool
    From $810 per night (USD)

    VRBO

    Luxury Ranch 2 Master Kg Bed w\/ heated Salted Pool

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    13

    The Luxury Ranch is a tropical getaway in Orlando where life revolves around the sunshine, swimming pool, and airy sunro ...

    From $810 per night (USD)

    VRBO

    Details
  • Sunshine Escape Guesthouse ☀
    From $161 per night (USD)

    Expedia

    Sunshine Escape Guesthouse ☀

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Clean and comfortable guesthouse centrally located in Orlando. It is perfect for business travelers, baecation for coupl ...

    From $161 per night (USD)

    Expedia

    Details
  • Cozy Condo
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    VRBO

    Cozy Condo

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    ...

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    VRBO

    Details
  • Advent health all white unit
    Click For Pricing

    Expedia

    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

    Expedia

    Details
  • Unit A Cheerful 2 Bedroom
    From $180 per night (USD)

    VRBO

    Unit A Cheerful 2 Bedroom

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    Enjoy a stylish experience at this centrally-located place in the Heart of Maitland. Close to dining options, Enzian The ...

    From $180 per night (USD)

    VRBO

    Details
  • Unit B  2 Bedroom with Herb Garden
    From $320 per night (USD)

    Expedia

    Unit B 2 Bedroom with Herb Garden

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    Enjoy a stylish experience at this centrally-located place in the Heart of Maitland. Close to dining options, Enzian The ...

    From $320 per night (USD)

    Expedia

    Details
  • Casa Jardin
    From $414 per night (USD)

    VRBO

    Casa Jardin

    Bedrooms:
    6
    Bathrooms:
    3
    Sleeps:
    6

    3 bedrooms with 3 bathrooms home overlooking an extra large backyard with a mature landscape surrounding the pool area. ...

    From $414 per night (USD)

    VRBO

    Details
  • Renovated College Park home Sleeps10 close to WP
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    Expedia

    Renovated College Park home Sleeps10 close to WP

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Enjoy a conveniently stylish experience at this centrally-located newly renovated place. This modest concrete block dupl ...

    Click For Pricing

    Expedia

    Details
  • City Charmer
    From $194 per night (USD)

    VRBO

    City Charmer

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Come stay on the quiet side of Orlando, just a stone throw away to Baldwin Park. This half duplex has 2 bedrooms and 2 f ...

    From $194 per night (USD)

    VRBO

    Details
  • Bungalow on quiet street close to trendy cafes, pubs, and parks. Dogs welcome!
    From $170 per night (USD)

    VRBO

    Bungalow on quiet street close to trendy cafes, pubs, and parks. Dogs welcome!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy the best of Florida living in this cute bungalow beside popular Baldwin Park. The open floor plan with vintage har ...

    From $170 per night (USD)

    VRBO

    Details
  • Perfect Private Winter Park Getaway Near Theme Parks!
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    VRBO

    Perfect Private Winter Park Getaway Near Theme Parks!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover the very best of Orlando from the comfort & convenience of this perfect private retreat! Ideally situated in be ...

    Click For Pricing

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    Details
  • Orlando Tropical Oasis
    From $331 per night (USD)

    Expedia

    Orlando Tropical Oasis

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    About this space Welcome to Orlando Tropical Oasis! Our four bedroom, two bathroom pool home is centrally located in the ...

    From $331 per night (USD)

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    Details
  • Stylish Winter Park Flat: Minutes from Park Avenue\n\n
    From $248 per night (USD)

    VRBO

    Stylish Winter Park Flat: Minutes from Park Avenue\n\n

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This cozy vacation Flat is located in Winter Park, Florida, a charming and affluent suburb of Orlando. The interior is t ...

    From $248 per night (USD)

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    Details
  • Luxury 3BD in Downtown Orlando
    From $196 per night (USD)

    Expedia

    Luxury 3BD in Downtown Orlando

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    NEW to VEBO! Home features modern and stylish furnishings, fully equipped kitchen, and spacious living area. Bedrooms su ...

    From $196 per night (USD)

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    Details
  • scape to sunny Florida.
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    VRBO

    scape to sunny Florida.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Relax with the whole family at this peaceful place to stay. 3 bedroom, 2 bathroom home . Master bedroom has a king size ...

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    Details
  • The Studio in the Heart of Orlando
    From $155 per night (USD)

    Expedia

    The Studio in the Heart of Orlando

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to our charming studio suite located in the heart of Orlando! Nestled in a serene oasis, our property offers a p ...

    From $155 per night (USD)

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    Details
  • Gorgeous Lake Howell Townhouse
    From $160 per night (USD)

    VRBO

    Gorgeous Lake Howell Townhouse

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beautifully renovated townhouse on gorgeous Lake Howell. Kick back and relax in this calm, stylish space. Centrally loc ...

    From $160 per night (USD)

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    Details
  • **Travel Themed Property with Backyard Oasis**
    From $984 per night (USD)

    Expedia

    **Travel Themed Property with Backyard Oasis**

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    14

    Summary: Welcome to "The Terminal" – a unique 6 bedroom, 3 bath paradise that takes you on a global adventure without le ...

    From $984 per night (USD)

    Expedia

    Details
  • House close to Downtown Orlando has Walking trail and next to Baldwin Park Lake
    From $180 per night (USD)

    VRBO

    House close to Downtown Orlando has Walking trail and next to Baldwin Park Lake

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Fully remodeled townhouse, 3 bedrooms and 2.5 bathrooms, all the rooms upstairs one Fulton downstairs in leaving room. M ...

    From $180 per night (USD)

    VRBO

    Details
  • Vacation Villa next to pool
    From $121 per night (USD)

    Expedia

    Vacation Villa next to pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Cute one bedroom Villa located in the backyard where the pool is studio style Murphy bed 1/2 bath opens right out to the ...

    From $121 per night (USD)

    Expedia

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

    VRBO

    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)

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    Details
  • Cozy lakeside cottage in the heart of Orlando.
    From $450 per night (USD)

    VRBO

    Cozy lakeside cottage in the heart of Orlando.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    This lakeside Cottage with amazing views is conveniently located within minutes to Winter Park, Downtown Orlando, and Ro ...

    From $450 per night (USD)

    VRBO

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

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    Details
  • Charming Winter Park 3 Bedroom Villa with Pool
    From $180 per night (USD)

    Expedia

    Charming Winter Park 3 Bedroom Villa with Pool

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    This villa is centrally located in East Winter Park just off 436 between Aloma and Howell Branch Road with easy access t ...

    From $180 per night (USD)

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    Details
  • Winter Park Pool Home 4 beds 2 bath
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    Winter Park Pool Home 4 beds 2 bath

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Centrally located. Quiet neighborhood. Swimming pool with diving board and lots of toys, floaties. Pool table recently u ...

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    Details
  • Stunning Orlando Getaway
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    Expedia

    Stunning Orlando Getaway

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    The whole group will enjoy easy access to everything from this centrally located Orlando location. This 1950s beautifull ...

    Click For Pricing

    Expedia

    Details
  • Mills 50 District\/Audobon Park Area 2 Bedroom
    From $156 per night (USD)

    VRBO

    Mills 50 District\/Audobon Park Area 2 Bedroom

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Two bedroom, one bath 1/2 duplex in prime area of Orlando. Big bedroom has queen bed. Smaller bedroom has a twin and a f ...

    From $156 per night (USD)

    VRBO

    Details
  • BEAUTIFUL 2 bedroom, LUXURY backyard & amenities
    From $188 per night (USD)

    Expedia

    BEAUTIFUL 2 bedroom, LUXURY backyard & amenities

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Both bedrooms include a therapeutic-grade queen size bed, nightstands, and dressers for storing your personal items. The ...

    From $188 per night (USD)

    Expedia

    Details
  • Serenity Heaven 3 Bed
    From $161 per night (USD)

    VRBO

    Serenity Heaven 3 Bed

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    🏡Welcome! You will have access to three bedrooms, a private bathroom, a living room, a dining room and a fully equipped ...

    From $161 per night (USD)

    VRBO

    Details
  • 2 Bed CozyHeaven Retreat
    From $137 per night (USD)

    VRBO

    2 Bed CozyHeaven Retreat

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    🏡Welcome! You will have access to two bedrooms, a private bathroom, a living room, a dining room and a fully equipped k ...

    From $137 per night (USD)

    VRBO

    Details
  • College Park 5Star Guesthouse Villa - QUIET-PRIVATE-mins to DT and Winter Park
    From $296 per night (USD)

    VRBO

    College Park 5Star Guesthouse Villa - QUIET-PRIVATE-mins to DT and Winter Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Central to Downtown/Eola/Winter Park. Tranquil bamboo lined perimeter provides relaxing setting in much desired COLLEGE ...

    From $296 per night (USD)

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    Details
  • Chris & Tish Cozy Apartment 2 bedrooms, a bonus room.  2 beds for 3 people. Q&T
    From $98 per night (USD)

    Expedia

    Chris & Tish Cozy Apartment 2 bedrooms, a bonus room. 2 beds for 3 people. Q&T

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Imagine a quiet, secluded-long driveway tucked away house. This apartment overseas the entire property. The apartment ...

    From $98 per night (USD)

    Expedia

    Details
  • test 1 test 1
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    VRBO

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    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    I will write a description I will write a description I will write a description I will write a description I will write ...

    Click For Pricing

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

    Expedia

    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)

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    Details
  • THE HIDEAWAY AT COLLEGE PARK
    From $174 per night (USD)

    VRBO

    THE HIDEAWAY AT COLLEGE PARK

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    Experience “The Hideaway at College Park”, a unique private oasis, tucked away in one of the most sought after walkable ...

    From $174 per night (USD)

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    Details
  • Downtown Cottage
    From $189 per night (USD)

    Expedia

    Downtown Cottage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Get the best of both worlds with a cozy cottage feel right in the heart of downtown Orlando. Many walkable restaurants a ...

    From $189 per night (USD)

    Expedia

    Details
  • Cozy 2-Bedroom Bungalow near Theme Parks & Orlando's Top Michelin-rated spots
    From $403 per night (USD)

    VRBO

    Cozy 2-Bedroom Bungalow near Theme Parks & Orlando's Top Michelin-rated spots

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to our newly renovated bungalow in the heart of Orlando's vibrant Mills 50 neighborhood! This charming retreat b ...

    From $403 per night (USD)

    VRBO

    Details
  • Landing at The Yard at Ivanhoe - 1 Bedroom in Northeast Orlando
    From $138 per night (USD)

    VRBO

    Landing at The Yard at Ivanhoe - 1 Bedroom in Northeast Orlando

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The Yard at Ivanhoe is a popular property in the Northeast Orlando neighborhood of Orlando where Landing offers fully fu ...

    From $138 per night (USD)

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    Details
  • Landing at Azul Baldwin Park Apartments - 1 Bedroom in Northeast Orlando
    From $120 per night (USD)

    VRBO

    Landing at Azul Baldwin Park Apartments - 1 Bedroom in Northeast Orlando

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Azul Baldwin Park Apartments is a lively property in the Northeast Orlando neighborhood of Orlando where Landing offers ...

    From $120 per night (USD)

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    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)

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

    VRBO

    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)

    VRBO

    Details
  • Cozy Winter Park Cottage
    From $326 per night (USD)

    VRBO

    Cozy Winter Park Cottage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    9

    Welcome to our charming Winter Park Getaway in Orlando, Fl. This cozy retreat offers all you need for a memorable short- ...

    From $326 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
  • Orlando room near Winter Park Village !!
    From $161 per night (USD)

    VRBO

    Orlando room near Winter Park Village !!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    we offer comfortable accommodations at the value you deserve. The friendly service at our hotel gives you more for your ...

    From $161 per night (USD)

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    Details
  • GardenHouse @AudubonPark Sleeps 8
    From $372 per night (USD)

    VRBO

    GardenHouse @AudubonPark Sleeps 8

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Take it easy at this unique and tranquil getaway. Located in Orlando's garden district, GardenHouse is conveniently loca ...

    From $372 per night (USD)

    VRBO

    Details
  • Lake Front Home near Winter Park!
    From $208 per night (USD)

    Expedia

    Lake Front Home near Winter Park!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Beautiful Casita Eulalia located north of Downtown Orlando in the heart of Maitland FL. This Casita is the pe ...

    From $208 per night (USD)

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    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
  • Canterbury Carriage House- private space
    From $127 per night (USD)

    Expedia

    Canterbury Carriage House- private space

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    This quiet getaway is on historic Dubsdread golf coarse and just minutes from Winter Park shopping and dining. The spac ...

    From $127 per night (USD)

    Expedia

    Details