Winter Park, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Winter Park, Florida on RentalSaver.com!

Winter Park Rentals

From $165 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 $165 per night (USD)
VRBO
From $215 per night (USD)
Expedia
Tranquil Hideaway: 2-Bedroom Retreat near Mills/50
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to your charming duplex in Orlando, where you'll discover a delightful blend of comfort and character. Nestled n ...
From $215 per night (USD)
Expedia
From $183 per night (USD)
VRBO
Modern Comfort: Mills/50 Hideaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to our charming duplex in the heart of downtown Orlando! This delightful 2-bedroom apartment is located in the v ...
From $183 per night (USD)
VRBO
From $130 per night (USD)
Expedia
Charming 2BR/2BA Winter Park Cottage, steps from Park Ave
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our charming 2-bedroom, 2-bathroom home nestled in the heart of Winter Park! Located just a short stroll away ...
From $130 per night (USD)
Expedia
From $325 per night (USD)
VRBO
GardenHouse @AudubonPark Sleeps 8
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Take it easy at this unique and tranquil getaway. Located in Orlando's garden district, GardenHouse is conveniently loca ...
From $325 per night (USD)
VRBO
From $242 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 $242 per night (USD)
Expedia
From $131 per night (USD)
VRBO
Lakefront Condo w/ Pool & Views: 7 Mi to Orlando!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to 'Executive Lakefront Oasis,' a fully remodeled vacation rental near Orlando's top attractions! Designed for sn ...
From $131 per night (USD)
VRBO
From $81 per night (USD)
Expedia
Adorable 1 Bedroom in the perfect location!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our fully renovated, pet-friendly apartments are located in one of the most sought-after neighborhoods in the area, just ...
From $81 per night (USD)
Expedia
From $123 per night (USD)
VRBO
Perfect 4-Bedroom in a prime location!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This 4 Bedroom 2 Full Bathroom Ranch Home Is Immaculate! Enjoy The Open Floor Plan W/ Vaulted 15ft Ceilings & Large Wind ...
From $123 per night (USD)
VRBO
From $156 per night (USD)
Expedia
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 $156 per night (USD)
Expedia
From $141 per night (USD)
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 ...
From $141 per night (USD)
VRBO
From $161 per night (USD)
Expedia
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)
Expedia
From $328 per night (USD)
VRBO
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 $328 per night (USD)
VRBO
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)
Expedia
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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 ...
Click For Pricing
VRBO
From $137 per night (USD)
Expedia
LUXURY AND LOCATION!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Three blocks to Park Ave and two block ...
From $137 per night (USD)
Expedia
From $160 per night (USD)
VRBO
Gorgeous Lake Howell Townhouse
Bedrooms:
1
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)
VRBO
From $592 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 $592 per night (USD)
Expedia
From $262 per night (USD)
VRBO
Cozy Winter Park Cottage
Bedrooms:
2
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 $262 per night (USD)
VRBO
From $214 per night (USD)
Expedia
House close to Downtown Orlando has Walking trail and next to Baldwin Park Lake
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Fully remodeled townhouse, 3 bedrooms and 2.5 bathrooms, all the rooms upstairs one Fulton downstairs in leaving room. M ...
From $214 per night (USD)
Expedia
From $121 per night (USD)
VRBO
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)
VRBO
From $215 per night (USD)
Expedia
Fire Pit + Grill + 2MI to DT + Long Term Stays!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Come and relax in our newly remodeled, stylish home. Moments away from craft beer bars, brewery, AdventHealth O ...
From $215 per night (USD)
Expedia
From $450 per night (USD)
VRBO
Cozy lakeside cottage in the heart of Orlando.
Bedrooms:
2
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
From $222 per night (USD)
VRBO
Comfortable House in the lovely Winter Park, Olando Fl .
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Easy access to drive in and out, ample parking available. A good open yard space is available at the back of the house f ...
From $222 per night (USD)
VRBO
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VRBO
Landing at Enders Place at Baldwin Park - 3 Bedrooms in Northeast Orlando
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enders Place at Baldwin Park is a charming property in the Northeast Orlando neighborhood of Orlando where Landing offer ...
Click For Pricing
VRBO
From $198 per night (USD)
VRBO
Charming Home Winter Park, Near Rollins College, Lake Baldwin Park, Orlando FL
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover the convenience of this exceptional locale strategically situated just 5-7 minutes away from the vibrant Park A ...
From $198 per night (USD)
VRBO
Click For Pricing
VRBO
Landing at Juno at Winter Park - 3 Bedrooms in Downtown Winter Park
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Juno at Winter Park is a vibrant property in the Downtown Winter Park neighborhood of Winter Park where Landing offers f ...
Click For Pricing
VRBO
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Expedia
Landing at Enders Place at Baldwin Park - 2 Bedrooms in Northeast Orlando
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enders Place at Baldwin Park is a lively property in the Northeast Orlando neighborhood of Orlando where Landing offers ...
Click For Pricing
Expedia
From $189 per night (USD)
VRBO
Chris & Tish Cozy Apartments -1 bedroom with queen size bed.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Imagine a quiet, secluded-long driveway tucked away house. Central AC unit. The Apartment is equipped with a kitchenet ...
From $189 per night (USD)
VRBO
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Expedia
Landing at Enders Place at Baldwin Park - 1 Bedroom in Northeast Orlando
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enders Place at Baldwin Park is a sought-after property in the Northeast Orlando neighborhood of Orlando where Landing o ...
Click For Pricing
Expedia
From $183 per night (USD)
VRBO
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 $183 per night (USD)
VRBO
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Expedia
Cozy 4-bedroom house with WiFi, AC in peaceful Winter Park
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to this lovely house in Winter Park. With 4 bedrooms, including 3 queen beds and 1 king bed, this fantastic prop ...
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Expedia
From $271 per night (USD)
VRBO
Elegant & Spacious Historic Winter Park Home with Pool + Spa
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Historic Winter Park home, located within a beautiful neighborhood. The home is spacious, charming and elegantly-appoint ...
From $271 per night (USD)
VRBO
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Expedia
Landing at Azul Baldwin Park Apartments - 1 Bedroom in Northeast Orlando
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Azul Baldwin Park Apartments is a charming property in the Northeast Orlando neighborhood of Orlando where Landing offer ...
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Expedia
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VRBO
Landing at Azul Baldwin Park Apartments - 2 Bedrooms in Northeast Orlando
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Azul Baldwin Park Apartments is a charming property in the Northeast Orlando neighborhood of Orlando where Landing offer ...
Click For Pricing
VRBO
From $116 per night (USD)
Expedia
Cozy and Chic Winter Park Studio which is conveniently located just for you
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Light, airy, and perfectly appointed studio. Enjoy this fully furnished and centrally-located location. This space provi ...
From $116 per night (USD)
Expedia
From $178 per night (USD)
VRBO
Orlando 3BR Getaway • Comfort & Work-Friendly
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Save 25% on this peaceful 3BR Orlando duplex—perfect for families, groups, or remote workers. Enjoy spacious living area ...
From $178 per night (USD)
VRBO
From $147 per night (USD)
VRBO
Kid-Friendly 2BR Orlando Home w/ Private Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Family fun awaits! This 2BR Orlando home features a private pool, full kitchen, and spacious living areas—perfect for up ...
From $147 per night (USD)
VRBO
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
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
From $1092 per night (USD)
VRBO
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 $1092 per night (USD)
VRBO
From $346 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 $346 per night (USD)
Expedia
From $311 per night (USD)
VRBO
Modern, Charming Home in the heart of Winter Park- Perfect for a couples retreat or small group!
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Escape to our charming 3BD/1BA home in Winter Park, FL—modern, cozy, and pet-friendly! Perfect for families, couples, an ...
From $311 per night (USD)
VRBO
$Beautiful Mid Term Home in the Elegance of Winter Park!\n\n$
From $178 per night (USD)
Expedia
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)
Expedia
From $169 per night (USD)
VRBO
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 $169 per night (USD)
VRBO
From $245 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 $245 per night (USD)
VRBO
From $540 per night (USD)
VRBO
Queen Room Near All Saints Episcopal Church ORL
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in Winter Park, Florida, This property offers free WiFi and an outdoor pool. Rollins College is located 650 metr ...
From $540 per night (USD)
VRBO
From $866 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 $866 per night (USD)
Expedia
From $84 per night (USD)
VRBO
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 $84 per night (USD)
VRBO
From $286 per night (USD)
Expedia
The Bird House Spa Winter Park
Bedrooms:
2
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 $286 per night (USD)
Expedia
From $394 per night (USD)
VRBO
Lakefront Paradise Near Attractions
Bedrooms:
3
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 $394 per night (USD)
VRBO
From $77 per night (USD)
Expedia
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 ...
From $77 per night (USD)
Expedia
From $431 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 $431 per night (USD)
VRBO
From $91 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 $91 per night (USD)
Expedia
From $317 per night (USD)
VRBO
Upscale 3/2 Townhome | King Bed | Patio | Wifi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come experience luxury in Winter Park in our upscale two-story townhome! ✓ Private Entrance & Self-Check In ✓ Perfect f ...
From $317 per night (USD)
VRBO
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
From $283 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 $283 per night (USD)
VRBO
From $146 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 $146 per night (USD)
VRBO
From $346 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 $346 per night (USD)
VRBO
From $322 per night (USD)
Expedia
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 $322 per night (USD)
Expedia
From $426 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 $426 per night (USD)
VRBO
From $112 per night (USD)
Expedia
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 $112 per night (USD)
Expedia
From $165 per night (USD)
VRBO
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 $165 per night (USD)
VRBO
From $272 per night (USD)
Expedia
Winter Park: 3B 2B Home with King Bed, Gym, & Fenced Yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This comfortable and modernized 3 bed 2 bath home in WInter Park is perfect for those traveling for a family event such ...
From $272 per night (USD)
Expedia
From $385 per night (USD)
VRBO
Ayianna's Luxury Home.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Our prime location is a gateway to endless world of excitement. Just moment away from the trendy Park Ave, You'll be spo ...
From $385 per night (USD)
VRBO
From $182 per night (USD)
Expedia
The beautiful Melrose Cottage - 25% monthly rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to our Melrose Cottage in Winter Park. This delightfully curated property features 2 bedrooms with a king and qu ...
From $182 per night (USD)
Expedia
From $179 per night (USD)
VRBO
Stylish & Cozy King Bed Retreat @ Baldwin Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Fully furnished home @ Baldwin Park & near Winter Park! This cozy upgraded home is just minutes from downtown Orlando, B ...
From $179 per night (USD)
VRBO
From $136 per night (USD)
Expedia
Quaint Key West Pool Bungalow
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience Winter Park like a local in this superb 1-bedroom bungalow. This enchanting property offers all the comforts ...
From $136 per night (USD)
Expedia
From $157 per night (USD)
VRBO
City Cottage with Mid Century Modern Vibe
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Premium home with Mid Century Modern vibe. Beautiful furnishings and decor to make you feel completely comfortable. Rel ...
From $157 per night (USD)
VRBO
From $212 per night (USD)
Expedia
Cozy 4/3 House with Pool in fabulous Winter Park with AC, WiFi
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to this charming house in Winter Park. This beautiful property offers 4 bedrooms, 3 full bathrooms with bathtub ...
From $212 per night (USD)
Expedia
From $176 per night (USD)
VRBO
Cozy 3/2 House with Pool with AC, WiFi in Winter Park FL
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience Winter Park like a local in this brilliant house with pool. The house has 3 queen size bedrooms, 2 full bath ...
From $176 per night (USD)
VRBO
From $131 per night (USD)
Expedia
2ba/1bd - College Park, Orlando. Minutes from ORMC & Advent Health Hospitals
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Peaceful and centrally-located place in the charming town of College Park, Orlando FL. Walking distance to restaurants, ...
From $131 per night (USD)
Expedia
Click For Pricing
VRBO
Spacious Home in Downtown Orlando
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
About this space Nestled in one of the most coveted neighborhoods near Downtown Orlando (Ivanhoe Village), you'll be wit ...
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VRBO
From $110 per night (USD)
VRBO
Spacious half 1/1 duplex in amazing location!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Be in Disney, or Universal in 30 minutes. Everything you need to feel at home and have peace. Right on I75, and right ne ...
From $110 per night (USD)
VRBO
From $289 per night (USD)
VRBO
Amazing lakefront mid-modern 3-bed Winter Park home surrounded by Natural Beauty
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience Winter Park like a local in this 3 bedroom 2.5 bath home. The bedrooms feature 2 queen beds and 1 king bed, e ...
From $289 per night (USD)
VRBO
From $195 per night (USD)
Expedia
Vibrant Orlando Lakefront Cat Lover's Retreat with Pool & Gardens
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
The Cat House: A Mid-Century Lakefront Retreat with Feline Flair Welcome to your tranquil escape in the heart of Orland ...
From $195 per night (USD)
Expedia
From $264 per night (USD)
VRBO
Charming Home in College Park close to golf + car
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Your family will be close to everything when you stay at this centrally-located College Park DUPLEX . Nestled next to Du ...
From $264 per night (USD)
VRBO
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Expedia
Home away from home • sleeps 8 • 10 min hospital • 15 min to Universal
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Welcome to your home away from home at 232 Emory Pl, Orlando, FL 32804—a warm and welcoming bungalow in the heart of Col ...
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Expedia
From $266 per night (USD)
VRBO
Coastal Bungalow ~ Firepit, Pool, Gazebo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Stay at this elevated coastal retreat with a neutral palette, turquoise accents, and natural wood touches. This 3 bed, 2 ...
From $266 per night (USD)
VRBO
From $474 per night (USD)
Expedia
Modern 4 bed/4 bath Lake Home
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Get ready to relax in this 4-bedroom house in Maitland. This superb property boasts 2 king beds, 1 queen bed, and 1 full ...
From $474 per night (USD)
Expedia
From $122 per night (USD)
VRBO
Charming Flat in Winter Park
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Your cozy getaway awaits in Winter Park at this excellent apartment. This lovely space features a bedroom with a comfort ...
From $122 per night (USD)
VRBO
From $190 per night (USD)
Expedia
Family Fun 3-bedroom house with gym, games, toys, outdoor hangout and coffee
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Modern Family Retreat | Winter Park, FL 30 min → Disney & Universal 8 min → Downtown Winter Park Fast Wi‑Fi • Self‑check ...
From $190 per night (USD)
Expedia
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VRBO
Charming 3-bedroom house with WiFi, AC in welcoming Winter Park
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
This charming house in Winter Park offers 3 cozy bedrooms with a mix of a king, full, and queen beds. With 3 bathrooms f ...
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VRBO
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Expedia
Cozy 1-bedroom/private bath with WiFi, AC in delightful Orlando
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience Orlando like a local in this shared 1-bedroom apartment. Private room/bathroom/storage. This beautiful space ...
Click For Pricing
Expedia
From $192 per night (USD)
VRBO
Charming bungalow with plunge pool located steps away from trendy Mills 50 area.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Tucked away in the heart of Colonialtown, Orlando, this charming boho-inspired cottage is the perfect retreat for your s ...
From $192 per night (USD)
VRBO
From $191 per night (USD)
Expedia
Cozy 1920s Cabin | Near Disney & Orlando Nightlife
Bedrooms:
1
Bathrooms:
2
Sleeps:
11
Stay near Orlando’s top attractions in this charming 2BR, 1BA Victorian-style retreat. Blending vintage charm with moder ...
From $191 per night (USD)
Expedia
From $347 per night (USD)
VRBO
Modern 3BR/3BA home in Prime Winter Park Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Spacious 3BR/3BA townhome in the heart of Winter Park, FL 🌴 Perfect for families, remote workers, or extended stays. Ea ...
From $347 per night (USD)
VRBO
From $166 per night (USD)
VRBO
Large 3 bedroom with King Bed!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience tranquility in this stylish Mid-Century modern townhome, nestled in a quiet neighborhood just 8 minutes from ...
From $166 per night (USD)
VRBO
From $319 per night (USD)
VRBO
Spacious 3BR Pool House on Mills 50 · Central, Walkable, Perfect for Long Stays
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Orlando is waiting for you at this 3-bedroom house. Nestled in a tranquil neighborhood, this perfect retreat offers 2 qu ...
From $319 per night (USD)
VRBO
From $339 per night (USD)
Expedia
Downtown Mid-Century House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this centrally located mid-century modern home nestled among Spanish palms in the heart of downtown Orlando. E ...
From $339 per night (USD)
Expedia
From $293 per night (USD)
VRBO
Winter Park Gem, 2BR Near Parks, 3MI to Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to our cozy and inviting 2-bedroom, 1-bathroom home. This charming property offers a comfortable and co ...
From $293 per night (USD)
VRBO
From $404 per night (USD)
Expedia
Spacious Modern Japandi Retreat - Winter Park
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Experience serene luxury in this spacious Japandi-style home in beautiful Winter Park. Blending Scandinavian warmth with ...
From $404 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Citrus Oasis: 4BR Pool Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape to our Citrus Oasis! This beautiful 4-bedroom, 2-bath home offers a fully equipped kitchen, spacious bedrooms, a ...
From $240 per night (USD)
VRBO
From $138 per night (USD)
Expedia
Peaceful RV with AC in Winter Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Nestled in Winter Park, this delightful recreational vehicle offers a cozy retreat for guests. With 2 bedrooms including ...
From $138 per night (USD)
Expedia

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Results: 194 Rentals