Winter Park Rentals
From $135 per night (USD)VRBO
Stay near Winter Park action at our 2-bedroom apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
In the heart of Winter Park, this charming 2-bedroom apartment offers non-stop chances for unwinding and exploring. Unwi ...
From $135 per night (USD)VRBO
From $132 per night (USD)Expedia
Walk The Downtown Village of Winter Park!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is a downstairs end apartment with a back door that opens directly onto the pool deck near the hot tub. The apartme ...
From $132 per night (USD)Expedia
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Stroll to Park Avenue from Vintage Lake-View House
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This cozy, quaint Winter Park home was built in 1925. The house has updated appliances and plenty of space. There are tw ...
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From $154 per night (USD)Expedia
Three Blocks to Park Ave, 2 Blocks to WP Village!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Three blocks to Park Ave and two block ...
From $154 per night (USD)Expedia
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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 ...
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From $255 per night (USD)Expedia
You're Pampered Here - Just 3 Blocks From Park Avenue!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Modern, clean and unique. Fastest internet speed available: 139MBPS download and 21.5 MBPS upload! Second floor penthous ...
From $255 per night (USD)Expedia
From $147 per night (USD)VRBO
Mid Century Modern Cottage in The Heart of Winter Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Furnished Mid Century Modern Short/Long term rental located in charming Olde Winter Park. Two bedrooms and one and half ...
From $147 per night (USD)VRBO
From $214 per night (USD)Expedia
Winter Park Oasis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Your backyard oasis awaits you, with queen size 10in memory foam swing mattress, full outdoor kitchen, 65in TV along wit ...
From $214 per night (USD)Expedia
From $230 per night (USD)VRBO
Cute bungalow minutes walk from Park Avenue.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Just what you have been waiting for; beautiful cottage home in the heart of Winter Park! 2 bedroom/2 bath only steps aw ...
From $230 per night (USD)VRBO
From $143 per night (USD)Expedia
Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Location!!! Beautifully appointed 2 bedroom, 2 bath second floor apartment overlooking a beautiful pool area with balcon ...
From $143 per night (USD)Expedia
From $106 per night (USD)VRBO
Winter Park charm. Close to Park Ave
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Private 2 bedroom guest suite with its own entry and a separate sitting room. Tandem bedroom include 1 queen sized bed ...
From $106 per night (USD)VRBO
From $348 per night (USD)Expedia
Stylish Boutique Guest house in Winter Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Indulge the senses in the calming aesthetics of this newly constructed guest house. The residence features room for 4 g ...
From $348 per night (USD)Expedia
From $132 per night (USD)VRBO
Light, Bright and Full of Delight! 2 Blocks to Park Ave
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy this PRIVATE and Sparkling clean entire home, first floor 2 bedroom/1 full bath luxury apartment near Park Avenue! ...
From $132 per night (USD)VRBO
From $138 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 $138 per night (USD)VRBO
From $251 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 $251 per night (USD)VRBO
From $402 per night (USD)VRBO
Winter Park Pool home close to Lake Virginia, Rollins College & Park Ave.
- Bedrooms:
- 2
- 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 $402 per night (USD)VRBO
From $155 per night (USD)VRBO
Walk To Park Ave, Heated Pool, Hot Tub, Grill Station, Modern and Comfortable!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is a downstairs end apartment with a back door that opens directly onto the pool deck near the hot tub. The apartme ...
From $155 per night (USD)VRBO
From $281 per night (USD)Expedia
Just 3 Blocks to Park Ave Shops/ Restaurants, 2 From The Winter Park Village!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Modern, clean and unique. Second floor penthouse unit overlooking the pool area. Gorgeous acacia wood floors, quartz c ...
From $281 per night (USD)Expedia
From $293 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 $293 per night (USD)VRBO
From $147 per night (USD)Expedia
Luxury Living Just 3 Blocks From Park Ave!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful Acacia wood flooring, with marble in the bathrooms and porcelain tile in the kitchen. Quartz countertops, ceil ...
From $147 per night (USD)Expedia
From $242 per night (USD)VRBO
Great Family Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Our home has high quality furniture, linens, cookware and tableware for your family dinners. There are large and small ...
From $242 per night (USD)VRBO
From $294 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 $294 per night (USD)VRBO
From $144 per night (USD)VRBO
Urban Retreat 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 $144 per night (USD)VRBO
From $142 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 $142 per night (USD)Expedia
From $128 per night (USD)VRBO
Cozy Comfort Just 2 Blocks From Park Ave!
- 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 $128 per night (USD)VRBO
From $377 per night (USD)VRBO
Contemporary Award Winning Hotel w/Rooftop Close to Parks & Rollins College
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our 323 square foot King Room is appointed with handsome contemporary furnishings, including an armoire, mini fridge, fl ...
From $377 per night (USD)VRBO
From $377 per night (USD)VRBO
ADA Compliant Room - Contemporary Furnishings - Rooftop Pool - Close to Parks
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our Classic King ADA is wheelchair-accessible. The room is appointed with handsome contemporary furnishings, including a ...
From $377 per night (USD)VRBO
From $412 per night (USD)VRBO
Private Balcony in Award Winning Hotel, Roof-top Pool, Close to Rollins College
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Classic King with Balcony room measures 323 square feet and has the added feature of a balcony with French doors tha ...
From $412 per night (USD)VRBO
From $377 per night (USD)VRBO
Award Winning Boutique Hotel Close to Parks & Rollins College, Rooftop Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our Classic Queen room is 358 square feet and appointed with two pillowtop Queen size beds, luxury linens and handsome c ...
From $377 per night (USD)VRBO
From $412 per night (USD)VRBO
Private Balcony - Award Winning Accommodations w/Rooftop Pool, Close to Parks!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our Classic Queen with Balcony room is 358 square feet and appointed with two pillowtop Queen size beds, luxury linens a ...
From $412 per night (USD)VRBO
From $416 per night (USD)VRBO
Rooftop Pool, Close to Parks & Rollins College - Award Winning Accommodations
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our Premier ADA Queen is a larger room at 448 square feet and is wheelchair-accessible. The room features an additional ...
From $416 per night (USD)VRBO
From $462 per night (USD)VRBO
Large Room Award Winning Hotel w/Rooftop Pool - Close to Parks & Rollins College
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our Parlor King is a larger room at 435 square feet and features a separate Parlor seating area with a sleeper sofa and ...
From $462 per night (USD)VRBO
From $405 per night (USD)VRBO
ADA Compliant Room in Award Winning Hotel w/Rooftop Pool - Close to Parks!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Our Premier ADA Queen is a larger room at 448 square feet and is wheelchair-accessible. The room features an additional ...
From $405 per night (USD)VRBO
From $225 per night (USD)VRBO
Cozy Retreat + Pet Friendly + 8 minutes to Park Ave - Downtown Winter Park
- Bedrooms:
- 1
- 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 $225 per night (USD)VRBO
From $193 per night (USD)VRBO
Winter Park Oasis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy your stay at the Winter Park Oasis! This cozy 2 bedroom private unit, is in a charming and historic neighborhood! ...
From $193 per night (USD)VRBO
From $195 per night (USD)VRBO
GREAT LOCATION 🏡
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Location, location, location - this immaculate Olde Winter Park home is ready for you to relax and enjoy Winter Park and ...
From $195 per night (USD)VRBO
From $249 per night (USD)VRBO
Ideal Location, Charming 4 bedroom home w Pool, fenced yard.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Traditional Old Winter Park home ready for your event, special occasion, vacation, wedding, golf weekend, or executive r ...
From $249 per night (USD)VRBO
From $179 per night (USD)VRBO
Winter Park Bungalow & Outdoor Oasis - Rollins College, Park Ave & Fenced Yard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This charming bungalow in the heart of Winter Park's upscale Forest Hills neighborhood is the perfect retreat for your n ...
From $179 per night (USD)VRBO
From $448 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 $448 per night (USD)VRBO
From $185 per night (USD)Expedia
Home Away from Home- Winter Park
- Bedrooms:
- 1
- 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 $185 per night (USD)Expedia
From $184 per night (USD)VRBO
Quaint Winter Park East End Market Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our Winter Park home behind East End Market ! You will fall in love with this area which is full of friendly ...
From $184 per night (USD)VRBO
From $132 per night (USD)VRBO
Quaint Key West Pool Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Historic Winter Park Florida. Central Florida's gem Winter Park is filled with history, whimsy and magic as i ...
From $132 per night (USD)VRBO
From $125 per night (USD)VRBO
6 Mi to Downtown Orlando: Quiet Home w/ Sunroom
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Soak up the Florida sun and explore the Orlando area with ease from this 2-bed, 1-bath vacation rental in Winter Park! Y ...
From $125 per night (USD)VRBO
From $141 per night (USD)VRBO
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 $141 per night (USD)VRBO
From $140 per night (USD)VRBO
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 $140 per night (USD)VRBO
From $292 per night (USD)VRBO
LUXURY 𝕄𝕚𝕕 ℂ𝕖𝕟𝕥𝕦𝕣𝕪 𝕄𝕠𝕕𝕖𝕣𝕟 ᴠᴀᴄᴀᴛɪᴏɴ in 𝒲𝒾𝓃𝓉𝑒𝓇 𝒫𝒶𝓇𝓀
- Bedrooms:
- 2
- 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 $292 per night (USD)VRBO
From $174 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 $174 per night (USD)VRBO
From $109 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 $109 per night (USD)Expedia
From $88 per night (USD)VRBO
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 $88 per night (USD)VRBO
From $100 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 $100 per night (USD)Expedia
From $183 per night (USD)VRBO
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 $183 per night (USD)VRBO
From $143 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 $143 per night (USD)Expedia
From $314 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 $314 per night (USD)VRBO
From $118 per night (USD)VRBO
Fantastically Exclusive - Temporarily Reduced
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Call for availability; flexible booking. Fantastically exclusive property designed and formally owned by a well-known Wi ...
From $118 per night (USD)VRBO
From $355 per night (USD)VRBO
3-bedroom house in quaint Winter Park with cool vibes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Your cozy getaway awaits in Winter Park at this beautiful house. With three bedrooms featuring a king bed, two full beds ...
From $355 per night (USD)VRBO
From $388 per night (USD)Expedia
Winter Park Spacious Unit - 118
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Summary: Minimum 30 days required by HOA. Experience the ultimate lakefront living in our stunning 2/1 Winter Park Cond ...
From $388 per night (USD)Expedia
Click For PricingVRBO
Charming Remodeled Cottage | Walk to Park Ave
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Charming Remodeled Cottage | Walk to Park Ave & Downtown Winter Park Welcome to your comfortable, newly remodeled Winte ...
Click For PricingVRBO
From $213 per night (USD)VRBO
Fantastic, quiet home minutes from Park Ave.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this beautifully updated tropical retreat featuring bright open living spaces, warm hardwood floors, and styli ...
From $213 per night (USD)VRBO
From $667 per night (USD)VRBO
3b/2ba Winter Park Residence w Music Studio & Office
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
5 minute drive or 15 minute walk to Park Ave. Incredibly spacious with two offices on top of the 3 bedrooms and 2 bathro ...
From $667 per night (USD)VRBO
From $607 per night (USD)Expedia
Bali-inspired Oasis in the Heart of Winter Park
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Only available for July + 1st week of Aug! Escape to a brand-new custom-built luxury oasis inspired by the beauty of Bal ...
From $607 per night (USD)Expedia