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 $164 per night (USD)
VRBO
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 $164 per night (USD)
VRBO
From $255 per night (USD)
Expedia
Best Winter Park Home close to Rollins College, Advent Health & Park Avenue !
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Beautiful furnished and fully equipped kitchen 4-bedroom, 3-bath home which sits on a large fenced corner lot in a high ...
From $255 per night (USD)
Expedia
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VRBO
Winter Park Getaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Simplicity at its finest. I host like I live and like I like to be hosted- with chocolates and snacks and fluffy towels ...
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VRBO
From $244 per night (USD)
Expedia
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 $244 per night (USD)
Expedia
From $161 per night (USD)
VRBO
Mid Century Luxury, 1 block from Park Ave (#3)
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This 2nd floor apartment is nestled under oaks on a quiet cobblestone street in downtown Winter Park. There are only 3 u ...
From $161 per night (USD)
VRBO
From $161 per night (USD)
Expedia
Mid Century Luxury, 1 block from Park Ave (#2)
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This ground floor apartment is nestled under oaks on a cobblestone street in downtown Winter Park. There are only 3 unit ...
From $161 per night (USD)
Expedia
From $92 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 $92 per night (USD)
VRBO
From $157 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 $157 per night (USD)
Expedia
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
From $345 per night (USD)
Expedia
Best Home by Winter Park Hospital, Rollins College and Park Ave !
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
BeautifuL furnished and fully equipped kitchen 3-bedroom, 2-bath home which sits on a large fenced corner lot in a highl ...
From $345 per night (USD)
Expedia
From $170 per night (USD)
VRBO
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 $170 per night (USD)
VRBO
From $281 per night (USD)
Expedia
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)
Expedia
From $172 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 $172 per night (USD)
VRBO
From $199 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 $199 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 $91 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 $91 per night (USD)
VRBO
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Expedia
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 ...
Click For Pricing
Expedia
From $234 per night (USD)
VRBO
Ideal Location, Charming 4 bedroom home w Pool, fenced yard, 25% off thirty days
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 $234 per night (USD)
VRBO
From $192 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 $192 per night (USD)
VRBO
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
From $206 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 $206 per night (USD)
VRBO
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
From $241 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 $241 per night (USD)
Expedia
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
From $180 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 $180 per night (USD)
Expedia
From $201 per night (USD)
VRBO
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 $201 per night (USD)
VRBO
From $248 per night (USD)
Expedia
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 ...
From $248 per night (USD)
Expedia
From $152 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 $152 per night (USD)
VRBO
From $146 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 $146 per night (USD)
Expedia
From $116 per night (USD)
VRBO
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)
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 $77 per night (USD)
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 ...
From $77 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 $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 $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 $173 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 $173 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 $161 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 $161 per night (USD)
VRBO
From $162 per night (USD)
Expedia
Modern, fabulous two-bedroom with parking in Winter Park
Bedrooms:
1
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 $162 per night (USD)
Expedia
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
From $129 per night (USD)
Expedia
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 $129 per night (USD)
Expedia
From $282 per night (USD)
VRBO
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 ...
From $282 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 $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
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
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 ...
Click For Pricing
VRBO
From $215 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 $215 per night (USD)
Expedia
Click For Pricing
VRBO
A DEAL By The Month! Walk to Rollins & Park Ave
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
It's your own private one-room structure with a private entrance next to a parking space. It's much like a hotel room in ...
Click For Pricing
VRBO
From $122 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 $122 per night (USD)
Expedia
From $125 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 $125 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $115 per night (USD)
VRBO
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 $115 per night (USD)
VRBO
From $120 per night (USD)
Expedia
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 $120 per night (USD)
Expedia
From $186 per night (USD)
VRBO
CHARMING - Cozy Retreat Near Lake Killarney in 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 $186 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 $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 $394 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 $394 per night (USD)
VRBO
From $404 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 $404 per night (USD)
VRBO
From $431 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 $431 per night (USD)
VRBO
From $415 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 $415 per night (USD)
VRBO
From $442 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 $442 per night (USD)
VRBO
From $465 per night (USD)
VRBO
Rooftop Pool, Close to Parks & Rollins College - Award Winning Accommodations
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 $465 per night (USD)
VRBO
From $510 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 $510 per night (USD)
VRBO
From $472 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 $472 per night (USD)
VRBO
From $375 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 $375 per night (USD)
VRBO
From $489 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 $489 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $128 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 $128 per night (USD)
VRBO
From $148 per night (USD)
VRBO
Coastal Feel - Modern Appeal
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
2 bedroom 2 bath, 1350 sqft detached home Family friendly layout with master bedroom suite, shared bedroom (2 twin beds) ...
From $148 per night (USD)
VRBO
From $144 per night (USD)
VRBO
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 $144 per night (USD)
VRBO
From $114 per night (USD)
Expedia
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 $114 per night (USD)
Expedia
From $1161 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 $1161 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 $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 $97 per night (USD)
Expedia
Private Patio: College Park Cottage in Orlando!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Pets Welcome w/ Fee | Furnished Patio | Shaded Property Nestled just 3 miles from downtown, this welcoming 2-bedroom, 1 ...
From $97 per night (USD)
Expedia
$8th Green Cottage \A relaxing Oasis in the city\ Guesthouse$
From $148 per night (USD)
VRBO
8th Green Cottage \"A relaxing Oasis in the city\" Guesthouse
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The 8th Green Cottage is a relaxing oasis in the heart of Orlando. Located less than 10 minutes from downtown. Sitting o ...
From $148 per night (USD)
VRBO
From $228 per night (USD)
Expedia
Charming Clean Home near East End Market Large fenced yard - 25% off thirty days
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Winter Park home ready for your event, vacation or executive rental. Updated kitchen, granite countertops, wood floors, ...
From $228 per night (USD)
Expedia
From $166 per night (USD)
VRBO
A comfortable home close to the city, yet tucked away from the noise.
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Perfect for those who want to kick back as well as those who are ready for Orlando fun.... Theme parks, beaches, shoppin ...
From $166 per night (USD)
VRBO
From $369 per night (USD)
Expedia
Casa Bella
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Casa Bella offers new fixtures and equipment . A double car garage . 3 King size master bedrooms with their own full bat ...
From $369 per night (USD)
Expedia
From $194 per night (USD)
VRBO
Mid-Century Modern Gem Near Downtown/Winter Park/Baldwin Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Recent renovations makes this mid-century modern cottage feel like a dream and you can't beat the location! Cozy and inv ...
From $194 per night (USD)
VRBO
From $88 per night (USD)
Expedia
17'coachman clipper tiny travel trailer
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This little 17' narrow travel trailer is perfect for those that want to "camp" for a few days with out having to set up ...
From $88 per night (USD)
Expedia
From $349 per night (USD)
VRBO
Casa Feliz
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Spacious and comfortable 3 bedroom 2 bathroom home with a fully enclosed pool in Maitland. Very quiet cul-de-sac with pl ...
From $349 per night (USD)
VRBO
From $267 per night (USD)
Expedia
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)
Expedia
From $369 per night (USD)
VRBO
Casa Winter Park
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Casa Winter Park accommodates the need for personal space while enjoying, at the same time, the gathering with several f ...
From $369 per night (USD)
VRBO
From $198 per night (USD)
VRBO
Old World Charm of College Park/Winter Park
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcoming and spacious home located in a highly sought after College Park / Winter Park district of Central Florida. It' ...
From $198 per night (USD)
VRBO
From $181 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 $181 per night (USD)
VRBO
From $235 per night (USD)
VRBO
Modern 2BR Lake House in Exclusive Area – No Smoking
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nestled in prestigious Maitland neighborhood, this stylish and comfortable retreat offers the perfect blend of relaxatio ...
From $235 per night (USD)
VRBO
From $208 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 $208 per night (USD)
VRBO
Click For Pricing
Expedia
Amazing College Park private walled in estate
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Amazing private Mediterranean walled estate located across from the historic DubsDread golf course! Centrally located in ...
Click For Pricing
Expedia
From $217 per night (USD)
VRBO
Temporary living that feels like home where you can relax and be yourself.
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Fully furnished, charming and comfortable, 4 bedroom - 2 bath, short-term home has new linens, new beds (1 King, 2 queen ...
From $217 per night (USD)
VRBO
From $311 per night (USD)
Expedia
★Modern DT Home★King Bed☀️Patios✔Long Stays⚡️WiFi★
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy your peaceful stay in a quiet neighborhood in this beautiful Mid-Century modern townhome, just 8 minutes from dow ...
From $311 per night (USD)
Expedia
From $283 per night (USD)
VRBO
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 $283 per night (USD)
VRBO
From $436 per night (USD)
Expedia
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 $436 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 $133 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 $133 per night (USD)
VRBO
From $451 per night (USD)
Expedia
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 $451 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 $730 per night (USD)
Expedia
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 $730 per night (USD)
Expedia

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Winter Park Rentals

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Results: 194 Rentals