
Lake Killarney Rentals

- From $542 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 $542 per night (USD)VRBO
- From $223 per night (USD)
Expedia
Charming house with AC, fitness equipment, & WIFI in the city of Orlando.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Consider this house your home away from home while you visit Orlando. This cool property offers a tremendous fitness roo ...
From $223 per night (USD)Expedia
- Click For Pricing
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 ...
Click For PricingVRBO
- From $76 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 $76 per night (USD)Expedia
- From $267 per night (USD)
VRBO
Comfy Home in Winter Park, can accommodate up 6 guests!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our home is located in Winter Park and can serve as a central base to live like a local. You can enjoy all of the great ...
From $267 per night (USD)VRBO
- From $140 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 $140 per night (USD)Expedia
- From $186 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 $186 per night (USD)VRBO
- From $90 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 $90 per night (USD)Expedia
- From $124 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 $124 per night (USD)VRBO
- From $161 per night (USD)
Expedia
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 $161 per night (USD)Expedia
- From $156 per night (USD)
VRBO
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 $156 per night (USD)VRBO
- From $155 per night (USD)
Expedia
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 $155 per night (USD)Expedia
- From $336 per night (USD)
VRBO
Stylish Boutique Guest house in Winter Park
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Indulge the senses in the calming aesthetics of this newly constructed guest house. The residence features room for 4 g ...
From $336 per night (USD)VRBO
- From $169 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 $169 per night (USD)Expedia
- Click For Pricing
VRBO
Amazing College Park private walled in estate
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
Amazing private Mediterranean walled estate located across from the historic DubsDread golf course! Centrally located in ...
Click For PricingVRBO
- 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 $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 $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 $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
- 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 $183 per night (USD)
VRBO
Modern Elegance In The Heart Of Winter Park - 2 beds\/2 baths
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Location!!! Beautifully appointed 2 bedroom, 2 bath second floor apartment overlooking a beautiful pool area with balcon ...
From $183 per night (USD)VRBO
- From $139 per night (USD)
Expedia
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)Expedia
- From $208 per night (USD)
VRBO
Just 3 Blocks to Park Ave Shops\/ Restaurants, 2 From The Winter Park Village!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Modern, clean and unique. Second floor penthouse unit overlooking the pool area. Gorgeous acacia wood floors, quartz c ...
From $208 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 $150 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 $150 per night (USD)VRBO
- From $286 per night (USD)
VRBO
LUXURY 𝕄𝕚𝕕 ℂ𝕖𝕟𝕥𝕦𝕣𝕪 𝕄𝕠𝕕𝕖𝕣𝕟 ᴠᴀᴄᴀᴛɪᴏɴ in 𝒲𝒾𝓃𝓉𝑒𝓇 𝒫𝒶𝓇𝓀
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
NEW CONSTRUCTION Luxury Home north of Downtown Orlando in the heart of Winter Park steps from Winter Park Village near t ...
From $286 per night (USD)VRBO
- From $1884 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 $1884 per night (USD)VRBO
- From $324 per night (USD)
Expedia
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 $324 per night (USD)Expedia
- Click For Pricing
VRBO
Charming 2-bedroom apartment with AC and WiFi in enchanting Winter Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Located in Winter Park, this apartment is a dream. With 2 nice bedrooms, AC, WiFi, a hair dryer, an iron, and a washing ...
Click For PricingVRBO
- From $209 per night (USD)
Expedia
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)Expedia
- From $146 per night (USD)
VRBO
Home Away from Home- Winter Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy our newly renovated home in Winter Park. We are centrally located and within minutes from Rollins College and Park ...
From $146 per night (USD)VRBO
- From $121 per night (USD)
VRBO
Winter Park College quarters historic district
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The College Quarters in Winter Park is located in the charming city of Winter Park Historic District. Located within blo ...
From $121 per night (USD)VRBO
- From $162 per night (USD)
VRBO
Modern, fabulous two-bedroom with parking in Winter Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our newly renovated duplex home is stylish and well-appointed with everything you need for a getaway or a longer visit. ...
From $162 per night (USD)VRBO
- From $193 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 $193 per night (USD)Expedia
- From $162 per night (USD)
VRBO
Cozy 4-bedroom house with WiFi, AC in peaceful Winter Park
- Bedrooms:
- 3
- 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 ...
From $162 per night (USD)VRBO
- From $271 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 $271 per night (USD)Expedia
- From $100 per night (USD)
VRBO
Charming 4-bedroom House with WiFi, AC in welcome to Winter Park Area
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Consider this house your home away from home while you visit Winter Park. This lovely property features 1 bedroom 1 Bath ...
From $100 per night (USD)VRBO
- From $165 per night (USD)
Expedia
Disney, Universal, Sea World, Cozy Bungalow Home easy access to I-4...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy Winter Park home features 2 bedrooms and 1 bath. Conveniently located off of I-4. Close to downtown Orlando/Winter ...
From $165 per night (USD)Expedia
- From $182 per night (USD)
VRBO
The beautiful Melrose Cottage
- Bedrooms:
- 3
- 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)VRBO
- From $342 per night (USD)
Expedia
Mills House @WP. Sleeps 11 Renovated. Queen beds
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 11
Enjoy a stylish experience at this centrally-located place. MillsHouse is conveniently located for a foodie adventure. T ...
From $342 per night (USD)Expedia
- From $110 per night (USD)
VRBO
6 Mi to Downtown Orlando: Quiet Home w\/ Sunroom
- Bedrooms:
- 1
- Bathrooms:
- 3
- 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 $110 per night (USD)VRBO
- Click For Pricing
Expedia
Cottage on Cornell - Quaint & Cozy w\/Outdoor Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
Newly renovated guest suite using original reclaimed materials to create a modern vintage farmhouse vibe. Centrally loca ...
Click For PricingExpedia
- From $144 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 $144 per night (USD)VRBO
- From $115 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 $115 per night (USD)Expedia
- From $120 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 $120 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $219 per night (USD)
VRBO
CHARMING - Cozy Retreat Near Lake Killarney in Winter Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come and stay awhile at the Killarney Retreat, built in the 50s, tucked away from the hub of city, yet just a short driv ...
From $219 per night (USD)VRBO
- Click For Pricing
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 PricingExpedia
- 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
- Click For Pricing
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 PricingExpedia
- From $198 per night (USD)
VRBO
New Renovated House Near Everything
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Lovely comfortable and clean home with large “zin” yard in an area that is near the best of the best: Restaurants, Whole ...
From $198 per night (USD)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 $246 per night (USD)
VRBO
You're Pampered Here - Just 3 Blocks From Park Avenue!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Modern, clean and unique. Fastest internet speed available: 139MBPS download and 21.5 MBPS upload! Second floor penthous ...
From $246 per night (USD)VRBO
- From $147 per night (USD)
Expedia
Private Poolside Guest House In Winter Park\/Orlando
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beautiful and comfortable two-story cottage/detached guest house, centrally-located within an historic neighborhood. Loc ...
From $147 per night (USD)Expedia
- From $341 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 $341 per night (USD)VRBO
- From $375 per night (USD)
VRBO
Winter Park Pool home close to Lake Virginia, Rollins College & Park Ave.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
One month minimum to rent (30 nights). A hidden gem, this meticulous sun-filled 3 BR + Office/2.5 bath home offers ult ...
From $375 per night (USD)VRBO
- 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)VRBO