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 $210 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 $210 per night (USD)
VRBO
From $235 per night (USD)
Expedia
Charming Clean Home near East End Market Large fenced yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Winter Park home ready for your event, vacation or executive rental. Updated kitchen, granite countertops, wood floors, ...
From $235 per night (USD)
Expedia
From $156 per night (USD)
VRBO
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 $156 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 $353 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 $353 per night (USD)
VRBO
From $183 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 $183 per night (USD)
Expedia
From $178 per night (USD)
VRBO
Breezy Pool Home!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to beautiful Breezy Winter Park Home where you can relax and enjoy! The home is situated in a short drive to Dow ...
From $178 per night (USD)
VRBO
From $278 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 $278 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 $180 per night (USD)
Expedia
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 $180 per night (USD)
Expedia
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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 $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
From $315 per night (USD)
VRBO
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 $315 per night (USD)
VRBO
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 $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
Click For Pricing
Expedia
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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Expedia
From $373 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 $373 per night (USD)
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
Click For Pricing
VRBO
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 Pricing
VRBO
From $360 per night (USD)
Expedia
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 $360 per night (USD)
Expedia
From $181 per night (USD)
VRBO
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 $181 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 $266 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 stays with access to all the best of Central Florida. Ten mi ...
From $266 per night (USD)
VRBO
From $326 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 $326 per night (USD)
Expedia
From $147 per night (USD)
VRBO
Cottage Retreat in the City
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
QUICK LOOK Recently Constructed, 1-Bedroom Cottage in College Park, a quaint downtown Orlando neighborhood Available Ni ...
From $147 per night (USD)
VRBO
From $254 per night (USD)
Expedia
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)
Expedia
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 $167 per night (USD)
Expedia
Top 1% College Park GuestHouse Villa/Oasis - Mins to DT ORL/Winter Park & Eola
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
***Update January 2025*** EV Level 2 Charger FREE to our guests. 9X faster than Level 1. Located adjacent our Guest park ...
From $167 per night (USD)
Expedia
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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 ...
Click For Pricing
VRBO
From $247 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 $247 per night (USD)
Expedia
From $262 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 ADU retreat offers the perfect blend of relax ...
From $262 per night (USD)
VRBO
From $252 per night (USD)
Expedia
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 $252 per night (USD)
Expedia
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 $363 per night (USD)
Expedia
Private Luxury Pool / Smart-home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Owners have freshly renovated September 2023 Investing over ($75,000) adding the following - Brand new single slope met ...
From $363 per night (USD)
Expedia
From $172 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 $172 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
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VRBO
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 ...
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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 $134 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 $134 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
Click For Pricing
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
From $480 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 $480 per night (USD)
VRBO
From $461 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 $461 per night (USD)
VRBO
From $515 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 $515 per night (USD)
VRBO
From $497 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 $497 per night (USD)
VRBO
From $531 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 $531 per night (USD)
VRBO
From $628 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 $628 per night (USD)
VRBO
From $613 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 $613 per night (USD)
VRBO
From $561 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 $561 per night (USD)
VRBO
From $196 per night (USD)
Expedia
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 $196 per night (USD)
Expedia
From $198 per night (USD)
VRBO
Temporary living that feels like home where you can relax and be yourself.
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Fully furnished, charming and comfortable, 4 bedroom - 2 bath, short-term home has new linens, new beds (1 King, 2 queen ...
From $198 per night (USD)
VRBO
From $172 per night (USD)
Expedia
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)
Expedia
From $209 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 $209 per night (USD)
VRBO
From $332 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 $332 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
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Expedia
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 ...
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Expedia
From $170 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 $170 per night (USD)
VRBO
From $427 per night (USD)
Expedia
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)
Expedia
From $401 per night (USD)
VRBO
Modern and fabulous tropical oasis, central to everything!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Make memories at this unique and family-friendly property in the heart of Audubon Park. Hang out in a tropical garden sh ...
From $401 per night (USD)
VRBO
From $1086 per night (USD)
Expedia
Luxury Ranch 2 Master Kg Bed w/ heated Salted Pool
Bedrooms:
3
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 $1086 per night (USD)
Expedia
From $100 per night (USD)
VRBO
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 $100 per night (USD)
VRBO
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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 ...
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Expedia
From $138 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 $138 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 $134 per night (USD)
VRBO
Beautiful Direct Fish & Ski Lakefront Town home In N. Orlando with Pool & WiFi
Bedrooms:
2
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 $134 per night (USD)
VRBO
From $237 per night (USD)
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 ...
From $237 per night (USD)
Expedia
From $320 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 $320 per night (USD)
VRBO
From $211 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 $211 per night (USD)
Expedia
From $104 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 $104 per night (USD)
VRBO
From $187 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 $187 per night (USD)
VRBO
From $321 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 $321 per night (USD)
VRBO
From $249 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 $249 per night (USD)
Expedia
From $82 per night (USD)
VRBO
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 $82 per night (USD)
VRBO
From $123 per night (USD)
Expedia
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)
Expedia
From $159 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 $159 per night (USD)
VRBO
From $198 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 $198 per night (USD)
Expedia
From $145 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 $145 per night (USD)
VRBO
From $884 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 $884 per night (USD)
Expedia
From $295 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 $295 per night (USD)
VRBO
From $253 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 $253 per night (USD)
Expedia
From $400 per night (USD)
VRBO
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 $400 per night (USD)
VRBO
Click For Pricing
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 $178 per night (USD)
VRBO
Modern 3BR Duplex | Kitchen, Wi-Fi & Pet-Friendly
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Save 25% on this peaceful 3BR Orlando duplex—ideal for families, groups, or remote workers. Relax in spacious living are ...
From $178 per night (USD)
VRBO
From $157 per night (USD)
VRBO
2BR Orlando Escape | Close to Disney + Pool & Pets
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Family-friendly 2BR Orlando home with private pool, full kitchen, and roomy living areas for up to 6 guests. Kids will l ...
From $157 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 $863 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 $863 per night (USD)
Expedia
From $290 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 $290 per night (USD)
VRBO
From $224 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 $224 per night (USD)
Expedia
From $1248 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 $1248 per night (USD)
VRBO
From $90 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 $90 per night (USD)
Expedia
From $287 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 $287 per night (USD)
VRBO
From $456 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 $456 per night (USD)
Expedia
From $138 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 $138 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 $112 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 $112 per night (USD)
VRBO
From $120 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 $120 per night (USD)
Expedia
From $351 per night (USD)
VRBO
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 $351 per night (USD)
VRBO
From $190 per night (USD)
Expedia
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 $190 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 $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

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Results: 117 Rentals