Europe / Italy / Tuscany

Nestled in the renowned “Chianti Classico” winemaking region just outside Florence, Villa Realgrande offers a unique 15th-century experience.

up to 10
up to 22
from 7
Min. Nights


Meticulously restored, the main villa boasts original frescoes and opulent interior décor against a backdrop of picturesque Tuscan vineyard-lined hills. Only a 25-minute drive from Florence, the villa seamlessly blends old-world charm with modern luxury, featuring ten bedrooms for up to 22 guests. Immerse yourself in history and culture while enjoying five-star comfort, surrounded by artwork and furnishings from around the world. Explore perfectly restored frescoed rooms, relax in the awe-inspiring loggia with views of the Duomo, and indulge in various spaces, including dining rooms, outdoor terraces, and a superb wellness area with a heated pool, gym, sauna, and steam bath.

Living Spaces
Ground Floor

  • Large, luxurious and beautiful main piano salon and formal dining room, both leading onto a gorgeous, fully furnished frescoed terrace with glorious views
  • Large kitchen

First Floor

  • Fully furnished frescoed terrace with amazing views
  • Small service eat-in kitchen

Outdoor Featrures
Villa Realgrande reigns over 750 acres of vineyards, olive groves and Tuscan forest. It features spectacular frescoed terraces with beautiful lounges, tables and outdoor furnishings, a swimming pool, sculpture garden and beautiful garden surroundings.

Special Characteristics 
Immerse yourself in a truly unforgettable experience at this historically beautiful estate, where five-star service ensures lasting memories. The main villa, adorned with restored 15th-century frescoes and a curated mix of antiques and contemporary art from South Africa, is a masterpiece of restoration and decoration. Producing its own olive oil and fine wines, the property embodies a legacy of unparalleled luxury. Guests can live in the lap of modern comfort within the same villa that once hosted Florence’s ruling aristocrats. Realgrande, featured in renowned magazines like Vanity Fair and Food & Wine, offers exceptional spaces for grand entertainment, making it an ideal venue for weddings and special events.


10 Bedrooms, 10 Bathrooms

Sleeps 22 Guests

  • Spa / Sauna
  • Hair Dryer
  • Separate Kitchen
  • Dishwasher
  • Fully Equipped
  • Elevator
  • Helipad
  • Vineyard View
  • Parking Space
  • Al Fresco Dining
  • Fireplace
  • DVD player
  • Cable
  • Stereo
  • Television
  • CD Player
  • Wi-Fi


Bedroom Details

Bedroom 1 (Ground Floor): Royal Suite: Spectacular master king bedroom royal suite with en-suite mosaic-covered, priceless marble Jacuzzi tub and his and hers bathrooms
Bedroom 2 (Ground Floor): Deluxe queen bedroom with en-suite marble bathroom
Bedroom 3 (Ground Floor): Deluxe queen bedroom with en-suite marble bathroom
Bedrooms 4 & 5 (First Floor): Two bedroom Duplex Suite – two separate bedrooms (1 King and 1 Twin/Queen) with en-suite bathrooms with tubs
Bedrooms 6 - 9 (First Floor): 5 Royal duplex suites with en-suite bathrooms, one of which has 1 extra bedroom and bathroom
Bedroom 10 (First Floor Mezzanine): Deluxe queen bedroom with en-suite marble bathroom

Pool Details

Private gated garden and outdoor pool
Indoor pool heating is an additional cost

Staff and Services

Final cleaning
Daily housekeeping from 10:00 am to 2:00 pm/6 days per week
Mid-week bedroom and bathroom linen change
Welcome drink and snack on arrival
Daily buffet breakfast
Wi-Fi Internet connection
Villa manager: 6 days a week; 8 hours a day
Local concierge service: 4 hours a day; 6 days a week
Garden and pool maintenance

Staff and Services (at Additional Cost)

Extra linen change
Chef service – No third-party suppliers allowed: the services will be provided by the villa management and in-house staff
Cost of food and beverages
Personal laundry and ironing service
Babysitting service
Grocery delivery service
Specialty Sky TV channels (On-Demand)
Telephone/fax charges
Anything else not specifically listed under “Included with rent”

Location Details

Lucca - 1 hour
Siena - 50 minutes
Florence - 30 minutes
Rome - 2 hours and 45 minutes
San Casciano val di Pesa - 12 minutes

Villa Notes

Copies of passports must be provided in advance for all guests to expedite check-in process.
Sorry, no pets
Check-in: after 4:00 pm
Check-out: before/by 10:00 pm
All extra services to be paid locally, prior to departure, unless otherwise arranged
Important note regarding Chef/ Cook Services: All Chef/Cook services need to be arranged by your Concierge. Only Villa approved Chef/Cooks can be used. This also pertains to In-Villa cooking lessons.
Due to limited transportation in outlying and rural areas, a rental car is essential for stays at countryside villas in Italy. We are more than happy to arrange a car for you during your stay, please just let us know at time of booking.
Please note that Italy villas rent from Saturday to Saturday. Exceptions may be possible on a case by case basis and upon request.
Most villas in Italy require the cost of extra services be paid upon arrival in cash. Please check with your Villa Specialist or Concierge for details.

Rates and Availability

Tax Service Charge Details*
Visitor’s tax: The Italian government might require the payment of a Visitor’s Tax (approximately €1.50 – €6.00 per person, per day, depending on the location) and may be applied for the first ten days in the destination. This tax is payable locally, in Euro cash.
A food and beverage deposit will be required in advance when guests choose to add the private chef service; amount to be advised at time of service reservation
If guests wish to engage the staff for extra hours or to have additional staff this will be at extra charge
Heating of indoor pool, if requested, is additional
Security Deposit Details
€15,000 Pre-collected A €149 Accidental Damage Waiver applies to every reservation.
Accidental Damage Waiver
A $149 Accidental Damage Waiver applies to every reservation.
Minimum Stay Details

Minimum night stay may vary by villa. Please contact a villa specialist to confirm.

Check-In Times
Check in: 4:00 PM - Check out: 10:00 AM

Exclusive Offers

Discover the ultimate in luxury travel with a private villa experience in more than 52 destinations around the world. From a fully-staffed, beachfront estate in Turks & Caicos to an authentic retreat in the rolling hills of Italy, your one-of-a-kind villa vacation awaits. And now, you'll receive up to $2,000 cash back on your 2023 or 2024 getaway when you take advantage of our exclusive Cyber Week offer. Don't wait to unlock the extraordinary - secure your dream villa today.

Here's how you earn.

Base Villa Cost Cash Back*
$5,000 - $15,000 $150
$15,001 – $25,000 $250
$25,001 – $35,000 $350
$35,001 – $50,000 $500
$50,001 – $75,000 $750
$75,001 – $100,000 $1,000
$100,001 + $2,000


Book now and unlock your next villa escape.

Offer valid for new bookings made between 11/19/23 – 12/10/23 travel from 11/19/23 - 12/31/24. Amount is based on the base villa cost only. Minimum booking value applies. Cash back will be paid in a Villas of Distinction Visa® Prepaid Card upon deposit. Villas of Distinction Visa® Prepaid Card is issued by MetaBank®, N.A., Member FDIC, pursuant to a license from Visa U.S.A. Inc. No cash access or recurring payments. Can be used everywhere Visa debit cards are accepted. Card valid for up to 12 months; unused funds will forfeit after the valid thru date. Card terms and conditions apply. Offer is valid for travel advisors’ clients. The Villas of Distinction Prepaid Card will be mailed directly to the travel advisors’ client within 30 days of deposit. Client mailing address must be provided. May not be combinable with other offers. All offers are subject to availability and may not apply to all villas or travel dates. Other restrictions may apply; please call for full details.



Our stay here at Machiavelli has been absolutely magical! From the beautiful villa to the warm and lovably staff, everything has been wonderful. Our three children felt comfortable and welcomed and loved playing on the grounds among the beautiful landscape and sculptures. The wonderful staff went out of their way to make certain that all members of our family felt comfortable and pampered! Tuscany is absolutely breathtaking and Villa Machiavelli has been a special place in which we were able to fully immerse ourselves in our surroundings. We can't thank you all enough for making our time here memorable and unforgettable! - Felix B.

Villa information may change without notice and should be confirmed with our villa rental specialists.