Nestled in the heart of Tuscany, Provincia di Arezzo is a tapestry of rolling green valleys, medieval hill towns, and vibrant markets. This is a destination where vacation rentals feel like a home away from home and where every alley whispers a story from centuries past. If you’re seeking sunlit holidays, welcoming hosts, and authentic Tuscan experiences, you’ll find them here—from the art-filled streets of Arezzo city to the tranquil vineyards of Cortona and beyond. Whether you want a family-friendly villa with a pool, a charming casale tucked into olive groves, or a boutique agriturismo where farm-to-table meals are part of the daily rhythm, this region offers a spectrum of vacation rentals and holiday homes that fit every style and budget. For easy planning and access to a wide selection of accommodations in the area, consider searching on searchandstay.com, your go-to website to find places to stay in the Province of Arezzo and throughout Toscana.
Destinations in the Province of Arezzo you won’t want to miss
Arezzo city — art, markets, and timeless streets
Arezzo city is a gateway to Tuscan culture with a pulse that blends ancient artistry and lively modern life. The city center unfurls around monumental churches, museums, and the expansive Piazza Grande, where you can soak up sun, sip a cappuccino, and watch local life unfold. Staying in a vacation rental in Arezzo puts you steps away from the world-famous Piero della Francesca frescoes in the Basilica di San Francesco and the powerful views from the Concezione Coglievina. The vibrant weekly market is a color-splashed invitation to mingle with locals—perfect for anyone seeking an authentic Italian experience. When you’re not wandering the cathedrals or markets, you can join a guided food tour or take a cooking class in a nearby agriturismo to understand the Tuscan table from field to fork. If you prefer a relaxed day, a stroll along the ancient city walls and a sunset from one of the overlook points will reward you with photogenic memories. For accommodations, you’ll find a range of villa rentals, elegant apartments, and family-friendly holiday homes that keep you close to the center while offering a peaceful retreat after a day of exploration.
Travelers often pair their Arezzo stay with day trips into Val di Chiana or the Casentino for a broader taste of the region. Easy rail and road links mean you can base yourself in Arezzo and still cover Cortona, Anghiari, and Sansepolcro in day trips if you crave variety in a single Tuscan itinerary. For booking convenience and a curated inventory of places to stay, searchandstay.com is a trusted resource to discover accommodations in the Arezzo province and across Toscana.
Cortona — hilltop charm, art, and panoramic skies
Perched on a limestone ridge with sweeping views over the valley below, Cortona is a magnet for travelers who crave dramatic scenery and intimate Tuscan storytelling. The town’s winding lanes lead to Renaissance palazzi, evocative museums, and a lively piazza where locals gather for aperitivi. A stay in a Cortona villa rental or a restored farmhouse enables you to wake up to sunlit rooftops and the distant hum of market stalls. In Cortona you’ll find excellent opportunities for wine tastings along DOC Cortona routes, olive oil tours that reveal the region’s fruity notes, and hands-on cooking classes that showcase Tuscan classics like ribollita, pappardelle al cinghiale, and almond biscotti. Day trips from Cortona often include a visit to nearby vineyards, a stop at Lake Trasimeno for a lakeside lunch, or a stroll through nearby villages like Castiglione del Lago for more architectural charm. When you’re ready to relax, your Cortona accommodation can be a boutique guesthouse or a serene hillside villa that frames the sunset with terracotta rooftops and olive groves.
For travelers seeking diverse experiences, Cortona makes a brilliant base: short scenic drives to the Val di Chiana’s markets, longer excursions into the Casentino forests, and easy access to Arezzo’s historical sites. Searchandstay.com offers a range of Cortona-area vacation rentals and house rentals that balance proximity to attractions with tranquility in the Tuscan countryside.
Anghiari — a medieval jewel with sweeping views
Anghiari sits high above the Tiber valley, where stone houses cling to the hillside as if trying to touch the sky. The town’s fortified walls and narrow lanes feel like stepping into a living postcard. Anghiari is ideal for travelers who love photography, local crafts, and a slower pace that still sparkles with energy during the warm Tuscan evenings. An Anghiari stay can be wonderfully paired with day trips to nearby forests and rivers for easy hikes, fishing shores, and picnics among olive groves. In the evenings, you can enjoy trattorie serving hearty Tuscan comforts—pancetta, ribollita, and peppery pecorino—paired with wines from nearby vineyards. Choosing a vacation rental in Anghiari means embracing authentic regional life, often in charming stone houses with courtyards that invite morning coffee and evening aperitifs with fellow travelers. For accommodation options in Anghiari and the surrounding area, searchandstay.com curates a diverse selection of properties to suit lovers of culture, cuisine, and nature alike.
Anghiari’s annual events and medieval ambiance make it an inviting stop for a multi-town itinerary through the Arezzo province. Combine Anghiari with Cortona for a day that alternates hilltop views with cellar doors and market strolls, then unwind in a cozy farmhouse rental that feels both rustic and refined.
Castiglion Fiorentino — walls, squares, and hillside charm
Castiglion Fiorentino presents a quintessential Tuscan town with a Romanesque church, a lively central square, and a network of narrow lanes that reward careful wandering. A stay here gives you a slice of rural life with easy access to vineyards and olive groves. The town is also a gateway to activities like cycling through the Val di Chiana, guided hikes to hidden chapels, and culinary experiences that showcase the robust flavors of Tuscan country cooking. Agriturismi and farmhouses around Castiglion Fiorentino offer family-friendly spaces with pools, gardens, and opportunities to learn about farming cycles, from grape harvests to olive picking. When you’re not exploring the historic core, you can hop into a car for a short drive to Cortona or Arezzo for museums, markets, and signature Tuscan sunsets. For travelers seeking a blend of culture and countryside, Castiglion Fiorentino presents a balanced, welcoming base. Look for villa rentals and country homes on searchandstay.com to compare options and find the perfect match for your travel party.
Holiday rentals in Castiglion Fiorentino often feature outdoor spaces designed for social evenings, making it easy to connect with hosts and fellow guests while savoring the local produce and regional wines.
Sansepolcro — birthplace of Renaissance light
Sansepolcro, known for its Palladian-inspired architecture and the artistic legacy of Piero della Francesca, offers a luminous blend of culture and countryside. A day here might begin with a visit to the frescoed churches, followed by a stroll along the town’s quiet streets and a lunch of handmade pasta and casalinga cheese. Staying in Sansepolcro can mean a comfortable, well-equipped villa or a tasteful apartment near the historic center, placing you within easy reach of museums, galleries, and artisan shops. Local experiences include guided tours of the painter’s sites, time in nearby workshops learning traditional paper-making, and food tastings that highlight the region’s chestnuts, cured meats, and honey. As with other towns in the Arezzo province, Sansepolcro serves as a gateway to outdoor adventures in the Casentino forests and to scenic drives through the Valtiberina. Booking through searchandstay.com gives you access to a curated mix of accommodations that suit solo travelers, couples, and families who value comfort and convenience after full days of discovery.
Combine a Sansepolcro stay with a scenic drive to nearby natural reserves for hiking or cycling, followed by a sunset meal in a village trattoria—the kind of day that makes a Tuscan itinerary feel effortless and joyful.
Casentino (foreste Casentinesi) — forests, monasteries, and trails
The Casentino is more than a landscape; it’s an invitation to immersion. The Foreste Casentinesi, Monte Falterona, Campigna National Park preserves ancient beech and fir forests, tranquil streams, and a spectacular mix of wildlife. This is where hikers, families, and nature lovers find a different tempo—one defined by fresh air, meadows, and the distant echo of cowbells. Nestled in this alpine Tuscan corner are farmhouses and agriturismi that emphasize sustainable living and farm-based experiences. A Casentino base makes it easy to visit the medieval hermitages, the Camaldolese monastery, and the waterfalls that tumble through wooded canyons. After a day of outdoor adventures, you can unwind in a rustic stone cottage or a modern villa with sweeping forest views. If your travel style loves a balance of nature, culture, and comfortable lodging, a Casentino stay is a natural fit. Check searchandstay.com for Casentino-area properties that blend accessibility with immersion in the region’s tranquil charm.
Seasonal activities here include forest hikes in spring, wildlife watching, and autumn photography of changing foliage. In winter, the region feels extra intimate, with cozy fireplaces, hot chocolate, and close proximity to towns offering cultural events and regional cuisine.
Where to stay — vacation rentals, house rentals, and more
Provincia di Arezzo caters to every traveler’s lodging preference—villas with panoramic views, historic casali restored into elegant holiday homes, agriturismi that pair comfortable accommodations with farm-to-table meals, and modern apartments that keep you connected to the pulse of local life. If you’re planning a family gathering, a long weekend with friends, or a romantic escape, you’ll find properties that suit your needs—from spacious multi-bedroom houses with private pools to intimate studios perched above terraced olive groves. The region’s vacation rentals often come with terraces or gardens ideal for al fresco dining, outdoor grills for Tuscan barbecues, and sun-soaked pools that make summer days effortless. For travelers who value authentic experiences, many hosts offer cooking classes, wine tastings, and guided walks as part of the stay, giving you a richer sense of place. Access to reliable Wi-Fi, fully equipped kitchens, and convenient parking is common across the portfolio, making it easy to plan day trips to Cortona, Arezzo, Anghiari, and Sansepolcro while returning to a comfortable home base each night.
When you book through searchandstay.com, you can filter by property type, price range, and location within the Province of Arezzo to find exactly what you want—whether it’s a family-friendly villa near the Val di Chiana, a secluded casale surrounded by olive groves, or a boutique apartment in a historic center. The site curates a robust selection of holiday rentals and house rentals across Toscana, with options that emphasize hospitality, accessibility, and value. Take advantage of guest reviews, clear photographs, and host communications to select a stay that aligns with your travel rhythm and budget. After you choose your base, you’ll be ready to dive into the region’s experiences with confidence and curiosity.
Local experiences and activities to shape your Arezzo adventure
- Art and history tours in Arezzo city, Cortona, and Sansepolcro, including guided visits to frescoes, palazzi, and museums that showcase Renaissance masters and medieval artisans.
- Wine and olive oil experiences along Cortona DOC routes and surrounding vineyards—tasting flights paired with local cheeses and rustic bread.
- Hands-on Tuscan cooking classes at agriturismi or in small cooking schools—learn to make handmade pici, ribollita, and cantucci with fresh, seasonal ingredients.
- Olive oil tastings and farm visits to see the harvest cycle, production methods, and bottling practices that give Tuscan extra-virgin olive oil its distinctive flavor.
- Nature and outdoor activities in the Casentino forests: hiking, bird watching, and family-friendly trails that lead to ancient monasteries and picturesque viewpoints.
- Hot air balloon experiences over the Tuscan countryside, offering a bird’s-eye view of vineyards, olive groves, and hill towns as dawn light spills across the valleys.
- Cooking demonstrations and market tours in local towns where you can shop with residents and learn about seasonal produce, pecorino, and seasonal fruits.
- Bike and e-bike routes through rolling hills and vales, with stops at traditional taverns for a tasting and a chat with locals.
- Festivals and sagre (seasonal food festivals) that celebrate chestnuts, truffles, wine, and regional specialties—an engaging way to connect with community and taste authentic flavors.
- Heritage walks in medieval towns like Anghiari and Castiglion Fiorentino, where stone walls, viewpoints, and plazas become open-air museums.
To discover these experiences and arrange your stays around them, look for accommodations on searchandstay.com that place you near the activities you love. The platform helps you pair your lodging with the region’s rich calendar of houses, markets, and events, ensuring you never miss a moment of Arezzo’s hospitality.
Seasonal itineraries — what to book and what to do, anytime
Spring
Spring in the Province of Arezzo is a time of fresh olives, early wine releases, and flowers that perfume stone towns. It’s ideal for walking tours, outdoor markets, and day trips to Cortona’s hillside landscapes. A spring stay might feature a villa with a courtyard garden and a nearby winery for a tasting after a morning hike. Outdoor dining becomes the norm as temperatures rise and the countryside comes alive with birdsong and new growth.
Summer
Summer invites long days by a pool, sunset aperitifs on a terrace, and late-evening strolls through the old towns. It’s a peak season for farm stays and coastal excursions to nearby lakes and valley towns. Choose a vacation rental with a pool, easy access to cycling routes, and a well-equipped kitchen for family feasts featuring tomatoes, basil, and fresh mozzarella. The region’s markets are especially welcoming, offering local produce, breads, and cheeses to complement your summer barbecues.
Autumn
Autumn is harvest time. It’s perfect for food lovers who want truffle hunts, chestnut festivals, and wine sipping by thermally warmed stone walls. Stay in a cozy casale or a hillside villa to harvest the warm glow of Tuscan light while savoring roasted chestnuts and porcini mushrooms. Day trips to Cortona and Anghiari are stunning with autumn colors, and olive harvest experiences create a flavorful behind-the-scenes look at olive oil production.
Winter
Winter in Arezzo province brings quiet streets, candlelit dinners, and the comfort of a crackling fireplace in a country home. Cozy accommodations with modern comforts are popular, and you can still enjoy guided tours, museum visits, and regional cuisine in warm havens after a day exploring nearby towns. If you’re seeking a peaceful, culturally rich retreat, winter can be the ideal time to savor Tuscan hospitality with fewer crowds while still enjoying excellent access to vineyards, galleries, and historic architecture.
Practical tips for planning your Arezzo adventure
- Best time to visit: late spring (April–June) and early autumn (September–October) offer pleasant weather, fewer crowds, and vibrant seasonal offerings in markets and restaurants.
- Getting around: a car is the most convenient way to explore the province, with easy day trips to Cortona, Anghiari, and Casentino. Some towns have limited parking in the historic centers, so consider a centrally located base with accessible parking.
- Where to stay: look for vacation rentals with private outdoor spaces, kitchens, and reliable wi‑fi. Agriturismi can offer authentic experiences and meals, while villa rentals provide space for gatherings and kids’ rooms for a comfortable family stay.
- Local etiquette: Tuscan hosts are welcoming and keen to share recommendations. A quick “buon giorno” or “grazie” goes a long way, and bringing a small gift like locally produced wine or olive oil is a thoughtful gesture when visiting a family-run agriturismo.
- Food and markets: don’t miss the weekly markets in Arezzo and nearby towns. They’re perfect for tasting regional cheeses, cured meats, and seasonal vegetables, and they provide a glimpse into daily life that you can’t replicate in a tourist restaurant.
- Booking and planning: use searchandstay.com to compare listings across the Province of Arezzo and Toscana, read guest reviews, and find properties that align with your travel dates, group size, and preferred activities.
With its blend of ancient charm and lively modernity, the Province of Arezzo invites you to design a vacation rental experience that’s as social as it is scenic. From Arezzo city’s fountains to Cortona’s sunlit hills, from Anghiari’s arched streets to the Casentino’s forest trails, you’ll discover a Tuscany that invites connection, conversation, and joyful exploration. Whether you’re booking a family villa, a romantic casale, or a stylish apartment for friends, the region offers a spectrum of options to ensure a memorable, inclusive, and immersive stay. For a curated pool of accommodations in the Arezzo area, searchandstay.com is a practical partner to help you find the right fit for your next Tuscan escape.