Province of Arezzo, Tuscany, Italy Rentals for Summer Holidays

Why Arezzo is the perfect destination for a summer holiday

Summer in the Province of Arezzo is a tapestry of colors, flavors, and experiences. The climate is Mediterranean with hot, sunny days and cooler evenings that invite long strolls along ancient town walls and through fragrant olive groves. The landscape is a mosaic of vineyards, sun-kissed fields of grain, and chestnut forests that glow gold at dusk. It’s a destination where you can rent a country villa with a pool for a family vacation, or book a stylish apartment within the historic center for a romantic getaway, all while staying within reach of world-class art, timeless architecture, and dramatic natural scenery.

For holiday accommodation at, you’ll discover a spectrum of options—from short term rental homes and compact apartments to elegant farmhouses and expansive villas. If you’re looking for a holiday rental that combines privacy with shared spaces for social gatherings, there are many properties offering outdoor dining terraces, wood-burning ovens, and swimming pools surrounded by olive groves. For stays that feel rooted in the land, agriturismo stays provide an authentic connection to local farming cycles, where you can learn about olive harvests, grape pressing, and seasonal kitchen gardens while savoring meals prepared with ingredients grown on-site.

Travelers seeking a destination that balances culture with outdoor adventure will find endless opportunities for activities and things to do. The summer calendar is alive with markets, processions, historical reenactments, and music events. Day trips to nearby hill towns reveal treasured art, Romanesque churches, and views that stretch to the horizon. And with direct access to scenic walking trails, ridge-top viewpoints, and quiet country lanes, you can pair cultural exploration with outdoor exploration for the ultimate Italian summer experience.

Where to stay in the Province of Arezzo: accommodation in Arezzo and beyond

In this region, accommodation in Arezzo ranges from stylish city-center flats to rustic farmhouses tucked into hillside vineyards. If you’re after holiday accommodation at a slower pace, there are agriturismi where a chef might bring a tasting of local olive oil and wines to your dining table. For those who crave convenience and proximity to historic sights, boutique hotels and fully equipped vacation rentals in town centers provide easy access to museums, markets, and trattorie. Here are some standout categories to guide your search for places to stay in Arezzo province:

• Historic center apartments and lofts in Arezzo city, offering convenient access to Piazza Grande, the Cathedral complex, and narrow winding lanes lined with artisan shops.
• Elegant villas and country houses in the countryside, set among olive groves and vineyards with private pools and expansive terraces for entertaining guests.
• Agriturismo stays on working farms, where you can participate in winemaking or olive oil production and enjoy farm-to-table meals featuring fresh ingredients.
• Rustic-chic Tuscan farmhouses (casedelle or casali) ideal for families or groups seeking privacy, space, and a retreat-like atmosphere.
• Charming bed and breakfast properties that pair personalized service with local character.
• Loft-style apartments and modern vacation rentals near major towns for those who want great access combined with contemporary comforts.

When planning a stay, consider the vibe you want: a home base in the heart of Cortona’s winding lanes with sunset views across the Val di Chiana, or a tranquil agriturismo where mornings begin with birdsong and a stroll through a fruit orchard. A short-term rental in the Arezzo countryside can feel like stepping into a painting, while a stay in town keeps you close to markets, cafés, and spontaneous evenings with locals. For a truly immersive experience, look for properties that offer authentic Tuscan features—terracotta floors, exposed wooden beams, fireplaces, and sun-drenched terraces.

Tip: if you’re planning a multi-town itinerary, consider staying in two or three different places to experience the variety of the province without long commutes. A couple of nights in Arezzo city, followed by a week in a countryside villa near Cortona or Anghiari, can provide a balanced and enriching experience of both culture and nature.

Top destinations within the province for your summer itinerary

The Province of Arezzo is peppered with towns and landscapes that each tell a unique story. Here are some highlights that frequently shape visitor itineraries and inspire memorable stays:

• Arezzo city – A thriving hub with a gem of a medieval center, frescoed churches, and a weekly antiques market that attracts collectors from across Italy. The city’s architecture blends Roman, medieval, and Renaissance layers, inviting exploration on foot between cathedrals, palazzi, and tepidity of street cafés.
• Cortona – Perched on a Tuscan hillside above the Tiber Valley, Cortona offers sweeping views, charming lanes, and a lively cultural calendar. It’s renowned for its Etruscan origins and a superb blend of galleries, eateries, and artisan workshops—an ideal backdrop for a memorable holiday rental with a panoramic terrace.
• Anghiari – Known for its preserved medieval feel and panoramic vistas, Anghiari is a photographer’s dream and a gateway to serene countryside trails. Antiquities, local crafts, and a sense of timeless pace make a short-term rental here feel like a private retreat.
• Bibbiena and Casentino Valley – A gateway to forested valleys, Romanesque churches, and the forested slopes of Foreste Casentinesi. It’s a stimulating place for nature lovers who want long walks, fresh air, and quiet evenings after exploring the surrounding villages.
• Poppi and the Casentino – Home to the dramatic Poppi Castle, this area offers a mix of history, outdoor activity, and a welcoming rural atmosphere that’s perfect for a relaxed summer break with a touch of drama.
• Castiglion Fiorentino and Monte San Savino – Small towns with a strong sense of local identity, winding lanes, and local eateries that celebrate seasonal produce and regional wines.
• Lucignano – A hill town with a compact medieval core, circular layout, and intimate squares where you can linger over gelato and a glass of Rosso di Cortona or local wines.

Each destination brings its own flavor to a summer itinerary. If a day’s plan means visiting a hill town followed by a sunset stroll along a farm-dotted lane, you’ll find that each stop in Arezzo province offers something distinct—yet all are easily connected by a network of scenic country roads and well-kept highways that make exploring by rented car wonderfully convenient.

Local experiences and things to do that make your stay memorable

To truly capture the essence of Arezzo, immerse yourself in experiences that go beyond sightseeing. This is a place where food, arts, and landscapes merge into a vivid, shareable memory—perfect for an energetic, social traveler who loves to connect with locals and fellow travelers alike.

• Food and wine tastings – Explore the palate of Tuscany with guided tastings featuring Rosso di Cortona and other regional wines. Savor extra-virgin olive oil fresh from the press, accompanied by crusty bread, pecorino, and locally cured meats. A cooking class in a rural villa can teach you how to prepare classic dishes using seasonal ingredients.
• Markets and culinary routes – Weekly markets in towns like Arezzo, Cortona, and nearby villages offer a feast of fresh produce, cheeses, honey, and handmade pastas. Joining a guided market tour lets you sample regional specialties and bring home edible souvenirs to remind you of your stay.
• Art and architecture tours – The Arezzo province is a living museum. In Arezzo city, you can visit the Basilica of San Francesco to see the famous politi-painted stories, the Cathedral of Saint Donatus, and the Medicean Fortress. Outside the city, Cortona’s churches and museums preserve Etruscan and Renaissance legacies that reveal centuries of Tuscan culture.
• Outdoor adventures – Foreste Casentinesi, Monte Falterona, and Campigna National Park offers forest trails for all levels, waterfalls, and shaded paths perfect for daytime escapes. Hiking, mountain biking, and birdwatching are popular, and many rental properties include maps and local route tips to help you plan day trips.
• Hill-town strolls at golden hour – The light in Arezzo’s hills during late afternoon is magical. A walk along town walls and through narrow lanes reveals terracotta tones, flower boxes, and unobstructed views over valleys that seem to glow at sunset.
• Antiques and crafts – The antiques markets and artisan workshops offer unique finds, from hand-painted ceramics to leather goods and textiles. If you’re staying in a villa, you can create a private shopping route to collect handmade pieces as memories of your holiday.
• Festivals and live music – Summer calendars are full of concerts, street performances, and historical parades in towns across the province. Attending a local festival is a wonderful way to meet residents and understand the region’s cultural heartbeat.
• Cooking and farm-to-table experiences – Some agriturismi host farm-to-table dinners where you can dine on seasonal dishes made with produce harvested that day. It’s a convivial way to socialize, sample regional flavors, and learn about Tuscan farming practices first-hand.

For travelers who enjoy staying active and connected, several properties in the area can arrange guided activities such as guided bike tours along winding country roads, sunrise photography routes, or wine-and-woods experiences that strengthen your sense of place while keeping the vacation vibe light and social.

Planning your stay: practical tips for a smooth summer vacation

To make the most of your time in Arezzo, a little planning goes a long way. Here are practical tips to help you find the right holiday accommodation, secure a comfortable stay, and maximize your Italian summer experience.

• Timing and seasonality – Peak tourist season in Arezzo runs from late spring through early autumn. If you’re after a livelier atmosphere with longer days for exploring and dining outdoors, plan for July or August. For quieter countryside tranquility, consider late spring or early autumn remain pleasantly warm with fewer crowds.
• Choosing a location – Decide whether you want a stay in the historical heart of a town like Arezzo or Cortona (closer to museums and cafés) or a countryside villa with expansive views and private outdoor spaces. If you prefer a blend of both, a rural property within a short drive of a town is an excellent compromise.
• Type of accommodation – Short term rental apartments offer flexibility and kitchen facilities for self-catering. Villas and farms provide more space for families or groups and often include private pools. Agriturismi deliver immersion in local agriculture and meals prepared with on-site produce. Budget, space, and desired experiences should guide your choice.
• Accessibility and transport – Renting a car makes it easier to hop between hill towns and countryside landscapes. If you prefer not to drive, look for accommodations near train stations in Arezzo city or other accessible towns; many properties offer easy shuttle options or private drivers for day trips.
• Amenities to look for – A private pool, reliable Wi-Fi, full kitchen, air conditioning, and laundry facilities often are the most sought-after amenities for summer stays. If you’ll be cooking, check for a well-equipped kitchen; if you’ll be staying with children, a secure outdoor space and proximity to markets are valuable.
• Local experiences – Seek out hosts and properties that can arrange wine tastings, olive oil tastings, guided walks, or cooking classes. A thoughtful host can introduce you to hidden gems and personal favorites not listed in standard guides.

When booking, balance convenience with immersion. You don’t need to sacrifice comfort to enjoy genuine Tuscan life. A well-chosen short term rental can serve as your home base in Arezzo, letting you step out each morning to fresh air, historic streets, and a landscape that invites exploration and play.

Food, wine, and the sensory joy of a Tuscan summer

Food in Arezzo province is not just sustenance; it’s a language of community, family, and seasonal abundance. Summer introduces a bounty of tomatoes, basil, zucchini, fresh peaches, and stone fruit that pair beautifully with wines from the area. A vacation rental here isn’t complete without a kitchen moment—grilled vegetables, a simple pasta with local olive oil, and a leisurely outdoor meal beneath a starry night sky.

The region is known for Rosso di Cortona, a ruby to deep red wine with fruity notes and a satisfying structure that pairs with hearty Tuscan dishes. You’ll also find IGT wines and Chianina beef specialties in trattorie near Arezzo and Cortona. If you’re staying in a farm stay, you might watch the winemaker’s ritual, taste the harvest, and learn how a season’s climate shapes the wine’s character. Food lovers will relish the chance to discover local cheeses, fresh burrata, pecorino with honey, and traditional soups that echo grandma’s recipes from generations past.

For a social and educational twist, join a farmer-to-table experience at a rural estate. Learn about heirloom tomatoes, zucchini blossoms filled with ricotta, and herbs grown on site. Finish your evening with a fireside chat about olive oil production and the artistry of aging balsamic-like flavors in a Tuscan way. These experiences become more than meals; they become shared stories that you carry home as part of your holiday memory.

Day trips and itineraries: how to weave the province into a memorable summer

Are you dreaming of a curated summer itinerary that blends culture, nature, and leisure? The Province of Arezzo makes it easy to craft days that feel purposeful yet relaxed. Here are some example itineraries to spark ideas for your holiday rental stay:

• Galleria and Piazza Grande day – Base yourself in Arezzo city or a nearby countryside villa. Spend the morning at the historic center, the cathedral, and the frescoes in San Francesco. Enjoy lunch at a trattoria in the city, then take an afternoon stroll along the city walls with views over the Val di Chiana. Finish the day with a sunset gelato in Piazza Grande and a drink at a rooftop bar.
• Etruscan and medieval trail – Begin in Cortona with its Etruscan roots and medieval lanes. From there, head to Anghiari’s winding streets and artful overlooks. In the evening, return to a countryside villa to unwind by the pool with a glass of wine from the local region.
• Foreste Casentinesi expedition – Drive into Casentino and hike among forests where pine and beech meet, and where panoramic viewpoints reward your effort. Pack a picnic and enjoy a shaded meal near a stream. Return to your rental for a relaxing night with a wood-fired pizza oven at your disposal.
• Wine-and-town-hopping – Tour Cortona, Castiglion Fiorentino, and Lucignano for wine tastings, olive oil tastings, and opportunities to meet winemakers and artisans. End with a culinary night in your accommodation, featuring local cheeses, cured meats, and a rustic loaf of bread.
• Market and cooking class circuit – Visit town markets to pick fresh ingredients, then attend a cooking class back at your rental or at a local agriturismo. Learn to prepare a Tuscan feast and savor the dishes with newly formed travel friends.

These itineraries are adaptable to different group sizes and pace. If you’re traveling with children or friends who love social experiences, choose accommodations that include spaces for group meals, outdoor games, or shared terraces to keep the energy high and the conversations flowing.

Booking guidance for a seamless experience

To secure a great stay in the Arezzo region, consider a few essential steps that help you maximize your time and minimize stress. Good planning, clear expectations, and reliable communication will ensure your accommodation supports your summer adventures rather than complicating them.

• Research the neighborhood – If you’re after a quiet countryside retreat, look for properties with easy access to walking trails or shaded seating areas. If you want lively evenings near cafés and markets, prioritize towns with vibrant nocturnal life and short walking routes from your door.
• Confirm amenities – Verify essential features for your needs: air conditioning for hot afternoons, a pool for family fun, a fully equipped kitchen for flexible meals, and parking if you’ll rent a car. For families, ensure child-friendly amenities such as cribs or safety gates if needed.
• Understand check-in and check-out – Communicate clearly about arrival times, access codes, and what to do with extra towels or linens. A smooth handover reduces stress when you’re juggling luggage and a jet lag rhythm.
• Ask about local services – A good host or property manager may provide recommended drivers, cooking classes, or guided tours. Don’t hesitate to ask for curated itineraries or last-minute activity suggestions that align with your interests.
• Plan with flexibility – Summer plans can shift. Leave some days open to linger in a town you fall in love with, or to change plans if weather turns sunny and perfect for outdoor adventures.

Where you search for accommodations matters. For a wide selection of options across the Province of Arezzo, consider visiting an accommodations-focused platform that highlights properties in Tuscany and more specifically the Arezzo area. For a comprehensive set of listings, you can use the following resource to find accommodations in the area: Search and Stay.

Additionally, this site specializes in short term rental options, ideal for travelers who want flexibility in dates and durations—the right choice for a summer vacation that doesn’t bind you to a fixed schedule. If you’re seeking a destination with a rich mix of history, landscape, and modern comforts, the Arezzo province is a superb fit for a stay that’s as social as it is serene.

Local traditions, culture, and seasonal highlights

One of the most compelling aspects of staying in the Arezzo province is the living culture that welcomes visitors as if they were old friends. From small-town festivals to late-night gelato runs, the rhythm of summer blends hospitality with regional identity. Seasonal markets offer a daily ceremony of flavors and textures—herbs, cheese, cured meats, fresh fruit, and oven-baked breads that fill the air with an irresistible aroma. If you’re staying at a rural villa, you’ll hear the residents speak in warm, inviting tones as they share a table for a communal meal or invite travelers to join in an impromptu outdoor music session or a backyard barbecue under the stars.

Beyond culinary pleasures, Arezzo’s artistic and historical layers are accessible through walkable routes that reveal art, sculpture, and architectural marvels. The province’s churches, palazzos, and archaeological sites preserve a lineage that dates back to Etruscan times and beyond. For a traveler who loves to capture memories with photos, the landscapes—cascading hills, cypress lines along country roads, fields of sunflowers that shimmer in late afternoon light—offer countless moments to remember and share with friends back home.

Staying connected: how to weave social experiences into your holiday

If you’re an energetic and inclusive traveler who thrives on connecting with people, Arezzo’s hospitality and its communities will feel natural. Look for accommodations that encourage social experiences—shared outdoor dining spaces, communal kitchens, or hosts who organize group tastings, farm tours, or cooking demonstrations. These elements help create a sense of belonging and make your holiday more than a simple lodging arrangement. It becomes a portal into a lively social circle where you can meet travelers from around the world and locals who are excited to share their customs and favorite places.

Additionally, choosing a rental in a central or easily reachable town can increase opportunities for spontaneous gatherings—perhaps a night at a local trattoria with a host’s recommended wine pairing, or a sunset walk with new friends through old town streets. The social fabric of Arezzo’s villages and towns invites you to join in, learn, and contribute to experiences that transcend a typical vacation and become lasting memories.

Concluding thoughts: Arezzo as your summer home away from home

The Province of Arezzo in Tuscany is more than a picturesque backdrop for a summer vacation; it’s a living, breathing destination that invites you to immerse yourself in its rhythms, savor its flavors, and participate in its traditions. From the comfort of thoughtfully chosen holiday rentals to the energy of lively town centers and the quiet majesty of the countryside, Arezzo offers a balance that’s rare and compelling. Whether you seek a romantic escape or a family-friendly adventure, a weekend with friends or a longer-term stay that lets you slow down and savor life, the region’s landscapes, culinary treasures, and welcoming people create a setting where every day feels like a new discovery.

For travelers who want a curated experience with options for flexible stays, the province offers a wide range of accommodations that fit different budgets and styles. And for those who want to take the guesswork out of finding the right place to stay, a centralized listing hub like the one mentioned above can be a valuable starting point to explore holiday accommodation at, vacation rentals, and short term rental options in the Arezzo area. The province’s charisma remains constant, while your summer story unfolds with new friends, new flavors, and a renewed sense of wonder. So pack your bags, bring your curiosity, and prepare for a summer of discovery in Arezzo.

When you’re ready to start your search for accommodations in the area, consider perusing listings on Search and Stay. It’s a convenient gateway to holiday accommodation at, vacation rentals, and vacation-stay options across Arezzo’s towns and countryside, helping you find the perfect short term rental that matches your style, pace, and plans for a memorable summer.

Final tips for a successful Arezzo summer stay

Before you go, remember:

• Book early to secure your preferred type of accommodation—whether it’s a hillside villa with a pool or a central apartment near the markets.
• Explore a mix of towns and the countryside to experience the full range of Arezzo’s landscapes and cultural offerings.
• Include at least one hands-on local experience—such as olive oil tasting, a cooking class, or a guided hike—to deepen your connection with the region.
• Pack comfortable walking shoes, a light jacket for cooler evenings, and a reusable water bottle to stay hydrated during long days outdoors.
• Respect local customs and learn a few phrases in Italian; even basic greetings go a long way in building connections with hosts and shopkeepers.

With a thoughtful plan and a sense of adventure, your summer stay in the Province of Arezzo will be memorable for all the right reasons: sun, landscapes, authentic flavors, and a welcoming sense of place that makes every day feel like a celebration of life in Tuscany.