Reggello, part of the Metropolitan City of Florence in Tuscany, Italy, is the kind of place where every day feels like a mini-holiday. Picture rolling hills, olive groves, and sun-kissed vineyards stretching toward the horizon, with charming stone villages tucked along winding lanes. This is the region where vacation rentals and holiday rentals become more than just a place to sleep—they’re your launchpad for friendship-filled adventures, lazy picnics, and spontaneous night markets. If you’re hunting for pet friendly rentals and want to travel with your four-legged pal, Reggello and its surroundings are especially welcoming. Use searchandstay.com to discover a curated selection of accommodations in the area that combine comfort, style, and that Tuscan vibe you crave.
Whether you’re planning a weekend with friends or a longer Tuscan break, Reggello offers a versatile base. It’s close enough to Florence for day trips but far enough away to feel like a countryside escape. The landscape invites outdoor activities, slow breakfasts on the terrace, and sunset views over cypress-lined horizons. The town spares you the crowds of the big tourist hubs while still offering excellent food, wine, and authentic Tuscan experiences. For pet lovers, there are plenty of pet friendly rentals that provide flexible layouts, private outdoor spaces, and easy access to trails and parks where dogs are welcome. If you’re searching for accommodations in the area, searchandstay.com is a user-friendly platform that highlights pet friendly options and makes it simple to compare villas, farmhouses, apartments, and agriturismi tailored to groups of friends seeking a mix of adventure and relaxation.
Where to stay in Reggello and nearby villages
Reggello itself is scattered with rustic farmhouses (casali), country villas, and compact but stylish apartments that suit different travel styles. Look for terms like casale, agriturismo, or villa to capture the classic Tuscan vibe. The Leccio area, just a short drive from the The Mall Firenze shopping outlet, offers convenient access to shopping without sacrificing countryside charm. Pet friendly rentals in this zone often come with enclosed gardens, private patios, or fenced yards—perfect for travelers who want to bring their four-legged companions along for adventures through olive groves or along quiet country lanes.
Nearby villages such as Vallombrosa, with its pine-clad hills and historic abbey, add a layer of natural beauty to your stay. Vallombrosa is known for forest trails that suit both easy ambles and longer hikes, making it ideal for active travelers who want to pair mornings on the trail with afternoon wine tastings. When you search for accommodations on searchandstay.com, you’ll find listings that emphasize proximity to Vallombrosa and other scenic routes, so you don’t have to compromise on either comfort or scenery.
Another great option is to base your group in a larger villa or farmhouse that accommodates friends, with multiple bedrooms, private pools, and communal spaces where meals and laughter can flow. Look for features like open-plan kitchens, outdoor al fresco dining areas, and pet friendly arrangements. In Tuscany, a well-chosen vacation rental is more than a place to sleep—it’s where you’ll gather after a day of exploring markets, hiking, or wine tasting, and where you’ll create those shared memories that make holidays with friends so special.
Pet friendly rentals and tips for traveling with dogs or cats
Pet friendly rentals are increasingly common in Reggello and the surrounding countryside. The key is to find a property that suits your pet’s energy level and your plans. Many villas and casali offer fenced yards, private terraces, and direct access to green spaces, making it easy to start the day with a dog walk and end it with a sunset stroll. When you’re searching for accommodations on searchandstay.com, filter for pet friendly options and check for practical details such as fenced gardens, tiled or easy-to-clean floors, and proximity to walking trails.
Before you book, consider these pet-friendly features:
- Fenced or walled outdoor space for dogs to roam safely.
- Nearby parks or nature trails suitable for pets and owners alike.
- Ground-floor or accessible entry to minimize stairs with crates or carriers.
- Local veterinary clinics or emergency numbers in case of travel hiccups.
- Pet-friendly amenities at the property, such as bowls, beds, or security for small pets.
In Tuscany, many hosts welcome pets with open arms, but it’s wise to confirm house rules, leash requirements in shared spaces, and any pet-related fees before confirming your stay. A good strategy is to plan early, especially in peak season, to secure a property that combines the right layout, privacy, and pet-friendly perks. With searchandstay.com, you can compare listings side by side, read reviews from fellow guests, and find a pet friendly rental that aligns with your vacation goals.
Activities and local experiences you’ll love
Reggello is a playground for active travelers who love to mix outdoor adventures with delicious food and relaxed social moments. Here are some top experiences to consider during your stay, whether you’re traveling with friends, a partner, or a furry companion:
Outdoor adventures and nature escapes
The countryside around Reggello is peppered with scenic trails, olive groves, and country lanes just begging to be explored on foot, by bike, or on a relaxed drive. Vallombrosa forest, with its shaded paths and evergreen air, is a favorite for morning hikes or sunset strolls. If you enjoy longer hikes, you can plan a day that threads through forested hills, offering panoramic views of the Arno valley and Florence’s iconic skyline in the distance. For a more leisurely pace, plan a picnic on a hillside and let the group savor fresh bread, local cheese, and a bottle of Tuscan red while watching the light change over the vineyards.
Water lovers aren’t left out—there are gentle rivers and streams in the surrounding countryside where you can dip your toes or watch the kids build island-shaped sandcastles while the adults unwind with a cool drink. If you’re traveling with a dog, these open-air moments are ideal for a group stroll, a fetch session, and post-walk dog-friendly snacks. Remember to bring water, a collapsible bowl, and bags for waste, and check that the trail you choose is suitable for your pet’s energy level and age.
Wine, olive oil, and farm-to-table experiences
Tuscany’s heart beats in its kitchens and cellars, and Reggello makes it easy to savor the best of both worlds. The region around Reggello offers hillside wineries and olive oil producers where you can tour vineyards and mills, sample a flight of local wines, and discover the notes of Sangiovese, Canaiolo, and Cabernet blends that pair beautifully with Tuscan dishes. Many small producers welcome visitors for guided tastings, often paired with bruschetta, pecorino cheese, and house-made bread. If you’re staying in a villa, you could even arrange a private chef for a Tuscan dinner featuring local ingredients from farm to table, a perfect centerpiece for a night of friends and laughter.
The area is also known for olive oil tastings, where you’ll learn about the cold-press process, the differences between extra virgin olive oils, and the ways local producers infuse olives with herbs for unique flavors. A culinary-focused day can be a highlight of your trip, especially when you pair it with a shopping stint at markets in nearby towns or a stop at a local bakery for sweet treats after a long day of exploration.
Markets, culture, and day trips to Florence and Chianti
Many visitors use Reggello as a gateway to Florence and the wider Chianti region. A day trip to Florence is a must for art lovers—the city’s treasure-filled galleries, architectural masterpieces, and lively street life create a perfect balance to the quiet countryside. From Reggello, you can drive or catch a convenient train or bus to Florence’s historic center, where you can stroll the Arno River embankment, explore the Duomo and Uffizi, and then return to the tranquility of your Tuscan base.
Chianti, with its rolling vineyards and medieval villages, is ideal for scenic drives, motorbike routes, or guided wine tours. Towns like Greve in Chianti, Panzano, and Castellina offer beautiful viewpoints, wine tastings, and a taste of rural Tuscan life. If you’re up for a day of exploration with friends, plan a route that lets you stop at a couple of wineries, enjoy a long lunch outdoors, and finish with a sunset aperitivo in a hilltop town.
Local experiences and seasonal activities
Throughout the year, Reggello hosts markets, festivals, and seasonal events that celebrate local produce, crafts, and traditions. Look for weekly markets offering fresh fruits, vegetables, cheeses, and baked goods, as well as seasonal festivals featuring food stalls, live music, and street performances. Participating in these events is a wonderful way to connect with locals, taste authentic flavors, and create memories with friends that go beyond the usual tourist checklist.
For those who love a bit of culture with their fun, you’ll find small concerts, theatrical performances, and organized walking tours in the surrounding villages. Some hosts may even arrange private guided tours focusing on the history of the area, or culinary tours that explore the evolution of Tuscan cuisine—from rustic peasant dishes to refined traditional plates.
Sample itinerary: four days of friends, food, and exploration
Day 1: Arrival and settling in. Choose a pet friendly villa or casale in or around Leccio, settle into the outdoor space, and plan a relaxed dinner on the terrace. If you’re up for a stroll, take a gentle evening walk to a nearby village, then enjoy a welcome meal featuring local bread, cheese, and a glass of Chianti Classico. Day 2: Vallombrosa forest hike and a winery visit. Start with a morning walk through Forest of Vallombrosa, then head to a nearby winery for a guided tasting and a light lunch. Return to your rental for a sunset aperitif and a home-cooked meal or a casual pizza night in the village. Day 3: The Mall Firenze and olive oil tasting in the Leccio area. Spend part of the day shopping at The Mall Firenze or explore local markets, followed by an olive oil tasting and a cooking class back at your accommodation. Day 4: Florence day trip. Spend a full day exploring Florence’s cathedrals, museums, and the Arno river, then return to Reggello for a final Tuscan dinner under the stars.
These are just starting points. Your group can tailor days to include more hiking, more winery experiences, or longer downtime at your rental. The beauty of Reggello lies in its flexibility: you can be active all day or simply unwind with friends while savoring Italian flavors and the serenity of the Tuscan countryside. When you’re ready to book your stay, searchandstay.com helps you find vacation rentals and holiday rentals that align with your travel style, including pet friendly options that welcome furry companions on your adventures.
Practical tips for a smooth trip
Getting there is part of the experience. Reggello is most easily reached by car, which gives you the freedom to explore hillside towns and countryside at your own pace. If you’re flying into Italy, you’ll likely land in Florence or Pisa and then drive or take a private transfer to Reggello. Once you’re settled, local taxis and rideshares can handle shorter trips, but having a car makes day trips and shopping runs much more convenient.
When booking pet friendly rentals, confirm the pet policy with the host, including any size or breed restrictions, pet fees, and whether there are any areas that are off-limits to animals. Check whether the property has leash-friendly outdoor spaces and whether there are nearby trails or parks where your pet can exercise. It’s also wise to bring along essential pet items—food and water bowls, a portable bed, a leash and harness, waste bags, and any medications your pet might need. If your dog is crate-trained, consider ensuring the rental has a safe indoor space where your pet can rest comfortably while you’re out for a day of exploring.
Food safety and dining out while traveling with pets can require a little planning. Many Tuscan restaurants welcome well-behaved dogs outdoors, but it’s best to verify in advance. In more rural areas, daytime meals might happen at agriturismi or family-run trattorie where the ambiance is casual and the doors are open to al fresco dining—an ideal match for a group of friends looking to enjoy long lunches and late, relaxed dinners. When you’re not cooking at your rental, you can enjoy markets and eateries in Reggello and nearby villages where seasonal produce and regional specialties shine.
Why Reggello is the perfect base for vacation and pet friendly holidays
Reggello offers a balanced blend of countryside charm and easy access to some of Tuscany’s most beloved destinations. Its proximity to Florence means you can sprinkle your itinerary with a city break, world-class art, and Renaissance architecture, while the surrounding hills, vineyards, and olive groves deliver the relaxing, restorative atmosphere that makes Tuscany so appealing. For travelers who want to travel with friends and bring a pet along, Reggello is particularly well-suited: there are plenty of pet friendly rentals that reflect the region’s rustic elegance, and the slower pace invites long conversations over wine and plates of antipasti.
Finding the right accommodation is essential for a memorable trip. Platforms like searchandstay.com curate a range of vacation rentals and holiday rentals in Reggello and the surrounding area. The site highlights pet friendly listings, shows availability, and helps you compare options based on your preferred location, travel dates, and budget. By focusing on pet friendly rentals and family-friendly features, you can ensure that everyone in your group—from humans to dogs—feels welcome and comfortable from the moment you arrive.
In the end, Reggello isn’t just a place to stay; it’s a gateway to your next memorable holiday with friends. You’ll wake up to gentle light over olive trees, spend afternoons exploring markets or hiking with your crew, and fall into easy evenings of conversation, good food, and shared laughter. The region’s warmth—culinary warmth, people warmth, and place warmth—stays with you long after you’ve packed your bags. And when you’re ready to plan, remember that searchandstay.com can help you find vacation rentals and holiday rentals that fit your vision—especially the pet friendly options that keep every member of your travel party engaged and included.
Whether you’re chasing scenic viewpoints, a foodie itinerary, or a sunset that looks straight out of a postcard, Reggello delivers. It’s a destination where holiday rentals become experiences: a stone-walled villa with a terrace for al fresco dinners, a casale with a private garden to unwind after a day of adventures, or a modern apartment with a balcony overlooking the valley—each offering a base for memorable times with friends and four-legged companions. For pet friendly travelers and groups of friends seeking a Tuscany escape that blends nature, culture, food, and easy Florence access, Reggello is a destination that delivers on all fronts, and searchandstay.com is your partner for finding the right place to call home during your Tuscan holiday.