
Vacation rentals in Villa
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Top-rated vacation rentals in Villa
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Florence Sunset Hills • Giogoli
Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

Charming Tuscan Villa with View forFamily&Friends
Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visits & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

Palazzo Monaci - Piscina nelle crete Senesi
Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

Villa di Geggiano - Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Tuscan cottage with an heavenly view
Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni è un antica e storica proprietà risalente al 1600 situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare servizio navetta e esperienze esclusive su misura per voi . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello colline e vigneti con tramonti unici.

colonica da sogno nel chianti, giardino panoramico
“DIMORA BADIA A PASSIGNANO” Vivrete una vacanza rilassante e ristorativa nel cuore del chianti classico. soggiornerete in un antico fienile totalmente restaurato in pietra con grande giardino recintato e un antico gazebo, adatto a gruppi numerosi e famiglie. le camere sono comode e spaziose per 8 persone. la ristrutturazione è stata eseguita finemente, tenendo conto di ogni minimo particolare estetico per poter farvi respirare l’antica tradizione toscana mixata con la comoda modernità.

Casa al Gianni - Il Fienile di Simignano
Trasformato da un antico fienile, questo rifugio lussuoso offre 5 camere, 4 bagni, grande cucina attrezzata, ampio living, un ampio giardino privato con parcheggio, hot tub, patio con divani, BBQ, fire pit e cucina esterna. Ideale per chi cerca un'esperienza unica, unisce fascino rustico a comfort moderni. Perfetto per famiglie o gruppi, promette serate magiche sotto le stelle, tra relax nell'hot tub e cene all'aperto. Una fuga memorabile vi aspetta in questo angolo di paradiso!

Private Chianti Cottage, Garden & Vineyard Views
Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

La Loggia
Immerse yourself in the authentic Tuscan dream. "La Loggia" is a charming home in the heart of Chianti Classico, just 300 meters on foot from the historic center of Radda. It offers the perfect blend of countryside quietness and village convenience, featuring a large private garden with breathtaking panoramic views over vineyards and a beautiful glass-enclosed loggia. The perfect oasis to relax and enjoy the sunset after exploring Siena, Florence, and nearby wineries.

Il Castello di Ferrano - Castle in Tuscany
Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.
Popular amenities for Villa vacation rentals
Other great vacation rentals in Villa

Luxury Medieval Tower • Exclusive Chianti Stay

Casa San Ripa: Relax Oasis with Private Pool

Happy Stay in a Tuscany Escape in a Country Home

Apartment Comfort | Quiet Escape in Tuscany

Villa le Scope 5*

Poggiolo

Luxury Penthouse overlooking Piazza del Campo

Cipressini 2 - piscina e vista mozzafiato
Frequently Asked Questions
What are the best places to stay in Villa?
Stay in central town apartments for easy access to cafes and shops, or choose countryside villas and farmhouses for a peaceful retreat amid nature. Many accommodations blend traditional style with modern comforts.
What are the best things to do in Villa with kids?
Families can explore outdoor parks, join farm visits, or participate in simple cooking classes designed for younger guests. Many find joy in gelato stops, open-air picnics, and gentle countryside strolls.
What are some of the best things to do in Villa?
Explore local wineries, join culinary workshops, or wander through historic town centers with narrow streets and artisan shops. Seasonal festivals and market days provide a glimpse into Villa’s traditions.
How is the weather in Villa?
Villa experiences mild winters with temperatures around 33–49°F (0–9°C), and warm, dry summers reaching 89°F (31°C). Spring and autumn bring comfortable temperatures and a mix of sunshine and refreshing rain, making them appealing for outdoor activities.
When is the best time to visit Villa?
Spring and early autumn in Villa are often recommended for comfortable temperatures and vibrant landscapes. Summer draws visitors for outdoor events, while winter has a quieter pace and festive village atmospheres.
What are the best places to visit in Villa?
Explore Villa’s historic piazzas, step into small museums, or relax in peaceful public gardens. Nearby churches and artisan studios also capture the local character.
What are some hiking trails in Villa?
Villa has scenic hiking options through rolling hills, vineyards, and woodland paths. Explore routes that pass olive groves and quiet villages, or venture onto parts of the surrounding countryside’s networks for panoramic views and gentle terrain.
What are some family activities we can do in Villa?
Enjoy outdoor picnics, visit small farms for animal encounters, or join hands-on cooking workshops geared toward families. Wandering local markets and exploring historical squares also provide activities for all ages.
What are some of the best day trip ideas from Villa?
From Villa, travelers often explore medieval towns, historic estates, and hillside vineyards. Art cities, thermal baths, and regional markets around Tuscany provide a rich mix of nature, history, and culinary discovery.
Are there any pet friendly accommodations available in Villa?
Villa has accommodations where pets are welcome, including countryside stays and some central apartments. Many hosts provide details about garden access or nearby walking paths, which can make travel with pets more comfortable.
What are some local tips for visiting Villa?
Locals suggest visiting traditional markets for regional produce and handcrafted goods. Wearing comfortable shoes helps on cobblestone streets, and learning a few Italian phrases is appreciated by residents.
What is Villa known for?
Villa is known for its Tuscan landscapes, locally rooted cuisine, and cultural heritage. The area has vineyards, Renaissance-era architecture, and traditional festivals that highlight community traditions.
What are the best hidden gems to explore in Villa?
Seek out family-run wineries, lesser-known chapels, and tranquil gardens tucked away in quiet corners of Villa. Local artisan workshops and hillside picnic spots reveal a quieter side of the area.
What are the best foods to try in Villa?
Villa’s cuisine is rooted in Tuscan flavors—try dishes like ribollita soup, handmade pici pasta, and locally produced cheeses. Olive oil, truffle specialties, and traditional desserts such as cantucci with vin santo are frequently suggested.
What should I bring for a trip to Villa?
Pack comfortable walking shoes, layers for changing weather, and a hat for sun protection in summer. A reusable water bottle and a camera help capture and enjoy the experience.
What is the nightlife in Villa like?
Villa’s nightlife centers around local wine bars, relaxed trattorias, and occasional live music in town squares. In summer, open-air gatherings and cultural performances become part of the evening scene.
What are the most popular events or festivals in Villa?
Villa frequently hosts traditional food festivals, grape harvest celebrations in early autumn, and local fairs featuring arts and crafts. Guests also gather for music performances and community events during the summer months.
Are there family friendly vacation rentals in Villa?
Villa has family-friendly rentals, including countryside villas, farmhouses, and spacious apartments. Some properties feature gardens or pools and amenities suited for guests of all ages.
Destinations to explore
- Cathedral of Santa Maria del Fiore
- Lake Trasimeno
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Mugello Circuit
- Mercato Centrale
- Stazione Santa Maria Novella
- Uffizi Gallery
- Fortezza da Basso
- Spiagge Bianche
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Del Chianti
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Piazza della Signoria
- Medici Chapel
- Basilica of Santa Croce
- Stadio Artemio Franchi





