
Vacation rentals in Pian dell'Olmino
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Top-rated vacation rentals in Pian dell'Olmino
Guests agree: these stays are highly rated for location, cleanliness, and more.

Casa al Gianni - The Simignano Barn
Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!
4.97 out of 5 average rating, 198 reviews
Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient family-run property from the 1600s located in the beautiful hills of Chianti in Tuscany, with the possibility of arranging a private shuttle and local experiences directly with our family. The apartment is available for 2 adults with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with incomparable sunsets.
5.0 out of 5 average rating, 352 reviews
Casa Lida [Garden+Parking]
Welcome to Casa Lida, your peaceful retreat in the heart of Tuscany. Independent two-story apartment on Via Francigena, in Colle di Val d'Elsa: a base for discovering Siena, San Gimignano, Monteriggioni, Volterra, and the Chianti vineyards. Two bedrooms and two bathrooms, equipped kitchen, fireplace, and heating. Outside, there is a large private garden with a terrace for outdoor breakfasts and dinners, and parking. Fast Wi-Fi. Ideal for couples, families, and those seeking peace and authenticity.
5.0 out of 5 average rating, 84 reviews
Villa dei 2 Ulivi (Abbadia Isola)
FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) A.k.A FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn (ABB)
4.97 out of 5 average rating, 174 reviews
La Casina di Piano Colle di Val d'Elsa
In the heart of Tuscany between Siena, Florence, San Gimignano, you will find a welcoming place where you can rest, and share your itinerary with owners who, like you, love to travel. You will have an equipped kitchen with a living room, 2 bedrooms for a total of 4 beds, with the possibility of reaching 5. Bathroom with hairdryer, wifi, air conditioning, garden, luggage and bike storage, free parking. A few meters away are all the useful services, pharmacy, laundromat, refreshments.
4.94 out of 5 average rating, 106 reviews
Siena, House in the heart of Tuscany
Holiday home in the medieval village of Colle di Val d'Elsa, at 115 Via Gracco del Secco in Tuscan style on 2 floors, 3 bedrooms, 3 bathrooms, fireplace and wood-burning oven. Voucher from 5 euros per person per day for breakfast at Mario Barone bakery. Recently renovated and furnished with care and value. Wifi and air conditioning. Next to the Spa Hotel San Lorenzo. Ample nearby public parking. At 15 minutes from San Gimignano, 20 fm Volterra, 40 fm Florence, 25 fm Siena.
4.96 out of 5 average rating, 23 reviews
The Bottom
A newly built apartment with a private entrance and a small outdoor garden, located in a residential complex of only four apartments in the heart of Via Francigena, a short distance from the SentierElsa River Park and the Caldane. It is located 24 km from Siena, 45 km from Florence, 10 km from Monteriggioni, and 15 km from San Gimignano. Ideal as a base for those who want to visit Tuscany's most iconic places and are looking for a dynamic and convenient vacation.
4.96 out of 5 average rating, 28 reviews
CANONICA 43 Luxury villa in the heart of Tuscany
CANONICA 43 Spacious and modern apartment, immersed in the Tuscan countryside. In an unspoiled nature, you will spend a vacation in an atmosphere of peace and relaxation. It is an excellent starting point for visiting small villages, famous cities of art, for walks in the woods or for beautiful bike rides pedaling through the rolling hills that surround it. You can taste Tuscan dishes in the typical restaurants of the area or organize a barbecue in the garden
5.0 out of 5 average rating, 80 reviews
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.
4.98 out of 5 average rating, 107 reviews
Florence & Siena • Terrace • Private Parking • A/C
Imagine waking up to sunlight filling the apartment and enjoying breakfast overlooking the Tuscan hills. Bright top-floor apartment with elevator, panoramic terrace and 180° open views, between Florence and Siena, in a quiet private area with no through traffic. Perfect for families, with parking, air conditioning, fast Wi-Fi, fully equipped kitchen and all the comforts to explore Tuscany’s villages, wineries, art cities and iconic landscapes.
5.0 out of 5 average rating, 31 reviews
Tenuta Uzielli an elegant countryside villa
Located amidst olive groves and vineyards, just 7.5 km away from the enchanting thirteenth-century village of Monteriggioni, Villa Tenuta Uzielli, initially built in 1843, has recently undergone renovation. Tenuta Uzielli is the perfect place to relax and explore the Chianti region for a family and friends vacation. Monteriggioni, Siena, San Gimignano, Montalcino, and Florence are all easily accessible destinations by car.
5.0 out of 5 average rating, 20 reviews
Villa with pool in Chianti Area
Amazing Entire Tuscan apartment in an indipendet part of our family Villa in the Chianti! Panoramic 360° view, independent entrance, parking, private garden with BBQ, big SWIMMING POOL, 4 Bedrooms, large living area with big tuscan fireplace, equipped kitchen and laundry. High speed WIFI. Between Siena and Florence in a strategic position close to the main Chianti roads and many characteristic villages!!
4.95 out of 5 average rating, 73 reviewsPopular amenities for Pian dell'Olmino vacation rentals
Other great vacation rentals in Pian dell'Olmino

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5.0 out of 5 average rating, 21 reviews
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Il Fienile del Borgo – Monteriggioni
4.96 out of 5 average rating, 26 reviews
Private House for 4P – La Capanna Di Azzurra
4.96 out of 5 average rating, 26 reviewsDestinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Stazione Santa Maria Novella
- Cala Violina
- Mugello Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Fortezza da Basso
- Gulf of Baratti
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden





