
Montespertoli Rentals

- From $1277 per night (USD)
VRBO
Villa Certaldo Summar
- Bedrooms:
- 10
- Bathrooms:
- 9
- Sleeps:
- 18
Summary: Villa Certaldo is a great villa for large groups of family or friends. It can sleep up to 18 guests in total in ...
From $1277 per night (USD)VRBO
- From $1250 per night (USD)
VRBO
FABULOUS 9BR-8.5BA VILLA W PRIVATE HEATED POOL, IN PRIME LOCATION NEAR FLORENCE!
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 18
*** For weddings, please see the conditions at the bottom of this page *** * Please Note * The property can comfortably ...
From $1250 per night (USD)VRBO
- From $1563 per night (USD)
VRBO
Villa Luce in Tuscany by Fantasia Villas
- Bedrooms:
- 10
- Bathrooms:
- 9
- Sleeps:
- 18
Villa Luce is the perfect place for holidays in Tuscany for groups. The villa with swimming pool near Florence has 9 do ...
From $1563 per night (USD)VRBO
- From $160 per night (USD)
Expedia
Holiday apartment Empoli for 1 - 4 persons with 2 bedrooms - Farmhouse
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Farm stay in Empoli Refrigerators and microwaves are provided. Bathrooms include showers.
From $160 per night (USD)Expedia
- From $126 per night (USD)
VRBO
holiday home in San Casciano
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
Experience authentic Tuscan atmosphere in San Casciano in Val di Pesa, where this 1-bedroom holiday home is located. The ...
From $126 per night (USD)VRBO
- From $1128 per night (USD)
Expedia
[VILLA SAN JACOPO ⭐⭐⭐⭐⭐] Pool | Vineyards | Olive trees
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 17
An enchanting medieval parish church dating back to the year 1000, surrounded by the marvelous Chianti hills. Once the ...
From $1128 per night (USD)Expedia
- From $211 per night (USD)
VRBO
Casa Cassiodoro F: A graceful apartment surrounded by vineyards and olive groves, with Free WI-FI.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Casa Cassiodoro F is a graceful apartment surrounded by vineyards and olive groves. It sleeps four people. It is approxi ...
From $211 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Beautiful home in Montelupo Fiorentino
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to this beautiful property with countryside views. The beautiful vacation home awaits you in Montelupo Fioren ...
From $175 per night (USD)Expedia
- From $217 per night (USD)
VRBO
Casa Cassiodoro A: A characteristic age-old farm house surrounded by vineyards and olive groves, with Free WI-FI.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Casa Cassiodoro A is a characteristic age-old farm house surrounded by vineyards and olive groves. It sleeps six people. ...
From $217 per night (USD)VRBO
- From $1356 per night (USD)
Expedia
Villa La Fiana - Five Bedroom Villa, Sleeps 10
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Villa La Fiana is a restored ancient farmhouse deep within the countryside between Florence and Siena. Sitting within a ...
From $1356 per night (USD)Expedia
- From $491 per night (USD)
VRBO
San Martino, Certaldo, Florence and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
Retreat to this quiet spot high in the vine-covered hills south-west of Florence. It’s a peaceful place yet also a gatew ...
From $491 per night (USD)VRBO
- From $165 per night (USD)
Expedia
Country House \/ Farm House in Castelfiorentino with 3 bedrooms sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Agriturismo Cabbiavoli located in Castelfiorentino consists of two farmhouses and two barns, divided in turn into apar ...
From $165 per night (USD)Expedia
- From $181 per night (USD)
VRBO
Cosy apartment in villa with WIFI, pool, panoramic view and parking, close to San Gimignano
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Agriturismo Vallone a Cabbiavoli is located 5 km (3 mi) from Castelfiorentino, Italy and only 25 km (15 mi) from San Gim ...
From $181 per night (USD)VRBO
- From $422 per night (USD)
Expedia
Tognazzi Casa Vacanze - Panoramic Villa - Villa with private pool and hot tube
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Panoramic Villa is located in Certaldo, in the heart of Tuscany, a few kilometers from the major tourist attractions of ...
From $422 per night (USD)Expedia
- From $1035 per night (USD)
VRBO
Unique views Tuscan countryside!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 11
Villa del Colle, strategically oriented at the top of one of the most perfectly situated Florentine Chianti hills, offer ...
From $1035 per night (USD)VRBO
- From $1010 per night (USD)
Expedia
Villa Alma - Homelike Villas
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 11
Villa Alma, strategically positioned on the top of one of the perfectly situated Chianti hills, offers our guests breath ...
From $1010 per night (USD)Expedia
- From $505 per night (USD)
VRBO
Villa Mea - Homelike Villas
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Villa Mea enjoys a 360° panorama from a green and tranquil hill, opening directly to spectacular views of the stunning T ...
From $505 per night (USD)VRBO
- From $1253 per night (USD)
Expedia
Amazing florentine Villa Casale with 2 private pool and chiledren playgarden strategically ori...
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 17
Originally built in the year 1000AD, our villa has undergone a lengthy and meticulously conceived restoration. Today, as ...
From $1253 per night (USD)Expedia
- From $186 per night (USD)
VRBO
Belvilla by OYO Focolare
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 7
Reside amid utter comfort in this rustic farmhouse in the Italian Castelfiorentino for a wonderful holiday with the fami ...
From $186 per night (USD)VRBO
- From $143 per night (USD)
Expedia
Belvilla by OYO Cipressi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Submit yourself to the true beauty of nature in this rural apartment in the Italian Castelfiorentino and enjoy a wonderf ...
From $143 per night (USD)Expedia
- From $94 per night (USD)
VRBO
Belvilla by OYO Fontana
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Reside comfortably in this rural apartment in the Italian Castelfiorentino for a wonderful holiday with the family. Ther ...
From $94 per night (USD)VRBO
- From $544 per night (USD)
Expedia
Tenuta Cambiano - Colombaie ,Tuscany
- Bedrooms:
- 6
- Bathrooms:
- 9
- Sleeps:
- 17
Beautiful property with swimming pool and tennis court located roughly 40km from Florence. The property is a part of a ...
From $544 per night (USD)Expedia
- From $589 per night (USD)
VRBO
Private Villa with A\/C, WIFI, private pool, TV, patio, panoramic view, close to San Gimignano
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Large stone villa in the Tuscan countryside in Lucardo, on the edge of Chianti. Furnished in characteristic rustic count ...
From $589 per night (USD)VRBO
- From $1480 per night (USD)
Expedia
Villa in Castelfiorentino with 6 bedrooms sleeps 12
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
HARMONIC EMOTION In a casket of purity at the foot of historic Florence, stands an extraordinary residence: Villa del Du ...
From $1480 per night (USD)Expedia
- From $601 per night (USD)
VRBO
Betony Cottage - Tuscan cottage with private pool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
BETONY COTTAGE - FLORENCE AREA Located in the countryside of Montelupo Fiorentino, town famous for its pottery, Betony ...
From $601 per night (USD)VRBO
- From $1192 per night (USD)
Expedia
Villa Luisa - Farmhouse with private pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
VILLA LUISA - FLORENCE AREA Villa Luisa is a wonderfully renovated farmhouse with an 11th Century tower as central stru ...
From $1192 per night (USD)Expedia
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VRBO
Vrbo Property
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
<p>This vacation home lets you experience it all. </p><p>While you're here, you can enjoy all the comforts of home and m ...
Click For PricingVRBO
- Click For Pricing
Expedia
Chalet for romantic getaways in the heart of Tuscany and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
<p>Located in Empoli, this welcoming vacation home brings it all within your reach. With convenient onsite parking, you' ...
Click For PricingExpedia
- From $135 per night (USD)
VRBO
Maramaldo Tignatello,Shared Pool, Chianti, Castelfiorentino, Italy
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A beautiful, 1st floor apartment, overlooking the swimming pool and gorgeous Tuscan countryside. It is one of 7 properti ...
From $135 per night (USD)VRBO
- From $100 per night (USD)
Expedia
Maramaldo Morellino, Shared Pool, Chianti, Castelfiorentino, Italy
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
A unique, ground-floor apartment which sleeps 3 people. The apartment is one of 7 on a beautiful agriturismo, which is a ...
From $100 per night (USD)Expedia
- From $134 per night (USD)
VRBO
Maramaldo Sangiovese Shared Pool, Chianti, Castelfiorentino, Italy
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
On the 1st floor of a beautifully renovated farmhouse, this apartment overlooks the magnificent Tuscan countryside. On a ...
From $134 per night (USD)VRBO
- From $105 per night (USD)
Expedia
Maramaldo Galestro, Shared Pool, Chianti, Castelfiorentino, Italy
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
A little piece of heaven in Tuscany! Climb up your private brick staircase to reach the front door of this charming apar ...
From $105 per night (USD)Expedia
- From $121 per night (USD)
VRBO
Maramaldo Brunello, Shared Pool, Chianti, Castelfiorentino, Italy
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
This idyllic, semi-detached cottage for 3 people, surrounded by vineyards and olive groves, offers a peaceful retreat at ...
From $121 per night (USD)VRBO
- From $110 per night (USD)
Expedia
Maramaldo GalloNero, Shared Pool, Chianti, Castelfiorentino, Italy
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
A charming rural retreat for 3 people, this pretty semi-detached cottage is one of 7 apartments on an idyllic agriturism ...
From $110 per night (USD)Expedia
- From $140 per night (USD)
VRBO
Maramaldo Sassicaia, Shared Pool, Chianti, Castelfiorentino, Italy
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
A sun-filled, ground-floor apartment, which retains some of its original features, including beautiful terracotta floors ...
From $140 per night (USD)VRBO
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Expedia
Maggiano - Lucardo ,Tuscany
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Large stone villa in the Tuscan countryside in Lucardo, on the edge of Chianti. Furnished in characteristic rustic count ...
Click For PricingExpedia
- From $324 per night (USD)
VRBO
Stunning private villa with WIFI, private pool, A\/C, TV, patio, panoramic view and parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Independent cottage in a renovated old hayloft with a private pool, located in the Tuscan hills near Montelupo Fiorentin ...
From $324 per night (USD)VRBO
- From $1315 per night (USD)
Expedia
Villa Sun & Sun 2 Pools by BelcantoVillas
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 17
In one of the most beautiful panoramic hills near Florence, there is this pleasant and large holiday structure made up o ...
From $1315 per night (USD)Expedia
- From $906 per night (USD)
VRBO
Villa in Montelupo Fiorentino with 6 bedrooms sleeps 11
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 11
On top of one of the most perfectly situated Florentine Chianti hills, the villa offers stunning views of the Tuscan val ...
From $906 per night (USD)VRBO
- From $454 per night (USD)
Expedia
Villa Sunflower - By Belcantovillas
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
In the Montelupo Fiorentino countryside only 30 minutes from Florence you come across this charming Tuscan villa rental: ...
From $454 per night (USD)Expedia
- From $158 per night (USD)
VRBO
L' Ulivo by Interhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
House "L'Ulivo". 3 km from the centre of Castelfiorentino, 11 km from the centre of San Miniato, 40 km from the centre o ...
From $158 per night (USD)VRBO
- Click For Pricing
Expedia
beautiful cottage surrounded by nature
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This cottage is a beautiful cottage surrounded by nature located on the top of one of the most beautiful hills of the Fl ...
Click For PricingExpedia
- From $740 per night (USD)
VRBO
[VILLA CHIANTI FLORENCE ⭐⭐⭐⭐⭐] Vineyards | Olive Trees
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 16
Forget all your worries in this expansive oasis of serenity—a typical Tuscan farmhouse, a timeless place surrounded by c ...
From $740 per night (USD)VRBO
- From $1351 per night (USD)
Expedia
The Hill Below - Imagine a place just for you
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 17
<p>Close to cycling, fishing, and more, this pet-friendly villa brings it all within reach. Jump into your car and make ...
From $1351 per night (USD)Expedia
- From $526 per night (USD)
VRBO
Luxury, Sustainability and Eco Pool in Style Apt.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Medieval Origin and Modern Sustainability. Complete renovation according to Bio-Building rules. Period furniture, origin ...
From $526 per night (USD)VRBO
- From $717 per night (USD)
Expedia
Luxury, Sustainability and Eco Pool in Frangi Apt.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Medieval Origin and Modern Sustainability. Complete renovation according to Bio-Building rules. Period furniture, origin ...
From $717 per night (USD)Expedia
- From $379 per night (USD)
VRBO
Home with pool and views in Chianti near Florence
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
<p>Located in Barberino Tavarnelle, this welcoming apartment brings it all within your reach. With convenient onsite par ...
From $379 per night (USD)VRBO
- From $269 per night (USD)
VRBO
CasAle Martignana 💜
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
CasAle is immersed in the green Tuscan countryside. It is part of a farm inside a family estate and was the nest where w ...
From $269 per night (USD)VRBO
- From $230 per night (USD)
VRBO
Casa Cassiodoro L: A graceful apartment surrounded by the greenery, with Free WI-FI.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Casa Cassiodoro L is a graceful apartment surrounded by the greenery. It sleeps six people. It is approximately 90 squar ...
From $230 per night (USD)VRBO
- From $144 per night (USD)
VRBO
Apartment\/ flat - Tavarnelle val di pesa
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
(Text automatically translated) Ideally located, very quiet, in the heart of Chianti, near Florence, Siena, San Gimignan ...
From $144 per night (USD)VRBO
- From $159 per night (USD)
VRBO
Holiday apartment Empoli for 2 - 5 persons with 2 bedrooms - Farmhouse
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
ED Refnr. 2773076 The “Martignana Alta” agritourism is located in the Matrignana estate. With its 30 hectares of land a ...
From $159 per night (USD)VRBO
- From $68 per night (USD)
VRBO
Whole house FARMHOUSE and single rooms, garden, whirlpool, pizza grill ovens
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
For Family, Couple and Group (until 15 persons) large house, country style, large dining room, fireplace in a large livi ...
From $68 per night (USD)VRBO
- From $1448 per night (USD)
VRBO
Holiday house Montelupo Fiorentino for 1 - 16 persons with 8 bedrooms - Holiday house
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 16
ED Refnr. 3048161 In the heart of Tuscany, a luxury property where you can live the summer all year long…Originally bui ...
From $1448 per night (USD)VRBO