Montespertoli, Tuscany Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Montespertoli, Tuscany on RentalSaver.com!

Montespertoli Rentals

Filter

Popular Areas

From $1268 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 $1268 per night (USD)
VRBO
From $1767 per night (USD)
Expedia
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 $1767 per night (USD)
Expedia
From $1322 per night (USD)
VRBO
[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 $1322 per night (USD)
VRBO
From $569 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 $569 per night (USD)
Expedia
Click For Pricing
VRBO
Vrbo Property
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This vacation home lets you experience it all. While you're here, you can enjoy all the comforts of home and m ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Chalet for romantic getaways in the heart of Tuscany and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located in Empoli, this welcoming vacation home brings it all within your reach. With convenient onsite parking, you' ...
Click For Pricing
Expedia
From $145 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 $145 per night (USD)
VRBO
From $103 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 $103 per night (USD)
Expedia
From $136 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 $136 per night (USD)
VRBO
From $121 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 $121 per night (USD)
Expedia
From $133 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 $133 per night (USD)
VRBO
From $117 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 $117 per night (USD)
Expedia
From $159 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 $159 per night (USD)
VRBO
From $566 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 $566 per night (USD)
Expedia
$Private Villa with WIFI, private pool, A\/C, TV, patio, panoramic view, close to San Gimignano$
From $682 per night (USD)
VRBO
Private Villa with WIFI, private pool, A\/C, 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 $682 per night (USD)
VRBO
From $1538 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 $1538 per night (USD)
Expedia
From $669 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 $669 per night (USD)
VRBO
From $1132 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 $1132 per night (USD)
Expedia
From $134 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 $134 per night (USD)
VRBO
From $1189 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 $1189 per night (USD)
Expedia
From $540 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 $540 per night (USD)
VRBO
From $1519 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 $1519 per night (USD)
Expedia
From $1146 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 $1146 per night (USD)
VRBO
From $505 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 $505 per night (USD)
Expedia
From $1529 per night (USD)
VRBO
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 $1529 per night (USD)
VRBO
From $201 per night (USD)
Expedia
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 $201 per night (USD)
Expedia
From $152 per night (USD)
VRBO
Apartment in Chianti with swimming pool
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 $152 per night (USD)
VRBO
Click For Pricing
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 Pricing
Expedia
From $883 per night (USD)
VRBO
[CASALE FORNACE FLORENCE ⭐⭐⭐⭐⭐] Vineyards | Olive Trees | Pool
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 $883 per night (USD)
VRBO
From $1762 per night (USD)
Expedia
The Hill Below - Imagine a place just for you
Bedrooms:
8
Bathrooms:
8
Sleeps:
17
Close to cycling, fishing, and more, this pet-friendly villa brings it all within reach. Jump into your car and make ...
From $1762 per night (USD)
Expedia
Click For Pricing
VRBO
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 Pricing
VRBO
From $574 per night (USD)
Expedia
Beautiful home in Montelupo Fiorentino
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Please note that: Bed linen and towels are included in the room rate in 2025. Consumption costs are not included in ...
From $574 per night (USD)
Expedia
Click For Pricing
VRBO
Villa Majolica - Five Bedroom Villa, Sleeps 11
Bedrooms:
5
Bathrooms:
5
Sleeps:
11
With beautiful valley views, surrounded by vineyards, olive groves and forested hills, Villa Majolica is a gem of a Tusc ...
Click For Pricing
VRBO
From $1332 per night (USD)
Expedia
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 $1332 per night (USD)
Expedia
From $244 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 $244 per night (USD)
VRBO
From $1577 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 $1577 per night (USD)
Expedia
From $510 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 $510 per night (USD)
VRBO
From $189 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 $189 per night (USD)
Expedia
$Country House \/ Farm House in Castelfiorentino with 3 bedrooms sleeps 6$
From $171 per night (USD)
VRBO
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 $171 per night (USD)
VRBO
From $191 per night (USD)
Expedia
Beautiful apartment in villa with pool, WIFI, panoramic view and parking, close to San Gimignano
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Agriturismo Vallone a Cabbiavoli is a lovely holiday home with WiFi internet, air conditioning and pool. The villa / far ...
From $191 per night (USD)
Expedia
From $265 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 $265 per night (USD)
VRBO
From $279 per night (USD)
Expedia
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 $279 per night (USD)
Expedia
$Apartment\/ flat - Tavarnelle val di pesa$
From $207 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 $207 per night (USD)
VRBO
From $168 per night (USD)
Expedia
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 $168 per night (USD)
Expedia
From $71 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 $71 per night (USD)
VRBO
From $681 per night (USD)
Expedia
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 $681 per night (USD)
Expedia
From $745 per night (USD)
VRBO
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 $745 per night (USD)
VRBO
Click For Pricing
Expedia
Luxury, Sustainability and Eco Pool
Bedrooms:
9
Bathrooms:
10
Sleeps:
5
While you're here, you can enjoy all the comforts of home and more, including a dishwasher and free WiFi, as well as ...
Click For Pricing
Expedia
From $514 per night (USD)
VRBO
Home with pool and views in Chianti near Florence
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Located in Barberino Tavarnelle, this welcoming apartment brings it all within your reach. With convenient onsite par ...
From $514 per night (USD)
VRBO
From $1763 per night (USD)
Expedia
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 $1763 per night (USD)
Expedia

Search Your Destination Now!

Montespertoli Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 550 Rentals