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Villa vacation rentals in Monteriggioni

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Top-rated villa rentals in Monteriggioni

Guests agree: these villas are highly rated for location, cleanliness, and more.

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Guest favorite
A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.
Villa in Castellina in Chianti

Villa Padronale - IlVillinoFarmhouse

Intero piano superiore della Villa Padronale appena ristrutturata in stile tradizionale toscano.Gli alti soffitti con le travi a vista rendono il posto accogliente e perfetto per famiglie o gruppi di amici.Nella casa si trovano due grandi camini(in salotto e cucina)funzionali.Alloggio privato, non condiviso. La casa ha una ampia terrazza coperta,giardino con divani,bbq,firepit,parking privato. La piscina tra gli ulivi e i vigneti e' ideale per il relax ha un accesso privato alla zona condivisa

FamilyLocationAccuracy

4.93 out of 5 average rating, 254 reviews
Superhost
The exterior of a charming stone villa is showcased, with a refreshing swimming pool in the foreground. Lush green grass surrounds the pool area, and a shaded gazebo with seating is positioned nearby. Rolling hills and a clear blue sky form a picturesque backdrop.
Villa in Greve in Chianti

Villa La Doccia, Greve in Chianti.

Villa La Doccia si trova a circa 8 minuti di auto dal centro di Greve in Chianti, in Località Casole, nel cuore della splendida campagna del Chianti. La villa è situata in una zona tranquilla e silenziosa, all’interno di una piccola azienda agricola circondata da vigneti e uliveti, dove gli ospiti possono godere della natura e dei tipici paesaggi toscani. La posizione è ideale per chi desidera rilassarsi immerso nella campagna ma allo stesso tempo essere vicino al centro di Greve in Chianti

FamilyValueView

4.85 out of 5 average rating, 179 reviews
Top guest favorite
A charming stone villa is set amidst a lush green lawn. The building features wooden window shutters and a terracotta tile roof. A covered porch, adorned with flower pots, offers a welcoming outdoor space, complemented by a backdrop of blooming plants and trees.
Villa in Barberino Tavarnelle

CasaDiManuela:TotallyPrivateChiantiVilla withTub

CasaDiManuela:TotallyPrivateVilla in Chianti withTub Jacuzzi The villa, immersed in the Chianti countryside, was obtained from an old farmhouse and then renovated with extreme care and attention to detail. Original terracotta floors and ceilings with ancient exposed beams, old traditional Tuscan furniture, flowery fabrics that dress beds and armchairs, paintings, antique china and lived objects recovered from markets and junk dealers will frame your living room. Nothing here is by chance.

FamilyLocationQuiet

4.97 out of 5 average rating, 105 reviews
Guest favorite
Villa in Monteriggioni

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)

FamilyLocationWalkability

4.97 out of 5 average rating, 174 reviews
Top guest favorite
A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.
Villa in Montecatini Val di Cecina

Torre dei Belforti

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

LocationFamilyWalkability

4.99 out of 5 average rating, 137 reviews
Top guest favorite
A heated jacuzzi is situated under a shaded pergola, surrounded by lush greenery and colorful flowers. The serene outdoor space is complemented by a gravel path leading towards vineyards in the background, inviting relaxation and privacy.
Villa in San Casciano In Val di Pesa

Il Vichiaccio: Florence Villa with Jacuzzi

Cozy Chianti Villa near Florence. This 135sqm stone house has a rustic kitchen with a fireplace. It sleeps 9 guests in 3 rooms, but for groups of 11, a 4th bedroom is included. Smaller groups can add it for extra comfort (extra fee). Enjoy the private garden with a covered dining area, a patio with armchairs and parking. The ground floor is fully wheelchair-friendly (kitchen, bedroom, bath). Plus, A/C and a private Jacuzzi (extra fee) for relaxing under the stars!

LocationFamilyLong stay

4.95 out of 5 average rating, 202 reviews
Top guest favorite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle

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.

FamilyValueNearby

4.98 out of 5 average rating, 105 reviews
Top guest favorite
Bright seating area features two white armchairs and a patterned ottoman, surrounded by large glass arches that open to a lush garden. Natural light floods the space, enhancing the exposed stone walls and wooden ceiling beams, complemented by a large potted plant.
Villa in San Casciano in Val di Pesa

Luxury Villa in the very heart of Chianti

The views, the views, oh my word the VIEWS! Originating in the early 12th century this spectacular home once served as the bakery for the entire village. Now fully renovated, the entrance and ground level have been opened with glass arches allowing natural light to illuminate the exposed walls, 4 large bedrooms, 3 with ensuite baths ( including a jacuzzi ). Only Minutes away from the famous Wineries of Chianti, this is THE Spot for a glass amongst friends.

LocationFamilyParking

4.97 out of 5 average rating, 119 reviews
Top guest favorite
An inviting villa surrounded by lush greenery and vibrant flowers, featuring blooming rose bushes and olive trees. The gravel pathway leads to the entrance, showcasing a two-story structure with balconies. Sunlight highlights the colorful landscape, creating a serene atmosphere.
Villa in Impruneta

La Torre

Antica villa toscana, bellissima, con giardino privato esclusivo, completamente ristrutturata, immersa nelle splendide e dolci colline toscane. La villa ha una vista mozziafiato, molto soleggiata, ben arredata e dotata di tutti i comfort, silenziosa e non isolata. La casa si trova a Bagnolo, piccola frazione di Impruneta alle porte del Chianti, zona di uliveti, vigneti e pace. La casa si trova a circa 10 km in macchina dal centro di Firenze.

LocationFamilyAmenities

5.0 out of 5 average rating, 188 reviews
Guest favorite
Villa in Monteroni d'Arbia

"Villa Daisy" con vista su Siena

Meravigliosa villa con ingresso indipendente all'interno del podere "Caggiolo", riportato alla luce con curata e profonda ristrutturazione che ha mantenuto intatti i lineamenti tipici di un podere toscano. Splendida vista panoramica su Siena. Situato alle Ville di Corsano, a soli 14 km dalla città. Luogo ideale per trascorrere giorni in totale relax e godere delle meraviglie che questa zona offre (Chianti, Val d'Orcia, Crete Senesi..).

LocationFamilyTV

4.95 out of 5 average rating, 171 reviews
Guest favorite
Villa in Siena

Villa Capanna, Private Pool, Breathtaking Views

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.

LocationValueBreakfast

4.89 out of 5 average rating, 307 reviews
Top guest favorite
A well-maintained garden surrounds a refreshing pool, bordered by manicured grass. A comfortable seating area, featuring two lounger chairs and a shaded umbrella, provides a serene spot for relaxation. Soft greenery and flowering shrubs form a natural backdrop, enhancing the tranquil atmosphere.
Villa in Tignano

Villa Isabella

Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

LocationFamilyGetting around

4.96 out of 5 average rating, 207 reviews

Popular amenities for Monteriggioni villa rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Private villa rentals

Guest favorite
A charming stone villa stands surrounded by green grass and trees, featuring ivy-covered walls. The exterior is complemented by a pathway made of light-colored stones leading to seating arrangements. Clear blue skies are visible above, enhancing the tranquil outdoor setting.
Villa in Siena

La Villa della Brigata Spendereccia!

LocationFamilyPool

5.0 out of 5 average rating, 27 reviews
Top guest favorite
The exterior of the villa is shown against a clear blue sky, featuring textured walls with traditional diamond-shaped brick patterns. Large windows provide natural light, while a shaded patio with seating and table is visible, surrounded by well-maintained greenery and trees.
Villa in San Gimignano

Fabulous 3Br Villa with 360° Views!

LocationFamilyBathroom

4.95 out of 5 average rating, 75 reviews
Guest favorite
An aerial view showcases the rustic villa surrounded by lush green fields and rolling hills. The exterior features terracotta roofing, a garden area with lounge chairs, and a shaded patio space for outdoor dining, all under a partly cloudy sky.
Villa in Siena

Capanna di Elfo - Capanna Di Elfo

LocationValueHospitality

4.97 out of 5 average rating, 60 reviews
Top guest favorite
An aerial view showcases a charming Tuscan farmhouse surrounded by lush vineyards and tall trees. The property features a private pool and a well-maintained garden, offering a serene landscape typical of the Chianti hills.
Villa in Noce

Villa storica con piscina privata in Toscana

LocationFamilyIndoor spaces

5.0 out of 5 average rating, 35 reviews
Guest favorite
Villa in Badia a Passignano

Guardia di Badia a Passignano

LocationAmenitiesView

4.86 out of 5 average rating, 7 reviews
Superhost
Villa in Lilliano

Country house with pool and garden by Vacavilla

FamilyLocationView

4.84 out of 5 average rating, 25 reviews
Top guest favorite
Villa in Barberino Tavarnelle

Luxury Villa in Chianti • Private Natural Pool

FamilyValueComfort

5.0 out of 5 average rating, 30 reviews
Top guest favorite
A serene outdoor area features a turquoise swimming pool surrounded by chaise lounges. Vibrant pink roses bloom near the edge, while lush greenery provides a natural backdrop. A stone villa with a tiled roof is visible in the distance, highlighting the tranquil setting.
Villa in Gaiole in Chianti

Sestuccia

LocationFamilyNearby

4.99 out of 5 average rating, 74 reviews

Luxury villa rentals

Top guest favorite
An aerial view captures a charming stone villa surrounded by lush greenery and neatly arranged gardens. A spacious swimming pool is visible, complemented by outdoor seating areas and pergolas, all against the backdrop of rolling hills and cloudy blue skies.
Villa in San Gimignano

Tuscan Villa with Pool & Jacuzzi, San Gimignano

FamilyLocationPool

4.98 out of 5 average rating, 90 reviews
Guest favorite
Villa in Gaiole in Chianti

Lucignano Secondo - La Villa

FamilyLocationKitchen

4.91 out of 5 average rating, 33 reviews
Top guest favorite
A private swimming pool is surrounded by a spacious stone patio, featuring comfortable sun loungers and shaded seating areas. Potted plants are placed around the pool, enhancing the tranquil outdoor space that is framed by trees and the rustic charm of the stone house.
Villa in Volterra

Romantic Villa with private pool - "Il Pollaio"

LocationFamilyIndoor spaces

5.0 out of 5 average rating, 47 reviews
Top guest favorite
Bright pink flowers frame a tranquil infinity pool, with rolling green hills visible in the background. The landscape is dotted with tall trees and stretches toward distant mountains under a clear blue sky.
Villa in Barberino Tavarnelle

Valluccia 51

ValueFamilyCheck-in

5.0 out of 5 average rating, 49 reviews
Top guest favorite
The villa is depicted with a stone exterior, surrounded by olive trees and rolling vineyards. A circular pool is featured in the foreground, offering a tranquil spot for relaxation. Umbrellas provide shade over lounge chairs nearby, enhancing the serene outdoor space.
Villa in Radda in Chianti

Villa con piscina nel Chianti - Castellare Petroso

LocationFamilyGrill

5.0 out of 5 average rating, 33 reviews
Guest favorite
Villa in Monteroni d'Arbia

Villa panoramica nelle crete senesi, vista Siena.

LocationFamilyDecor

5.0 out of 5 average rating, 52 reviews
Top guest favorite
An aerial view captures the charming layout of ancient stone houses surrounded by lush greenery and cypress trees. A swimming pool is visible, accompanied by well-maintained gardens featuring various relaxation areas. The surrounding landscape reveals vineyards and rolling hills typical of the Chianti scenery.
Villa in Castellina in Chianti

I CIPRESSINI DEL CASTELLACCIO (Cip 1 + Cip 2)

LocationFamilyAmenities

5.0 out of 5 average rating, 16 reviews
Top guest favorite
An arch adorned with blooming wisteria frames a lush garden, featuring greenery and vibrant flowers. A terracotta pot sits nearby, while a picturesque tower rises in the background, adding a historic charm to the tranquil outdoor setting.
Villa in Florence

Villa Holm stunning view 10 mn walk to city centre

LocationFamilyHospitality

5.0 out of 5 average rating, 53 reviews

Villa rentals with a pool

Top guest favorite
A private swimming pool is surrounded by vibrant flowers and lush greenery. Multiple lounge chairs are positioned under umbrellas for shade. A seating area is visible in the background, along with a well-maintained pathway and rustic stone walls, enhancing the serene outdoor setting.
Villa in Poggibonsi

Villa L'Olivo w/Private pool (Close San Gimignano)

FamilyLocationLaundry

4.99 out of 5 average rating, 98 reviews
Guest favorite
The crystal-clear swimming pool reflects the blue sky, bordered by a well-kept garden. In the background, a stone farmhouse features green shutters and a classic tiled roof. The pool area is complemented by shaded seating, offering a serene and private atmosphere.
Villa in Gaiole in Chianti

Podere il Trebbio

ValueLocationShared spaces

4.92 out of 5 average rating, 88 reviews
Top guest favorite
A spacious patio area is surrounded by vibrant purple flowers and greenery, creating a serene outdoor environment. The rustic stone house features large glass doors, complemented by a shaded umbrella and seating area. A grassy lawn adds to the charm of this inviting setting.
Villa in Radicondoli

Casa di Leo Romantic House

FamilyLocationWifi

5.0 out of 5 average rating, 65 reviews
Superhost
A serene swimming pool is surrounded by lush greenery and rustic buildings. Several guests enjoy the cool water, while sun loungers offer a comfortable place to relax. Tall trees provide natural shade, enhancing the peaceful outdoor setting.
Villa in Greve in Chianti

Put down your luggage, this is just the beggining!

FamilyValueCondition

4.89 out of 5 average rating, 97 reviews
Guest favorite
A crystal-clear swimming pool is framed by a large, well-kept lawn, inviting relaxation. Surrounding the pool are sun loungers, with rustic buildings visible in the distance beneath a clear blue sky, enhancing the serene atmosphere.
Villa in Colle di Val d'Elsa

Villa with pool in the heart of Tuscany

FamilyLocationHospitality

4.94 out of 5 average rating, 48 reviews
Superhost
A rustic Tuscan farmhouse, restored with care, features a tall tower and expansive windows. Surrounding greenery includes cypress trees and shrubs, complementing the natural landscape. The lawn offers open space for relaxation, enhancing the serene atmosphere of the property.
Villa in Buonconvento

Beautiful tuscan country house

LocationValuePool

4.9 out of 5 average rating, 21 reviews
Top guest favorite
A charming entrance is framed by a wrought iron gate, opening to a gravel pathway leading to a spacious courtyard surrounded by greenery and stone buildings. Lush trees and flowering plants enhance the inviting outdoor space, reflecting the historical character of the restored barn.
Villa in Certaldo

Villa Gelsomino, your dream in Tuscany

FamilyLocationBathroom

4.94 out of 5 average rating, 32 reviews
Top guest favorite
A vibrant outdoor area features a pergola draped with greenery, providing shade over a comfortable seating arrangement. Flowering plants and shrubs surround the patio, enhancing the natural beauty of the villa's exterior, which exhibits warm hues under the sunlight.
Villa in Peccioli

Dream in Tuscany, Villa with pool

LocationValueHospitality

4.99 out of 5 average rating, 82 reviews

Destinations to explore