
Villa vacation rentals in San Gimignano
Find and book unique villas on Airbnb
Quick stats about villa rentals in San Gimignano

Total vacation rentals
Explore 70 vacation rentals in San Gimignano

Nightly prices starting at
San Gimignano vacation rentals start at $130 per night before taxes and fees

Verified guest reviews
Over 1,500 verified reviews to help you choose

Family-friendly vacation rentals
70 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
70 of San Gimignano vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across San Gimignano rentals

4.8 Average rating
San Gimignano stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated villa rentals in San Gimignano
Guests agree: these villas are highly rated for location, cleanliness, and more.

Villa Il Vecchio Pozzo in Toscana
Immersa nella natura dove è possibile rilassarsi alla vista di un magnifico panorama. Gambassi Terme è situato al centro della Toscana a pochi km dalle principali città d'arte (Firenze, Siena, Pisa). Il centro storico è raggiungibile anche a piedi e nei periodi estivi vengono organizzate varie feste paesane e spettacoli vari. L'appartamento è composto da cucina, soggiorno, divano, camino, bagno, una camera matrimoniale e una camerina con due letti singoli. Sul retro c'è un loggiato con vista mozzafiato e la piscina con lettini e ombrelloni. La presenza dell'ampio giardino e la vicinanza all'orto di famiglia munito di animali domestici (galline, piccioni e papere) ne fanno un luogo ideale anche per una famiglia con bambini. Immerso nella campagna dove è possibile rilassarsi in pace e tranquillita' alla vista di un magnifico scorcio ,ma facilmente raggiungibile anche a piedi il centro dove ci sono supermarket,bar. ecc
LocationFamilyParking

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
FamilyLocationOutdoor spaces

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
ValueFamilyAccess

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.
LocationValueCleanliness

Il Vichiaccio: Accessible Chianti Villa & Jacuzzi
Cozy Chianti getaway 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!
FamilyValueLong stay

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.
LocationFamilyBackyard

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.
FamilyLocationLong stay

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.
ValueLocationParking

"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..).
FamilyValueCondition

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.
FamilyLocationCheck-in

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.
FamilyLocationLaundry

Colonica nel Chianti
Splendida porzione di casa colonica immersa nel Chianti con bellissima piscina, circondata da vigne e olivi, perfettamente arredata con vasto giardino e posti macchina. Si trova a 20 minuti da Firenze, 40 da Siena e 50 da Pisa, in pochi minuti si raggiunge Certaldo (città natale di Boccaccio) e Vinci (città natale di Leonardo Da Vinci). la casa è a metà strada tra Montespertoli e San Casciano (7km).
ValueFamilyComfort
Popular amenities for San Gimignano villa rentals
Private villa rentals

CasaDiManuela:TotallyPrivateChiantiVilla withTub
LocationFamilyAccess

Giardino Incantato
LocationValueComfort

Villa dei 2 Ulivi (Abbadia Isola)
FamilyLocationOutdoor spaces

Tuscany Country House Villa Claudia
ValueFamilyHeating

Fabulous 3Br Villa with 360° Views!
ValueLocationHeating

Chiesino Dei Vaioni
ValueLocationIndoor spaces

Romantic Villa with private pool - "Il Pollaio"
FamilyLocationQuiet

Villa Holm stunning view 10 mn walk to city centre
LocationFamilyDecor
Luxury villa rentals

Villa Gourmet Food, Pizza, Chef, Pool and Nature
ValueFamilyAir conditioning

Villa Poggio a Mandria in Chianti
LocationValueGrill

Farmhouse , pool, 13 px. Lucca 10km
FamilyLocationView

Luxury Villa on Chianti Wine Estate
LocationFamilyGrill

Luxury Villa in Chianti • Private Natural Pool
LocationValueBathroom

[Villa with Pool] Luxury Villa with Pool
LocationFamilyGrill

Casa Colombaia, in the Chiantishire
FamilyLocationWifi

Sestuccia
LocationFamilyGetting around
Villa rentals with a pool

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

Villa Indipendente in Toscana - Montecatini Terme
LocationFamilyView

Lilium,delux farmhouse in the chianti hills
ValueLocationAmenities

Tenuta Uzielli an elegant countryside villa
LocationFamilyOutdoor spaces

Intera villa in Toscana: spa, piscina e cinema
FamilyLocationCheckout

Villa Fonticina: Private Pool & Secluded Woods
LocationFamilyView

Exclusive villa with pool jacuzzi wifi and green
FamilyLocationKitchen

[Le rondini in Tuscany] Exclusive View Pool Villa
FamilyLocationBackyard
When is the best time to visit San Gimignano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $712 | $639 | $598 | $592 | $636 | $743 | $749 | $622 | $541 | $425 | $207 | $632 |
| Avg. temp | 44°F | 46°F | 51°F | 57°F | 65°F | 73°F | 78°F | 78°F | 70°F | 61°F | 52°F | 45°F |
Destinations to explore
- House rentals San Gimignano
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- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Basilica of Santa Maria Novella
- Mugello Circuit
- Cala Violina
- Stazione Santa Maria Novella
- Pisa Centrale Railway Station
- Mercato Centrale
- Spiagge Bianche
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Gulf of Baratti
- Fortezza da Basso
- Parco delle Cascine
- Piazza della Repubblica
- Del Chianti
- Piazzale Michelangelo
- Piazza della Signoria
- Palazzo Vecchio
- Pitti Palace
- Boboli's Garden
- Things to do San Gimignano
- Tastings San Gimignano
- Cooking San Gimignano
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- Nature and outdoors San Gimignano
- Food and drink San Gimignano
- Art and culture San Gimignano
- Outdoors San Gimignano
- Food tours San Gimignano
- Things to do Siena
- Sightseeing Siena
- Art workshops Siena
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- Art and culture Siena
- Entertainment Siena
- Museums Siena
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- Food tours Siena
- Cultural tours Siena
- Outdoors Siena
- Landmarks Siena
- Nature and outdoors Siena
- Wildlife Siena
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- Cooking Siena
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- Sports activities Siena
- Things to do Tuscany
- Water sports Tuscany
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- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Food and drink Italy
- Food tours Italy
- Cooking Italy
- Flying Italy
- Cultural tours Italy
- Wellness Italy
- Art and culture Italy
- Nature and outdoors Italy
- Tastings Italy
- Wildlife Italy
- Landmarks Italy
- Sports activities Italy
- Museums Italy
- Performances Italy
- Art workshops Italy
- Dining Italy
- Sightseeing Italy
- Galleries Italy
- Tours Italy
- Outdoors Italy
- Architecture Italy
- Water sports Italy
- Entertainment Italy
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes







