
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 ﺩ.ﺇ 477 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 L'Olivo w/Private pool (Close San Gimignano)
Villa L’Olivo si trova nella campagna Toscana, a circa 10 chilometri da San Gimignano e a pochi minuti dai supermercati ed i vari servizi presenti a Poggibonsi. La nostra Villa è un ottimo punto di partenza per scoprire tutte le bellezze della Toscana, ma è anche un luogo ideale per chi ama concedersi una pausa dalla vita frenetica della città. A Villa L’Olivo, puoi prenotare una cena con chef privato, direttamente in villa, per goderti una cena toscana in tutta tranquillità. Scrivici per info!
FamilyLocationPool
4.99 out of 5 average rating, 101 reviews
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
ValueFamilyNearby
4.93 out of 5 average rating, 256 reviews
Tuscany Country House Villa Claudia
Vivi l’incanto della nostra Country House: un antico casale toscano di pregio, finemente restaurato, con vista mozzafiato sul borgo di Canneto (785 d.C.). Immersa nel verde di San Miniato e dotata di ogni lusso moderno, la villa è un rifugio esclusivo per rigenerarsi. Scegli tra il relax totale nella Jacuzzi in giardino, tour enogastronomici d'eccellenza o visite alle vicine città d’arte toscane. Un’esperienza sensoriale indimenticabile tra storia e natura. Prenota il tuo sogno in Toscana!
LocationFamilyTV
4.94 out of 5 average rating, 134 reviews
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.
ValueFamilyIndoor spaces
4.97 out of 5 average rating, 106 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)
ValueFamilyDecor
4.97 out of 5 average rating, 174 reviews
Villa Gourmet Food, Pizza, Chef, Pool and Nature
Villa Gourmet Typical farmhouse in the heart of Tuscany with 6 bedrooms that can comfortably accommodate up to 14 guests. - Exclusive saltwater infinity pool - Gourmet cuisine - Large garden with private parking - Two Free Charging Station (3,75 KW) - Veranda with table and Weber barbecue by the pool - Children's play area and table tennis - Football pitch - Home Restaurant service available - Cooking class and pizza workshop using a wood-fired oven - Shuttle Services
FamilyLocationView
4.98 out of 5 average rating, 127 reviews
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.
FamilyLocationWalkability
4.99 out of 5 average rating, 138 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.
ValueLocationPool
4.98 out of 5 average rating, 107 reviews
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.
LocationFamilyAir conditioning
4.98 out of 5 average rating, 120 reviews
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.
ValueLocationBeach
5.0 out of 5 average rating, 190 reviews
"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..).
LocationValueSleep quality
4.95 out of 5 average rating, 174 reviews
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.
ValueLocationAccess
4.89 out of 5 average rating, 309 reviewsPopular amenities for San Gimignano villa rentals
Private villa rentals

Villa Il Vecchio Pozzo in Toscana
LocationFamilyBathroom
4.94 out of 5 average rating, 146 reviews
Il Vichiaccio: Florence Villa with Jacuzzi
FamilyLocationAmenities
4.95 out of 5 average rating, 202 reviews
In the Heart of Tuscany near Florence
ValueLocationParking
4.97 out of 5 average rating, 559 reviews
Farmhouse , pool, 13 px. Lucca 10km
FamilyValueLong stay
4.99 out of 5 average rating, 148 reviews
Fabulous 3Br Villa with 360° Views!
FamilyLocationCleanliness
4.95 out of 5 average rating, 75 reviews
Exclusive Tuscan Villa with private pool
LocationFamilyBeach
5.0 out of 5 average rating, 16 reviews
Tuscan Villa with Pool & Jacuzzi, San Gimignano
LocationFamilyKitchen
4.98 out of 5 average rating, 90 reviews
Romantic Villa with private pool - "Il Pollaio"
FamilyLocationCleanliness
5.0 out of 5 average rating, 48 reviewsLuxury villa rentals
Le Maggioline Your Tuscany country house
LocationFamilySleep quality
4.98 out of 5 average rating, 142 reviews
Charming Villa in Stone in Tuscany, Borgo ai Lecci
FamilyLocationComfort
4.97 out of 5 average rating, 116 reviews
Poggio del Fattore-Villa with pool,hilltop,Chianti
ValueFamilyCheckout
4.99 out of 5 average rating, 131 reviews
Guardia di Badia a Passignano
LocationViewWalkability
4.86 out of 5 average rating, 7 reviews
L'Apparita del Peruzzi | Villa | Private Pool & AC
LocationFamilyAir conditioning
5.0 out of 5 average rating, 22 reviews
Private Villa with semi-Olympic pool and Tennis
FamilyValueBreakfast
4.98 out of 5 average rating, 50 reviews
I CIPRESSINI DEL CASTELLACCIO (Cip 1 + Cip 2)
FamilyLocationPool
5.0 out of 5 average rating, 17 reviews
Casale del timignano, private villa with huge gard
LocationFamilyHeating
4.86 out of 5 average rating, 21 reviewsVilla rentals with a pool

Country house with view over San Gimignano hills
FamilyLocationWalkability
4.95 out of 5 average rating, 20 reviews
Tenuta la Cipresseta | Casa Cipresso
LocationFamilyPets
4.98 out of 5 average rating, 41 reviews
Podere Ulimeto
ValueLocationBathroom
4.9 out of 5 average rating, 77 reviews
Villa Gelsomino, your dream in Tuscany
FamilyValueAmenities
4.94 out of 5 average rating, 32 reviews
Villa Montefalcone: Charm, Private Pool, and Chef
ValueFamilyHot tub
4.98 out of 5 average rating, 42 reviews
Tenuta Uzielli an elegant countryside villa
FamilyLocationAmenities
5.0 out of 5 average rating, 20 reviews
La Villa della Brigata Spendereccia!
FamilyLocationKitchen
5.0 out of 5 average rating, 28 reviews
Tuscany Villa + private pool and garden estate
FamilyLocationIndoor spaces
5.0 out of 5 average rating, 43 reviewsWhen is the best time to visit San Gimignano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 2,615 | ﺩ.ﺇ 2,347 | ﺩ.ﺇ 2,196 | ﺩ.ﺇ 2,174 | ﺩ.ﺇ 2,336 | ﺩ.ﺇ 2,729 | ﺩ.ﺇ 2,751 | ﺩ.ﺇ 2,284 | ﺩ.ﺇ 1,987 | ﺩ.ﺇ 1,561 | ﺩ.ﺇ 760 | ﺩ.ﺇ 2,321 |
| Avg. temp | 7°C | 8°C | 11°C | 14°C | 18°C | 23°C | 25°C | 25°C | 21°C | 16°C | 11°C | 7°C |
Destinations to explore
- Rentals with a hot tub San Gimignano
- Family-friendly rentals San Gimignano
- House rentals San Gimignano
- Vacation home rentals San Gimignano
- Farmstay rentals San Gimignano
- Rentals with pools San Gimignano
- Luxury rentals San Gimignano
- Pet-friendly rentals San Gimignano
- Rentals with breakfast San Gimignano
- Bed and breakfasts San Gimignano
- Apartment rentals San Gimignano
- Cottage rentals San Gimignano
- Condo rentals San Gimignano
- Hotel rooms San Gimignano
- Villa rentals Siena
- Villa rentals Tuscany
- Villa rentals Italy
- 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
- Things to do San Gimignano
- Tastings San Gimignano
- Cooking San Gimignano
- Outdoors San Gimignano
- Food tours San Gimignano
- Things to do Siena
- Tastings Siena
- Museums Siena
- Food tours Siena
- Cultural tours Siena
- Art workshops Siena
- Outdoors Siena
- Dining Siena
- Landmarks Siena
- Wildlife Siena
- Cooking Siena
- Things to do Tuscany
- Water sports Tuscany
- Flying Tuscany
- Cooking Tuscany
- Wildlife Tuscany
- Landmarks Tuscany
- Tastings Tuscany
- Galleries Tuscany
- Outdoors Tuscany
- Museums Tuscany
- Workouts Tuscany
- Art workshops Tuscany
- Food tours Tuscany
- Shopping and fashion Tuscany
- Dining Tuscany
- Performances Tuscany
- Cultural tours Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Cooking Italy
- Cultural tours Italy
- Flying Italy
- Tastings Italy
- Wildlife Italy
- Food tours Italy
- Museums Italy
- Performances Italy
- Wellness Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Landmarks Italy
- Architecture Italy
- Outdoors Italy
- Water sports Italy







