
Vacation rentals with a pool in San Gimignano
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Quick stats about vacation rentals with a pool in San Gimignano

Total vacation rentals
Explore 490 vacation rentals in San Gimignano

Nightly prices starting at
San Gimignano vacation rentals start at $50 per night before taxes and fees

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Over 12,170 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 230 rentals that welcome pets

Rentals with dedicated workspaces
150 properties have a dedicated workspace

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

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

4.7 Average rating
San Gimignano stays receive an average rating of 4.7 out of 5 from guests
Top-rated rentals with a pool in San Gimignano
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni è un antica proprietà del 1600 a gestione familiare situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare navetta privata e esperienze locali direttamente con la nostra famiglia . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello e vigneti con tramonti unici.
ValueLocationAmenities

Palazzo Monaci - Piscina nelle crete Senesi
Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.
FamilyValueSolo travel

TREEhouse/casaBARTHEL
casaBARTHEL is a perfect place for a vacation and an artist residency, immersed in the Tuscan landscape only 15' from the florentine Duomo. Come and live with us; enjoy the olive trees, the kitchen garden, our horse Astro and our family life style, away from the working rhythm. By providing wifi only in the communal courtyard we suggest to take a break from been connected with elsewhere and enjoy the 'here and now' . But if you need to work you can rent a portable private connection from us.
FamilyValueView

Infinity pool in Chianti 1
Sulle colline del Chianti, porzione di antica casa colonica in pietra del 1800, situata a S. Filippo una piccola frazione di Barberino Tavarnelle, a metà strada tra Firenze e Siena, a 30 minuti di macchina dall'aeroporto di Firenze, a 1 ora da quello di Pisa. Tre camere da letto, due bagni, ampia sala con camino, cucina abitabile e sala da pranzo. Vista magnifica sulle colline da ogni finestra! Splendida piscina a sfioro con zona idromassaggio, non riscaldata e aperta da Aprile a Ottobre.
ValueFamilyBathroom

Stone House with Exclusive Pool Codilungo in Chianti
Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.
ValueLocationAmenities

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.
LocationValueAmenities

SuiteLouise.pool, Hot Tub,homeGym & private Garden
SuiteLouise, in the chianti region is the perfect retreat for those seeking design,comfort and authentic tuscan vibes.Relax in the outdoor lounge,enjoy a bbq in the rose garden, or unwind in the private hot tub or home gym. Feel at home embraced by the rolling tuscan hills, whille i help you create tailor-made stays with 10+experiences. Contact me to craft your tuscan escape and create unforgettable memories in this strategic and amazing area between Florence and Siena.
ValueFamilyParking

Il Castello di Ferrano - Castle in Tuscany
Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.
ValueLocationDecor

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.
FamilyValueHospitality

Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.
FamilyValueWifi

Cercis - La Palmierina
E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.
FamilyValueIndoor spaces

A Big Dream in a Little Tower.
The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.
ValueFamilyView
Popular amenities for San Gimignano rentals with a pool
House rentals with a pool

Private Chianti Cottage, Garden & Vineyard Views
LocationFamilyGetting around

Vacanza immersa nella campagna Toscana 'Canaiolo'
ValueFamilyView

I Limoni Apartment in Tuscany
FamilyLocationLayout

Ancient Barn in Chianti with Pool
LocationFamilyHiking

Tuscany stoned house with private pool
LocationFamilyTV

Explore Chianti from a Charming Stone House
ValueLocationView

Paluffo Torre House
LocationValueShared spaces

Agriturismo Casa Giulia di Sopra
FamilyLocationKitchen
Condo rentals with a pool

Appartamento Loggiato 3 in toscana vicino Siena
FamilyValueSleep quality

Adalberto Apartment inside the Manor of Fulignano
ValueFamilyGetting around

Scenic Stilish Country
LocationFamilyTV

House between Firenze, Arezzo, chianti e Siena
FamilyValueCleanliness

Residenza Vintage con Piscina nel Chianti
LocationValueLong stay

Poggiolieto Suite - on hills 10' from city center
FamilyValueWalkability

Manuela appartamento con piscina in agriturismo
FamilyValueNearby

La Casetta
FamilyLocationWifi
Home rentals with a private pool

Villa il Palagio nelle campagne toscane
LocationFamilyIndoor spaces

Suite Casa Luigi con piscina esclusiva
LocationFamilyOutdoor spaces

Farmhouse , pool, 13 px. Lucca 10km
ValueFamilyIndoor spaces
Historic villa x8 with exclusive pool
FamilyLocationComfort

Villa Fonteintanata Ground floor
LocationFamilyGrill
When is the best time to visit San Gimignano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $211 | $222 | $180 | $193 | $222 | $228 | $208 | $212 | $200 | $184 | $170 | $212 |
| 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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- Rentals with pools Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- 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
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- Outdoors San Gimignano
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- Things to do Siena
- Sightseeing Siena
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- Things to do Tuscany
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- Things to do Italy
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- Cooking Italy
- Flying Italy
- Cultural tours Italy
- Wellness Italy
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- Tastings Italy
- Wildlife Italy
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- Sports activities Italy
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- Architecture Italy
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- 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
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- 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







