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Condo holiday rentals in San Gimignano

Find and book unique condos on Airbnb

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Popular amenities for San Gimignano condo rentals

Weekly condo rentals

Guest favourite
Condo in Asciano
4.91 out of 5 average rating, 152 reviews

Appartamento Loggiato 3 in toscana vicino Siena

JanRating, 5 stars2 weeks ago
We hebben een onvergetelijke 14 dagen doorgebracht op deze droomplek. Het huis is prachtig gelegen op een heuvel met 360 graden kilometers ver schitterend uitzicht. Het is goed bereikbaar en centraal gelegen zodat vele bekende plekken in Toscane goed bereikbaar zijn. Het appartement heeft alles wat je nodig hebt om te koken, zelfs is er een Bialetti Moka koffiezetter aanwezig voor de liefhebber maar ook een gewoon koffiezetapparaat. De Coop supermarkt en bakker zijn binnen 15 minuten rijden te vinden. Anna, Francesca en hun team houden alles op en top schoon, ze zijn goed bereikbaar en spreken goed Engels. Ook hun moeder komt dagelijks langs om te controleren af alles in orde is. Bij het zwembad is het heerlijk vertoeven met een uitzicht waar je nooit genoeg van krijgt. Alles is uitstekend geregeld, iedereen heeft zijn eigen plekken buiten. Een top plek!
Top Guest favourite
Condo in Centro Storico
4.99 out of 5 average rating, 186 reviews

Casa degli Allegri

JesseRating, 5 stars4 days ago
My stay at Antonio's Airbnb was an absolute dream, largely thanks to their incredible hospitality and super communicative nature. From the moment I booked, he was on top of everything, providing clear instructions and quickly answering any questions I had. But what truly set this experience apart were the thoughtful, personal touches. The curated playlist waiting for me was the perfect soundtrack to my trip, and their insider recommendations on local hotspots led me to some truly hidden gems I would never have discovered otherwise. It felt less like a rental and more like visiting a friend who genuinely wanted me to have the best time in Florence. I highly recommend Antonio's place for anyone looking for a seamless, enriching, and truly memorable stay!
Guest favourite
Condo in Gambassi Terme
4.89 out of 5 average rating, 234 reviews

A View Over Tuscany's Countryside

JonathanRating, 5 stars3 weeks ago
El apartamento y Filippo fueron maravillosos!!! con vistas muy lindas a viñedos que te hacen sentir verdaderamente en la Toscana! Filippo ha sido uno de los mejores anfitriones que hemos tenido, sin duda te sentiras como en casa con su buen trato y calidez y con todo lo que ofrece su apartamento, la cocina muy bien equipada, la cama muy comoda perfecta para descansar despues de un intenso dia de aventuras toscanas! Sin duda volveriamos!
Guest favourite
Condo in Chiusdino
4.87 out of 5 average rating, 103 reviews

Appartamento Chiusdino - Centro storico

NicholasRating, 5 stars1 month ago
Alloggio ottimo, casa come da foto e descrizione, locata in un piccolo paesino molto carino. Struttura pulita e ordinata, Host sempre disponibile per qualsiasi informazione e gentile.
Guest favourite
Condo in Pisa
4.98 out of 5 average rating, 202 reviews

"Mercanti" cozy attic in a tower house

KatjaRating, 5 stars2 weeks ago
Die Wohnung war sehr stilvoll eingerichtet und gut gelegen, um die Stadt zu Fuß zu erkunden. Die Küche war sehr gut ausgestattet und es hat Spaß gemacht dort zu kochen. Die Kommunikation mit Elisa war perfekt und wir durften sogar früher ein- und später auschecken. Das Bad war klein, aber funktional. Leider war uns nachts trotz Klimaanlage zu warm, da das Bett direkt unter das Dach gebaut ist. Die Wasserpumpe war zudem recht laut (auch wenn kein Wasser lief). Insgesamt können wir die Wohnung auf jeden Fall empfehlen, wenn man kein Problem mit steilen Treppen hat :)
Guest favourite
Condo in Figline e Incisa Valdarno
4.93 out of 5 average rating, 472 reviews

Casa Rebecca con piccola piscina privata

MonikaRating, 5 stars1 week ago
Das Ferienhaus und der Garten mit Pool ist wunderschön. Das Haus ist liebevoll im eingerichtet im Toskana Stil. Alles war sehr sauber und es hat an nichts gefehlt. Wir haben uns wie zu Hause gefühlt und haben in den Betten sehr gut geschlafen. Benedetta und ihr Vater sind sehr liebe und hilfsbereite Gastgeber, die uns jederzeit unsere Fragen beantwortet haben und sehr gute Empfehlungen für Besichtigungen und Restaurants gegeben haben. Als unser Auto repariert werden musste ist der Vater mit uns in die Werkstatt gefahren und war bei der Übersetzung behilflich. Danke nochmals für die selbstlose Hilfe. Wir werden diesen schönen Urlaub immer als das kleine Paradies in Erinnerung behalten, das von sehr lieben Menschen geführt wird. Wir können es nur empfehlen.
Guest favourite
Condo in Rifredi
4.92 out of 5 average rating, 167 reviews

VILLA LE PERGOLE - Florence

JennaRating, 5 stars1 week ago
Anna was a fantastic host, who treated us with the upmost respect and kindness. While her place is a bit difficult to find at first, once you're there, you're in one of the most beautiful scenes we've seen during our time in Italy. Also, it was close enough that we were still early able to travel into Florence each day we were there. Anna was so nice in providing us with breakfast each morning, which included apricot jam from her fruit trees and homemade bread. We would recommend this spot for anyone looking for a quiet place to stay outside of the busy city.
Superhost
Condo in Fiesole
4.88 out of 5 average rating, 189 reviews

Poggiolieto Studio - on hills 10' from city center

BethRating, 5 stars3 weeks ago
We had a lovely a time at the property. It was exactly as described and had amazing views. The host was very welcoming and was exceptionally helpful. It is fairly easily to get to the city centre from the property. There are two fairly regular buses and we were able to use a maps app pretty successfully to predict travel times.

Pet-friendly condo rentals

Top Guest favourite
Condo in Prato
4.94 out of 5 average rating, 157 reviews

Appartamento" Il teatro "- Prato centro storico

MatthewRating, 5 stars3 days ago
Sandra was the perfect hostess, what a lovely person and a lovely place, it felt like home, very quirky which I loved. Will definitely go again if I'm in Prato. Only criticism which was a very minor one was finding the place, but Sandra came and met us which was nice of her. Extremely happy with our stay, highly recommend
Top Guest favourite
Condo in Centro Storico
4.98 out of 5 average rating, 176 reviews

Dafne's House - Cozy & Lovely Apartment

AmyRating, 5 stars5 days ago
Aida's place was wonderful! We loved everything about it. It's very spacious and decorated beautifully. The air-conditioning was fantastic to come home to after long days sightseeing in very warm weather. We highly recommend Aida's place for a "home away from home."
Top Guest favourite
Condo in Siena
4.96 out of 5 average rating, 170 reviews

Elegant vintage decorated home in the old Siena

DeniseRating, 5 stars3 weeks ago
Perfectly located vintage decorated home within walking distance of historic center of Siena. We spent a month here and used her place as a center base to discover Tuscany. Close to shopping and restaurants. WiFi is excellent as my husband worked remotely for a few days a week. Kitchenette and washing machine were a big help as we cooked a few nights staying in. Mattress is very comfy and the apartment is very quiet. Church bells rang daily and drummers in the contrade practice for parades and Palio. Experience Medieval Siena here. We were very comfortable in Grazia’s place. Nice to have a 1/2 bath on main level, as bedroom and bathroom with shower is on the upper level. Grazia provides everything you could possibly want and has excellent suggestions for places to eat and sights to visit. She was indispensable helping us always responding within minutes if we had a question or needed help. Perfect place for the Tuscan vacation! Grazia is a wonderful and caring host!
Superhost
Condo in San Gimignano
4.85 out of 5 average rating, 113 reviews

Suite "La Rocca Romantica" in San Gimignano

Juan CruzRating, 5 stars13 months ago
I loved this place. Duccio (the host) told me that this used to be a convent around the 1500. The bed is really confortable and the water pressure and temperature is great. Also, you are at just around 100 meters from the main squares. Highly recommended!!
Guest favourite
Condo in Centro Storico
4.86 out of 5 average rating, 442 reviews

Stylish Terrace on Boboli Gardens

KellyRating, 5 stars2 weeks ago
We loved this space and when we come to Florence again we will most definitely book here. It was a cool, quiet oasis on the beautiful relaxing side of the Arno. The location was perfect with an easy walk to all the sites but also so quiet and peaceful. We loved the kitchen and cooked multiple days and sat on the sweet patio and enjoyed the local wine. The space was clean and cool and the layout was perfect for 2 people. There’s also a couch bed if another person or one or two children were there. Our hosts were so accommodating and friendly! We have so much love for this special spot in Florence.
Guest favourite
Condo in Scandicci
4.94 out of 5 average rating, 155 reviews

Florentine Hills "LE SCALETTE"

StephanieRating, 5 stars2 months ago
Lovely stay in Tuscany! Patrizia had started a warming fire going for us in the fireplace upon arrival, as the weather was chilly and rainy. The house was very cozy, artistically decorated, and well appointed -- it made us feel very much at home away from home. Gorgeous views of Tuscany from the bedroom windows, and a well cared for garden which had lemons, rosemary, basil and many flowering plants. Patrizia was the absolute best hostess and provided for all our needs during our stay. There was plenty of room for everybody in the house, and there was even a lovely little kitchen which was fully stocked (salt, pepper, spices, coffee, milk, and more!). Note there is not an oven, but we were able to cook breakfast every day, and even a few dinner meals for our small group in the mini kitchen (there is a mini fridge which fit a lot of perishable food for its size!, and a small induction stove top). Thank you for the perfect stay!
Guest favourite
Condo in Pienza
4.91 out of 5 average rating, 99 reviews

Amazing view of Val d'Orcia Pienza

JulianeRating, 5 stars4 weeks ago
Wir hatten einen tollen Aufenthalt in dieser Unterkunft. Ruhig gelegen mit allem Komfort für eine entspannte Urlaubswoche in Val D’Orcia. Der Ausblick vom Garten des Grundstücks ist einfach nur wunderschön!
Top Guest favourite
Condo in Montepulciano
4.98 out of 5 average rating, 320 reviews

Residenza In cerca d'Autore

WilliamRating, 5 stars2 weeks ago
We absolutely loved our week stay here and couldn't have been happier. It was spacious, beautifully furnished and steps away from nearby restaurants and shops. Best of all was the huge terrace –it had insanely gorgeous views of the Tuscany landscape which never got old. Looked forward to our morning coffee and early evening aperitivo with the views of the Tuscan landscape. The views were fabulous (including a nice sunrise if you're an early riser)! We didn't have reservations for dinner one night and wandered just across the street to Rosso Rubino Trattoria. The owners could not have been nicer, and the food was delicious. Berardino graciously held us a spot in the coveted "Parcheggio 7" and drove our luggage up the hill upon arrival. He gave us a tour of the apartment and several great recommendations. It was a very welcoming start to our stay. It was the perfect base for exploring Tuscany and hope to return soon.

Condo rentals with a pool

Guest favourite
Condo in Cavriglia
4.88 out of 5 average rating, 150 reviews

Chianti La Pruneta, Michelangelo apartment

TomRating, 5 stars2 weeks ago
Lovely stay in this rural location. Comfortable, scenic, friendly hosts! Nice pool!! Clean and everything we needed! Massimo made us feel as comfortable as possible down to the details!! We loved Iris the dog too (and we think she loved us!) Recommend the meal which helped make my wife’s birthday very special.
Guest favourite
Condo in Monte San Savino
4.96 out of 5 average rating, 51 reviews

La Foresteria | Casa Granaio

RhiannonRating, 5 stars2 weeks ago
This place is even more beautiful than the photos show! We are travelling round Italy for our honeymoon and this has been our highlight. From the amazing grounds to the incredible food at the little restaurant it’s all been perfect. Thank you Marian for excellent communication and being so accommodating. What a fantastic place - Grazie!!
Guest favourite
Condo in Figline Valdarno
4.87 out of 5 average rating, 54 reviews

Agriturismo Casavecchia, l'Olivo

VerenaRating, 5 stars2 weeks ago
Wir hatten einen wunderschönen Aufenthalt in diesem tollen Anwesen, welches von zahlreichen Olivenbäumen umgeben ist. Alle waren sehr freundlich, hilfsbereit und haben uns tolle Tipps zum Essengehen etc. gegeben. Abends haben wir immer direkt dort gegessen - einfach empfehlenswert. Sehr leckere regionale Küche. Wer es entspannt und ruhig möchte ist dort super aufgehoben. Wir haben es geliebt und uns total wohl gefühlt. Alles in allem super top, wir kommen gerne wieder :).
Guest favourite
Condo in Sesto Fiorentino
4.95 out of 5 average rating, 100 reviews

Ginestra: Private Pool Overlooking Florence

LauraRating, 5 stars2 months ago
Rafaella's place was nothing short of amazing! We had such a great time her place had everything you could need and more. She and her husband were super responsive. My only wish is that I wish it was warmer so that we could have enjoyed their beautiful outdoor space more. They even gave our girls sweet easter eggs. Thanks for letting us stay in your lovely home.
Top Guest favourite
Condo in Castellina in Chianti
4.92 out of 5 average rating, 60 reviews

Apartment with terrace and stunning view

LeonRating, 5 stars2 weeks ago
Der Aufenthalt bei Raisa war unfassbar schön. Die Unterkunft und insbesondere die Aussicht ist noch viel schöner als auf den Bildern zu sehen. Raisa hat sich wahnsinnig viel Mühe gegeben uns alles zu angenehm wie möglich zu machen. Die Hunde (Saila und Yango) sind Mega knuffig, der Pool ist toll und das gesamte Anwesen echt malerisch. Mit dem Auto sind schöne Städtetrips etc. gut machbar und wir würden uns freuen irgendwann nochmal wieder zu kommen.
Guest favourite
Condo in Castelnuovo Berardenga
4.96 out of 5 average rating, 69 reviews

Castello di Orgiale Charme Residenz

ShellRating, 5 stars1 month ago
Property is amazing, host so friendly and helpful… Honestly we spent very little time on the property as we were exploring so much of Tuscany during our stay with the lovely location as our home base. But it was so beautiful to wake to every day and come “home” to late every evening :) During our 6 days, we explored Florence, hung out in Siena, hiked Chianti trails, visiting all over from Monteriggioni to San Gimignano to Volterra… and throughout Val d’Orcia from Montepulciano to Pienza , Pitigliano to Serano… and north to Lucca & Pisa. Just wonderful location :) Thank you so much!
Top Guest favourite
Condo in Barberino Tavarnelle
5 out of 5 average rating, 29 reviews

Entire house for couple with exclusive pool

JacekRating, 5 stars2 weeks ago
Wir haben hier eine wunderbare Woche verbracht. Die Aussicht ist atemberaubend und ein großes privates Pool ist Sahnehäubchen auf der Torte. Matteo ist sehr bemüht dein Aufenthalt unvergesslich zu machen und ist bei allem behilflich. Dabei respektiert er deine Privatsphäre und ist praktisch “ unsichtbar”. Die Wohnung selbst ist geräumig und modern eingerichtet mit allen Annehmlichkeiten. Klimaanlage ist top. Für mich als Frau eine große Ankleide war auch ein großer Pluspunkt. Draußen konnten wir uns an Gemüsegarten bedienen. Superpraktisch und gesund. Wir haben wenig gekocht, dafür viele großartige Restaurants in der nahen Umgebung besucht. Gleich am ersten Abend hat uns Matteo einen Tisch in einem Restaurant seines Freundes reserviert und das Essen war unglaublich lecker. In der Nähe würden wir auch La Sosta di Pio VII und Ristorante Triocco empfehlen. Besuche Volterra, Siena, Monterrigioni, Panzano, Castellina und Radda in Chianti und genieße die Aussichten und das Essen.
Superhost
Condo in San Gimignano
4.88 out of 5 average rating, 78 reviews

Charming Tuscan home with pool, garden & Air-Con

KarolRating, 5 stars1 week ago
Our stay at this beautiful place was a a bull's-eye! The views of the rolling hills were breathtaking, the house was spotless and full of charm, and the host Eleonora was incredibly welcoming and helpful. It was the perfect blend of rustic charm — we truly felt like we were living in a postcard. Beside it place is located close to beautiful San Gimignano, Florence, Siena! Can't wait to come back!

Quick stats about condo rentals in San Gimignano

  • Total rentals

    60 properties

  • Nightly prices starting at

    $83 NZD before taxes and fees

  • Total number of reviews

    2.9K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with a pool

    20 properties have a pool

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. San Gimignano
  6. Condo rentals