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Apartment holiday rentals in Montemassi

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Popular amenities for Montemassi apartment rentals

Weekly apartment rentals

Top Guest favourite
Apartment in Montalcino
4.96 out of 5 average rating, 68 reviews

Focolare per 4 persone con piscina a Montalcino

AlessandroRating, 5 stars2 weeks ago
Stupendo b/b immerso nella colline senesi. L'appartamento per 4 persone era pulito e in ordine con tutto il necessario per il soggiorno. L'area esterna è incantevole: viti, piante stupende e giardino curato. La piscina a sfioro - con vista - è sicuramente il punto forte: davvero impagabile la vista. L'host è stato cortese e disponibile anche a fronte di qualche inconveniente che si è verificato durante la permanenza. Uniche note negative: check in non disagevole. Al nostro arrivo, la chiave inserita nella key box era quella del monocale e non del nostro appartamento. Ergo, abbiamo dovuto contattare la responsabile e attendere l'arrivo - dopo 15 minuti circa - della domestica che ci ha fornito la chiave corretta. L'appartamento era pulito eccetto la presenza, vicino al lavabo, di molte formiche morte. Il lavabo era intasato e, pertanto abbiamo segnalato alla domestica che è intervenuta per sbloccare. Nel complesso, comunque, posto davvero bello che merita la visita.
Guest favourite
Apartment in Sticciano Scalo
4.9 out of 5 average rating, 21 reviews

Apartment "Tramonto" - Podere Scopaione

JacquelineRating, 5 stars2 weeks ago
Un angolo di pace immerso nel verde, e al rientro dalle ns scorribande motociclistiche, c'era sempre la piscina ad aspettarci! Comodo per visitare gli innumerevoli borghi circostanti e solo ad una mezz'ora dal mare. Per fare la spesa basta spostarsi in macchina 5 min. Io ed il nostro piccolo gruppo di amici ci siamo trovati davvero bene, speriamo di poter tornare presto.
Guest favourite
Apartment in Montalcino
4.95 out of 5 average rating, 87 reviews

La Casa di Bruna

MarcellaRating, 5 stars2 weeks ago
Luciana and her husband were very nice from the start, and came to greet us in the parking lot to present themselves and take us to the apartment. everything in the apartment was perfect and very clean and organized. very comfortable, quiet and has a nice view from the terrace. nothing to complain, perfect!
Guest favourite
Apartment in Monteroni d'Arbia
4.95 out of 5 average rating, 65 reviews

San Giovanni in Poggio, Crepuscolo app. 60 mq

ŁukaszRating, 5 stars1 month ago
Marvelous place, Sara is very friendly and helpful host. Can’t wait to visit this place again.
Top Guest favourite
Apartment in Siena
4.97 out of 5 average rating, 32 reviews

Palazzo del Papa Suites standard

TravisRating, 5 stars3 weeks ago
AMAZING stay. More beautiful than the photos. Spotless. 5 min drive to Siena. View of the wine country. Bed was more comfortable than my bed at home. Owner was extremely friendly and helpful.
Superhost
Apartment in San Vincenzo
5 out of 5 average rating, 5 reviews

La Torre-Luxury attic - BEACH FRONT - Tuscany

DaveyRating, 5 stars1 week ago
Beautiful beach views and an incredible terrace to enjoy them from. The bed was super comfortable, the place was spotless, and check-in was a breeze. Great host – friendly, responsive, and really flexible with our changing arrival time. Highly recommend! Vista mozzafiato sulla spiaggia e una terrazza incredibile da cui godersela. Il letto era super comodo, la casa impeccabile e il check-in facilissimo. Host eccezionale – gentile, reattivo e davvero flessibile con il nostro orario di arrivo variabile. Consigliatissimo!
Top Guest favourite
Apartment in San Gimignano
4.98 out of 5 average rating, 42 reviews

Herons Superior Apartment - Splendid view!

MicahRating, 5 stars2 weeks ago
Highly recommend anyone new to Italy to try San gimigano first. Staying here allowed us flexibility to explore other cities and had plenty of great spots in walking distance. Lorenzo provided fantastic recommendations and assisted with everything we asked for.
Top Guest favourite
Apartment in Piombino
4.98 out of 5 average rating, 57 reviews

Sea Retreat: Borgo alla Noce

StefanRating, 5 stars2 weeks ago
Super appartement op toplocatie in centrum van Piombino. Edoardo is jonge enthousiaste host, en kan je vele tips geven. Ook verhuurd hij boten om bijv. zelf naar Elba te varen. We zijn best kritisch, maar zelfs na een verblijf van 7 nachten geen negatieve zaken te melden over het appartement, Edoardo of Piombino. Mensen die van een balkon, terras of tuin houden moeten even verder kijken. Want dat heeft dit appartement niet dat wisten we uiteraard). We zouden zo weer gaan!

Private apartment rentals

Guest favourite
Apartment in Pogi
4.94 out of 5 average rating, 89 reviews

Borgo Iesolana Suite Superior

RobertRating, 5 stars2 weeks ago
5 Stars – A Tuscan Dream Come True! Our stay at Francesco’s private resort-style retreat in the hills of Tuscany was absolutely magical. The location is stunning—peaceful, picturesque, and the perfect escape into the beauty of the Italian countryside. The rustic room had so much charm and comfort, and the property itself was amazing, with not one but two beautiful pools to relax by. One of the highlights was the on-site restaurant. The free breakfast was far beyond the typical offering—not just muffins, but a full, authentic Italian breakfast that we looked forward to each morning. Dinner was just as impressive, showcasing delicious local flavors and warm hospitality. It was also a great jumping-off point for exploring the region—we took a lovely day trip to Siena with ease. This place is a hidden gem, and we’d return in a heartbeat. Highly recommended for anyone looking to experience the best of Tuscany!
Guest favourite
Apartment in Poggibonsi
4.95 out of 5 average rating, 61 reviews

Il Casale di Villore, Poggibonsi, Siena, Tuscany , Morellino Apt.

JohnRating, 5 stars1 month ago
We spend here 4 nights with our dog and felt right at home. I love nature and I love to cook and the kitchen being small has everything and a window on the Tuscan landscape, Considering we were not lucky with the weather Antonio gave us a few great tips what to do and we had an amazing time! Also special shoutout to sweet Tilda ❤️ we miss her already John Olya Floyd
Guest favourite
Apartment in Siena
4.89 out of 5 average rating, 129 reviews

Attico con vista su Siena

IrynaRating, 5 stars5 days ago
This penthouse in Siena completely stole our hearts! It was so spacious, peaceful, and beautifully designed—we truly didn’t want to leave. The views from the windows and terrace were absolutely breathtaking. I honestly think this is the best spot in all of Siena if you’re looking for stunning views of the city and countryside. The host was incredibly responsive and flexible, which made a huge difference for us. We were traveling with our two-year-old, and they went out of their way to accommodate his sleep schedule and make our check-in seamless. We’re so grateful for that extra care—it made our stay feel even more special. If you’re heading to Siena, don’t think twice—this place is pure magic.
Guest favourite
Apartment in Castelnuovo Berardenga
4.88 out of 5 average rating, 25 reviews

Colle ai Lecci: Design Apartment in Tuscany

GülcanRating, 5 stars2 weeks ago
Wir hatten eine unvergessliche Zeit hier - die Natur sowie die Anlage selbst sind wunderschön, etwas rustikal mit ein paar Erneuerungen, über die Ana viel erzählen kann. Man kann sich auf dem Gelände super verteilen, hat genug Privatsphäre falls erwünscht und kann die schönsten Sonnenuntergänge beobachten. Auch der Pool zwischen den Olivenbäumen ist traumhaft. Wir konnten von hier aus einige Städte wie Florenz und Siena besuchen, auch hier hatte Ana super Tipps für geeignete Restaurants parat. Wir kommen gerne wieder!
Guest favourite
Apartment in Castiglione d'Orcia
4.95 out of 5 average rating, 57 reviews

agriturismo famiglie con bambini in val d'orcia

LeaRating, 5 stars1 month ago
Il Poderuccio di Lucia si trova in un'ottima posizione ed è perfetto come punto di partenza per esplorare la bellissima Val d'Orcia. L'appartamento è spazioso, pulito, cucina provvista di tutto ed i letti erano comodi. Il bagno ha una doppia doccia..utile per famiglie con bambini piccoli. Fuori c'è un bel terrazzo con tavoli, sedie e sdraio..per chi volesse fermarsi ad ammirare il bellissimo panoramma sui colli della Val d'Orcia. Lucia è stata molto cordiale, accogliente e flessibile per il check-in/check-out. È stato un piacere conoscere lei e la sua bella famiglia. Per noi è stato un bel soggiorno e ci farebbe piacere ritornarci. Grazie!
Guest favourite
Apartment in Castiglione della Pescaia
4.88 out of 5 average rating, 25 reviews

Agriturismo Bandinelli #1 "Rotana"

DominikRating, 5 stars8 months ago
Wonderful stay at an authentic Tuscan farmhouse! We found exactly what we were looking for: a classic old farmhouse that perfectly reflects the atmosphere of Tuscany. The spacious garden and peaceful surroundings allowed us to fully relax and unwind. The rooms are beautifully decorated with great attention to detail – perfect for winding down after a long day. The rooms are a bit noisy, but it wasn't a major issue for us. Communication with David was excellent and straightforward. Hopefully, this won't be our last stay here!
Top Guest favourite
Apartment in Massa Marittima
4.96 out of 5 average rating, 28 reviews

La Casina del Corso

BradleyRating, 5 stars1 month ago
I had a great stay! The place looks better in person in my opinion. It smelled very nice and the space was clean. The local restaurants are good as well. I would definitely recommend to others. Thank you Catia & Antonio!
Top Guest favourite
Apartment in San Rocco a Pilli
5 out of 5 average rating, 55 reviews

Authentic Italian Apartment with Private Terrace

CatherineRating, 5 stars1 week ago
Such an amazing location overlooking the beautiful Tuscany countryside. Only a short drive to Siena and within an hour of many other Tuscany towns. The villa was extremely well appointed with a welcome pack along with coffee pods which were available for refill during our week stay. Would highly recommend staying here.

Apartment rentals with a hot tub

Superhost
Apartment in San Giovanni d'Asso
5 out of 5 average rating, 20 reviews

Podere Ferranino #Cimabue Townhouse

MartinRating, 5 stars10 months ago
Sehr schönes Haus, landestypisch eingerichtet dabei aber trotzdem modern. Besonders gefallen haben und die Betten und die angenehme sanfte aber effektive Klimatisierung. Sehr geräumig, so dass ein Aufenthalt mit 4 Personen sehr angenehm möglich ist. Es gibt sogar eine Lademöglichkeit für E-Fahrzeuge.
Top Guest favourite
Apartment in Radicondoli
4.95 out of 5 average rating, 22 reviews

SerenaHouse

MatthewRating, 5 stars5 days ago
Patrizios home was very well located in heart of town. I would like to point out that his flat was very clean. We used his flat to visit the nearby beautyfull villages.
Superhost
Apartment in Santa Luce
4.85 out of 5 average rating, 13 reviews

Artemisia Dreamscape with Wooden Hot Tub

RobertRating, 5 stars6 days ago
Our stay was fantastic! As a couple needing a break from a long start to the year, we couldn’t have asked for a better place to relax. Nestled in between fields and olive trees, we felt completely at home, the view from the deck was stunning and listening to the different sounds at night, from our private hot tub with a bottle of wine was perfect! We made several day trips to Volterra, Lucca and even Florence from the cabin, though definitely wake up early if you’re planning to venture further out! Would definitely recommend hiring a car if you’re going to stay here! 10 out of 10 stay! Thanks Pino!
Superhost
Apartment in Monterotondo Marittimo
4.76 out of 5 average rating, 37 reviews

Studio in Farmhouse, Swimming Pool, Restaurant.

ElenaRating, 5 stars1 month ago
Wir hatten eine schöne Zeit mit leckerem Essen und sehr freundlichen Gastgebern. Die Lage war wunderschön und die Zeit sehr entspannend. Vielen Dank :)
Guest favourite
Apartment in Seggiano
4.88 out of 5 average rating, 64 reviews

Romantic farmhouse, garden apartment with panorama

KatrinRating, 5 stars2 weeks ago
Wir verbrachten zauberhafte Tage bei Ulla. Das wunderschöne Haus, die liebevolle Einrichtung, der traumhafte Pool und die schöne Umgebung… all das hat uns so gut getan. Der Ausblick von der Terrasse ist sensationell. Man kann schöne Ausflüge unternehmen, wenn man möchte, wandern, Kultur erleben, Städte besuchen oder Restaurants. Ulla hatte dafür Unterlagen für uns bereitgestellt mit vielen Tipps. Die Zeit verging wie im Flug. Wer wirklich zur Ruhe kommen möchte, der ist hier gut aufgehoben. Wir kommen gerne wieder.
Guest favourite
Apartment in Montevarchi
4.91 out of 5 average rating, 104 reviews

Apartment with garden in the heart of Tuscany

DaniloRating, 5 stars1 month ago
Tutto perfetto. La posizione dell'appartamento è magnifica: immerso nel verde, offre una vista rilassante sulle colline circostanti. Allo stesso tempo è in una posizione strategica per chi desidera visitare i borghi storici del Valdarno e del Chianti. L’appartamento è curato, luminoso e pulito. Paola e la sua famiglia sono padroni di casa molto gentili e sempre disponibili a offrire consigli su attività e luoghi da visitare nella zona. Consigliatissimo!
Top Guest favourite
Apartment in Siena
4.94 out of 5 average rating, 109 reviews

Domus Nannini - L' Angolo di Paradiso Spa

DanyelleRating, 5 stars2 weeks ago
After another Airbnb mishap, Gianluca was so accommodating to allow to book and check in late last minute. He even met us there personally to be sure we got in okay. He even had the fold out couch ready with linens and provided a few breakfast items. The place was better than we’d hoped, location was fantastic, updated and perfectly clean! We would absolutely stay here again. This place will be one of the highlights of our trip!
Superhost
Apartment in Siena
4.91 out of 5 average rating, 132 reviews

Penthouse in Siena near Piazza del Campo and Palio

ElizabethRating, 5 stars1 month ago
We had a fabulous stay here, there was more than enough rooms and space to relax after a day of sightseeing. The view from the living room is gorgeous, the rooms are all charmingly decorated and it had all the amenities we needed: separate beds for 4 adults, large enough showers, laundry and kitchen as well as cosy living room. Federico was very friendly, responsive and made us feel at home immediately. Highly recommend!

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Grosseto
  5. Montemassi
  6. Apartment rentals