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House vacation rentals in Massa Marittima

Find and book unique houses on Airbnb

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Popular amenities for Massa Marittima house rentals

House rentals with a pool

Guest favorite
A serene outdoor area features a swimming pool surrounded by lush greenery and olive trees. Sun loungers are positioned on the wooden deck beside the pool, while a covered seating area provides shade. Scenic hills and a distant villa are visible in the background.
Home in Pistoia
4.92 out of 5 average rating, 133 reviews

dependance in villa Toscana

DustinRating, 5 stars2 weeks ago
My wife and I stayed at Marco’s for a week for our honeymoon. We both loved it. Pool was beautiful and peaceful. The property is fantastic the pictures don’t do it justice. As amazing as it looks in the photos it is 1000 times better in person. The front gate made everything feel so secure. Walking up the steps to the guest house we were hit with a nice floral smell with all the daisies growing everywhere. Such a peaceful and beautiful property. The view was stunning looking over the mountains. The place was perfect. The kitchen was everything we needed and more, the pull out couch allowed us to relax and watch tv at the end of the night. The patios were perfect for coffees and meals. And the bed was nice and comfortable. Marco left a flower pedal heart on the bed for us which was a nice personal touch. We met his parents (who stay in the main house) they were very kind and gave us our privacy. There was lots of information about the area and things to do. Wish we stayed longer
Guest favorite
The outdoor area features a serene swimming pool surrounded by well-maintained grass. Several sun loungers are arranged nearby under large umbrellas, offering shaded seating. An olive tree adds to the lush landscape, while expansive views of rolling hills are visible in the background.
Home in San Martino
4.94 out of 5 average rating, 212 reviews

Casa Bada - Barn

RaymondRating, 5 stars3 weeks ago
Great place and location. everything about the place and our stay was excellent.
Superhost
A clear stone pool is surrounded by lush greenery, with gentle slopes visible in the background. A sun umbrella offers shade nearby, while a well-maintained terrace provides a serene atmosphere. The scene captures the tranquil setting, ideal for relaxation and enjoying the surrounding nature.
Home in Pievescola
4.93 out of 5 average rating, 106 reviews

Antico Borgo Ripostena – n. 9 Frantoio

DanielRating, 5 stars2 weeks ago
Martina’s entire estate is very peaceful and extremely beautiful. Just remember that it is really off the beaten path. She was so passionate about the property and making people feel right at home. It was one of the more beautiful places we stayed in all of Italy. Make sure to bring food up there with you before going. It is at least 35 min to town, but this is one of those places it is almost not worth leaving. Wish we had more time to stay there.
Guest favorite
A shaded outdoor dining area features a large table surrounded by several chairs, nestled under a pergola with lush greenery. The shared swimming pool glistens in the background, framed by terracotta tiles and scenic views of the Tuscan landscape.
Home in San Miniato
4.92 out of 5 average rating, 133 reviews

Private villa/swimming pool in Tuscany

MārcisRating, 5 stars2 weeks ago
Everything was absolutely perfect! ⭐️ Location: Ideal base for exploring Tuscany — you’re right in the heart of it all. Whether you’re heading to Florence, Pisa, or the charming hill towns, everything is within easy reach. House: Well-equipped and comfortable, with all the listed amenities in perfect working order. After long days of sightseeing, the pool was a refreshing retreat. The panoramic view over the valley is truly breathtaking. Host: Lorenzo is an outstanding host — friendly, responsive, and fluent in English. He was proactive and helpful throughout our stay. The house includes a detailed guidebook he created with handpicked recommendations for local shops, markets, restaurants, farms, and sights. It made planning our days effortless. Bottom line: If this listing is available — don’t hesitate. Book it. 10/10 would recommend!
Guest favorite
A private pool is set within a well-kept garden, surrounded by lush greenery and gently sloping grass. The octagonal pool is framed by stone pathways and features a small tree at its center. The tranquil outdoor space invites relaxation and enjoyment.
Home in Gaiole in Chianti
4.86 out of 5 average rating, 264 reviews

Charming estate with views

LéaRating, 5 stars2 days ago
Nous avons adoré notre séjour chez Bernardino ! Le paysage est magnifique, l’endroit est très propre et la piscine est un vrai plus pour se détendre. Bernardino est un hôte attentionné, toujours à l’écoute et prêt à aider à tout moment. Merci pour cette belle expérience !
Top guest favorite
The exterior of a two-story yellow house is displayed, featuring green shutters and a charming balcony adorned with flower pots. Stone accents at the base contrast with the bright walls. A pathway leads to the entrance, surrounded by greenery and colorful flowers.
Home in Gallicano
4.99 out of 5 average rating, 105 reviews

Serenella

MichaelRating, 5 stars1 week ago
Natürlich! Hier ist die überarbeitete Version mit dem Zusatz zur Umgebung und dem Wunsch, wiederzukommen: ⸻ Die Unterkunft liegt in einer ruhigen, idyllischen Gegend und ist perfekt, um abzuschalten und zu entspannen. Das Haus war sauber und die Küche mit allem ausgestattet, was man im Alltag braucht. Die Kommunikation mit Ilaria war jederzeit freundlich und unkompliziert – alles hat super geklappt. Das Highlight ist der große, sehr gepflegte Garten mit vielen verschiedenen Pflanzen – ein richtig schönes, grünes Paradies. Der Pool macht das Ganze noch besser. Wir haben die Zeit dort sehr genossen und kommen gerne wieder!
Guest favorite
A private pool is surrounded by sun loungers, set on a wooden deck. The pool area features natural stone paving and is enclosed by a child-proof fence. Lush greenery and olive trees outline the space, providing a serene environment for relaxation.
Home in Lecchi in Chianti
4.96 out of 5 average rating, 137 reviews

Casa di Lyndall - Entire house with exclusive pool

LiannaRating, 5 stars1 week ago
Yet another fabulous stay! Thank you Lyndall for sharing your special space. Getting in on the village pizza night was a surprise bonus and so fantastic to enjoy the local community. Until next time :)
Superhost
A stone pathway leads to a charming rustic building, surrounded by greenery and blooming flowers. To the side, a flat stone table under a large tree provides a serene outdoor space, inviting relaxation amidst nature.
Home in Rietine
4.85 out of 5 average rating, 208 reviews

Gaiole in Chianti Poggio Casabianca

AlexRating, 5 stars4 weeks ago
Valeria und Simone haben eine super schöne und saubere Wohnung! Wir haben uns von Anfang an sehr wohlgefühlt. Die Wohnung bietet einen super Ausgangspunkt für zahlreiche Wanderungen und Ausflüge. Während unseres Aufenthaltes haben wir immer gute Tipps und Ratschläge von den beiden bekommen. Unser Hund hat sich auch sehr wohlgefühlt und da das Grundstück komplett eingezäunt ist, konnte er sich frei bewegen. Wir würden jederzeit wiederkommen. Es war eine unglaublich schöne Zeit!

Weekly house rentals

Top guest favorite
A private garden is surrounded by greenery, featuring a wooden deck with a dining table and chairs. A lounge chair rests on the grass, complemented by colorful flowers. Stone walls of the house provide a rustic backdrop, enhancing the serene atmosphere.
Home in Suvereto
4.96 out of 5 average rating, 48 reviews

The house in the Castle and the secret garden

RebeccaRating, 5 stars2 weeks ago
A beautiful place. You can see and feel it is not just a random vacation rental but feels like someones home and someone has put a lot of detail and love in the place. Once you talk with Diana, you understand even better: as the owner, so the home :) The house offers all you need to stay there (with your whole family) also for longer than only a few nights. The village is very cute and offers all you need, plus charming bars and restaurants. On top it is a great starting point to go and explore the area/ medieval towns/ nature parcs/ beaches. By car it felt like everything is reachable in max 20minutes. Further you can explore by bike and even start from the town on hikes so: if you get a chance to book, stop searching - hit the button and enjoy your time :)
Guest favorite
The image depicts a tranquil swimming pool with sparkling turquoise water, reflecting the surrounding greenery and a distant stone building. Tall cypress trees line the area, enhancing the serene landscape, while sun loungers are arranged neatly near the pool's edge.
Home in Asciano
4.97 out of 5 average rating, 34 reviews

Family Forest - Piscina nelle Crete Senesi

SylviaRating, 5 stars1 week ago
The area is incredible, peaceful and the view spectacular. Asciano has the delightful charm of an Italian village. The people were friendly and welcoming. Even got greeted by their local police who offered up their number in case we needed anything. I felt safe, and it felt as if I lived there for years. I’d say this is a piece of heaven on earth. Bellezza maestosa! Non vedo l'ora di visitare di nuovo la Toscana e la città di Asciano! Grazie!
Top guest favorite
A rustic kitchen area is nestled against a stone wall, featuring a wooden bar table with two round stools. Minimalistic shelves hold kitchen essentials, while light streams through a window, illuminating the space and connecting it with the adjoining sleeping area.
Home in Montemassi
4.96 out of 5 average rating, 49 reviews

Capezzuolo 33

BenRating, 5 stars1 week ago
This apartment was so beautiful and the views were even better. We had an amazing stay here as our base for exploring Tuscany - visiting the Val d’Orcia and the thermal baths were a highlight! Lucia and Marco met us on arrival and were extremely friendly and gave us plenty of advice and places to visit. There was an issue with the boiler but Lucia was straight on it and it was fixed by the time we were home for the day. Thank you so much!
Top guest favorite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Home in Barberino Tavarnelle
4.97 out of 5 average rating, 72 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

MeganRating, 5 stars2 weeks ago
How can we even put into words what an incredible experience this was! Antonella was kind and helpful, and her home is just stunning. She made us feel so at home even with our limited Italian. She prepared us a home cooked, four-course meal one night and it was absolutely delicious. She even gave us the leftovers so we could have them for breakfast the next day. The villa was breathtaking and in a perfect location to visit beautiful towns in Tuscany like Pienza, Montepulciano and San Gimignano. We especially loved the pool and visiting with the animals. This was a bucket list stay for us and worth every penny!
Top guest favorite
Home in Pereta
5 out of 5 average rating, 56 reviews

Bel Casale with sea view and the mediaeval village

DennisRating, 5 stars6 days ago
Die Kommunikation vor unserer Anreise war sehr gut, die Gastgeberin hat sehr schnell auf Nachrichten reagiert und sich selbst auch proaktiv bei uns gemeldet. Wir wurden sehr freundlich empfangen und durften sogar 1h früher einchecken. Uns wurde alles in und um das Haus gezeigt. Das Haus und der Garten + Pool waren sehr sauber. Die Klimaanlagen in den Schlafzimmern waren wichtig und haben auch gut funktioniert. In der Küche findet man alles was man benötigt. Der Garten ist schön groß und top gepflegt. Auch der große Pool mit dem wunderschönen Ausblick hat uns begeistert. Die Gastgeber, die ca. 50m neben an wohnen, haben sich jeden morgen um den Pool gekümmert und geprüft ob dort alles okay ist. Die Anfahrt war auch relativ einfach. Ca. 30 Minuten Autofahrt zum Haus gibt es einen großen Coop Supermarkt, wo wir einkaufen waren. Das Meer ist auch nur 30 Minuten mit dem Auto entfernt. Alles in allem waren wir sehr zufrieden und haben unseren Urlaub als 6 Personen Gruppe voll genossen!
Guest favorite
A bright interior space is shown, featuring a table with chairs set for breakfast. A cozy sofa is positioned nearby, and a cabinet holds decorative elements. A well-equipped kitchenette is visible, with dishes neatly arranged on the counter. A window offers a view of the outside garden.
Home in Roccastrada
5 out of 5 average rating, 5 reviews

Apartment in the countryside

Dr. SveaRating, 5 stars10 months ago
Außergewöhnlich schöne, mit viel Liebe und Geschmack eingerichtete Wohnung in einer wunderschönen, gepflegten Anlage! Der schöne, gepflegte Pool ist das i-Tüpfelchen, das die Anlage perfekt macht. Wir haben das viergängige Dinner unter Sternen sehr genossen, in der Umgebung gibt es aber auch so viele gute Restaurants, dass man gar nicht alle ausprobieren kann. Chiara und Stefano sind die perfekten Gastgeber, von ihnen kann man viel Interessantes erfahren! Sie legen auch viel Wert auf Nachhaltigkeit, die Anlage ist autark und im zugehörigen Weingut werden nur Bio-Weine produziert.
Top guest favorite
A spacious living area is presented, featuring a contemporary sectional sofa adorned with cushions. The room is highlighted by a stone accent wall and a modern fireplace. Large windows provide natural light, while a round coffee table sits centrally, enhancing the inviting feel of the space.
Home in Monteroni d'Arbia
5 out of 5 average rating, 13 reviews

Golden View - Casale da sogno in Toscana

KshitijaRating, 5 stars2 days ago
This has to be one of the nicest Airbnbs we’ve stayed it. The accommodation was luxurious in an absolutely stunning area of Tuscany. The rolling fields and cypress tree made a spectacular setting for this beautiful house. We had hired a car and this place was a 20 minute drive from Siena. Our only regret was not staying here longer.
Guest favorite
A logo featuring a house with a welcoming doorway, adorned with potted plants on either side. The design includes the text 'DEPENDANCE LA BANDITA' and 'ESTD 2023,' framed by delicate floral elements, suggesting a curated and inviting space.
Home in Marina di Castagneto Carducci
4.98 out of 5 average rating, 57 reviews

Dependance La Bandita

EllaRating, 5 stars1 week ago
We picked the location based on (very last minute) availability Airbnb’s. Both the city and Airbnb did not disappoint. The house was very chill and provided us with plenty of privacy and met all our needs. Azzurra was very helpful. And the city (with help of Azzuras tips) provided us with the relaxation we were looking for. Wish we booked a longer stay. Only recommendation for future guests, a car is required to navigate through the area.

Private house rentals

Top guest favorite
A covered outdoor patio is featured with a textured brick floor and stone walls. Comfortable seating arrangements made of wood overlook the garden, surrounded by greenery. Potted plants add a touch of color, with sunlight highlighting the inviting space.
Home in La Pesta
4.82 out of 5 average rating, 49 reviews

L' Alloro

AlessandroRating, 5 stars1 month ago
Abbiamo soggiornato presso “l’alloro” per cinque giorni (quattro notti) e ci siamo trovati molto bene. I proprietari sono cordiali, ci hanno dato tutte le informazioni utili per un soggiorno comodo e piacevole. Il luogo è riparato e molto tranquillo. L’abitazione è confortevole e pulita. Con noi c’era il nostro cane di taglia grande e non abbiamo trovato difficoltà. Nei paraggi c’è il lago dell’Accesa, molto comodo, ma in ogni caso non eravamo troppo distanti dalle spiagge di Follonica. Un’ottima esperienza.
Guest favorite
The image captures a tranquil outdoor area featuring a swimming pool surrounded by well-maintained grass and foliage. A shaded structure offers seating beside the pool, with steps leading into the water visible. Rolling hills and clear blue skies are seen in the background.
Home in Sovicille
4.94 out of 5 average rating, 78 reviews

Cozy country house Podere Scorno with pool

LucRating, 5 stars3 days ago
Nos 3 journées chez Virginia ont été une réussite Sienne à proximité,l'environnement extérieur et le coin piscine très appréciés Nous recommandons vivement
Top guest favorite
A panoramic view depicts rolling green hills extending toward the coastline. The azure sky is adorned with scattered clouds, while the sea glistens in the distance. A sheer curtain is visible in the foreground, framing the serene landscape.
Home in Campiglia Marittima
5 out of 5 average rating, 39 reviews

appartamento in casale

MeretRating, 5 stars2 weeks ago
We absolutely loved our wonderful stay at Susanna's and Carlo's. The apartment was well equipped, comfortable bed, welcoming interior, the views were stunning. It was really calm and it felt like home. Especially because Susanna and Carlo were such great hosts, friendly, helpful with good advice, they even organised to rent bikes for us. Also, the dog Peppe, gave us so much love, such a sweet dog, we really miss him. We witnessed the arrival of two cute cats and how they met Peppe. It was hard to leave. We absolutely recommend to stay there! Grazie mille per tutto, Susanna, Carlo and Peppe!
Guest favorite
The villa is positioned on a hillside, offering panoramic views of the rolling Tuscan countryside at sunset. Olive trees are scattered throughout the landscaped garden, with a covered terrace visible, inviting outdoor relaxation and dining. Warm light bathes the scene, enhancing the natural beauty.
Home in Castelmuzio
4.98 out of 5 average rating, 40 reviews

Casa Ora d"Oro - Panoramic Views

Jason AllenRating, 5 stars3 weeks ago
first I love his neighbors who checked us in. Cinzia was amazing. She not only showed us our place but took our kids to show us her farm. she also makes her own olive oil and gifted us with some! Wonderful Italian neighbors!! I contacted Rocky in advance and he provided me with specific recommendations for where we should go during a long drive we took. we went where he suggested and was not disappointed! Amazing quiet location with great near by wineries. would 100% recommend to everyone!
Top guest favorite
The image captures a scenic view from a terrace overlooking lush green mountains at dusk, with a village of Pruno nestled among the hills. Warm lights from the village twinkle gently against the backdrop of towering peaks, creating a tranquil atmosphere.
Home in Volegno
5 out of 5 average rating, 46 reviews

Casale del boscaccio La civetta

BiancaRating, 5 stars1 week ago
Da elisabetta siamo stati benissimo, tutti i servizi sono stati impeccabili, a partire dal check in dove elisabetta è stata flessibile riguardo all’orario è estremamente disponibile. la casa è perfettamente attrezzata di tutto il necessario e impeccabile a livello di pulizia. l’ ambientazione poi è da sogno. consiglio assolutamente un soggiorno, non ve ne pentirete!
Top guest favorite
Home in Pontassieve
4.96 out of 5 average rating, 82 reviews

La casina ridente in Toscana con vista mozzafiato

FelipeRating, 5 stars2 weeks ago
Stella nos recebeu muito bem, foi simpática e prestativa. A casa estava muito limpa e organizada. O espaço e aconchegante. O lugar é extraordinário, muito bonito, com natureza exuberante e uma vista maravilhosa. Stella recomendou lugares para visitar e restaurantes da região que gostamos muito. Somente elogios, nenhuma reclamação.
Top guest favorite
The bedroom features a spacious bed with a patterned bedspread. A wooden headboard adds warmth, complemented by two small bedside lamps. Large windows allow natural light to fill the space, with views of the surrounding landscape. Two paintings adorn the walls, enhancing the room's charm.
Home in Poggibonsi
4.92 out of 5 average rating, 59 reviews

Agriturismo Podere San Martino (apartment for two)

PaulineRating, 5 stars1 week ago
Onwijs fijn appartement dat goed koel blijft tijdens warme dagen. Uitzicht vanaf het prive terras was adembenemend en het appartement was smetteloos schoon. Alles behalve een weegschaal om de koffer te wegen was aanwezig, echter die was binnen een half uur geleend van de ontzettend vriendelijke eigenaresse (die overigens olijfolie en honing van eigen kweek aanbiedt).
Guest favorite
A bright kitchen features a large wooden window overlooking a leafy garden. Fresh flowers are arranged in a vase on the countertop, accompanied by a bowl of eggs. Natural light enhances the space, highlighting the white cabinetry and sink area.
Home in Colle di Val d'Elsa
4.94 out of 5 average rating, 64 reviews

Countryhometuscany - House with Garden -

GabrielleRating, 5 stars1 week ago
Beautiful property with warm, welcoming hosts. The bed was exceptionally comfortable, and everything is tastefully decorated The kitchen is fully equipped, perfect for cooking meals at home. The pool was a great temperature, immaculately clean, and came with stunning views of the surrounding countryside. The entire setting is peaceful and relaxing, yet only a 35-minute drive to Siena and 50 minutes to Florence. We especially loved watching the sunset at the nearby five-star Belmond hotel. We went for drinks at 7pm, enjoyed live music, and were surrounded by the heavenly scent of jasmine. There is no air conditioning but the fans were absolutely fine! Another highlight was La Speranza, a gorgeous deli serving excellent coffee, pastries, cheese, and wine. They kindly spoke English when we got stuck and made us feel so welcome.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Grosseto
  5. Massa Marittima
  6. House rentals