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Villa holiday rentals in Massa Marittima

Find and book unique villas on Airbnb

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Popular amenities for villa rentals in Massa Marittima

Private villa rentals

Guest favourite
Villa
4.96 out of 5 average rating, 23 reviews

Charming property, wi-fi, weddings ,cooking class

ColetteRating, 5 stars8 months ago
Our wedding at Villa Cini was truly magical. The venue’s blend of natural beauty and elegance provided the perfect backdrop for our stay during the week and our special day. The gardens and stunning views created a fairy tale atmosphere and allowed to us have both an Indian wedding and an Italian Civil one. The arches ballroom, offered a romantic and inviting ambiance. We are incredibly grateful to have a chosen a place which has passed down for generations and has such a heartfelt attention to detail. If you're looking for a dream wedding venue and a beautiful place to stay then look no further than Villa Cini.
Superhost
Villa
4.89 out of 5 average rating, 9 reviews

Elegant Chianti Villa w/ Stunning Views + Starlink

MartinaRating, 5 stars5 months ago
What a great place. Very quiet and beautiful views. We had a great time. We loved the serenity of the place. You do not hear anything but your own breathing😊. I can definitely recommend this house. You reach the house of road but that has its charme too!
Top guest favourite
Villa
5 out of 5 average rating, 14 reviews

Luxury Villa with swimming pool In Castagniccia

MischaRating, 5 stars18 months ago
Silvia and Philippe were very very friendly and reliable hosts. You had the feeling of being welcome at all times. Silvia was always immediately reachable with questions. The house was in perfect and clean condition, exactly as expected in the photos. The pool and location of the house offer a beautiful view and you could end the day by the pool or on the terrace in the evening, in peace. The closest village with a large supermarket was reachable in 10min, the nearest beach in about 25-30min drive. There's nothing to complain about and we'd come back anytime.
Guest favourite
Villa
4.82 out of 5 average rating, 17 reviews

Exclusive Villa with Private Pool and Air Cond.

KaraRating, 5 stars8 months ago
Our stay at Villa Chiara was nothing short of delightful. Nestled in the hills it offered a picturesque view of the Tuscan countryside. The villa itself was spacious and well maintained. It felt like home away from home. The pool and back patio are surrounded by lovely flowers, herbs and olive trees. Offering a spectacular view of the evening sunsets. The location was perfect to take short day trips to Siena, Florence and Montepulciano. Highly recommend for a serene, peaceful and relaxing getaway.
Superhost
Villa
5 out of 5 average rating, 3 reviews

EXCLUSIVE ENTIRE VILLA A STEP FROM THE SEA

manuelaRating, 5 stars29 months ago
Our stay at Villa Tina was memorable. Paolo and Laura are very good hosts and we didn't miss anything. Perfect for 2 families. Private beach access. Wonderful sea view. Highly recommend Paolo's place.
Top guest favourite
Villa
5 out of 5 average rating, 105 reviews

Poggio del Fattore-Villa with pool,hilltop,Chianti

VeraRating, 5 stars5 months ago
A truly stunning place with incredibly welcoming hosts. The villa exceeded our expectations in every way. The interior is filled with beautiful historic furniture, details, paintings, and books. The cozy fireplace in the living room added a special charm. We loved making pizza in our very own wood-fired oven, using the outdoor BBQ, and dining al fresco surrounded by breathtaking views. Every moment at Poggio del Fattore felt special, offering the perfect blend of comfort and authenticity. Highly recommended for anyone looking to experience the beauty of the Tuscan countryside in style!
Guest favourite
Villa
5 out of 5 average rating, 13 reviews

Villa "La Civetta" with pool, sauna and jacuzzi

BrynRating, 5 stars5 months ago
Lovely modern home in a beautiful, quiet town in southern Tuscany. We had a wonderful 8 days there with our 6 year old son.
Top guest favourite
Villa
5 out of 5 average rating, 10 reviews

Villa Leopoldina, 6 pax, Private Pool

MaximeRating, 5 stars6 months ago
Gigi’s place is one of the most peaceful places we’ve stayed in in Italy. The location is gorgeous and perfectly located between different towns to explore (Cortona, Arezzo, Montepulciano to name a few). A car is necessary but you can get to the town center for groceries and local produce in 10 minutes. We enjoyed spending our days by the pool, cooking and barbecuing in the garden. The kitchen was the most equipped I’ve ever seen for an Airbnb and the house was spotless. Extra supplies were left for us as well if we needed which was a nice touch. Gigi was always available for recommendations and extremely friendly. If you’re looking for calm and quiet this is your place!!

Luxury villa rentals

Superhost
Villa
4.88 out of 5 average rating, 17 reviews

VILLA ELBA 8 pers, 180° SEA VIEW, heated pool

GöranRating, 5 stars5 months ago
Erbalunga is a small, but very nice place, nice atmosphere, very local ambience, almost no tourists in sight, still a a lot of good restaurants. The view from the house is extraordinary! We ill bear this with us All in all a very nice experience
Superhost
Villa
5 out of 5 average rating, 15 reviews

Villa with pool,tennis court,village walk distance

EmelineRating, 5 stars6 months ago
Superb spacious and well-located villa with a great view! Awesome pool and tennis class Big tables for eating out There are enough sunbeds for everyone We had a lovely time at this beautiful villa It is just missing a large oven (there is a mini oven that troubleshoot well) and be careful the washing machine is in a residence next door and for a fee (€4 laundry detergent)
Top guest favourite
Villa
4.97 out of 5 average rating, 106 reviews

Luxury Villa in the very heart of Chianti

ScottRating, 5 stars4 months ago
Alec’s villa was even better than the pictures and description. We were greeted at the villa and had wonderful antipasto and wine with him. Everything was perfect. Alec was very responsive before, during, and after our stay. Both the villa and the host are highly recommended. Our whole family was extremely impressed. We would definitely stay here again if traveling to this region.
Luxe
Villa
5 out of 5 average rating, 5 reviews

Villa Montemaggio

HongmeiRating, 5 stars5 months ago
Absolutely gorgeous and luxurious place. Beautifully decorated, beautiful views, clean and also had an incredible kitchen. We loved it!
Guest favourite
Villa
4.86 out of 5 average rating, 22 reviews

Villa Lualdi

SallyRating, 5 stars5 months ago
Had a lovely week at the villa. Amazing place and beautiful views! Florence a short drive away, but we also enjoyed walking about 35 minutes to Fiesole for restaurants and views.
Superhost
Villa
4.85 out of 5 average rating, 20 reviews

Modern villa with a view

JohanRating, 5 stars4 months ago
We had a lovely stay in october, large spacious villa, with lots of space. Marvelous location with good restaurants reasonably close. Road up to villa not suitable for large cars, but can be solved with a bit of careful slow driving.
Top guest favourite
Villa
5 out of 5 average rating, 22 reviews

Luxury villa in Tuscany Panzano in Chianti

RobertRating, 5 stars5 months ago
I really don't want to say anything nice about Morten's home because I'd like to keep it a secret as much as possible. The more people that know how wonderful it is the harder it will be to reserve! We (six of us) were pretty much speechless for the first 15 minutes of being there. We felt like kids going into every room, looking at the paintings, furniture and wine collection. The views and grounds are spectacular and the pool was amazing. The area is perfect — easy drives to Sienna and Florence — and Panzano is a great small town with plenty to do. Morten arranged chef/owner Mimmo from Enotecca Baldi to cook for us one night which was spectacular. Such a nice person and fantastic chef! The wine cellar, if you can find it, is very cool and if our schedule didn't conflict, we would have been able to see some of the harvesting procedures. Maybe next time. One more thing: the wines at La Festegiatta are no joke! Some of the best Chianti we had during our stay! Loved the Gran Selezione!
Superhost
Villa
4.64 out of 5 average rating, 11 reviews

Tenuta Lo Spugno

IsabellaRating, 5 stars7 months ago
This home is breath taking. The most beautiful home i’ve stayed in. Everything was very well thought out. The road up is bumpy so I suggest a bigger car or 4 wheel drive- but besides that everything was amazing! The host was lovely and we organized for the chef to come and cook and it was delicious! I would definitely come back to this beautiful place again and recommend it to everyone!

Villa rentals with a pool

Top guest favourite
Villa
4.9 out of 5 average rating, 39 reviews

Villa Angiolina

ErinRating, 5 stars4 months ago
Villa Angiolina is truly beautiful!!! The view is incredible and everything was spotless and beautifully decorated. Our host was lovely and gracious and responded very quickly to all communications. She even arranged for an amazing pizza party with a private chef that was just one or the memorable moments from our time at the Villa. If this Villa is available…just book it!!! You will be glad that you did!!!!
Superhost
Villa
4.86 out of 5 average rating, 7 reviews

Villa Iris with Swimming Pool

KateRating, 5 stars5 months ago
I have so much positive to say about this place! Despite what some reviews mention about the drive, it's absolutely worth it. There's a small restaurant just 2-3 minutes away, easy access to the city, and you're only about an hour from Pisa and some beaches. The house was perfect—everything well thought out and worth every penny. The pool was amazing, and the host was very responsive. If you're visiting in autumn or spring, bring warm clothes for the chilly evenings. We were sad to leave, and I can't wait to come back to this dreamy property!
Superhost
Villa
4.87 out of 5 average rating, 23 reviews

Charming Villa -private swimming pool -16 people.

LauraRating, 5 stars7 months ago
Beautiful house in a stunning location. Pool was great. Perfect for a large family. Owners were very helpful and available when needed. Rooms were hot overnight but this is expected in peak summer in Italy.
Guest favourite
Villa
4.85 out of 5 average rating, 27 reviews

Villa "I Nespoli" with above ground pool

MarcoRating, 5 stars6 months ago
We had a wonderful week in Vincenzo's house. We were 2 families with children (5 in total). The spaces in the house were perfect for welcoming everyone. The location, a 15-minute drive from the beaches of Lido di Camaiore and 35 minutes from beautiful Lucca, turned out to be perfect. Out of the chaos, surrounded by greenery and tranquility. Vincenzo is also a super host! Friendly and available. Absolutely recommended.
Top guest favourite
Villa
4.97 out of 5 average rating, 37 reviews

Villa La Poggerina, private pool and amazing view

BryanRating, 5 stars6 months ago
A rare circumstance where both property and hosts exceeded our expectations. The house is spacious with lovely views and a patio and pool for exclusive use by guests. It is well stocked and appointed, including a pool table and multi-game arcade machine. Much appears recently renovated. For those wanting to cook traditional wood-fired pizzas, there are two outdoor ovens, plenty of wood, and a host at the ready to provide assistance as needed. Emanuele and his wife are excellent hosts - gracious and welcoming yet non-intrusive. They had a fantastic charcuterie board and wine ready on our arrival and helped us with guidance and reservations multiple times throughout the week. They live in the house next door, but you wouldn't know it. All in all, one of our best AirBnB experiences in nearly a decade of stays - very highly recommended!
Superhost
Villa
4.85 out of 5 average rating, 27 reviews

Piccola Casa with pool

FaranakRating, 5 stars6 months ago
Amazing place to chill out and enjoy the nature. The pool was amazing and the house was very clean. We had an excellent time there, Thank you Anto❤️
Superhost
Villa in Provincia di Arezzo
4.91 out of 5 average rating, 43 reviews

Villa near Florence: Pool, AC, Vast natural garden

JackRating, 5 stars6 months ago
Stunning villa in a beautiful setting. Francesco gave excellent directions & the peace & tranquility out in the Tuscan countryside was wonderful. Francesco was exceptionally responsive & gave great local advice. We loved the little towns nearby and can’t wait to return soon. Highly recommended. Jack.
Guest favourite
Villa
4.92 out of 5 average rating, 61 reviews

Villa laying on Tuscany hill

KimRating, 5 stars5 months ago
The Airbnb is absolutely gorgeous. There were so many areas to lounge outside with beautiful views. The double beds were a little bit hard but the single beds were more comfortable. The grocery stores are very close to pick up any things that were not stocked at the accommodation. You must have a car to get to this location as it is on the hill on a very narrow winding road.

Destinations to explore

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