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Villa vacation rentals in Massa Marittima

Find and book unique villas on Airbnb

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Popular amenities for Massa Marittima villa rentals

Private villa rentals

Guest favorite

Villa in Bucine

4.96 out of 5 average rating, 23 reviews

Charming property, wi-fi, weddings ,cooking class

ColetteRating, 5 stars7 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.
Guest favorite

Villa in Pergine Valdarno

4.82 out of 5 average rating, 17 reviews

Exclusive Villa with Private Pool and Air Cond.

KaraRating, 5 stars7 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 in Marlia

4.87 out of 5 average rating, 23 reviews

Charming Villa -private swimming pool -16 people.

LauraRating, 5 stars6 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.
Superhost

Villa in Capoliveri

5 out of 5 average rating, 3 reviews

EXCLUSIVE ENTIRE VILLA A STEP FROM THE SEA

manuelaRating, 5 stars28 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.
Superhost

Villa in Reggello

4.69 out of 5 average rating, 13 reviews

Villa, A/C,saltwater pool,sauna,near Mall outlet

MariaRating, 5 stars9 months ago
Luxurious large villa in beautiful Tuscany perfectly suited for a large party. Large, clean rooms and a well equipped kitchen as well as ample space for meals and lounging. Rurally located at end of simple road with its own little park and stunning views. Most of Tuscany within an hours drive or less (Florence, Siena, Chianti, Montepulciano, etc.) Our host Elena was very communicative and helpful and made our visit highly enjoyable. Well recommended!!
Guest favorite

Villa in San Leolino

5 out of 5 average rating, 105 reviews

Poggio del Fattore-Villa with pool,hilltop,Chianti

VeraRating, 5 stars3 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 favorite

Villa in Castelfranco di sotto

5 out of 5 average rating, 14 reviews

Villa Montefalcone: Charm, Private Pool, and Chef

JulieRating, 5 stars4 months ago
Wow. Best Airbnb I’ve ever stayed in. From booking to checkout everything was smooth and easy. The property was amazing , grounds were amazing, house was absolutely stunning. The communication from the team was perfect. We hired a sommelier for a night through the Airbnb and it was the best experience. You really need a car or hire a driver through the Airbnb. Lucce and Pisa are close. We loved montecarlo(nearby village) with all the various great vineyards. All in all a great experience. Hopefully will be back soon. Thank you to a great team.
Guest favorite

Villa in Seccheto

4.82 out of 5 average rating, 39 reviews

Villa in Solana, Elba Island - Seccheto

Priya PhilipRating, 5 stars5 months ago
The accommodation was in great condition, with freshly washed sheets and bathroom kits closed and provided by the laundry room. We were in a group of 9 and the house had comfortable spaces for everyone, both internally and on the small outdoor garden. The host has always been absolutely available to us, both at check-in and when we called him for advice or other reasons. Attention only and exclusively to the location, very panoramic and in an absolutely quiet place, but walking from the beach, although not impossible, involves a walk with a steep climb.

Luxury villa rentals

Superhost

Villa in Pietrasanta

4.86 out of 5 average rating, 85 reviews

Palatine 1 Colina Pietrasanta Forte dei marmi

MarinaRating, 5 stars5 months ago
Here is the final version of the review: --- We had a wonderful stay! The property offers a breathtaking view of the sea that we enjoyed every day, especially at the fantastic sunsets. The pool was beautiful and very well maintained, perfect for relaxing. The surroundings were quiet and peaceful, which really helped us relax. We also particularly liked the olive trees on the property, which gave the whole thing a special charm. The hosts were always available and very helpful. Highly recommended to anyone looking for a quiet getaway with fantastic amenities!
Guest favorite

Villa in Palaia

5 out of 5 average rating, 8 reviews

Villa La Gemma

DeryaRating, 5 stars4 months ago
The stay was beautiful! The villa was amazing, the view, the furniture, the rooms and the pool. We felt so lucky to be there. Rooms were new and clean. Every detail has been taken care of. Christina was incredibly helpful and always available. We'd be stuck without them. Unfortunately, we had more private problems and every time she helped us and brought us solutions. We, me and my friends, this stay was memorable!
Guest favorite

Villa in Camaiore

4.97 out of 5 average rating, 60 reviews

Villa Le Silerchie

UlrikeRating, 5 stars3 months ago
We were there with two families/4 days - in October, which is unfortunately more the usual rainy season in Tuscany. Nevertheless, we always had pleasantly mild temperatures, even sunny days, and a great vacation. The house is just wonderful, there is just nothing missing! After the sauna, we were also able to use the pool well, and for us "northern lights" the temperatures were summery and perfect for excursions (so not too hot ). The location is totally idyllic and ideal for excursions to Lucca, Pisa, Pietrasanta but also to smaller mountain villages in the vicinity (Metato, etc.).
Luxe

Villa in Radda in Chianti

5 out of 5 average rating, 5 reviews

Villa Montemaggio

HongmeiRating, 5 stars4 months ago
Absolutely gorgeous and luxurious place. Beautifully decorated, beautiful views, clean and also had an incredible kitchen. We loved it!
Guest favorite

Villa in Fiesole

4.86 out of 5 average rating, 22 reviews

Villa Lualdi

SallyRating, 5 stars4 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.
Guest favorite

Villa in Capannori

4.92 out of 5 average rating, 12 reviews

Villa with swimming pool, air conditioning, Wi-Fi

Marie VintherRating, 5 stars3 months ago
We had a lovely stay. Fantastic house. Easy and fast communication. Elena recommended two restaurants which were all absolutely fantastic.
Guest favorite

Villa in Impruneta

5 out of 5 average rating, 136 reviews

VILLA Amazing pool , tennis , 7km Florence,

AnnRating, 5 stars2 months ago
Exceptional villa just outside of Florence! Our family of 6 spent 5 blissful nights in this amazing home and loved every minute! The property/view is breathtaking! The villa is filled with comfortable furnishings/linens/beds! The tennis court, hot tub and outside kitchen made for extra-special fun! We visited late November but could still take advantage of all of the amazing outdoor spaces/activities and views!! We used the villa as a home-base for exploring Florence and Tuscany and it was absolutely PERFECT for us in every way!!! And the icing on the cake: Cinzia and Chef Patrizia are both INCREDIBLE!!! Cinzia’s hospitality was exceptional and Chef Patrizia wowed us with her incredible cooking skills and warm and positive presence. We booked her for 3 memorable meals (one of which was a cooking lesson that thrilled all ages!)! She is our new best friend and we can’t wait to go back to visit the beautiful villa and lovely people that captured our hearts!!!
Superhost

Villa in Florence

4.8 out of 5 average rating, 40 reviews

Villa with great view over Florence, pool, Wi-Fi

TinaRating, 5 stars4 months ago
Lorenzo was a fantastic host. Any question we had he answered straight away. The villa was lovely, peaceful and the views were amazing. When we arrived at the villa Mario was there to meet us. He then drove us to the supermarket and helped us with our shopping, he couldn’t have been more helpful! The bus stop is just up the road so getting into Florence was easy. At the end of our holiday Mario drove us to the airport as we were having trouble getting a taxi. Nothing was too much trouble. This was a holiday to remember! Thank you Lorenzo & Mario

Villa rentals with a pool

Guest favorite

Villa in Montecucco

4.9 out of 5 average rating, 39 reviews

Villa Angiolina

ErinRating, 5 stars3 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 in Rosignano Solvay-Castiglioncello

4.8 out of 5 average rating, 134 reviews

Villa with cliffside pool

SolveigRating, 5 stars3 months ago
The place is an absolute place to yearn. The view of the sea priceless. We were lucky enough to stay alone on the property almost the entire time. The amenities are functional and you have everything you need. Everything was clean and tidy, there is nothing to complain about. The decor is familiar with personal things of the family but that's exactly what I love about AirBnB. I was very reminded of my former family weekend house. We certainly weren't here last time and I thank Fabio&Valentina for sharing this wonderful place with others.
Superhost

Villa in Petrognano

4.86 out of 5 average rating, 7 reviews

Villa Iris with Swimming Pool

KateRating, 5 stars4 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!
Guest favorite

Villa in La Poggerina

4.97 out of 5 average rating, 37 reviews

Villa La Poggerina, private pool and amazing view

BryanRating, 5 stars4 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 in Camaiore

4.85 out of 5 average rating, 27 reviews

Piccola Casa with pool

FaranakRating, 5 stars5 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❤️
Guest favorite

Villa in Montaione

4.95 out of 5 average rating, 22 reviews

Private Villa with semi-Olympic pool and Tennis

SuzanneRating, 5 stars3 months ago
Francesca’s home was beautiful and in a breathtaking, peaceful location. There is a short, beautiful walk with Mountain View’s and olive groves to an incredible pool and pool house. She was incredibly helpful in helping us not only access the home, but also in providing us local recommendations. The meal that Ettore prepared for us was one of the highlights of our trip.
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 stars5 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.
Superhost

Villa in Castel San Niccolò

4.67 out of 5 average rating, 3 reviews

Podere Varlunga

SylwiaRating, 5 stars33 months ago
everything was ok, place is clean and really nice

Destinations to explore

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