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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23
In four months
Dec 19 - Dec 21

Browse Select Montescudaio Villas

Historic villa in the heart of Tuscany. Surrounded by nature.
Outdoor pool

Historic villa in the heart of Tuscany. Surrounded by nature.

9.8 out of 10, Exceptional, (42)
"Really great property to stay in for our family of 16. Clemente responded quickly to queries & had useful suggestions & tips for visiting restaurants & towns/villages. Loved our stay & would hope to return again."
Historic villa in the heart of Tuscany. Surrounded by nature.
Fantastic new villa near the sea in one of the most beautiful areas of Tuscany
Outdoor dining

Fantastic new villa near the sea in one of the most beautiful areas of Tuscany

10.0 out of 10, Exceptional, (12)
"Wir hatten einen wundervollen Urlaub in einem außergewöhnlich tollen Haus in der Nähe von Pomaia. Wir haben das Haus mit 10 Personen und einem Kleinkind bewohnt und es fehlte an nichts. Die Gastgeber Sabine und Klaus sind unglaublich freundlich, hilfsbereit und schaffen direkt eine Wohlfühlatmosphäre. Angefangen bei einem herzlichen Empfang in der Bar in Pomaia, über einen perfekten Poolservice alle 2-3 Tage, zahlreichen Tipps und Tischreservierungen haben wir diesen Service und die sehr...
Fantastic new villa near the sea in one of the most beautiful areas of Tuscany
Villa Cresci with pool 5 minutes from spa center
Outdoor pool

Villa Cresci with pool 5 minutes from spa center

Villa Cresci with pool 5 minutes from spa center
Villa Osservatorio for up to 11 with private pool, 15mins to San Gimignano
Exterior

Villa Osservatorio for up to 11 with private pool, 15mins to San Gimignano

10.0 out of 10, Exceptional, (44)
"Great property - well located for interesting day trips."
Villa Osservatorio for up to 11 with private pool, 15mins to San Gimignano
Villa near San Gimignano, with pool, air conditioning, and beautiful views
Outdoor pool

Villa near San Gimignano, with pool, air conditioning, and beautiful views

Villa near San Gimignano, with pool, air conditioning, and beautiful views
3-person apartment in Tuscan farmhouse
Outdoor spa tub

3-person apartment in Tuscan farmhouse

10.0 out of 10, Exceptional, (4)
"Nice appartment. Great views of Tuscan countryside. Close to Riparbella which has restaurants and shops and about 10km to the coast."
3-person apartment in Tuscan farmhouse
Single Villa in the hills with private pool, garden and wood
Property grounds

Single Villa in the hills with private pool, garden and wood

10.0 out of 10, Exceptional, (56)
"Frederica was an incredible host, and the villa was perfect for our young family. Stunning location, the perfect holiday!"
Single Villa in the hills with private pool, garden and wood
Tuscany Villa with private pool and jacuzzi for Honeymoon and summer holiday
Exterior

Tuscany Villa with private pool and jacuzzi for Honeymoon and summer holiday

10.0 out of 10, Exceptional, (34)
"We all had a wonderful holiday. The villa was lovely and so well equipped. The garden, hot tub and especially the pool were amazing!! Gina and Franco were so kind to bring us wonderful treats during the stay and left a very generous welcome basket. Absolutely fantastic place for a holiday. We hope to return one day!"
Tuscany Villa with private pool and jacuzzi for Honeymoon and summer holiday
Luxury Villa + A/C Dépendance, Whirlpool, infinity Pool, Chef, Pizza, massage
Outdoor pool

Luxury Villa + A/C Dépendance, Whirlpool, infinity Pool, Chef, Pizza, massage

10.0 out of 10, Exceptional, (134)
"Wonderful outdoor space, lots of rooms and space, and amazing and helpful owner. Bellissimo!"
Luxury Villa + A/C Dépendance, Whirlpool, infinity Pool, Chef, Pizza, massage
Vallegaia estate, complete relaxation with swimming pool, tennis, football
Outdoor pool

Vallegaia estate, complete relaxation with swimming pool, tennis, football

9.6 out of 10, Exceptional, (54)
"The location, size, facilities and accuracy were all amazing. The kids loved the pool with the slide, hard to get them out of the water ! Owner was on hand whenever we needed anything. GREAT !"
Vallegaia estate, complete relaxation with swimming pool, tennis, football
Iane's house
Marina

Iane's house

8.0 out of 10, Very good, (9)
"The house is as described. It is one half of a house, that is rented as well, so there can be other people around. A downside is that the house is up a steep hill. The road is small and needs some courage, but is totally do-able. We mostly drove by car instead of walking up and down. An upside is the cute neighbours cat, which visites occasionally. The landlady is very kind and even asked during the stay if everything is alright. All in all a great stay 👍"
Iane's house
Villa for groups and families, with Private Pool in Monteverdi Marittimo
Outdoor pool

Villa for groups and families, with Private Pool in Monteverdi Marittimo

8.8 out of 10, Excellent, (12)
"A quiet, idyllic place to relax. We enjoyed it very much"
Villa for groups and families, with Private Pool in Monteverdi Marittimo
Villa Poggialto, breathtaking views, large pool and private spa in luxury
Outdoor pool, a heated pool

Villa Poggialto, breathtaking views, large pool and private spa in luxury

9.4 out of 10, Exceptional, (6)
"Your video is captivating BUT REALITY IS EVEN MORE STUNNINGLY BEAUTIFUL..AN OASIS OF PACE AND RELAX. Picturesque views of wooded hills surround enormous pool...swimming at sunset is an .unforgetable emotion plus there is the SPA.. great fun..even at cocktail hour..booking masseuse..an added joy! we all fell in love with..this glorious but functional property Bedrooms are spacious and insuite bathrooms are too. Kingsize beds are very comfotable. See you soon! Josephine"
Villa Poggialto, breathtaking views, large pool and private spa in luxury
Comfortable Tuscany Family House with Private Pool close to beach and wine area
Pool

Comfortable Tuscany Family House with Private Pool close to beach and wine area

Comfortable Tuscany Family House with Private Pool close to beach and wine area
Luxury stone house, large private pool and stunning seaview, 3 golf courses nearby
Outdoor dining

Luxury stone house, large private pool and stunning seaview, 3 golf courses nearby

10.0 out of 10, Exceptional, (2)
"We had a great stay. Perfect areas outside the house, great pool and many spot to sit outside. The best spot for our family was the terrasse and the pool. A unique view from the terrasse and pool area. We solid love to come back. "
Luxury stone house, large private pool and stunning seaview, 3 golf courses nearby
House with 6 Bedrms, 5 Bathrms, 5min walk trough a private grove to the beach
Outdoor dining

House with 6 Bedrms, 5 Bathrms, 5min walk trough a private grove to the beach

9.8 out of 10, Exceptional, (19)
"After a busy week in the city, this was the perfect change of pace. The house fit our large family, the walk to the beach was easy, the grounds were manicured and spacious. It was so relaxing. Desi was a fantastic host."
House with 6 Bedrms, 5 Bathrms, 5min walk trough a private grove to the beach
Master Apartment in Residence by the sea set in typical Mediterranean vegetation
Pool

Master Apartment in Residence by the sea set in typical Mediterranean vegetation

9.8 out of 10, Exceptional, (42)
"First time in Tuscany and totally in love! Property with beuatiful landscape, marvellous garden, beautiful pool, nice gym and helpful, friendly stuff. Sure that will be back in the future."
Master Apartment in Residence by the sea set in typical Mediterranean vegetation
country villa with private pool between Bolgheri & Castagneto 5 km from the sea
Property grounds

country villa with private pool between Bolgheri & Castagneto 5 km from the sea

8.6 out of 10, Excellent, (14)
"Schöne super große Unterkunft auf einem umzäunten Gelände. Pool ist super und ebenfalls umzäunt. Kleine Grillstelle und Outfoorküche die wir immer genutzt haben"
country villa with private pool between Bolgheri & Castagneto 5 km from the sea
Villa Picchio - Holiday Villa Rental in Castel San Gimignano, Chianti, Tuscany
Property grounds

Villa Picchio - Holiday Villa Rental in Castel San Gimignano, Chianti, Tuscany

9.6 out of 10, Exceptional, (39)
"Excellent."
Villa Picchio - Holiday Villa Rental in Castel San Gimignano, Chianti, Tuscany
Private villa with pool and Jacuzzi in Tuscany - Exclusive use
Exterior

Private villa with pool and Jacuzzi in Tuscany - Exclusive use

10.0 out of 10, Exceptional, (11)
"We have had the best time staying here! Myself, husband and family. The communication and help prior to staying was excellent. The accommodation is excellent, well equipped and very clean, well laid out but above all beautiful. The views from the house are stunning, as is the local area. Everything we imagined Tuscany would be. So many nice touches that are not depicted in the photo’s. The pool / hottub area is fantastic. Beds comfortable. Showers great. Shutters on windows for a good nights...
Private villa with pool and Jacuzzi in Tuscany - Exclusive use
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Montescudaio Hotel Reviews

Castelfalfi

Castelfalfi

10/10 Excellent
"It was the best resort we have ever visited. "
vito 5-night trip
Posted 2 days ago
Castelfalfi

Find out more about Montescudaio

Find out more about Montescudaio

Montescudaio Villas information

Number of reviews
191
Accommodation
685 Villas
Lowest Price
Highest Price