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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 509 Villas in Montescudaio with updated reviews, rates, and availability.

Beautiful six bed seven bath Tuscan farmhouse in the Volterra hills.
Exterior

Beautiful six bed seven bath Tuscan farmhouse in the Volterra hills.

Beautiful six bed seven bath Tuscan farmhouse in the Volterra hills.
Villa with view and private pool
Pool

Villa with view and private pool

10.0 out of 10, Exceptional, (20)
"We loved the villa and the location. We couldn’t have asked for a better view giving us a wonderful feeling of Tuscany. The closeness to Volterra, coupled with the great supermarket and lovely pizzerias made it special. Guilia was very responsive and helpful at all times. We would come back in a heartbeat. "
Villa with view and private pool
Luxury villa, infinity pool, chef, pizzaiolo, massages, yoga, grocery delivery
Pool

Luxury villa, infinity pool, chef, pizzaiolo, massages, yoga, grocery delivery

10.0 out of 10, Exceptional, (132)
"My family and I spent the last week at the villa and had a wonderful time despite some rainy weather. The villa is in a beautiful location, well maintained and extremely clean. We booked an onsite chef who prepared a fabulous dinner, we also booked the pizza chef who created the best pizza we had on the trip, he is a true artist! Valerio is an excellent host, very accessible and quickly responds to any questions or requests. We would not hesitate to stay here in the future. I highly...
Luxury villa, infinity pool, chef, pizzaiolo, massages, yoga, grocery delivery
Historic mill with private swimming pool
Living area

Historic mill with private swimming pool

Historic mill with private swimming pool
Country villa with pool 5 minutes from spa center
Exterior

Country villa with pool 5 minutes from spa center

Country villa with pool 5 minutes from spa center
Villa Casa Collina - Castelfalfi - Tuscany - Saltwater pool- Airco & VIP Service
Pool with seating area Villa Casa Collina

Villa Casa Collina - Castelfalfi - Tuscany - Saltwater pool- Airco & VIP Service

Villa Casa Collina - Castelfalfi - Tuscany - Saltwater pool- Airco & VIP Service
3-person apartment in Tuscan farmhouse
Room

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
Comfortable Tuscany Family House with Private Pool close to beach and wine area
Pool with 8 beach chairs and 3 umbrellas.

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

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

9.8 out of 10, Exceptional, (40)
"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
Casa Bianca Villa with sea view by ToscanaTour
Pool

Casa Bianca Villa with sea view by ToscanaTour

9.8 out of 10, Exceptional, (7)
"Very nice stay in a beautiful house with a great pool and extremely friendly support staff"
Casa Bianca Villa with sea view by ToscanaTour
Villa Osservatorio for up to 11 with private pool, 15mins to San Gimignano
Pool

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

10.0 out of 10, Exceptional, (43)
"Great property - well located for interesting day trips."
Villa Osservatorio for up to 11 with private pool, 15mins to San Gimignano
Villa "Cristina" with Sea View, Private Pool & Wi-Fi
Exterior

Villa "Cristina" with Sea View, Private Pool & Wi-Fi

9.2 out of 10, Wonderful, (7)
"This was the perfect experience. The house, which we found out had only become available this year for rentals, was wonderful. It was comfortably and stylishly furnished and had everything we needed. The only thing missing was an induction compatible coffee maker - which the gracious property owner hand-delivered to us! The property, a short walk from Riparbella, had wonderful views to the ocean and the breezes to match. The area is rich with wine-making and fun to explore. I would highly...
Villa "Cristina" with Sea View, Private Pool & Wi-Fi
Iane's house

Iane's house

8.0 out of 10, Very Good, (9)
"Bis auf die fehlende Klimaanlage alles empfehlenswert"
Iane's house
PODERE LIVRONE- WITH SWIMMING POOL
Pool

PODERE LIVRONE- WITH SWIMMING POOL

10.0 out of 10, Exceptional, (3)
"Wir hatten eine tolle Woche in der Unterkunft und würden jederzeit wieder buchen. Veronica ist eine super Gastgeberin, die stets für Fragen zur Verfügung steht und tolle Tipps gibt."
PODERE LIVRONE- WITH SWIMMING POOL
Vallegaia estate, complete relaxation with swimming pool, tennis, football
Porch view

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

9.8 out of 10, Exceptional, (53)
"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
Villa for groups and families, with Private Pool in Monteverdi Marittimo
Pool

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

8.6 out of 10, Excellent, (11)
"A quiet, idyllic place to relax. We enjoyed it very much"
Villa for groups and families, with Private Pool in Monteverdi Marittimo
Single Villa in the hills with private pool, garden and wood
Pool

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

9.8 out of 10, Exceptional, (50)
"We had a wonderful stay in Federica’s home. The property is very spacious and is in a stunning, peaceful rural setting nestled amongst the olive groves / vineyards nr Riparbella. Check in was very easy and Federica was always at the end of the phone for any questions we had. The pool was delightful and a welcome antidote to the July heat! We were travelling with our 7 month old baby and Federica provided a lovely cot for him. The kitchen was very well equipped and we made good use of the BBQ on...
Single Villa in the hills with private pool, garden and wood
Pisa Florence: charming vacation villa with private garden, swimming pool
Pool

Pisa Florence: charming vacation villa with private garden, swimming pool

9.4 out of 10, Exceptional, (6)
"The house is very spacious Just like the garden. We had to share the pool which we didn't know but that turbed out okay. The cutlery and crockery weren 't very clean maybe because the dishwasher didn't work properly. The host / property manager on the other hand was great and helpen us a lot with everything. We had a wonderfull week!"
Pisa Florence: charming vacation villa with private garden, swimming pool
Extra privacy, Dog friend, Special Children, Unspoiled nature, Sea
Outdoor dining

Extra privacy, Dog friend, Special Children, Unspoiled nature, Sea

8.8 out of 10, Excellent, (5)
"Nonostante il breve periodo di permanenza la struttura era splendida, in un’incantevole scenario di alta collina. Il proprietario estremamente affabile e disponibile per ogni nostra necessità."
Extra privacy, Dog friend, Special Children, Unspoiled nature, Sea
Villa with pool, enclosed garden and beautiful sea view
Outdoor dining

Villa with pool, enclosed garden and beautiful sea view

10.0 out of 10, Exceptional, (8)
"Beautiful location a short walk from the amazing little village of Casale"
Villa with pool, enclosed garden and beautiful sea view
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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Other property types in Montescudaio

Hu Montescudaio Village
Water park

Hu Montescudaio Village

3.0 star property
9.4 out of 10, Exceptional, (16)
"Camping bellissimo e davvero ben curata. Le casette ben fatte, curate in ogni dettaglio e pulite. Abbiamo trascorso due giorni bellissimi e abbiamo già prenotato due date alla riapertura!!"
Hu Montescudaio Village
Fattoria La Steccaia
Outdoor spa tub

Fattoria La Steccaia

Fattoria La Steccaia
a family holiday home with plenty of space for the whole family.
Exterior

a family holiday home with plenty of space for the whole family.

8.4 out of 10, Very Good, (5)
"Super schön, vor allem super hilfsbereit, nachdem wir einen Unfall mit dem Auto hatten. So nette Leute , dadurch war der Urlaub wie ein Traum. Trotz aller Miseren, wir kommen wieder , einfach nur schön."
a family holiday home with plenty of space for the whole family.
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.