
Holiday rentals near Fortress of Tentennano
We found 2,211 holiday rentals — enter your dates for availability
Choose the perfect private holiday rental within close proximity to Fortress of Tentennano. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as a fireplace and garden. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Fortress of Tentennano
Showing deals for:26 Dec - 2 Jan
Image gallery for Hortulanus private Luxury Estate

1010 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Hortulanus private Luxury Estate
Seggiano, Toscana
9% off
Price is AU$25,947
AU$25,947
for 7 nights, 1 home
AU$3,707 per night
includes taxes & fees
Image gallery for Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.

1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.
San Giovanni d'Asso, Provincia di Siena
9% off
Price is AU$23,819
AU$23,819
for 7 nights, 1 villa
AU$3,403 per night
includes taxes & fees
Image gallery for WP RELAIS BORGO VIGNALUNGA, 46 HECTARES OF LAND IN THE HEART OF VAL D'ORCIA

1010 out of 10, Exceptional, (36 reviews)
Exceptional
(36 reviews)
WP RELAIS BORGO VIGNALUNGA, 46 HECTARES OF LAND IN THE HEART OF VAL D'ORCIA
Castiglione d'Orcia, Provincia di Siena
9% off
Price is AU$17,952
AU$17,952
for 7 nights, 1 villa
AU$2,565 per night
includes taxes & fees
Image gallery for Farmhouse, private garden and fenced swimming pool on Tuscany-Umbria border

1010 out of 10, Exceptional, (50 reviews)
Exceptional
(50 reviews)
Farmhouse, private garden and fenced swimming pool on Tuscany-Umbria border
Citta della Pieve, Umbria
9% off
Price is AU$5,964
AU$5,964
for 7 nights, 1 home
AU$852 per night
includes taxes & fees
Image gallery for Wonderful new villa in Maremma, near Montalcino and Castiglione della Pescaia

9.69.6 out of 10, Exceptional, (25 reviews)
Exceptional
(25 reviews)
Wonderful new villa in Maremma, near Montalcino and Castiglione della Pescaia
Montalcino, Toscana
9% off
Price is AU$6,247
AU$6,247
for 7 nights, 1 villa
AU$892 per night
includes taxes & fees
Image gallery for FARMH. PODERE CUNINA 25 KM SUD SIENA / MONTALCINO PRENDENDO LEZIONI DI CUCINA

1010 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)
FARMH. PODERE CUNINA 25 KM SUD SIENA / MONTALCINO PRENDENDO LEZIONI DI CUCINA
Buonconvento
8% off
Price is AU$2,956
AU$2,956
for 7 nights, 1 room
AU$422 per night
includes taxes & fees
Image gallery for Montalcino,private villa with pool in Tuscany,stunning wiews!

9.89.8 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)
Montalcino,private villa with pool in Tuscany,stunning wiews!
Montalcino, Tuscany
18% off
Price is AU$10,524
AU$10,524
for 7 nights, 1 villa
AU$1,503 per night
includes taxes & fees
Image gallery for Dream vacation home in an absolutely peaceful location

9.69.6 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)
Dream vacation home in an absolutely peaceful location
Sinalunga, Siena
9% off
Price is AU$4,666
AU$4,666
for 7 nights, 1 room
AU$667 per night
includes taxes & fees
Image gallery for Casa di Sotto, Podere Ampella: a beautiful holiday house in the heart of Tuscany

1010 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Casa di Sotto, Podere Ampella: a beautiful holiday house in the heart of Tuscany
Montalcino, Siena
9% off
Price is AU$3,849
AU$3,849
for 7 nights, 1 home
AU$550 per night
includes taxes & fees
Image gallery for Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena

1010 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)
Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena
Montepulciano
9% off
Price is AU$7,309
AU$7,309
for 7 nights, 1 villa
AU$1,044 per night
includes taxes & fees
Image gallery for Villa Banditello, secluded, panoramic view over Montepulciano valley.

1010 out of 10, Exceptional, (24 reviews)
Exceptional
(24 reviews)
Villa Banditello, secluded, panoramic view over Montepulciano valley.
Torrita di Siena, Tuscany
9% off
Price is AU$3,706
AU$3,706
for 7 nights, 1 home
AU$529 per night
includes taxes & fees
Image gallery for Idyllic guest house in Tuscan country house style with swimming pool

1010 out of 10, Exceptional, (24 reviews)
Exceptional
(24 reviews)
Idyllic guest house in Tuscan country house style with swimming pool
Sinalunga, Siena
8% off
Price is AU$1,929
AU$1,929
for 7 nights, 1 home
AU$276 per night
includes taxes & fees
Image gallery for PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - LAST WEEKS AVAILABLE

9.89.8 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - LAST WEEKS AVAILABLE
Chiusi, Toscana
7% off
Price is AU$4,824
AU$4,824
for 7 nights, 1 villa
AU$689 per night
includes taxes & fees
Image gallery for Podere Maiano - Private Pool Villa with 9 Bdrs and Spa

9.89.8 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Podere Maiano - Private Pool Villa with 9 Bdrs and Spa
Buonconvento, Tuscany
5% off
Price is AU$21,873
AU$21,873
for 7 nights, 1 villa
AU$3,125 per night
includes taxes & fees
Image gallery for Agriturismo Il Salarco: Apartment

9.69.6 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Agriturismo Il Salarco: Apartment
Montepulciano, Tuscany
9% off
Price is AU$1,870
AU$1,870
for 7 nights, 1 home
AU$267 per night
includes taxes & fees
Image gallery for Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia

1010 out of 10, Exceptional, (40 reviews)
Exceptional
(40 reviews)
Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia
Pienza, Siena
9% off
Price is AU$6,779
AU$6,779
for 7 nights, 1 villa
AU$968 per night
includes taxes & fees
Image gallery for Private and cozy retreat in Montalcino with private pool surrounded by vineyards

9.49.4 out of 10, Exceptional, (64 reviews)
Exceptional
(64 reviews)
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Montalcino, Tuscany
9% off
Price is AU$2,872
AU$2,872
for 7 nights, 1 villa
AU$410 per night
includes taxes & fees
Image gallery for CHARMING HOUSE IN HISTORIC TOWN CENTRE - ART-STUDIO In Cerca D'Autore

1010 out of 10, Exceptional, (79 reviews)
Exceptional
(79 reviews)
CHARMING HOUSE IN HISTORIC TOWN CENTRE - ART-STUDIO In Cerca D'Autore
Montepulciano, Toscana
9% off
Price is AU$3,822
AU$3,822
for 7 nights, 1 apartment
AU$546 per night
includes taxes & fees
Image gallery for Hilltop house in the heart of Tuscany with private pool

9.89.8 out of 10, Exceptional, (92 reviews)
Exceptional
(92 reviews)
Hilltop house in the heart of Tuscany with private pool
Montalcino, Siena
9% off
Price is AU$2,855
AU$2,855
for 7 nights, 1 villa
AU$408 per night
includes taxes & fees
Image gallery for Guest House Corso

1010 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Guest House Corso
Montepulciano, Provincia di Siena
13% off
Price is AU$3,075
AU$3,075
for 7 nights, 1 home
AU$439 per night
includes taxes & fees
Image gallery for FARMH. PODERE CUNINA 25 KM SUD SIENA DAVANTI AL MONTALCINO TENENDO CUCINE CLAS

1010 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
FARMH. PODERE CUNINA 25 KM SUD SIENA DAVANTI AL MONTALCINO TENENDO CUCINE CLAS
Buonconvento
8% off
Price is AU$1,813
AU$1,813
for 7 nights, 1 room
AU$259 per night
includes taxes & fees
Image gallery for AUTUMN agr.LA GUINZA) Ideal for a large family. Guaranteed relaxation and nature

9.89.8 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
AUTUMN agr.LA GUINZA) Ideal for a large family. Guaranteed relaxation and nature
Arcidosso
14% off
Price is AU$2,095
AU$2,095
for 7 nights, 1 apartment
AU$299 per night
includes taxes & fees
Image gallery for Villa Mulinello, secluded, panoramic view over Montepulciano valley.

1010 out of 10, Exceptional, (35 reviews)
Exceptional
(35 reviews)
Villa Mulinello, secluded, panoramic view over Montepulciano valley.
Torrita di Siena, Tuscany
9% off
Price is AU$3,458
AU$3,458
for 7 nights, 1 home
AU$494 per night
includes taxes & fees
Image gallery for Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome

1010 out of 10, Exceptional, (111 reviews)
Exceptional
(111 reviews)
Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome
Cetona
9% off
Price is AU$6,583
AU$6,583
for 7 nights, 1 room
AU$940 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Fortress of Tentennano
Il Casale Di Manuele 12, Emma Villas
Sleeps 12 · 6 bedrooms · 7 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
64 reviews(64 reviews)
Villa in Montalcino, exclusive for you, stunning view!!!
Sleeps 11 · 5 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
84 reviews(84 reviews)
Hilltop house in the heart of Tuscany with private pool
Sleeps 5 · 2 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
92 reviews(92 reviews)
The House of Alice, charm and relaxation
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
64 reviews(64 reviews)
Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia
Sleeps 13 · 4 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
40 reviews(40 reviews)
Top rated rentals - Fortress of Tentennano
Excellent
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Very helpful host and beautiful apartment.
Lani W.
Stayed Apr 2025
Monticchiello
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
A wonderful quiet apartment with everything you need . Comfortable bed, good a/c, good shower, well equipped kitchen, lovely host. All uphill from the car park but that’s what you expect in a hilltop village. Excellent restaurants in the village. Not far from Pienza . And a washing machine and dryer!
Linda M.
Stayed Apr 2025
Beautiful stay
1010 out of 10
Exceptionalexceptional
54 reviews(54 reviews)
We received a warm welcome from the family and a thorough explanation of the facilities, the surrounding area and places of interest. Fabrizio communicated easily with us using the translation phone app. The apartment is very clean, well equipped and offers a genuine Italian experience. Simply wonderful.
Murray H.
Stayed Oct 2024
Beautiful cottage
1010 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
The cottage was used in conjunction with the Villa on the property , for our family holiday , and provided beautiful accommodation in every way .
Thank you Luca and team .
Mike and family
MICHAEL P.
Stayed May 2024
Great place
1010 out of 10
Exceptionalexceptional
54 reviews(54 reviews)
A great apartment in a lovely Tuscan village. Host was extremely helpful and available at all times. Would recommend.
Sharon B.
Stayed Apr 2024
Absolutely Fabulous
1010 out of 10
Exceptionalexceptional
95 reviews(95 reviews)
My family and I had been planning a trip to Tuscany for over 10 years, then one day we just decided it was time to go, so after much research, I found this gorgeous villa in Arcidosso, and booked it. I have never looked back. From the moment I booked the villa, it just felt right. Margo and Marco met us in Arcidosso where they escorted us to the villa. I fell in love with it from the moment I saw it. It was better to look at in real life than the pictures. It was absolutely perfect. The villa was equipped with everything you needed for a perfect stay. Marco and Marta had left us a bottle of red wine, some pasta and sauce which was a lovely touch as we had arrived in Arcidosso late. We stayed a week and that was certainly not long enough. We didn’t get to experience the pool as we were out most days and the two days we stayed at the villa it was a cooler day. Marta gave us a list of places to visit which we did all but two. If you have time, I recommend the little town called Pitigliano, it was so gorgeous. She also gave us a list of restaurants to go to as well as where the nearest supermarket was. I also needed the hair dresser as we had been travelling for 5 weeks and I needed a freshen up, so Marta booked the hairdressers for me. She was always there, on hand if we needed anything. On check out, M & M called by to pick up the keys. It was sad leaving the villa but equally sad having to say goodbye to Marta and Marco. They were super hosts. 100% recommend this villa.
Sue S.
Stayed Sept 2023
Fabulous in every way
1010 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
Just divine location, magnificent view...friendly hosts and lovely Tuscan house. We loved our stay with our 8 month old baby!
Stephanie B.
Stayed May 2019
Absolutely stunning! Highly recommend!
1010 out of 10
Exceptionalexceptional
75 reviews(75 reviews)
My family and I stayed here in late September and had a fabulous time. The house has everything you need including a bbq (we are Australians so this is essential on a holiday), pool and an AMAZING view. The house is close enough to Sarteano to feel part of the village but far away enough to be very quiet and secluded! It provided a great base to explore the beautiful hill towns in this part of Italy!!
Lauren B.
Stayed Sept 2018
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- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value