
Vacation rentals near Crete Senesi
We found 3,658 vacation rentals — enter your dates for availability
Discover a selection of vacation rentals within easy reach of Crete Senesi that can be your home away from home. Whether you’re traveling with friends, family, or even pets, vacation homes have the best amenities for hanging out with the people that matter most, including parking and a TV. No matter what you're looking for, you'll be sure to find a rental that has what everyone needs, including accessible or non-smoking choices.
Vacation rentals with weekly discounts - Crete Senesi
Showing deals for:Nov 14 - Nov 21
Image gallery for Winery Villa in the heart of Nobile Vineyards.

1010 out of 10 rating
Exceptional
(14 reviews)
Winery Villa in the heart of Nobile Vineyards.
Montepulciano, Toscana
10% off
Price is CA $662
CA $662
CA $5,310 total
CA $5,310 total
includes taxes & fees
Image gallery for FARMH. PODERE CUNINA 25 KM SUD SIENA / MONTALCINO PRENDENDO LEZIONI DI CUCINA

1010 out of 10 rating
Exceptional
(19 reviews)
FARMH. PODERE CUNINA 25 KM SUD SIENA / MONTALCINO PRENDENDO LEZIONI DI CUCINA
Buonconvento
10% off
Price is CA $218
CA $218
CA $1,908 total
CA $1,908 total
includes taxes & fees
Image gallery for Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.

1010 out of 10 rating
Exceptional
(12 reviews)
Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.
San Giovanni d'Asso, Provincia di Siena
10% off
Price is CA $2,911
CA $2,911
CA $21,565 total
CA $21,565 total
includes taxes & fees
Image gallery for Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.

1010 out of 10 rating
Exceptional
(10 reviews)
Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
Radda in Chianti, Provincia di Siena
5% off
Price is CA $2,151
CA $2,151
CA $16,127 total
CA $16,127 total
includes taxes & fees
Image gallery for Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena

1010 out of 10 rating
Exceptional
(17 reviews)
Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena
Montepulciano
10% off
Price is CA $728
CA $728
CA $5,688 total
CA $5,688 total
includes taxes & fees
Image gallery for Mulino della Solaia, Arceno Rentals Club, Luxury Villa in Tuscany, pool, wifi

1010 out of 10 rating
Exceptional
(14 reviews)
Mulino della Solaia, Arceno Rentals Club, Luxury Villa in Tuscany, pool, wifi
Monticiano, Toscana
15% off
Price is CA $1,879
CA $1,879
CA $13,975 total
CA $13,975 total
includes taxes & fees
Image gallery for Idyllic guest house in Tuscan country house style with swimming pool

1010 out of 10 rating
Exceptional
(23 reviews)
Idyllic guest house in Tuscan country house style with swimming pool
Sinalunga, Siena
10% off
Price is CA $226
CA $226
CA $1,874 total
CA $1,874 total
includes taxes & fees
Image gallery for Stunning Villa: 24 guests, private SwimmingPool

9.89.8 out of 10 rating
Exceptional
(28 reviews)
Stunning Villa: 24 guests, private SwimmingPool
Sovicille, Provincia di Siena
15% off
Price is CA $1,993
CA $1,993
CA $14,806 total
CA $14,806 total
includes taxes & fees
Image gallery for Casa di Sotto, Podere Ampella: a beautiful holiday house in the heart of Tuscany

1010 out of 10 rating
Exceptional
(8 reviews)
Casa di Sotto, Podere Ampella: a beautiful holiday house in the heart of Tuscany
Montalcino, Siena
10% off
Price is CA $357
CA $357
CA $2,813 total
CA $2,813 total
includes taxes & fees
Image gallery for Borgo dei Fondi – Tuscan Oasis with Pool, Just Minutes from Siena

9.69.6 out of 10 rating
Exceptional
(35 reviews)
Borgo dei Fondi – Tuscan Oasis with Pool, Just Minutes from Siena
Siena, Tuscany
7% off
Price is CA $248
CA $248
CA $1,949 total
CA $1,949 total
includes taxes & fees
Image gallery for Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia

1010 out of 10 rating
Exceptional
(38 reviews)
Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia
Pienza, Siena
10% off
Price is CA $699
CA $699
CA $5,460 total
CA $5,460 total
includes taxes & fees
Image gallery for Montalcino,private villa with pool in Tuscany,stunning wiews!

9.89.8 out of 10 rating
Exceptional
(16 reviews)
Montalcino,private villa with pool in Tuscany,stunning wiews!
Montalcino, Tuscany
26% off
Price is CA $838
CA $838
CA $7,138 total
CA $7,138 total
includes taxes & fees
Image gallery for Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment

9.29.2 out of 10 rating
Wonderful
(25 reviews)
Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment
Civitella in Val di Chiana, Province of Arezzo
10% off
Price is CA $395
CA $395
CA $3,370 total
CA $3,370 total
includes taxes & fees
Image gallery for Private and cozy retreat in Montalcino with private pool surrounded by vineyards

9.49.4 out of 10 rating
Exceptional
(61 reviews)
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Montalcino, Tuscany
10% off
Price is CA $313
CA $313
CA $2,605 total
CA $2,605 total
includes taxes & fees
Image gallery for Luxury Tuscan Villa in Val d'Orcia, close to Montepulciano, Pienza, and Pools!

9.49.4 out of 10 rating
Exceptional
(9 reviews)
Luxury Tuscan Villa in Val d'Orcia, close to Montepulciano, Pienza, and Pools!
Chianciano Terme, Tuscany
5% off
Price is CA $676
CA $676
CA $5,414 total
CA $5,414 total
includes taxes & fees
Image gallery for Lake House, Farm in the hills between Arezzo Florence Siena, Garden, Pool

9.49.4 out of 10 rating
Exceptional
(9 reviews)
Lake House, Farm in the hills between Arezzo Florence Siena, Garden, Pool
Pergine Valdarno, Tuscany
15% off
Price is CA $137
CA $137
CA $1,174 total
CA $1,174 total
includes taxes & fees
Image gallery for BEAUTIFUL VILLA with private Pool in the heart of Chianti

1010 out of 10 rating
Exceptional
(25 reviews)
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Castelnuovo Berardenga
7% off
Price is CA $1,354
CA $1,354
CA $10,256 total
CA $10,256 total
includes taxes & fees
Image gallery for Tuscan village in SIena. farmhouse surrounded by garden,pool and panoramic view

1010 out of 10 rating
Exceptional
(43 reviews)
Tuscan village in SIena. farmhouse surrounded by garden,pool and panoramic view
Asciano, Toscana
5% off
Price is CA $384
CA $384
CA $3,096 total
CA $3,096 total
includes taxes & fees
Image gallery for Country Farmhouse with Magnificient Gardens near Siena, Tuscany

9.69.6 out of 10 rating
Exceptional
(24 reviews)
Country Farmhouse with Magnificient Gardens near Siena, Tuscany
Siena, Toscana
10% off
Price is CA $374
CA $374
CA $3,120 total
CA $3,120 total
includes taxes & fees
Image gallery for Beautiful Private & Luxurious Tuscan Villa Near Siena/Scenic Views/Crete Senesi

1010 out of 10 rating
Exceptional
(86 reviews)
Beautiful Private & Luxurious Tuscan Villa Near Siena/Scenic Views/Crete Senesi
Castelnuovo Berardenga
5% off
Price is CA $615
CA $615
CA $4,764 total
CA $4,764 total
includes taxes & fees
Image gallery for Apartment in renovated farmhouse in typical Chianti Tuscan village

9.89.8 out of 10 rating
Exceptional
(8 reviews)
Apartment in renovated farmhouse in typical Chianti Tuscan village
Castelnuovo Berardenga, Toscana
10% off
Price is CA $163
CA $163
CA $1,575 total
CA $1,575 total
includes taxes & fees
Image gallery for Relax Palazzo Monaci

1010 out of 10 rating
Exceptional
(10 reviews)
Relax Palazzo Monaci
Asciano, Tuscany
5% off
Price is CA $292
CA $292
CA $2,417 total
CA $2,417 total
includes taxes & fees
Image gallery for Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

1010 out of 10 rating
Exceptional
(14 reviews)
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany
Siena, Toscana
10% off
Price is CA $422
CA $422
CA $3,225 total
CA $3,225 total
includes taxes & fees
Image gallery for Portion Farmhouse nestled in the heart of Chianti with private pool,

9.89.8 out of 10 rating
Exceptional
(54 reviews)
Portion Farmhouse nestled in the heart of Chianti with private pool,
Gaiole in Chianti, Tuscany
5% off
Price is CA $384
CA $384
CA $3,067 total
CA $3,067 total
includes taxes & fees
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Find the best place to stay - Crete Senesi
Beautiful old stone house with a fantastic view
Sleeps 4 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
relaxation between nature and history
Sleeps 4 · 1 bedroom · 1 bathroom
8.48.4 out of 10
Very goodvery good
5 reviews(5 reviews)
Family farmhouse in Chianti, ideal for those traveling with animals!
Sleeps 4 · 1 bedroom · 1 bathroom
Gite Montemirello, with garden and swimming pool
Sleeps 5 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
54 reviews(54 reviews)
Charming 2 Br Flat In City Center Siena Close To Piazza Del Campo
Sleeps 3 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
57 reviews(57 reviews)
Top rated rentals - Crete Senesi
Perfect Location in Montepulciano
1010 out of 10
Exceptionalexceptional
49 reviews(49 reviews)
We spent 12 days in Montepulciano on a cycling trip and the location was perfect. Located just a few steps from the main street in the Old City you have quick access to the shops, restaurants, and historic sites - not to mention a spectacular view of the Val D’Orcia valley to the east. Royce (owner) was attentive to all questions and requests.
Paul E.
Stayed Jun 2025
Fantastic time, Central location
1010 out of 10
Exceptionalexceptional
82 reviews(82 reviews)
We were a group of 4 couples and found there was plenty of room for all of us. The property as better in person than we had expected. We had a car so it was really easy to get around and see all the towns nearby. Very beautiful property with great vistas. So relaxing to hang out at the pool or the deck.
Elfrieda S.
Stayed Sep 2024
Tuscan retreat
1010 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
We had a group of 11 stay and could not have loved our time more. The location was a great central spot to drive to different towns. We loved relaxing by the pools in the afternoons and our dinners al fresco. An incredible place to spend your vacation.
Shannon H.
Stayed Jul 2024
Beautiful !
1010 out of 10
Exceptionalexceptional
90 reviews(90 reviews)
Lovely cosy converted barn, very comfortable, and just right for 6 adults. Breathtaking views !
D W.
Stayed Apr 2024
Heart warming hospitality
1010 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
Anna Maria & her daughter Lorella met us on arrival. They both were warm & welcoming. They ensured we were very comfortable with the property & surrounding amenities before they left. The property was better than described on VRBO’s site. The charm of the stone farm house can’t be appreciated in pictures. Living the experience is the only way to truly get a feeling of Tuscan living. Although the property was 9 kms from Cortona it was an easy country drive to town. We appreciated leaving the busyness of the surrounding tourist attractions and going back to the quiet farmhouse at the end of the day! Fratticciola is a small community but the local people were accepting & friendly! The hosts were exceptional. Anna Maria’s wine, vin Santa & cantucci was a nice welcoming gift. During our visit she ensured we had everything we needed & dropped off goodies from time to time. Lorella was only a text message away. She was very helpful with information on the surrounding area. This review cannot do justice in describing how exceptional Anna Maria & her family were as hosts. We will return!
Wade B.
Stayed Apr 2024
We wanted to stay forever
1010 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
We have stayed in many unique VRBOs around the world and this one rated with the very best of those in a rural setting. The view is incredible and we never tired of it. The villa is clean and comfortable with great WiFi, and the walk up to Pienza is easy for those reasonably fit and good exercise...it meant we could eat more :) Best of all were Luciana and her husband, and Fabio, who were always helpful and quick to respond to anything we needed. It was our great pleasure to meet them, and I am sure we will be staying with them again in the future. Grazie mille!
Darlene B.
Stayed Oct 2023
Perfect stay in a perfect villa with a perfect host.
1010 out of 10
Exceptionalexceptional
53 reviews(53 reviews)
Fabrizio was very welcoming, helpful when needed. The house is simply incredible, well located and well furnished. Awesome view, could not wish for more.
Simon L.
Stayed Sep 2023
Spectacular
1010 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
Our stay was absolutely amazing. The Villa, the vineyard, Montalcino, the Tuscan Hills…all breathtaking. The pictures do not do it justice. We would sit and stare at the surrounding beauty. David was a great host and very helpful and showed us the cellar, which was very interesting. We did a wine tasting at Tenuta di Nozzole in Greve and Ilaria, our host, was so lovely and informative. Angela made our check in go so smoothly.
Just a magical trip for us all.
Highly recommended.
Loved it.
Kristi A.
Stayed Sep 2023
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value