Location

Dates

Guests

Vacation rentals in Province of Siena, Tuscany, Italy

Villa dei 2 Ulivi (Abbadia Isola)

(R6) living room with 2 double sofa beds

Gas BBQ, for your perfect Fiorentina steak

Villa dei 2 Ulivi (Abbadia Isola)

Villa dei 2 Ulivi (Abbadia Isola)

6 bedrooms·4 baths

Monteriggioni • Tuscany

5(232 reviews)

€1,566.00 EUR total for 3 nights

Sep 21 – 24, 2026

Free cancellation

Luxury Serviced Family Villa - Pool/Hot Tub *A/C* image 1

Main entrance w/ parking for 4-6 cars.

Tuscan sunset view from downtown Montepulciano

Living room + Samsung Frame 65" smart TV.

Dining room table + chairs for 10-12 + bar seating (multiple children's/high chairs available).

Luxury Serviced Family Villa - Pool/Hot Tub A/C

6 bedrooms·3 baths

Montepulciano • Tuscany

5(23 reviews)

$1,993/ night(excl. fees & taxes)

Apartment in the historic center | Campagnatico image 1

Apartment in the historic center | Campagnatico image 2

Apartment in the historic center | Campagnatico image 3

Apartment in the historic center | Campagnatico image 4

Apartment in the historic center | Campagnatico image 5

Apartment in the historic center | Campagnatico

1 bedroom·1 bath

Campagnatico • Tuscany

4.7(23 reviews)

€290.40 EUR total for 3 nights

Sep 16 – 19, 2026

Luxury villa, chef, massage, yoga, home shopping

Luxury villa, chef, massage, yoga, home shopping

Luxury villa, chef, massage, yoga, home shopping

Luxury villa, chef, massage, yoga, home shopping

Luxury villa, chef, massage, yoga, home shopping

Luxury villa, chef, massage, yoga, home shopping

5 bedrooms·5 baths

Volterra • Tuscany

5(18 reviews)

€5,600.00 EUR total for 7 nights

Oct 24 – 31, 2026

Free cancellation

Kitchen / Entrance

The Corte del Podestà image 5

The Corte del Podestà

1 bedroom·1 bath

Sarteano • Tuscany

5(12 reviews)

$432.00 USD total for 3 nights

Sep 21 – 24, 2026

comfortable living room on the ground floor

kitchen on the ground floor

entrance, living room and study corner on the ground floor

kitchen on the ground floor

kitchen and living room on the ground floor

Your oasis in the heart of Tuscany

1 bedroom·1 bath

Arezzo • Tuscany

4.85(65 reviews)

€258.00 EUR total for 3 nights

Sep 7 – 10, 2026

La Smarrita

5 bedrooms·7 baths

Province of Arezzo • Tuscany

€1,324.00 EUR total for 4 nights

Oct 18 – 22, 2026

Aerial photography

Aerial photography

Casa Frati

4 bedrooms·4 baths

Castiglione d'Orcia • Tuscany

€1,237.00 EUR total for 3 nights

Sep 16 – 19, 2026

Nido del Sorbino

Nido del Sorbino

Nido del Sorbino

Nido del Sorbino

Nido del Sorbino

Nido del Sorbino

1 bedroom·1 bath

Castiglion Fiorentino • Tuscany

€768.00 EUR total for 7 nights

Oct 17 – 24, 2026

Sissi

3 bedrooms·3 baths

San Gimignano • Tuscany

€1,746.00 EUR total for 7 nights

Sep 20 – 27, 2026

Antico Borgo S Lorenzo Cipresso

Antico Borgo S Lorenzo Cipresso

Antico Borgo S Lorenzo Cipresso

Antico Borgo S Lorenzo Cipresso

Antico Borgo S Lorenzo Cipresso

Antico Borgo S Lorenzo Cipresso

2 bedrooms·1 bath

Colle di Val d'Elsa • Tuscany

€723.00 EUR total for 3 nights

Sep 7 – 10, 2026

Le Buche

3 bedrooms·2 baths

Tuscany

€1,107.00 EUR total for 4 nights

Sep 15 – 19, 2026

Kitchen / Dining Room

Aerial photography

Boccaccio

2 bedrooms·1 bath

San Donato • Toscana

Val d'Orcia

5 bedrooms·5 baths

Radicofani • Tuscany

€1,356.00 EUR total for 3 nights

Sep 7 – 10, 2026

Podere dei Venti

Podere dei Venti

Podere dei Venti

Podere dei Venti

Podere dei Venti

Podere dei Venti

6 bedrooms·6 baths

Castel del Piano • Tuscany

€1,731.00 EUR total for 5 nights

Sep 19 – 24, 2026

Kitchen / Dining Room

Poggio all'Aia

4 bedrooms·4 baths

Casole d'Elsa • Tuscany

€892.00 EUR total for 3 nights

Sep 30 – Oct 3, 2026

Aerial photography

Il Lamone

2 bedrooms·1 bath

Ambra • Tuscany

€920.00 EUR total for 5 nights

Oct 3 – 8, 2026

Casale Il Poggino

Casale Il Poggino

Casale Il Poggino

Casale Il Poggino

Casale Il Poggino

7 bedrooms·6 baths

Tuscany

$837 – $1,451/ night(excl. fees & taxes)

Antico Borgo San Lorenzo - Fico

Antico Borgo San Lorenzo - Fico

Antico Borgo San Lorenzo - Fico

Antico Borgo San Lorenzo - Fico

Antico Borgo San Lorenzo - Fico

Antico Borgo San Lorenzo - Fico

2 bedrooms·1 bath

Colle di Val d'Elsa • Tuscany

€653.00 EUR total for 3 nights

Sep 7 – 10, 2026

Antico Borgo S LorenzoAlbicocco

Antico Borgo S LorenzoAlbicocco

Antico Borgo S LorenzoAlbicocco

Antico Borgo S LorenzoAlbicocco

Antico Borgo S LorenzoAlbicocco

Antico Borgo S LorenzoAlbicocco

1 bedroom·1 bath

Colle di Val d'Elsa • Tuscany

€729.00 EUR total for 4 nights

Oct 19 – 23, 2026

Antico Borgo San Lorenzo-Alloro

Antico Borgo San Lorenzo-Alloro

Antico Borgo San Lorenzo-Alloro

Antico Borgo San Lorenzo-Alloro

Antico Borgo San Lorenzo-Alloro

Antico Borgo San Lorenzo-Alloro

1 bedroom·1 bath

Colle di Val d'Elsa • Tuscany

€547.00 EUR total for 3 nights

Sep 7 – 10, 2026

Antico Borgo San Lorenzo

Antico Borgo San Lorenzo

Antico Borgo San Lorenzo

Antico Borgo San Lorenzo

Antico Borgo San Lorenzo

Antico Borgo San Lorenzo

18 bedrooms·13 baths

Colle di Val d'Elsa • Tuscany

€9,926.00 EUR total for 4 nights

Oct 19 – 23, 2026

Le Sodole - Petunia

Le Sodole - Petunia

Le Sodole - Petunia

4 bedrooms·4 baths

San Gimignano • Tuscany

Casa Grande

5 bedrooms·4 baths

Scansano • Tuscany

€701.00 EUR total for 3 nights

Sep 27 – 30, 2026