Search Vacation Homes in Castel San Gimignano

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Castel San Gimignano vacation homes

Front of property
Agriturismo La Ferrozzola

Vacation Home in Castellina in Chianti

Agriturismo La Ferrozzola
9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola
Fridge, oven, stovetop, dishwasher
Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi

Vacation Home in Poggibonsi

Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi
10.0 out of 10, Exceptional, (2)
"Pros: Tutto stupendo la casa la posizione è. La dolcezza della proprietaria"
Italy
Anonymous traveler
The price is AED 340
AED 488 total
includes taxes & fees
22 Dec - 23 Dec
Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi
Outdoor pool
Casa Vacanze Le Case

Vacation Home in San Gimignano

Casa Vacanze Le Case
9.0 out of 10, Wonderful, (8)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is AED 388
AED 448 total
includes taxes & fees
11 Jan - 12 January 2026
Casa Vacanze Le Case
Interior
Chianti Craft House Badia a Passignano

Vacation Home in Barberino Tavarnelle

Chianti Craft House Badia a Passignano
9.8 out of 10, Exceptional, (9)
"The house is beautiful and clean. The host is very welcoming and helpful. What more could one ask for! Thanks for having us. "
United States
Elika M.
The price is AED 561
AED 815 total
includes taxes & fees
22 Dec - 23 Dec
Chianti Craft House Badia a Passignano
Spa
LOVE NEST SIENA YOUR LOVE NEST

Vacation Home in Toscana

LOVE NEST SIENA YOUR LOVE NEST
The price is AED 228
AED 559 total
includes taxes & fees
22 Dec - 23 Dec
LOVE NEST SIENA YOUR LOVE NEST
2 bedrooms, free WiFi, bed sheets
Tuscan House Relax in the heart of the Tuscan countryside

Vacation Home in Montespertoli

Tuscan House Relax in the heart of the Tuscan countryside
The price is AED 426
AED 516 total
includes taxes & fees
22 Dec - 23 Dec
Tuscan House Relax in the heart of the Tuscan countryside
Outdoor pool
House with pool for 4 pax

Vacation Home in Casole d'Elsa

House with pool for 4 pax
9.4 out of 10, Exceptional, (3)
"Besser kann man es nicht haben. Den Pool hatten wir gefühlt immer für uns alleine. Die Lage der Unterkunft erlaubt es uns schnell in Siena und San Gimignano zu sein, auch die anderen Sehenswürdigkeiten in der Region waren schnell zu erreichen. In der Unterkunft war es sehr ruhig, ideal um sich zu erholen. Traumhaft schön. Wir kommen gerne wieder. Ciao Oli"
Germany
Oliver E.
The price is AED 602
AED 1,174 total
includes taxes & fees
2 Jan - 3 January 2026
House with pool for 4 pax
Fridge, oven, stovetop, dishwasher
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi

Vacation Home in Certaldo

Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
10.0 out of 10, Exceptional, (1)
"Pros: Die familiäre Aufnahme und Unterstützung war sehr angenehm."
Germany
Anonymous traveler
The price is AED 472
AED 695 total
includes taxes & fees
30 Dec - 31 Dec
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
Interior
DOLCE CUORE LUXE APARTMENT FLORENCE CHIANTI AREA

Vacation Home in San Donato

DOLCE CUORE LUXE APARTMENT FLORENCE CHIANTI AREA
The price is AED 340
AED 989 total
includes taxes & fees
22 Dec - 23 Dec
DOLCE CUORE LUXE APARTMENT FLORENCE CHIANTI AREA
Exterior
Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

Vacation Home in Castelnuovo Berardenga

Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
10.0 out of 10, Exceptional, (1)
"Pros: The view and unique traditional apartment. Cons: -"
United States
Anonymous traveler
The price is AED 1,731
AED 2,106 total
includes taxes & fees
7 Jan - 8 January 2026
Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
Interior
Holiday Home 'La Casetta' with Private Terrace, Private Garden and Wi-Fi

Vacation Home in Volterra

Holiday Home 'La Casetta' with Private Terrace, Private Garden and Wi-Fi
The price is AED 359
AED 428 total
includes taxes & fees
22 Dec - 23 Dec
Holiday Home 'La Casetta' with Private Terrace, Private Garden and Wi-Fi
Terrace/patio
Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.

Vacation Home in Monteriggioni

Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.
10.0 out of 10, Exceptional, (12)
"Monteriggioni is the perfect location between Siena, San Gimignani, and roads to Chianti. The hosts Marcela, Enzo, and Alessandro really made us feel at home and comfortable. The property is beautiful, quiet, with unforgettable sunsets! Time at the pool is refreshing and relaxing, with beautiful views of the surrounding countryside. The authentic Italian kitchen was perfect for creating your own breakfasts and dinners. The bathrooms with showers have all you need, and the beds are really...
United States
Daniel D.
The price is AED 1,041
AED 1,480 total
includes taxes & fees
22 Dec - 23 Dec
Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.
Exterior detail
THE TOLOMEI - apartment in the heart of the main street

Vacation Home in Siena City Centre

THE TOLOMEI - apartment in the heart of the main street
8.0 out of 10, Very Good, (4)
"Excellent location, very nice apartment was just like the pictures. Painless check-in, we had a comfortable wonderful 3 days in Siena. The only negative was the drain in the master shower backs up, but there's a second bathroom so we just showered in there. Great place!"
United States
Serena F.
The price is AED 384
AED 654 total
includes taxes & fees
7 Jan - 8 January 2026
THE TOLOMEI - apartment in the heart of the main street
Pool
Holiday Home 'La Casina Di Borgo Mommialla' with Shared Pool, Wi-Fi and Air Conditioning

Vacation Home in Gambassi Terme

Holiday Home 'La Casina Di Borgo Mommialla' with Shared Pool, Wi-Fi and Air Conditioning
10.0 out of 10, Exceptional, (2)
"Pros: Very warm welcome by the accomodating host who was always helpful with tips for the . Very nice appartment with beautiful view and community pool."
United States
Anonymous traveler
The price is AED 1,574
AED 2,006 total
includes taxes & fees
10 Jan - 11 January 2026
Holiday Home 'La Casina Di Borgo Mommialla' with Shared Pool, Wi-Fi and Air Conditioning
TV
Casa di Via del Corallo Gerfalco – Charming Apartment in Medieval Village

Vacation Home in Località Gerfalco Montieri

Casa di Via del Corallo Gerfalco – Charming Apartment in Medieval Village
The price is AED 688
AED 817 total
includes taxes & fees
23 Dec - 24 Dec
Casa di Via del Corallo Gerfalco – Charming Apartment in Medieval Village
Interior
Your nest in the Tuscany countryside

Vacation Home in Certaldo - Firenze

Your nest in the Tuscany countryside
The price is AED 516
AED 946 total
includes taxes & fees
22 Dec - 23 Dec
Your nest in the Tuscany countryside
Fridge, microwave, oven, stovetop
Casa Erika, relax in Tuscany

Vacation Home in Partino

Casa Erika, relax in Tuscany
The price is AED 396
AED 516 total
includes taxes & fees
6 Jan - 7 January 2026
Casa Erika, relax in Tuscany
Pool
Casale Torricella: Relax Among Woods with Sea View

Vacation Home in Montieri

Casale Torricella: Relax Among Woods with Sea View
The price is AED 895
AED 895 total
includes taxes & fees
23 Dec - 24 Dec
Casale Torricella: Relax Among Woods with Sea View
Exterior
Farmhouse in the heart of Tuscany, in the magnificent scenery of the countryside

Vacation Home in Toscana

Farmhouse in the heart of Tuscany, in the magnificent scenery of the countryside
The price is AED 516
AED 611 total
includes taxes & fees
31 Dec - 1 January 2026
Farmhouse in the heart of Tuscany, in the magnificent scenery of the countryside
Exterior detail
Chateau / Country House

Vacation Home in Sovicille

Chateau / Country House
The price is AED 258
AED 400 total
includes taxes & fees
28 Dec - 29 Dec
Chateau / Country House
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Castel San Gimignano Hotel Reviews

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"Having booked with another local hotel - The Athena - who were completely obnoxious and unhelpful regarding the parking. I stumbled across this gem. The staff were so helpful and accomplished ~ first class customer service."
Stephen 1-night trip
Posted 4 days ago
Palazzo Ravizza

Explore a world of travel with Expedia