San Gimignano Vacation Homes

A narrow street with stone buildings, Italian flags, and a shop with ceramic plates.

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Our top choices for San Gimignano holiday homes

A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

1. Casa Vacanze Le Case

San Gimignano

Andrew

HK$794 total

includes taxes & fees

5 Nov - 6 Nov

A bedroom with a bed, a bench, a window with curtains, and two wall-mounted lights.

2. Comfortable double room with a bathroom in the historic center of San Gimignano.

San Gimignano City Centre

HK$1,300 total

includes taxes & fees

1 Nov - 2 Nov

A compact bedroom with a bed, a desk with a chair, a bookshelf, a radiator, and a TV.

3. Deluxe Room - A comfortable and elegant room in the heart of San Gimignano.

San Gimignano City Centre

HK$1,800 total

includes taxes & fees

2 Nov - 3 Nov

A stone building with a covered outdoor seating area and a brick pathway.

4. Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi

San Gimignano

Anne-Marie M.

HK$4,255 total

includes taxes & fees

1 Nov - 2 Nov

A pool with lounge chairs and umbrellas, surrounded by greenery and buildings.

5. Agriturismo I Borghi – Caffè Apartment with Pool in San Gimignano

San Gimignano

HK$2,573 total

includes taxes & fees

1 Nov - 2 Nov

A balcony with a table and chairs overlooking a vineyard.

6. Holiday Home 'Uva' with Guest-Only Pool, Wi-Fi and Air Conditioning

San Gimignano

A stone building with a hot tub, surrounded by greenery.

7. Farmhouse "Le Volpaie - Appartamento Maria" with Private Garden, Whirlpool & Wi-Fi

San Gimignano

Dale M.

HK$3,648 total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel room with a walk-in closet, a vanity with a mirror, and a red accent wall.

8. A beautiful, elegant, and sophisticated superior room in the heart of San Gimignano.

San Gimignano City Centre

HK$1,905 total

includes taxes & fees

1 Nov - 2 Nov

A swimming pool with a hot tub, outdoor seating, and a view of a hillside house.

9. Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden

San Gimignano

Valerie S.

HK$5,198 total

includes taxes & fees

1 Nov - 2 Nov

10. "Volpe" Apartment with Pool Reserved for Guests, Wi-Fi, and Air Conditioning

San Gimignano

Bruno G.

HK$4,587 total

includes taxes & fees

2 Nov - 3 Nov

11. Agriturismo I Borghi – Apartment Tabacco with Pool in San Gimignano

San Gimignano

HK$2,889 total

includes taxes & fees

1 Nov - 2 Nov

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building with a sloped roof.

12. Agriturismo I Borghi – Apartment Zenzero with Pool in San Gimignano

San Gimignano

HK$3,205 total

includes taxes & fees

1 Nov - 2 Nov

A swimming pool with a clear blue water, surrounded by a landscaped garden with various plants and trees.

13. Agriturismo I Borghi – Apartment Liquirizia with Pool in San Gimignano

San Gimignano

HK$3,679 total

includes taxes & fees

1 Nov - 2 Nov

14. Agriturismo I Borghi - Cacao Apartment with Pool in San Gimignano

San Gimignano

"Received no response or check in details! Holidu (third party) did not respond to our check in emails ! It was all AI and no response to provided chat ! Property listing did not advise that Car rental was a necessity for this property! Property itself was nice, but had a musty smell ! No coffee provided, no toilet paper, nominal given! Laundry facilities provided, and easy to use! Once we located property, check in was pretty smooth! Hotel doing check in were very helpful, restaurant...

nada

HK$3,508 total

includes taxes & fees

1 Nov - 2 Nov

An aerial view of a property with a swimming pool, a large house, and surrounding gardens.

15. 'La Ripa - Apartment Il Fienile' with Shared Pool & Wi-Fi

San Gimignano

A residential area with multiple houses, a swimming pool, and vineyard rows.

16. 'La Ripa - Apartment I Ghiri' with Shared Pool & Wi-Fi

San Gimignano

A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

17. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

HK$1,136 total

includes taxes & fees

8 Nov - 9 Nov

A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

18. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

Ruffoli

"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...

James

HK$1,412 total

includes taxes & fees

2 Nov - 3 Nov

A patio with a table and chairs, an umbrella, and a view of a green fence and plants.

19. Holiday home 'Sandra House Certaldo' with private garden and Wi-Fi

Certaldo

Anonymous traveller

HK$1,932 total

includes taxes & fees

15 Nov - 16 Nov

An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

20. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

Montespertoli

"We found sanctuary at this lovely farmhouse during the July heat wave--refreshing dip in the pool, relaxing dinner in the courtyard, restful sleep in the air-conditioned home. Got up to watch the sunrise over the vineyards, absolutely stunning scenery, and watched three hot air balloons also taking in the sights. Matteo was very welcoming, and we bridged the language barrier with a little help from Google translate. Wished we could have stayed longer!"

Susan A.

HK$2,959 total

includes taxes & fees

15 Nov - 16 Nov

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Top San Gimignano Hotel Reviews

Hotel Sovestro

10/10 Excellent

"Great location. Beautiful place to stay and an excellent restaurant on site."

Hotel Bel Soggiorno

10/10 Excellent

"It was a five star quality experience— charming and well maintained with ravishingly beautiful views and excellent service. It was well located with convenient parking nearby. I recommend upgrading for a room with a view. San Gimignano is good starting spot for bike trips— BikeMeUp— good resource for that."

Tenuta Decimo

10/10 Excellent

"Such a beautiful peaceful property, lovely to hear the birds after being in the cities Friendly and helpful staff, especially Maria who gave us excellent local advice especially to make sure that we got a Dondoli Gelato in San Gimignano- you were 💯 right Maria And Nicola at the restaurant- fantastic service I feel that coffee and tea making facilities in the room would be a great idea"

Hotel Casolare Le Terre Rosse

10/10 Excellent

"Absolutely lovely hotel. Best one we stayed at in Italy - in retrospect, we wish we booked to stay here a second night. The location is quiet and isolated so stars are visible at night, plenty of parking, and breakfast is worth the 20 EURS, best breakfast options we had during our stay. Highly recommend, 10/10."

Relais Santa Chiara Hotel by Double Hospitality

10/10 Excellent

"The biggest mistake we made... was leaving. What a wonderful place to stay and enjoy the Tuscan countryside. The proximity to Sam Gimignano was perfect. Short stroll of 7 minutes and you are there. Room was clean and comfortable. Great water pressure in the shower with plenty of hot water. Loved the charm of this hotel. Met by Gaia... so hospitable and helpful. She walked us out to show us where parking had been set aside for us as asked (I received welcome emails ahead of my stay and inquired about parking. All was neatly arranged.) We enjoyed dinner in the bar area twice. All meals were wonderful. But the breakfast spread was just delightful. So many choices of fresh food. Delicious!! Thank you for a wonderful stay. Molto bene!!! Gratzie mille, Gaia!!"

Mormoraia

8/10 Good

"Great location close to San Gimignano for day trips Siena, volterra, etc. Beautiful views and very peaceful. Very clean and comfortable hotel, with gorgeous 360 views from rooms. Unfortunately it’s very expensive to use the amenities, so we didn’t use them. The staff are very nice and helpful. The restaurant was OK. The breakfast was good but not great (coffee was great though). We enjoyed their wine."

Hotel Leon Bianco

8/10 Good

"This hotel was right in the main square, which was nice, and it was the only one of 5 that we stayed in on this trip that included breakfast, which was very nice, but the room felt dated. I mean, the town IS from the 13th century, so gees, what can I expect, but I expected the room to be a little nicer. I have a feeling we got a lesser room because we booked through Expedia, because I saw a few other rooms in my brother's travel group who booked directly with the hotel and theirs were much nicer. Also, do know that the walk from the P2 recommended parking to the hotel is quite an uphill, so bring small luggage!"

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