A city with historic towers and a vineyard.

Castel San Gimignano Vacation Rentals

Q: What are some of the best vacation rentals in Castel San Gimignano?

Villa with large garden in the Chianti hills : This vacation home rental outside of Castel San Gimignano is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

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Dates

November 2026

December 2026

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Our top choices for Castel San Gimignano vacation rentals

An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

1. Palazzo Pacini

Colle di Val d'Elsa

John

SAR 491 total

includes taxes & fees

7 Dec - 8 Dec

A view from a window overlooking a rural landscape with fields and a distant mountain range.

2. B&B Palazzo Tortoli

San Gimignano City Centre

Caroline

SAR 436 total

includes taxes & fees

1 Dec - 2 Dec

A building with a wooden door, windows with shutters, and flower boxes.

3. Donna Nobile

San Gimignano City Centre

Treena

SAR 350 total

includes taxes & fees

7 Nov - 8 Nov

An open wooden door leading to an outdoor patio with a table and chairs.

4. Palazzo al Torrione 2

San Gimignano City Centre

Klaus

SAR 481 total

includes taxes & fees

8 Nov - 9 Nov

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

5. Casa Vacanze Le Case

San Gimignano

Andrew

SAR 356 total

includes taxes & fees

15 Nov - 16 Nov

A narrow alleyway with brick walls, wooden barrels, and potted plants.

6. San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

San Gimignano City Centre

Glenn

SAR 674 total

includes taxes & fees

11 Nov - 12 Nov

A narrow street with stone buildings, wooden doors, and a brick pathway.

7. Materia Rooms San Gimignano

San Gimignano City Centre

Bradley

SAR 444 total

includes taxes & fees

18 Nov - 19 Nov

A reception desk with the word "SPORTLAND" prominently displayed.

8. Sportland

Colle di Val d'Elsa

Giorgio

SAR 208 total

includes taxes & fees

29 Nov - 30 Nov

A patio with wicker furniture and potted plants, overlooking a scenic landscape.

9. Affittacamere Le Ginestre

San Gimignano City Centre

Jorge

SAR 405 total

includes taxes & fees

8 Nov - 9 Nov

A vineyard with a stone building, a metal gate, and purple plants in the foreground.

10. Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!

San Gimignano City Centre

William

SAR 1,036 total

includes taxes & fees

7 Nov - 8 Nov

A yellow building with a dark door, potted plants, and a stone staircase leading to the entrance.

11. AlbergoDiffusoVolterra

Volterra

Mia

SAR 699 total

includes taxes & fees

8 Nov - 9 Nov

A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

12. Villa Montecastello

Monteriggioni

Alvaro

SAR 1,480 total

includes taxes & fees

20 Nov - 21 Nov

An outdoor courtyard with brick walls, arched doorways, and potted plants. There are metal tables and chairs arranged for outdoor dining.

13. San Gimignano Apartment in the Heart of the City for 3 People: Fast Wi-Fi, Concierge Service

San Gimignano City Centre

Julie B.

SAR 864 total

includes taxes & fees

8 Nov - 9 Nov

A narrow cobblestone street with historic buildings, a chain-link fence, and a wooden door with a number plaque.

14. Colle di Val d'Elsa - Siena - Apt Rose - B

Colle di Val d'Elsa

"The host is excellent. Perfect English and Italian. Thoughtful and great communication. Parking instructions were accurate. The apartment was beautiful and the bed was comfortable. The apartment is walkable to dining and shopping. The street is steep and the nearby medievale hill town is steeper. While we loved walking up to the hill town everyday, we liked the variety of dining and shopping near the apartment."

Tamara C.

SAR 558 total

includes taxes & fees

8 Nov - 9 Nov

A stone-walled room with a wooden desk, a chair, a TV, and a large window with curtains.

15. Tenuta Sant'Ilario

Gambassi Terme

Sergio

SAR 503 total

includes taxes & fees

7 Nov - 8 Nov

A stone-walled room with a window overlooking a landscape.

16. Medieval Tower experience with Panoramic Rooftop, San Gimignano

San Gimignano City Centre

mark M.

SAR 1,918 total

includes taxes & fees

8 Nov - 9 Nov

A spacious room with a large bed, wooden bookshelves, a fireplace, and a wooden cabinet.

17. Casa Bardi Luxury Apartments with parking in San Gimignano Italy

San Gimignano City Centre

Roberto

SAR 1,507 total

includes taxes & fees

9 Nov - 10 Nov

A two-story stone house with a swimming pool, surrounded by greenery and a clear sky.

18. APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM

Monteriggioni

giuseppe z.

SAR 966 total

includes taxes & fees

7 Nov - 8 Nov

A stone building with a covered outdoor seating area and a tree with purple flowers.

19. Apartment 'Timignano in Agriturismo' with Mountain View, Pool among the Hills

Monteguidi

SAR 1,420 total

includes taxes & fees

7 Nov - 8 Nov

A statue in a garden with a pool and lounge chairs.

20. Private estate in Tuscany with a pool—5 charming villas at Tenuta Cantona,

Toscana

SAR 1,492 total

includes taxes & fees

7 Nov - 8 Nov

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Find vacation rentals that suit your style

Top Castel San Gimignano Hotel Reviews

A covered outdoor dining area with a table set for four, overlooking a scenic landscape with hills and a body of water.

Borgo Pignano Volterra Tuscany

Volterra

10/10 Excellent

Nithiwadee

A stone staircase leading to a gated entrance, surrounded by lush greenery and a well-maintained lawn.

Tenuta Decimo

San Gimignano

10/10 Excellent

FLOR

A dining area with tables and chairs, a chandelier, and wall-mounted lighting.

Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

10/10 Excellent

Fred

A well-maintained garden with a large urn, neatly trimmed hedges, and a building with warm lighting in the background.

Villa Sabolini

Colle di Val d'Elsa

10/10 Excellent

Mark

A swimming pool with lounge chairs and umbrellas, a building with a balcony, and a stone pathway.

Hotel Le Colline

San Gimignano

10/10 Excellent

Federico

An outdoor patio with round tables and chairs, set against a backdrop of mountains and a cloudy sky.

Villa San Lucchese

Poggibonsi

10/10 Excellent

Beautiful property with large rooms, parlors, great staff, great restaurant, etc. We arrived late and the kitchen was closed, but they made one call and re-opened it for us and served an amazing meal with late night enthusiasm on a beautiful deck. The rooms were large, nice baths and very comfortable beds. We wanted to stay another night to relax by the pool and enjoy the wonderful grounds, but they were booked so we had to move on as this was a last minute booking. Great breakfast in the...

Anonymous traveler

An outdoor patio with wicker furniture, a stone staircase, and a view of a historic building in the background.

Albergo Etruria

Volterra

10/10 Excellent

Steve

An outdoor dining area with tables and chairs, a stone wall, and a tree with green leaves.

Hotel Leon Bianco

San Gimignano City Centre

10/10 Excellent

We loved this place! Getting here was a bit tricky, as the map we were given in the welcome email was of bad quality, so it didn't take us to the correct place right away, but we figured it out, very minor. I'm sure you can ask for a better quality map. When we arrived to check in, we were greeted by Lisa, who was oh so very helpful! She showed us where laundry was, asked all questions we had about WIFI and other hotel things, recommended us 3 terrific places to eat dinner on each of our 3...

Todd

A table set for dining with a view of a vineyard.

La Cisterna

San Gimignano City Centre

10/10 Excellent

Old hotel in an old mountain top town. Given the limitations of this environment the Cisterna is a great little hotel that met all of our needs .The Cisterna is located in Cisterna Square in town close to sights, dining and a valley view walkway. The views to the valley from the rooms is amazing. The rooms are a good size and are modernized and comfortable. The staff is great (friendly and helpful). Many choices for dining close by (in the square) but others will require some minor hills and...

David

A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.

Hotel Borgo San Luigi

Monteriggioni

10/10 Excellent

James

A historic street with a hotel entrance featuring an arched doorway and potted plants.

Hotel L' Antico Pozzo San Gimignano

San Gimignano City Centre

10/10 Excellent

Dorothy

An outdoor dining area with tables set for two, overlooking a scenic landscape with mountains and trees.

Hotel Bel Soggiorno

San Gimignano City Centre

10/10 Excellent

Marianne B

A stone building with a sign reading "Vin Hotel." There are potted plants in front of the entrance.

Hotel Volterra In Superior

Volterra

10/10 Excellent

Lone Lady

A narrow cobblestone street lined with traditional brick buildings, outdoor seating with wicker chairs and tables, and hanging lanterns.

Hotel Il Castello

Certaldo Alto

10/10 Excellent

Kenneth

A neatly made bed with a tablet, two lamps, and towels on a floral-patterned bedspread.

Palazzo Mari

San Gimignano City Centre

10/10 Excellent

Pancho

An outdoor courtyard with stone walls, arched doorways, and potted plants.

Residenza d'Epoca Palazzo Buonaccorsi

San Gimignano City Centre

10/10 Excellent

The accomodations were awesome! I would highly recommend this hotel. She does not take credit cards and it is difficult to find. However, she will send you an e-mail prior to arrival with all these details as well as how to find the hotel. You can park out front while checking in and then you drive about 100 meters to a free parking lot .... very convenient. The City is wodnerful are easily walkable!

Anonymous traveler

A stone building with a swimming pool, outdoor seating, and trees.

Il Castagnolo Country B&B

San Gimignano

10/10 Excellent

Anonymous traveler

Frequently Asked Questions

Can I find a vacation rental in Castel San Gimignano?

Yes, we have vacation rentals close to top local attractions in Castel San Gimignano, or you can select a more secluded option if you're looking for a relaxing stay. Castel San Gimignano is known for its coffeehouses and local tours. Make sure you have time to check out the wineries while you're in the area.

What are some of the best vacation rentals in Castel San Gimignano?

Villa with large garden in the Chianti hills: This vacation home rental outside of Castel San Gimignano is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

How many vacation rentals will I find in Castel San Gimignano?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Castel San Gimignano stay.

What can I see and do in Castel San Gimignano?

Explore the area and family-friendly sights such as Chianti Observatory, or get out into nature at a spot like Val di Merse. In the larger area, you’ll find Sovestro in Poggio Winery and Casa e Torre Campatelli.

What are vacation rentals like in Castel San Gimignano?

Vacation rentals are privately owned accommodations you can book for several days or more in Castel San Gimignano. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family gatherings.

Castel San Gimignano Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Castel San Gimignano vacation rentals

1. Palazzo Pacini

2. B&B Palazzo Tortoli

3. Donna Nobile

4. Palazzo al Torrione 2

5. Casa Vacanze Le Case

6. San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

7. Materia Rooms San Gimignano

8. Sportland

9. Affittacamere Le Ginestre

10. Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!

11. AlbergoDiffusoVolterra

12. Villa Montecastello

13. San Gimignano Apartment in the Heart of the City for 3 People: Fast Wi-Fi, Concierge Service

14. Colle di Val d'Elsa - Siena - Apt Rose - B

15. Tenuta Sant'Ilario

16. Medieval Tower experience with Panoramic Rooftop, San Gimignano

17. Casa Bardi Luxury Apartments with parking in San Gimignano Italy

18. APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM

19. Apartment 'Timignano in Agriturismo' with Mountain View, Pool among the Hills

20. Private estate in Tuscany with a pool—5 charming villas at Tenuta Cantona,

Find vacation rentals that suit your style

Top Castel San Gimignano Hotel Reviews

Borgo Pignano Volterra Tuscany

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in Castel San Gimignano?

What are some of the best vacation rentals in Castel San Gimignano?

How many vacation rentals will I find in Castel San Gimignano?

What can I see and do in Castel San Gimignano?

What are vacation rentals like in Castel San Gimignano?