Castel San Gimignano Vacation Rentals

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

Tonight
Nov 21 - Nov 22
Tomorrow
Nov 22 - Nov 23
This weekend
Nov 21 - Nov 23
Next weekend
Nov 28 - Nov 30

Vacation Rentals in Castel San Gimignano

Outdoor pool, pool umbrellas, sun loungers
Chianti Village Morrocco

Chianti Village Morrocco

3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (108)
"Front desk was very helpful and very comfortable room. "
United States
Chris
Chianti Village Morrocco
Lobby lounge
ApartHotel Anghel

ApartHotel Anghel

Siena
8.4 out of 10, Very Good, (331)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is NT$2,417
NT$2,803 total
includes taxes & fees
Nov 26 - Nov 27
ApartHotel Anghel
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Siena City Centre
9.6 out of 10, Exceptional, (189)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Grand Apartment with Garden | Private kitchen | Full-size fridge, microwave, oven, stovetop
Regis Condo

Regis Condo

Siena City Centre
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
Regis Condo
Royal Apartment | View from room
Tuscasì Aparthotel

Tuscasì Aparthotel

Sovicille
9.0 out of 10, Wonderful, (24)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is NT$1,811
NT$2,100 total
includes taxes & fees
Nov 22 - Nov 23
Tuscasì Aparthotel
2 bars/lounges
Camping Boschetto Di Piemma

Camping Boschetto Di Piemma

3.0 star property
San Gimignano
8.8 out of 10, Excellent, (85)
"The mobile homes were a great alternative when Via Francigena hostels were full. Friendly people, swimming pool was wonderful , and an easy walk back and forth to San Gimignano."
United States
Martha
Camping Boschetto Di Piemma
Panoramic Suite, City View | View from room
Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi

Siena City Centre
9.6 out of 10, Exceptional, (116)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
The price is NT$5,273
NT$5,945 total
includes taxes & fees
Dec 2 - Dec 3
Residenza d'Epoca Palazzo Borghesi
Exterior
Camping Siena Colleverde

Camping Siena Colleverde

3.0 star property
Scacciapensieri
8.2 out of 10, Very Good, (159)
"Safe, great proximity to Siena without being too close, nice pool."
United States
Martha
Camping Siena Colleverde
Interior detail
Castello di Montegufoni

Castello di Montegufoni

Montespertoli
8.0 out of 10, Very Good, (31)
"This was a stunning castle to stay in. The frescoed ceilings were gorgeous. Loved every minute that we were there. The staff were wonderful. The only thing i would recommend is to add a vending machine and maybe to offer pastries in thr morning. "
United States
Cheryl
Castello di Montegufoni
Seasonal outdoor pool, pool umbrellas, sun loungers
Castello Del Nero - Podere San Filippo

Castello Del Nero - Podere San Filippo

Barberino Tavarnelle
9.8 out of 10, Exceptional, (38)
"Much nicer stay then the rooms at the Como"
United States
Anonymous traveler
Castello Del Nero - Podere San Filippo
Outdoor pool, pool umbrellas, sun loungers
Riserva di Fizzano Residence

Riserva di Fizzano Residence

3.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (23)
"Perfect location on the top of a hill surrounded by the beautiful vineyards of Chianti. Enjoy the view by the pool or the fabulous sunset with a glass of wine. The staff were friendly and the restaurant was 5 star. I highly recommend a stay to fulfill all your Tuscan dreams. "
United States
Eileen
Riserva di Fizzano Residence
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe
La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House

Siena City Centre
9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House
Exterior detail
La Casa di Ines

La Casa di Ines

San Gimignano City Centre
9.4 out of 10, Exceptional, (6)
"Love this town. Location is great "
United States
William
The price is NT$2,653
NT$3,099 total
includes taxes & fees
Dec 19 - Dec 20
La Casa di Ines
Terrace/patio
Porta Pispini Residence

Porta Pispini Residence

2.0 star property
Siena Historical Center
9.4 out of 10, Exceptional, (21)
"That’s not a hotel room, that’s small apartment with guest room and kitchen with washer and dishwasher Amazing window view Free parking Very clean 3 minutes walk from the city wall More than reasonable price "
United States
Gerard
Porta Pispini Residence
Deluxe Apartment | Living area | 50-inch Smart TV with cable channels
Casa Ciseri

Casa Ciseri

Siena City Centre
9.8 out of 10, Exceptional, (9)
"Beautiful property in the center of Siena! "
United States
Maura
The price is NT$8,092
NT$9,045 total
includes taxes & fees
Nov 25 - Nov 26
Casa Ciseri
Panoramic Apartment, Hill View (4) | Terrace/patio
Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi

Castellina in Chianti
8.0 out of 10, Very Good, (2)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is NT$3,715
NT$4,303 total
includes taxes & fees
Nov 26 - Nov 27
Casa Vacanze Squarcialupi
Property entrance
Palazzo Pacini

Palazzo Pacini

Colle di Val d'Elsa
9.8 out of 10, Exceptional, (98)
"Such a beautiful gem of a hotel. Steeped in Florentine style. Comfortable and classy. Definitely would recommend "
United States
George
The price is NT$4,347
NT$4,853 total
includes taxes & fees
Nov 23 - Nov 24
Palazzo Pacini
Seasonal outdoor pool, pool umbrellas, sun loungers
Villa San Filippo

Villa San Filippo

4.0 star property
Barberino Tavarnelle
8.4 out of 10, Very Good, (40)
"Conveniently situated between Florence and Siena in the heart of the Chianti region with stunning views. Friendly relaxed hosts who provide a substantial breakfast. Beautiful large swimming pool to cool off at the end of the day."
United Kingdom
Andrew
Villa San Filippo
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

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"The Grand Hotel Continental in Siena is a rare gem,elegant, inviting, and steeped in history. From the beautifully preserved interiors to the warm, attentive staff, every detail makes you feel genuinely cared for. Its central location is unbeatable, placing Siena’s most charming sights just steps away. A perfect blend of luxury and authentic Tuscan character, this hotel transforms a stay in Siena into something truly unforgettable. The foods were yummy took! "
Betty 4-night trip
Posted 2 days ago
Grand Hotel Continental Siena – Starhotels Collezione

Find out more about Castel San Gimignano

Search for holiday rentals in Castel San Gimignano on Expedia! You can easily find your home rentals, villas, holiday apartments in Castel San Gimignano using one of the methods below:

  • View our selection of featured holiday rentals in Castel San Gimignano
  • Use the map to find apartments and other holiday homes in the Castel San Gimignano neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Castel San Gimignano while they last

Look no further and take a look at our great range of rental properties in Castel San Gimignano!

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.

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

With 4 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 Sentierelsa Trail. In the larger area, you’ll find Sovestro in Poggio Winery and Piazza della Cisterna.

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.