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Vacation rentals in Castel San Gimignano

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Top-rated vacation rentals in Castel San Gimignano

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Apartment in San Gimignano

4.97 out of 5 average rating, 164 reviews

Casa Irene

Casa Irene is a lovely apartment in Tuscan style, located on the second and last floor of a building just 5 minutes walk from the center, 50 meters to Porta San Matteo and another 50 meters to Via Francigena. Given the secluded location, you can easily reach it by car to park in the immediate free parking. The apartment equipped with wifi and air conditioning is divided into living room/kitchen open space,bedroom and bathroom with shower and a habitable terrace overlooking the walls of San Gimignano

Dec 4 – 11

G$21,820 GYD per night
Guest favorite

Vacation home in Poggibonsi

4.94 out of 5 average rating, 105 reviews

Victoria Chianti Vacations 🍇🍷

Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

Mar 3 – 10

G$22,893 GYD per night
Guest favorite

Cottage in Geggiano

4.99 out of 5 average rating, 103 reviews

Villa di Geggiano - Guesthouse

The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idilic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa. PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR.

Nov 4 – 11

G$139,650 GYD per night

Popular amenities for Castel San Gimignano vacation rentals

Other great vacation rentals in Castel San Gimignano

Superhost

Farm stay in Simignano

4.81 out of 5 average rating, 100 reviews

Casa al Gianni - Hut

Nov 1 – 8

G$19,473 GYD per night
Guest favorite

Apartment in San Gimignano

4.89 out of 5 average rating, 131 reviews

Apartment Melogranowith great views

Apr 3 – 10

G$25,264 GYD per night
Guest favorite

Home in Poggibonsi

4.9 out of 5 average rating, 213 reviews

Tuscan Counrtry Detached House. Wi-Fi Free

Sep 7 – 14

G$19,005 GYD per night
Guest favorite

Villa in Castellina in Chianti

4.93 out of 5 average rating, 164 reviews

The Villino Farmhouse

Nov 3 – 10

G$107,658 GYD per night
Guest favorite

Apartment in Volterra

4.92 out of 5 average rating, 100 reviews

Apartment Rondine , "from stables to the stars "

Nov 30 – Dec 7

G$19,616 GYD per night
Guest favorite

Apartment in Castel San Gimignano

4.91 out of 5 average rating, 11 reviews

Between San Gimignano and Volterra

Jun 18 – 25

G$14,397 GYD per night
Guest favorite

Apartment in Castel San Gimignano

5.0 out of 5 average rating, 26 reviews

Casa Jasmine, in the center of art and relaxation

Apr 19 – 26

G$36,003 GYD per night
Guest favorite

Condo in San Gimignano

4.93 out of 5 average rating, 58 reviews

Beautiful & cozy apt with garden, pool & AC

Feb 8 – 15

G$22,395 GYD per night
Guest favorite

Villa in Colle di Val d'Elsa, Montegabbro

4.85 out of 5 average rating, 73 reviews

Special Offer

Oct 11 – 18

G$29,606 GYD per night
Superhost

Farm stay in San Gimignano

4.89 out of 5 average rating, 79 reviews

ECOLOGICAL FARMHOUSE "I VECCHI LECCI"

Feb 26 – Mar 5

G$34,298 GYD per night
Guest favorite

Farm stay in Colle di Val d'elsa

5.0 out of 5 average rating, 37 reviews

Your cottage in the Tuscan countryside

Feb 28 – Mar 7

G$15,486 GYD per night
Guest favorite

Tower in San Gimignano

4.92 out of 5 average rating, 91 reviews

Medieval tower experience with panoramic rooftop

Nov 28 – Dec 5

G$87,755 GYD per night

Destinations to explore