Holiday Rentals in Val d'Elsa

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Our top choices for Val d'Elsa holiday rentals

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (33)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
Tenuta Sant'Ilario

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (19)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
Casa di Campagna in Toscana

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (107)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is €119
includes taxes & fees
19 Jan - 20 Jan 2026
Palazzo al Torrione 2

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland

La Casa di Ines

La Casa di Ines
San Gimignano City Centre
9.6 out of 10, Exceptional, (7)
"Love this town. Location is great "
United States
William
The price is €86
includes taxes & fees
22 Dec - 23 Dec
La Casa di Ines

Borgo San Giusto

Borgo San Giusto
Empoli
9.4 out of 10, Exceptional, (38)
"The hotel stay was great."
United Kingdom
Jonathan
The price is €99
includes taxes & fees
10 Jan - 11 Jan 2026
Borgo San Giusto

B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (57)
"This is a great B&B its right in the heart of the town. The rooms are very clean and have historical character. The staff are so friendly and helpful. "
United States
April
The price is €124
includes taxes & fees
8 Jan - 9 Jan 2026
B&B Palazzo Tortoli

Affittacamere Le Ginestre

Affittacamere Le Ginestre
San Gimignano City Centre
7.8 out of 10, Good, (6)
"Spacious. Clean. Quite. Air conditioned. Comfort. The View. The best. "
United States
Jorge
Affittacamere Le Ginestre

Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
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 €110
includes taxes & fees
11 Jan - 12 Jan 2026
Casa Vacanze Le Case

Donna Nobile

Donna Nobile
San Gimignano City Centre
8.2 out of 10, Very good, (157)
"Very easy checkin, friendly staff. Loved the kitchen area!"
Canada
Treena
The price is €80
includes taxes & fees
22 Dec - 23 Dec
Donna Nobile

Affittacamere a 20 minuti da Firenze

Affittacamere a 20 minuti da Firenze
Empoli
8.2 out of 10, Very good, (19)
"Very basic lodgings - simple but good location between Florence & Pisa. Breakfast place right underneath the rooms made breakfast convenient. Parking was super simple & across the street, which is rare in Italy. "
United States
Scott
The price is €88
includes taxes & fees
25 Dec - 26 Dec
Affittacamere a 20 minuti da Firenze

san gimignano apartment in historical center, courtyard and fast free wifi

san gimignano apartment in historical center, courtyard and fast free wifi
San Gimignano City Centre
9.6 out of 10, Exceptional, (36)
"Great experience in a medieval villa converted to apartments. We were there for one night and enjoyed it very much!"
United States
Matthew E.
The price is €147
includes taxes & fees
6 Jan - 7 Jan 2026
san gimignano apartment in historical center, courtyard and fast free wifi

Antica Pieve B&B

Antica Pieve B&B
Barberino Tavarnelle
9.4 out of 10, Exceptional, (14)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
The price is €109
includes taxes & fees
10 Jan - 11 Jan 2026
Antica Pieve B&B

Borgo Antico Residence

Borgo Antico Residence
Certaldo Alto
10.0 out of 10, Exceptional, (3)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
The price is €111
includes taxes & fees
2 Jan - 3 Jan 2026
Borgo Antico Residence

Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi

Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi
Poggibonsi
10.0 out of 10, Exceptional, (2)
"Pros: Tutto stupendo la casa la posizione è. La dolcezza della proprietaria"
Italy
Anonymous traveller
The price is €114
includes taxes & fees
22 Dec - 23 Dec
Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi

Le Torri2 SanGimignanoApartments

Le Torri2 SanGimignanoApartments
San Gimignano City Centre
10.0 out of 10, Exceptional, (1)
"Muy bonito y acogedor "
Mexico
ROCIO
The price is €201
includes taxes & fees
6 Jan - 7 Jan 2026
Le Torri2 SanGimignanoApartments

Medieval tower experience with private rooftop, San Gimignano

Medieval tower experience with private rooftop, San Gimignano
San Gimignano City Centre
10.0 out of 10, Exceptional, (5)
"This was a perfect stop for the once in a lifetime tour of italy "
United States
mark M.
The price is €437
includes taxes & fees
6 Jan - 7 Jan 2026
Medieval tower experience with private rooftop, San Gimignano

Le Torri San Gimignano Apartments

Le Torri San Gimignano Apartments
San Gimignano City Centre
8.4 out of 10, Very good, (5)
"Loved this apartment. Felt like we were locals. Walked to everything. Outstanding communication with property manager. She was very helpful and accommodating. She was able to help us navigate how to return to our train station as transportation from here can be tricky if not planned in advance."
United States
Antonio M.
The price is €180
includes taxes & fees
22 Dec - 23 Dec
Le Torri San Gimignano Apartments

Colle di Val D'elsa - Siena - Apt Green - E

Colle di Val D'elsa - Siena - Apt Green - E
Colle di Val d'Elsa
10.0 out of 10, Exceptional, (1)
"Tutto bellissimo. Dal check in on line semplice e funzionale, l'apertura con il codice permette di arrivare quando si vuole. Alloggio esattamente come nelle foto, pulitissimo e dotato di tutto quello che serve anche per la preparazione dei cibi. Bagno particolare trasparente, pulitissimo e con doccia doppi. Vasca idromassaggio davanti al letto ... la chicca"
Italy
Stefano S.
The price is €150
includes taxes & fees
8 Jan - 9 Jan 2026
Colle di Val D'elsa - Siena - Apt Green - E

Cozy and bright apartment

Cozy and bright apartment
Montespertoli
The price is €198
includes taxes & fees
22 Dec - 23 Dec
Cozy and bright apartment
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.
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Top Val d'Elsa Hotel Reviews

Find out more about Val d'Elsa

Everything you need to know about Val d'Elsa holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Val d'Elsa holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Val d'Elsa holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Val d'Elsa holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Val d'Elsa. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Val d'Elsa holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Val d'Elsa holiday rentals we have selected for you start as low as €86 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Val d'Elsa rentals

At Expedia, we put the best Val d'Elsa holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Val d'Elsa rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Val d'Elsa holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Val d'Elsa. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.