Val d'Elsa 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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Our top choices for Val d'Elsa vacation rentals

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 ¥12,168
¥14,303 total
includes taxes & fees
Jan 9 - Jan 10, 2026
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 ¥14,902
¥16,943 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Borgo San Giusto

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

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 ¥19,821
¥22,721 total
includes taxes & fees
Jan 9 - Jan 10, 2026
B&B Palazzo Tortoli

Sportland

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

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (20)
"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

Two Bedroom Apartment

Two Bedroom Apartment
San Gimignano City Centre
9.8 out of 10, Exceptional, (11)
"Very well set up apartment and location was perfect. Parking is a bit of a challenge but if you don’t mind walking you will be ok. "
Canada
Bev P.
The price is ¥16,341
¥31,029 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Two Bedroom Apartment

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

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 ¥13,925
¥20,459 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Borgo Antico Residence

2bed, 1bath Garden apt in Chianti!

2bed, 1bath Garden apt in Chianti!
Frazione Mura, Montaione
10.0 out of 10, Exceptional, (3)
"We had a wonderful time staying at the house. The location is beautiful and peaceful, surrounded by nature and the house itself is charming and well cared for. The swimming pool and the tennis court were fantastic and made our stay even more enjoyable. It was the perfect place to relax and enjoy the Tuscan atmosphere. We truly enjoyed our stay and would love to return one day"
Germany
Cayit A.
The price is ¥14,505
¥34,701 total
includes taxes & fees
Jan 3 - Jan 4, 2026
2bed, 1bath Garden apt in Chianti!

2-BR 1 bath abode in the Chianti hills!

2-BR 1 bath abode in the Chianti hills!
Mura, Montaione
8.0 out of 10, Very Good, (1)
"Check in Vorgang schwierig, da Gastgeber vergessen hat, dass wir kommen. Dann aber hat alles gut geklappt.Die Wohnung ist sehr renovierungsbedürftig, mein Mann hat erstmal die Klospülung repariert. Sonst hat sie ihren Charme und ist gut ausgestattet Gewürzen und anderen LebensmittelnToll gelegen mit Pool und Tennisplatz"
Germany
Anke G.
The price is ¥11,016
¥30,478 total
includes taxes & fees
Jan 6 - Jan 7, 2026
2-BR 1 bath abode in the Chianti hills!

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 ¥14,828
¥21,841 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Palazzo al Torrione 2

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 ¥14,187
¥20,012 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Antica Pieve B&B

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 ¥12,518
¥14,688 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Donna Nobile

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 ¥22,216
¥36,904 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Le Torri2 SanGimignanoApartments

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 ¥18,360
¥33,048 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Le Torri San Gimignano Apartments

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 ¥16,524
¥26,255 total
includes taxes & fees
Jan 15 - Jan 16, 2026
san gimignano apartment in historical center, courtyard and fast free wifi

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 ¥12,558
¥25,410 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Colle di Val D'elsa - Siena - Apt Green - E

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 ¥16,570
¥19,145 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Casa Vacanze Le Case

Colle di Val d'Elsa - Siena - Apt Blue - C

Colle di Val d'Elsa - Siena - Apt Blue - C
Colle di Val d'Elsa
10.0 out of 10, Exceptional, (2)
"Super clean and a comfortable bed. Everything essential for making meals at home was provided. The host was very attentive and available by text. Housekeeping did an excellent job!"
United States
ALLAN
The price is ¥13,219
¥26,071 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Colle di Val d'Elsa - Siena - Apt Blue - C
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Val d'Elsa Hotel Reviews

Find out more about Val d'Elsa

Search for holiday rentals in Val d'Elsa on Expedia! You can easily find your home rentals, villas, holiday apartments in Val d'Elsa using one of the methods below:

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

Look no further and take a look at our great range of rental properties in Val d'Elsa!