A historic square with stone buildings, a prominent tower, and outdoor seating areas.

Val d'Elsa Holiday Rentals

  • 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

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Val d'Elsa holiday rentals

Terrace/patio

1. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is HK$894
HK$1,001 total
includes taxes & fees
2 Sept - 3 Sept
Palazzo Pacini
Balcony

2. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (109 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is HK$849
HK$1,205 total
includes taxes & fees
7 Aug - 8 Aug
Palazzo al Torrione 2
Garden view

3. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (44 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is HK$897
HK$1,041 total
includes taxes & fees
1 Sept - 2 Sept
Villa San Filippo
Aerial view

4. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (36 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is HK$1,849
HK$2,052 total
includes taxes & fees
24 Aug - 25 Aug
Riserva di Fizzano Residence
Exterior

5. Villa Montecastello

Villa Montecastello
Monteriggioni
7.0 out of 10, Good, (2 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is HK$1,497
HK$1,674 total
includes taxes & fees
4 Aug - 5 Aug
Villa Montecastello
View from room

6. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (64 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is HK$1,101
HK$1,256 total
includes taxes & fees
4 Aug - 5 Aug
B&B Palazzo Tortoli
Outdoor pool

7. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (11 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is HK$964
HK$1,106 total
includes taxes & fees
28 Aug - 29 Aug
Casa Vacanze Le Case
Food court

8. Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (67 reviews)
"Beautiful place, great position in the countryside, truly relaxing place, wish we could stay longer, definitely will return A***"
United States
Dean
The price is HK$1,531
HK$1,729 total
includes taxes & fees
30 Aug - 31 Aug
Borgo Il Poggiaccio
In-room safe, desk, laptop workspace, free WiFi

9. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
The price is HK$791
HK$916 total
includes taxes & fees
6 Aug - 7 Aug
Materia Rooms San Gimignano
Terrace/patio

10. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (86 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveller
The price is HK$444
HK$515 total
includes taxes & fees
23 Aug - 24 Aug
Camping Boschetto Di Piemma
Seasonal outdoor pool, pool loungers

11. Residence Arianna

Residence Arianna
Sovicille
9.8 out of 10, Exceptional, (6 reviews)
"We had a 4 night’s stay here and used it as our base for tours around Toscany. It is located in a quiet area outside Siena. The apartment was nice and clean. We used the kitchen for minor cooking and that worked well. There is a supermarket close by and small restaurants in the town. The AC was working great. The host was very keen to share information on good places to see and was eager to make our stay as pleasant as possible. The breakfast was very nice and they also have a restaurant where...
Denmark
Gitte Harrits
The price is HK$1,139
HK$1,280 total
includes taxes & fees
1 Sept - 2 Sept
Residence Arianna
Terrace/patio

12. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (25 reviews)
"A wonderful stay. "
United States
Sally
The price is HK$1,065
HK$1,199 total
includes taxes & fees
9 Aug - 10 Aug
Casa di Campagna in Toscana
Property grounds

13. 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
9.8 out of 10, Exceptional, (41 reviews)
"Beautiful location in San Gimignano! The owner was so attentive and provided great suggestions for our visit. Charming apartment that serviced all of are needs. Boboli bakery (25 yards from apartment) is amazing and a must! Enjoyable stay!"
United States
Curt G.
The price is HK$1,266
HK$1,808 total
includes taxes & fees
2 Sept - 3 Sept
san gimignano apartment in historical center, courtyard and fast free wifi
Porch

14. Donna Nobile

Donna Nobile
San Gimignano City Centre
8.2 out of 10, Very good, (166 reviews)
"Very easy checkin, friendly staff. Loved the kitchen area!"
Canada
Treena
The price is HK$682
HK$796 total
includes taxes & fees
5 Aug - 6 Aug
Donna Nobile
Terrace/patio

15. Affittacamere Le Ginestre

Affittacamere Le Ginestre
San Gimignano City Centre
7.8 out of 10, Good, (6 reviews)
"Spacious. Clean. Quite. Air conditioned. Comfort. The View. The best. "
United States
Jorge
The price is HK$978
HK$1,121 total
includes taxes & fees
4 Aug - 5 Aug
Affittacamere Le Ginestre
Exterior

16. Colle di Val d'Elsa - Siena - Apt Pink - B

Colle di Val d'Elsa - Siena - Apt Pink - B
Colle di Val d'Elsa
10.0 out of 10, Exceptional, (2 reviews)
"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."
United States
Tamara C.
The price is HK$1,148
HK$1,853 total
includes taxes & fees
1 Sept - 2 Sept
Colle di Val d'Elsa - Siena - Apt Pink - B
Property grounds

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

Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!
San Gimignano City Centre
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful home with all the amenities!! Excellent location and enjoyed walking this adorable town!! "
United States
William
The price is HK$1,058
HK$2,321 total
includes taxes & fees
4 Aug - 5 Aug
Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!
Exterior

18. DomuS Miniato

DomuS Miniato
San Miniato
10.0 out of 10, Exceptional, (2 reviews)
"Super clean, felt brand new with a beaaautiful view on the terrace! Quite a few stairs (heavy luggage :D) but definitely worth it! Sadly we only stayed two nights"
United Kingdom
Celesta
The price is HK$874
HK$980 total
includes taxes & fees
18 Aug - 19 Aug
DomuS Miniato
View from property

19. Antica Pieve B&B

Antica Pieve B&B
Barberino Tavarnelle
9.4 out of 10, Exceptional, (14 reviews)
"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 HK$1,109
HK$1,437 total
includes taxes & fees
26 Aug - 27 Aug
Antica Pieve B&B
Minibar, in-room safe, laptop workspace, soundproofing

20. Borgo San Giusto

Borgo San Giusto
Empoli
9.4 out of 10, Exceptional, (42 reviews)
"Lovely location and excellent staff. Restaurant on site is amazing! "
United Kingdom
Paul
The price is HK$1,183
HK$1,329 total
includes taxes & fees
3 Sept - 4 Sept
Borgo San Giusto
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 Val d'Elsa Hotel Reviews

La Cisterna

La Cisterna

10/10 Excellent
"We booked a room with valley view. Wow! Amazing balcony especially at night when the sun set and there was a breeze. The front desk staff were extremely friendly and helpful. We tried to drive to the hotel but gave up. Park inP2. It’s about a 10 minute walk uphill from there but once there you are in the center of it all. Both location wise but height wise. You’re at the top of the town. Plenty of restaurants, bars, and shops. Highly recommend."
Tim 3-night trip
Posted 2 days ago
La Cisterna

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!

Explore a world of travel with Expedia