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

Val d'Elsa Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Val d'Elsa vacation rentals

A narrow street with stone buildings, a tower, and an archway.

1. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
10.0 out of 10, Exceptional, (1 review)
"Fantastic all around experience. The rooms were beautiful and clean and this unique mix of rustic modern Italian styling. Located right in the heart of the old city made it very easy to walk everywhere. The service was fantastic, I was able to message the team and within a minute I got the help and had my questions answered. I’d definitely stay there again."
Canada
Bradley
$105 nightly
The price is $122
Nov 4 - Nov 5
Total with taxes and fees
Materia Rooms San Gimignano
An open wooden door leading to an outdoor patio with a table and chairs.

2. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 reviews)
"They were very helpful to me when I arrived. I difficulty accessing there messages to me. They put me at ease"
United States
Angela
$117 nightly
The price is $134
Nov 8 - Nov 9
Total with taxes and fees
Palazzo al Torrione 2
Outdoor pool

3. Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (9 reviews)
"The place is excellent! The owner and her daughter extremely friendly and kind! They helped us with everything we needed. I will definitely stay here again. I highly recommend this place!"
United States
Violeta
$122 nightly
The price is $138
Nov 11 - Nov 12
Total with taxes and fees
Residence Arianna
A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

4. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.6 out of 10, Excellent, (56 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
$91 nightly
The price is $107
Oct 28 - Oct 29
Total with taxes and fees
Villa San Filippo
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

5. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (102 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
$149 nightly
The price is $167
Oct 25 - Oct 26
Total with taxes and fees
Palazzo Pacini
A stone courtyard with a bench, potted plants, and a building in the background.

6. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.6 out of 10, Exceptional, (27 reviews)
"A wonderful stay. "
United States
Sally
$101 nightly
The price is $115
Nov 8 - Nov 9
Total with taxes and fees
Casa di Campagna in Toscana
A bedroom with a bed, a nightstand, a lamp, a radiator, and a curtain.

7. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.6 out of 10, Exceptional, (14 reviews)
"The property was perfect and the host was so nice and helpful. We would definitely stay there again."
United States
Andrew
$92 nightly
The price is $107
Nov 2 - Nov 3
Total with taxes and fees
Casa Vacanze Le Case
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

8. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (42 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
$195 nightly
The price is $217
Oct 19 - Oct 20
Total with taxes and fees
Riserva di Fizzano Residence
An interior with stone walls, wooden doors, and a bar area with stools and bottles.

9. Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (67 reviews)
"I loved the stay here. A great quiet place with an awesome restaurant and unbelievable staff. "
United States
Louie
$178 nightly
The price is $201
Oct 18 - Oct 19
Total with taxes and fees
Borgo Il Poggiaccio
A stone-walled room with a wooden desk, a chair, a TV, and a large window with curtains.

10. Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (37 reviews)
"Great place, difficult driving access but enjoyable"
United States
Sergio
$97 nightly
The price is $110
Nov 12 - Nov 13
Total with taxes and fees
Tenuta Sant'Ilario
A narrow alleyway with brick walls, wooden barrels, and potted plants.

11. San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service
San Gimignano City Centre
9.8 out of 10, Exceptional, (42 reviews)
"Authentic 13th century building with so much character and charm. The room was very unique and opened to a lovely courtyard. The location was great, and very close to the gate. A full Italian breakfast buffet was offered at a reasonable cost. Laundry service was also available. And the hosts were very friendly and helpful."
United States
Marilyn H.
$166 nightly
The price is $171
Oct 14 - Oct 15
Total with taxes and fees
San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

12. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (91 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveler
$48 nightly
The price is $56
Oct 18 - Oct 19
Total with taxes and fees
Camping Boschetto Di Piemma
A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

13. Borgo Antico Residence

Borgo Antico Residence
Certaldo Alto
10.0 out of 10, Exceptional, (3 reviews)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
$89 nightly
The price is $102
Oct 22 - Oct 23
Total with taxes and fees
Borgo Antico Residence
A stone building with outdoor seating and a view of the countryside.

14. Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
$159 nightly
The price is $179
Oct 15 - Oct 16
Total with taxes and fees
Antico Borgo Poggiarello
A reception desk with the word "SPORTLAND" prominently displayed.

15. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
$45 nightly
The price is $51
Oct 18 - Oct 19
Total with taxes and fees
Sportland
A building with a wooden door, windows with shutters, and flower boxes.

16. Donna Nobile

Donna Nobile
San Gimignano City Centre
8.2 out of 10, Very good, (168 reviews)
"Very easy checkin, friendly staff. Loved the kitchen area!"
Canada
Treena
$76 nightly
The price is $90
Nov 1 - Nov 2
Total with taxes and fees
Donna Nobile
An outdoor cafe area with tables and chairs, a red awning, and buildings with signs in the background.

17. DomuS Miniato

DomuS Miniato
San Miniato
10.0 out of 10, Exceptional, (3 reviews)
"Klein aber fein. Sehr gepflegt und geschmackvoll eingerichtet mit Liebe zum Detail. Herrliche Aussicht vom kleinen Balkon. Nur die Parkplatzsuche war am späten Freitag Abend schwierig, weil gefühlt die halbe Jugend der Toscana nach San Miniato in den Ausgang geht."
United States
Thomas
$88 nightly
The price is $99
Oct 27 - Oct 28
Total with taxes and fees
DomuS Miniato
A view from a window overlooking a rural landscape with fields and a distant mountain range.

18. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (66 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
$128 nightly
The price is $147
Oct 18 - Oct 19
Total with taxes and fees
B&B Palazzo Tortoli
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

19. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very good, (3 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
$178 nightly
The price is $199
Oct 18 - Oct 19
Total with taxes and fees
Villa Montecastello
A compact kitchen with a gas stove, a refrigerator, and a wooden dining table with chairs.

20. Nido con vista

Nido con vista
Radicondoli
$134 nightly
The price is $147
Nov 7 - Nov 8
Total with taxes and fees
Nido con vista
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

Hotel Sovestro

Hotel Sovestro

10/10 Excellent
"Friendly staff comfortable beds great location very good price"
Farzad 1-night trip
Posted 1 day ago
Hotel Sovestro

Find out more about Val d'Elsa

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

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

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