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

Val d'Elsa Vacation Rentals

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Our top choices for Val d'Elsa vacation rentals

1. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (104 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is CA $154
CA $173 total
includes taxes & fees
Dec 11 - Dec 12
Palazzo Pacini

2. 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
The price is CA $148
CA $171 total
includes taxes & fees
Nov 13 - Nov 14
Materia Rooms San Gimignano

3. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (67 reviews)
"Francesco, our host, is so nice and welcoming. We had the beat stay and our room had the most fantastic view. Excellent breakfast, place was super clean and quiet. We highly recommend."
Canada
Caroline
The price is CA $138
CA $160 total
includes taxes & fees
Dec 2 - Dec 3
B&B Palazzo Tortoli

4. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 reviews)
"Very friendly host 🙌 and great location"
Denmark
Klaus
The price is CA $132
CA $193 total
includes taxes & fees
Nov 14 - Nov 15
Palazzo al Torrione 2

5. 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
The price is CA $120
CA $140 total
includes taxes & fees
Nov 11 - Nov 12
Casa Vacanze Le Case

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
The price is CA $117
CA $134 total
includes taxes & fees
Nov 19 - Nov 20
Casa di Campagna in Toscana

7. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is CA $68
CA $78 total
includes taxes & fees
Nov 15 - Nov 16
Sportland

8. 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
The price is CA $108
CA $127 total
includes taxes & fees
Dec 8 - Dec 9
Donna Nobile

9. 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 CA $131
CA $152 total
includes taxes & fees
Nov 26 - Nov 27
Affittacamere Le Ginestre

10. Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (10 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
The price is CA $187
CA $210 total
includes taxes & fees
Nov 12 - Nov 13
Residence Arianna

11. Antica Pieve B&B

Antica Pieve B&B
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (15 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 CA $122
CA $172 total
includes taxes & fees
Dec 2 - Dec 3
Antica Pieve B&B

12. 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
The price is CA $501
CA $556 total
includes taxes & fees
Nov 21 - Nov 22
Villa Montecastello

13. 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
The price is CA $128
CA $144 total
includes taxes & fees
Nov 29 - Nov 30
DomuS Miniato

14. Borgo San Giusto

Borgo San Giusto
Empoli
9.4 out of 10, Exceptional, (48 reviews)
"A lovely overnight stay here! Staff were so accommodating to our limited Italian and the children. Would recommend"
United Kingdom
Lucy
The price is CA $111
CA $127 total
includes taxes & fees
Nov 15 - Nov 16
Borgo San Giusto

15. Affittacamere a 20 minuti da Firenze

Affittacamere a 20 minuti da Firenze
Empoli
8.4 out of 10, Very good, (26 reviews)
"Great location between Florence and Pisa. Also only a 5 minute walk to the train station that will take you to both cities. Great place to stay if looking for something quite and away from the crowds."
United States
Joshua
The price is CA $107
CA $123 total
includes taxes & fees
Dec 4 - Dec 5
Affittacamere a 20 minuti da Firenze

16. Nido con vista

Nido con vista
Radicondoli
The price is CA $212
CA $233 total
includes taxes & fees
Nov 13 - Nov 14
Nido con vista

17. Charming San Gimignano Apartment With City Views

Charming San Gimignano Apartment With City Views
San Gimignano City Centre
The price is CA $355
CA $529 total
includes taxes & fees
Nov 11 - Nov 12
Charming San Gimignano Apartment With City Views

18. IL VECCHIO CONVENTO

IL VECCHIO CONVENTO
San Gimignano City Centre
4.0 out of 10, (3 reviews)
"Unterkunft konnte wegen Wasserschaden nicht bezogen werden. Vermieter hat nicht geholfen eine Alternative zu finden…"
Germany
Bodo
The price is CA $191
CA $218 total
includes taxes & fees
Nov 20 - Nov 21
IL VECCHIO CONVENTO

19. Villa LE Cascine

Villa LE Cascine
Montaione
The price is CA $1,512
CA $4,043 total
includes taxes & fees
Nov 24 - Nov 25
Villa LE Cascine

20. Apartment in Chianti With Pool ID 450

Apartment in Chianti With Pool ID 450
Casole d'Elsa
The price is CA $560
CA $619 total
includes taxes & fees
Nov 13 - Nov 14
Apartment in Chianti With Pool ID 450
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Val d'Elsa. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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