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

Val d'Elsa Holiday Rentals

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Our top choices for Val d'Elsa holiday rentals

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 NZ$216
includes taxes & fees
2 Sept - 3 Sept
Palazzo Pacini

2. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (47 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is NZ$202
includes taxes & fees
13 Sept - 14 Sept
Villa San Filippo

3. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (88 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveller
The price is NZ$95
includes taxes & fees
10 Sept - 11 Sept
Camping Boschetto Di Piemma

4. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (110 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is NZ$262
includes taxes & fees
26 Aug - 27 Aug
Palazzo al Torrione 2

5. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is NZ$88
includes taxes & fees
6 Sept - 7 Sept
Sportland

6. 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 NZ$360
includes taxes & fees
26 Aug - 27 Aug
Villa Montecastello

7. 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 NZ$383
includes taxes & fees
8 Sept - 9 Sept
Riserva di Fizzano Residence

8. 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 NZ$240
includes taxes & fees
28 Aug - 29 Aug
Casa Vacanze Le Case

9. 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 NZ$422
includes taxes & fees
13 Sept - 14 Sept
Borgo Il Poggiaccio

10. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
The price is NZ$213
includes taxes & fees
18 Aug - 19 Aug
Materia Rooms San Gimignano

11. 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 NZ$261
includes taxes & fees
2 Sept - 3 Sept
Casa di Campagna in Toscana

12. 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, (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.
The price is NZ$314
includes taxes & fees
14 Aug - 15 Aug
san gimignano apartment in historical center, courtyard and fast free wifi

13. 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 NZ$167
includes taxes & fees
16 Aug - 17 Aug
Donna Nobile

14. 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 NZ$202
includes taxes & fees
3 Sept - 4 Sept
DomuS Miniato

15. 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 NZ$270
includes taxes & fees
12 Sept - 13 Sept
Residence Arianna

16. 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 NZ$370
includes taxes & fees
27 Aug - 28 Aug
B&B Palazzo Tortoli

17. Borgo al Cerro

Borgo al Cerro
Casole d'Elsa
9.2 out of 10, Wonderful, (25 reviews)
"Väldigt vackert ställe med bra placering mitt i Toscana. Rummet var väldigt fint, men bilderna från hemsidan var finare, så jag blev lite besviken när vi väl kom in. I övrigt var komplexets omgivningar och trädgård helt fantastisk. Barnen hade roligt med pingisbor och dart och det fanns trevlig grillplats att nyttja. "
Sweden
Frida
The price is NZ$412
includes taxes & fees
4 Sept - 5 Sept
Borgo al Cerro

18. 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
The price is NZ$273
includes taxes & fees
6 Sept - 7 Sept
Tenuta Sant'Ilario

19. 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 NZ$233
includes taxes & fees
14 Aug - 15 Aug
Affittacamere Le Ginestre

20. Apartment La Torre di Canonica Colle di val d'Elsa - Siena Via Francigena

Apartment La Torre di Canonica Colle di val d'Elsa - Siena Via Francigena
Colle di Val d'Elsa
10.0 out of 10, Exceptional, (1 review)
"Simply Amazing!"
United States
Rhett
The price is NZ$264
includes taxes & fees
29 Aug - 30 Aug
Apartment La Torre di Canonica Colle di val d'Elsa - Siena Via Francigena
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Val d'Elsa holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Val d'Elsa. 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 Val d'Elsa. 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 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 holiday 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 Val d'Elsa short-term rentals, that won’t be hard to do.

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