Val d'Elsa Vacation Rentals

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Our top choices for Val d'Elsa vacation rentals

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (30 reviews)
"The view was so incredible and the pool just like a dream. "
Canada
Sarah
The price is CA $306
CA $339 total
includes taxes & fees
May 27 - May 28
Riserva di Fizzano Residence

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is CA $261
CA $292 total
includes taxes & fees
Jun 4 - Jun 5
Villa Montecastello

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (24 reviews)
"A wonderful stay. "
United States
Sally
The price is CA $165
CA $186 total
includes taxes & fees
May 24 - May 25
Casa di Campagna in Toscana

Affittacamere a 20 minuti da Firenze

Affittacamere a 20 minuti da Firenze
Empoli
8.2 out of 10, Very good, (21 reviews)
"Very basic lodgings - simple but good location between Florence & Pisa. Breakfast place right underneath the rooms made breakfast convenient. Parking was super simple & across the street, which is rare in Italy. "
United States
Scott
The price is CA $115
CA $132 total
includes taxes & fees
May 25 - May 26
Affittacamere a 20 minuti da Firenze

Borgo San Giusto

Borgo San Giusto
Empoli
9.4 out of 10, Exceptional, (41 reviews)
"Lovely location and excellent staff. Restaurant on site is amazing! "
United Kingdom
Paul
The price is CA $218
CA $245 total
includes taxes & fees
Jun 7 - Jun 8
Borgo San Giusto

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
The price is CA $206
CA $230 total
includes taxes & fees
Jun 8 - Jun 9
Palazzo Pacini

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
The price is CA $242
CA $271 total
includes taxes & fees
May 24 - May 25
Antico Borgo Poggiarello

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 CA $182
CA $238 total
includes taxes & fees
May 25 - May 26
Antica Pieve B&B

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.4 out of 10, Very good, (42 reviews)
"Conveniently situated between Florence and Siena in the heart of the Chianti region with stunning views. Friendly relaxed hosts who provide a substantial breakfast. Beautiful large swimming pool to cool off at the end of the day."
United Kingdom
Andrew
The price is CA $115
CA $136 total
includes taxes & fees
Jun 4 - Jun 5
Villa San Filippo

Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (65 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 CA $207
CA $235 total
includes taxes & fees
May 30 - May 31
Borgo Il Poggiaccio

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (35 reviews)
"Great place, difficult driving access but enjoyable"
United States
Sergio
The price is CA $175
CA $197 total
includes taxes & fees
Jun 18 - Jun 19
Tenuta Sant'Ilario

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (109 reviews)
"Great location and beautiful room. Staff weren't that friendly but I think it would have been better if we spoke Italian."
Canada
Sophie
The price is CA $151
CA $214 total
includes taxes & fees
Jun 2 - Jun 3
Palazzo al Torrione 2

B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (61 reviews)
"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 CA $204
CA $232 total
includes taxes & fees
May 27 - May 28
B&B Palazzo Tortoli

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 $69
CA $79 total
includes taxes & fees
Jun 21 - Jun 22
Sportland

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
The price is CA $84
CA $138 total
includes taxes & fees
Jun 3 - Jun 4
Borgo Antico Residence

Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.0 out of 10, Wonderful, (8 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is CA $164
CA $189 total
includes taxes & fees
May 29 - May 30
Casa Vacanze Le Case

Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (4 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 CA $206
CA $232 total
includes taxes & fees
Jun 14 - Jun 15
Residence Arianna

Donna Nobile

Donna Nobile
San Gimignano City Centre
8.2 out of 10, Very good, (157 reviews)
"Very easy checkin, friendly staff. Loved the kitchen area!"
Canada
Treena
The price is CA $127
CA $147 total
includes taxes & fees
Jun 3 - Jun 4
Donna Nobile

Casa Michelangelo Certaldo

Casa Michelangelo Certaldo
CERTALDO
The price is CA $144
CA $247 total
includes taxes & fees
May 24 - May 25
Casa Michelangelo Certaldo

APART. OF CHARM, AIR CONDITIONING, FENCED POOL IN THE HEART OF CHIANTI-FLORENCE

APART. OF CHARM, AIR CONDITIONING, FENCED POOL IN THE HEART OF CHIANTI-FLORENCE
MONTERIGGIONI
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved Marcella & Enzo’s property. The pool was exactly what we needed to relax after a busy and hot few days in Rome & Venice. Just a 10 min drive from the train station. The home is set up very nicely with the 2 bedrooms and 2 bathrooms. We loved meeting the donkeys, having a quiet place to relax along with modern conveniences like a washing machine. We were treated like family. We hope to return in the future. Huge thank you! Breathtaking views. The cottage was picture perfect. "
United States
Anonymous traveller
The price is CA $431
CA $685 total
includes taxes & fees
May 25 - May 26
APART. OF CHARM, AIR CONDITIONING, FENCED POOL IN THE HEART OF CHIANTI-FLORENCE
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.