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Our top choices for Val d'Elsa holiday rentals

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (25 reviews)
"Perfect location on the top of a hill surrounded by the beautiful vineyards of Chianti. Enjoy the view by the pool or the fabulous sunset with a glass of wine. The staff were friendly and the restaurant was 5 star. I highly recommend a stay to fulfill all your Tuscan dreams. "
United States
Eileen
The price is ฿6,537
฿7,267 total
includes taxes & fees
15 Apr - 16 Apr
Riserva di Fizzano Residence

Borgo San Giusto

Borgo San Giusto
Empoli
9.4 out of 10, Exceptional, (39 reviews)
"Lovely location and excellent staff. Restaurant on site is amazing! "
United Kingdom
Paul
The price is ฿2,974
฿3,385 total
includes taxes & fees
1 Apr - 2 Apr
Borgo San Giusto

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 ฿5,731
฿6,418 total
includes taxes & fees
28 Apr - 29 Apr
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 ฿4,131
฿5,453 total
includes taxes & fees
18 Apr - 19 Apr
Antica Pieve B&B

Tenuta Cantona

Tenuta Cantona
Casole d'Elsa
The price is ฿5,643
฿8,366 total
includes taxes & fees
9 Apr - 10 Apr
Tenuta Cantona

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (21 reviews)
"Abbiamo trascorso una notte il 25 dicembre 2025 in questo agriturismo immerso nella campagna. Un vero angolo di pace, perfetto per staccare dalla routine e rilassarsi completamente. La struttura è curata nei minimi dettagli, pulitissima e accogliente, con un’atmosfera calda e familiare. I proprietari sono persone splendide, sempre disponibili e gentili, capaci di farti sentire come a casa fin dal primo momento. La cucina è semplicemente eccezionale: colazionei preparata con prodotti freschi e...
Italy
Roberta
The price is ฿3,313
฿3,758 total
includes taxes & fees
30 Mar - 31 Mar
Casa di Campagna in Toscana

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is ฿3,276
฿3,680 total
includes taxes & fees
19 Apr - 20 Apr
Palazzo Pacini

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (34 reviews)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
The price is ฿3,892
฿4,394 total
includes taxes & fees
30 Mar - 31 Mar
Tenuta Sant'Ilario

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.4 out of 10, Very good, (40 reviews)
"Wir hatten ein zweistöckiges Familienappartment mit drei Duschbädern, Küche, Wohnzimmer, zwei Schlafzimmern...sehr komfortabel. Alles war sauber und ordentlich, teilweise etwas in die Jahre gekommen, aber nicht störend. Tolle Poolanlage. Frühstück für deutsche Verhältnisse okay. Das Personal überaus freundlich und bemüht. Wir haben uns sehr wohl gefühlt. Kritikpunkt: auf der Terrasse gab es keine Sonnenschirme, was es uns leider unmöglich machte, dort auch mal etwas Zeit zu verbringen. "
Germany
Anonymous traveller
The price is ฿3,186
฿3,732 total
includes taxes & fees
1 Apr - 2 Apr
Villa San Filippo

Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (65 reviews)
"Trevlig personal. God mat o frukost. Fin miljö."
Sweden
Jörgen
The price is ฿5,042
฿8,235 total
includes taxes & fees
28 Apr - 29 Apr
Borgo Il Poggiaccio

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is ฿5,574
฿6,245 total
includes taxes & fees
3 Apr - 4 Apr
Villa Montecastello

Le Mascie Country House

Le Mascie Country House
Casole d'Elsa
9.2 out of 10, Wonderful, (9 reviews)
"We loved our stay. The property is quiet and private but is in close proximity to a small town. Very charming and the pool was an added bonus. "
United States
Misti
The price is ฿6,885
฿7,649 total
includes taxes & fees
30 Mar - 31 Mar
Le Mascie Country House

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is ฿1,673
฿1,916 total
includes taxes & fees
30 Mar - 31 Mar
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 ฿2,479
฿3,787 total
includes taxes & fees
30 Mar - 31 Mar
Borgo Antico Residence

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (108 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is ฿3,047
฿4,487 total
includes taxes & fees
30 Mar - 31 Mar
Palazzo al Torrione 2

Villa Mucellena

Villa Mucellena
Casole d'Elsa
Villa Mucellena

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 ฿4,611
฿5,262 total
includes taxes & fees
30 Mar - 31 Mar
B&B Palazzo Tortoli

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 ฿2,744
฿3,132 total
includes taxes & fees
12 Apr - 13 Apr
Affittacamere a 20 minuti da Firenze
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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