Val d'Elsa Vacation Home Rentals from CA $142: Search Top Private Vacation Homes for Rent

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

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Our top choices for Val d'Elsa vacation homes

A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

1. Casa Vacanze Le Case

San Gimignano

Andrew

CA $142 total

includes taxes & fees

Nov 2 - Nov 3

An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

2. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

Montespertoli

"We found sanctuary at this lovely farmhouse during the July heat wave--refreshing dip in the pool, relaxing dinner in the courtyard, restful sleep in the air-conditioned home. Got up to watch the sunrise over the vineyards, absolutely stunning scenery, and watched three hot air balloons also taking in the sights. Matteo was very welcoming, and we bridged the language barrier with a little help from Google translate. Wished we could have stayed longer!"

Susan A.

CA $529 total

includes taxes & fees

Nov 15 - Nov 16

A balcony with a view of a stone building and surrounding landscape.

3. A Nest with a View - A Romantic Getaway Within the City Walls

Radicondoli

CA $244 total

includes taxes & fees

Nov 5 - Nov 6

A bedroom with a bed, a bedside table with a book, a nightstand, and three framed pictures on the wall.

4. Comfortable double room with a bathroom in the historic center of San Gimignano.

San Gimignano City Centre

CA $232 total

includes taxes & fees

Oct 27 - Oct 28

A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and greenery.

5. House with pool for 4 pax

Pievescola

Judith C.

CA $437 total

includes taxes & fees

Oct 27 - Oct 28

A compact bedroom with a bed, a desk with a chair, a bookshelf, a radiator, and a TV.

6. Deluxe Room - A comfortable and elegant room in the heart of San Gimignano.

San Gimignano City Centre

CA $317 total

includes taxes & fees

Oct 28 - Oct 29

A patio with a table and chairs, an umbrella, and a view of a green fence and plants.

7. Holiday home 'Sandra House Certaldo' with private garden and Wi-Fi

Certaldo

Anonymous traveller

CA $311 total

includes taxes & fees

Nov 1 - Nov 2

A modern kitchen with white cabinets, a microwave, and a dining area with a round table and chairs.

8. New Listing

Dogana

CA $173 total

includes taxes & fees

Oct 27 - Oct 28

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Top Val d'Elsa Hotel Reviews

Hotel Sovestro

10/10 Excellent

"It was exactly what you would expect at a wine resort. Relaxing, refreshing, close to a whole bunch of wineries including the one right on property."

Relais Santa Chiara Hotel by Double Hospitality

10/10 Excellent

"The biggest mistake we made... was leaving. What a wonderful place to stay and enjoy the Tuscan countryside. The proximity to Sam Gimignano was perfect. Short stroll of 7 minutes and you are there. Room was clean and comfortable. Great water pressure in the shower with plenty of hot water. Loved the charm of this hotel. Met by Gaia... so hospitable and helpful. She walked us out to show us where parking had been set aside for us as asked (I received welcome emails ahead of my stay and inquired about parking. All was neatly arranged.) We enjoyed dinner in the bar area twice. All meals were wonderful. But the breakfast spread was just delightful. So many choices of fresh food. Delicious!! Thank you for a wonderful stay. Molto bene!!! Gratzie mille, Gaia!!"

Mormoraia

8/10 Good

"Great location close to San Gimignano for day trips Siena, volterra, etc. Beautiful views and very peaceful. Very clean and comfortable hotel, with gorgeous 360 views from rooms. Unfortunately it’s very expensive to use the amenities, so we didn’t use them. The staff are very nice and helpful. The restaurant was OK. The breakfast was good but not great (coffee was great though). We enjoyed their wine."

Hotel Leon Bianco

8/10 Good

"This hotel was right in the main square, which was nice, and it was the only one of 5 that we stayed in on this trip that included breakfast, which was very nice, but the room felt dated. I mean, the town IS from the 13th century, so gees, what can I expect, but I expected the room to be a little nicer. I have a feeling we got a lesser room because we booked through Expedia, because I saw a few other rooms in my brother's travel group who booked directly with the hotel and theirs were much nicer. Also, do know that the walk from the P2 recommended parking to the hotel is quite an uphill, so bring small luggage!"

Find out more about Val d'Elsa

Val d'Elsa Vacation Homes information

Number of reviews	25
Accommodation	421 Vacation Homes
Lowest Price	CA $142
Highest Price	CA $13,184

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Volterra Vacation Rentals

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Room 1

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Treat yourself

Be picky

Check prices for these dates

Our top choices for Val d'Elsa vacation homes

1. Casa Vacanze Le Case

2. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

3. A Nest with a View - A Romantic Getaway Within the City Walls

4. Comfortable double room with a bathroom in the historic center of San Gimignano.

5. House with pool for 4 pax

6. Deluxe Room - A comfortable and elegant room in the heart of San Gimignano.

7. Holiday home 'Sandra House Certaldo' with private garden and Wi-Fi

8. New Listing

9. Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi

10. Apartment in Chianti With Pool ID 513

11. Ebbio – Villa and Organic Farm in Monteriggioni

12. Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

13. Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi

14. Agriturismo I Borghi – Caffè Apartment with Pool in San Gimignano

15. Holiday Home 'Uva' with Guest-Only Pool, Wi-Fi and Air Conditioning

16. Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning

17. Farmhouse "Le Volpaie - Appartamento Maria" with Private Garden, Whirlpool & Wi-Fi

18. Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden

19. Peaceful House in the Heart of Tuscany, Near Florence and Siena

20. Apartment in Chianti With Pool ID 3939

Find vacation rentals that suit your style

Top Val d'Elsa Hotel Reviews

Hotel Sovestro

Relais Santa Chiara Hotel by Double Hospitality

Villa Sabolini

Tenuta Decimo

Mormoraia

Hotel Da Vinci

Hotel Leon Bianco

Castello di Casole, A Belmond Hotel, Tuscany

Hotel Pescille by Double Hospitality

Find out more about Val d'Elsa

Val d'Elsa Vacation Homes information

Explore a world of travel with Expedia

Val d'Elsa Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Val d'Elsa vacation homes

1. Casa Vacanze Le Case

2. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

3. A Nest with a View - A Romantic Getaway Within the City Walls

4. Comfortable double room with a bathroom in the historic center of San Gimignano.

5. House with pool for 4 pax

6. Deluxe Room - A comfortable and elegant room in the heart of San Gimignano.

7. Holiday home 'Sandra House Certaldo' with private garden and Wi-Fi

8. New Listing

9. Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi

10. Apartment in Chianti With Pool ID 513

11. Ebbio – Villa and Organic Farm in Monteriggioni

12. Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

13. Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi

14. Agriturismo I Borghi – Caffè Apartment with Pool in San Gimignano

15. Holiday Home 'Uva' with Guest-Only Pool, Wi-Fi and Air Conditioning

16. Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning

17. Farmhouse "Le Volpaie - Appartamento Maria" with Private Garden, Whirlpool & Wi-Fi

18. Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden

19. Peaceful House in the Heart of Tuscany, Near Florence and Siena

20. Apartment in Chianti With Pool ID 3939

Find vacation rentals that suit your style

Top Val d'Elsa Hotel Reviews

Hotel Sovestro

Find out more about Val d'Elsa

Val d'Elsa Vacation Homes information

Explore a world of travel with Expedia