Val d'Elsa Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Val d'Elsa vacation rentals

Aparthotel in San Gimignano City Centre

La Casa di Ines
9.6 out of 10, Exceptional, (7)
"Love this town. Location is great "
United States
William
The price is ¥12,100
¥14,223 total
includes taxes & fees
Dec 22 - Dec 23
La Casa di Ines
10.0 out of 10, Exceptional, (106)
"Great villa in a lovely location. We (8 adults and 2 children) really enjoyed our trip. It had everything we needed and a beautiful view from the pool! Thank you to Allesandro for helping us book things in the local area too. "
United Kingdom
Catherine T.
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
10.0 out of 10, Exceptional, (78)
"What an awesome place. Lovely house and backyard with pool. Leo is friendly , helpful and welcoming . Belforte is a small , quiet hilltop village but it is very accessible (by car) to other awesome spots- Siena, San Gimignano , Volterra and others. Highly recommended "
New Zealand
Adrian d.
"Casa di Leo" Bright And Romantic House Surrounded by Medieval Walls and Pool
10.0 out of 10, Exceptional, (108)
"Impeccable place very clean and the people who own the house are always there and very helpful gave us a great welcome where always available and very kindHouse had everything the views are extraordinary "
United States
Elena C.
- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
9.8 out of 10, Exceptional, (43)
"The property was absolutely charming. It really had that homey, Italian, Tuscan charm about it. The kids and my husband loved it too. I wish I had planned for more days there. We didn’t have time to partake in the cooking class or truffle hunting, but I guess that just leaves a reason to come back. The location was great too because it’s in the country away from the busy cities, but a close enough drive to all the various Tuscan sites.The owners were very nice and spoke good enough English....
United States
Gwen L.
Your panoramic house in Tuscany between vineyards and olive groves.

Residence in Barberino Tavarnelle

Castello Del Nero - Podere San Filippo
9.8 out of 10, Exceptional, (38)
"Much nicer stay then the rooms at the Como"
United States
Anonymous traveler
Castello Del Nero - Podere San Filippo

Camping in San Gimignano

Camping Boschetto Di Piemma
3.0 star property
8.8 out of 10, Excellent, (85)
"The mobile homes were a great alternative when Via Francigena hostels were full. Friendly people, swimming pool was wonderful , and an easy walk back and forth to San Gimignano."
United States
Martha
Camping Boschetto Di Piemma
9.8 out of 10, Exceptional, (30)
"What a Villa!! Four families with a total of 17 people, including kids aged between 12 and 19 stayed at the Villa and there was more than enough space for everyone to be comfortable. The kitchens were well stocked and the outdoor eating area was a great place to have a meal for all of us together. The pool, ping pong, hot tub and bocce provided lots to do when not sight seeing. Most importantly, Fabio was amazing!! Always available to assist or provide advice. And the meal he prepared for all...
Canada
Jonah D.
Stunning Villa: 24 guests, private SwimmingPool

Residence in Colle di Val d'Elsa

Palazzo Pacini
9.8 out of 10, Exceptional, (98)
"Such a beautiful gem of a hotel. Steeped in Florentine style. Comfortable and classy. Definitely would recommend "
United States
George
Palazzo Pacini
9.6 out of 10, Exceptional, (36)
"Great experience in a medieval villa converted to apartments. We were there for one night and enjoyed it very much!"
United States
Matthew E.
The price is ¥16,463
¥26,158 total
includes taxes & fees
Jan 6 - Jan 7, 2026
san gimignano apartment in historical center, courtyard and fast free wifi

Residence in Casole d'Elsa

Borgo al Cerro
9.2 out of 10, Wonderful, (23)
"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
Borgo al Cerro
10.0 out of 10, Exceptional, (119)
"It is a wonderful property, a beautiful villa with all expectations met, Caterina and Calorina were great hosts and looked after every detail. Location was great right in the middle of wine country "
Canada
Stephen L.
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.
9.8 out of 10, Exceptional, (48)
"We really enjoyed our stay. It was in a very quiet, out of the way picturesque place. Our host was great - had everything we needed and very helpful and great communication. Would definitely recommend and would stay here again. "
Canada
Danielle H.
Beautiful apartment in San Gimignano - RoccaiaCasa'70

Apartment in San Gimignano City Centre

Apartment 'Casa Vesta' with Wi-Fi and Air Conditioning
9.8 out of 10, Exceptional, (6)
"Calm, natural environment, history and toscany great ferlingd"
United States
Nuria Meritxell P.
The price is ¥40,077
¥49,897 total
includes taxes & fees
Dec 14 - Dec 15
Apartment 'Casa Vesta' with Wi-Fi and Air Conditioning
9.8 out of 10, Exceptional, (38)
"We had a group of 7 adult (19-64) family members staying here - property setting is spectacular with great views, gardens, pool , tennis court…. The house is spacious and well equipped - we ate every meal outside and took advantage of having a local chef come and cook for us one night. Very special time for us all / we will be back!"
Canada
Derek A.
San Gimignano - Panoramic garden and beautiful pool!
10.0 out of 10, Exceptional, (1)
"The villa has great charm and character, a huge living room where you can spend time with friends, as well as outdoor spaces and the swimming pool. It is an excellent point to visit San Gimignano Colle val d'elsa Florence and Siena. Thanks Luca for hosting us"
Italy
arianna p.
The timeless elegance with private pool

Vacation Home in COLLE VAL D' ELSA

Info House
9.8 out of 10, Exceptional, (12)
"All you need is available, peacefull and quiet."
Netherlands
Emile G.
Info House
10.0 out of 10, Exceptional, (40)
"Beautiful villa, stunning setting and wonderful, attentive hosts. We really enjoyed our time there. "
United Kingdom
Nicola S.
VILLA BELSOLE - Certaldo Tuscany HEATED POOL and electric car recharge
9.4 out of 10, Exceptional, (20)
"We stayed in apartment Falco which has great views over the valley.The apartment is exactly as listed,well equipped and spotlessly clean.It is perfectly placed for visiting all the top Tuscan towns and there are numerous local restaurants within easy reach. Fabio and Annemarie are wonderful hosts and we will definitely be visiting again. Thanks for a wonderful stay."
United Kingdom
Wendy M.
FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops

Residence in Casole d'Elsa

Villa Mucellena
Villa Mucellena
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Val d'Elsa Hotel Reviews

Find out more about Val d'Elsa

Search for holiday rentals in Val d'Elsa on Expedia! You can easily find your home rentals, villas, holiday apartments in Val d'Elsa using one of the methods below:

  • View our selection of featured holiday rentals in Val d'Elsa
  • Use the map to find apartments and other holiday homes in the Val d'Elsa neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Val d'Elsa while they last

Look no further and take a look at our great range of rental properties in Val d'Elsa!