Search Vacation Homes in Castel San Gimignano

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 1039 Vacation Homes in Castel San Gimignano with updated reviews, rates, and availability.

Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms
Outdoor dining

Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms

9.8 out of 10, Exceptional, (72)
"The house is picture perfect - and the views are absolutely stunning. As others have said, to get to it, you need to drive down a bit of bumpy dirt road (so having a SUV would be a wise choice), but once you get there l, the pure serenity and peacefulness of the Tuscan hills await you. It was so relaxing and quiet and really felt like you had it all to yourself. The house itself was great - 4 large bedrooms and 2 large bathrooms (especially for European standards) provided plenty of space to...
Luxury vacation home with fantastic views, pool, 4 bedrooms, 2 bathrooms
Country House & Spa - Inside Nature with panoramic views, Art Surrounded
Villanovia

Country House & Spa - Inside Nature with panoramic views, Art Surrounded

9.8 out of 10, Exceptional, (56)
"My wife and I found and booked this house for our family and friends to join us for a celebration, and not one part of our experience was disappointing. We showed up late Friday night after a longer day of travel than expected, and we had people at the house waiting for us. They were very gracious and kind and I was communicated with the entire way. I was given a tour of the house and grounds and then we settled in. The house itself is huge and absolutely gorgeous. It’s a picturesque home with...
Country House & Spa - Inside Nature with panoramic views, Art Surrounded
Tuscan villa with Florence, Pisa, Volterra & San Gimignano within 1 hour drive.
Property grounds

Tuscan villa with Florence, Pisa, Volterra & San Gimignano within 1 hour drive.

10.0 out of 10, Exceptional, (2)
"This house was lovely. There was plenty of space to spread out, screens on all windows to enjoy the breeze, beautiful Tuscany views from the comfortable balcony, and a wonderful new pool. The host was responsive, and we enjoyed our stay. The water pressure was great, and there was a good amount of comfortable furnishings, supplies, etc. The only challenge we had was that the internet was spotty at times and in some places, but the reality is we were there for R&R, so I am not sure that was...
Tuscan villa with Florence, Pisa, Volterra & San Gimignano within 1 hour drive.
Indipendendent house with private garden and swimming pool
Pool

Indipendendent house with private garden and swimming pool

10.0 out of 10, Exceptional, (55)
"If you like tuscan landscape as much as we do, this is the place to stay: the panoramic view is extraordinary and the house itself is well equipped and big enough for 4 people."
Indipendendent house with private garden and swimming pool
Holiday house with private pool and fenced garden
Terrace/patio

Holiday house with private pool and fenced garden

10.0 out of 10, Exceptional, (49)
"We really enjoyed our 10 day stay, beds were comfortable and everything was clean, the pool was fantastic with an amazing view. Lots of space for two couples to relax and unwind yet within an hour of all the major towns and attractions. Jurgen was responsive to our needs and even helped us with the pizza oven. We will definitely consider staying here again."
Holiday house with private pool and fenced garden
Tuscan style house, independent, panoramic swimming pool, whirlpool, wi fi.
Pool

Tuscan style house, independent, panoramic swimming pool, whirlpool, wi fi.

10.0 out of 10, Exceptional, (7)
"After an eight-day, April stay, we did not want to leave. Surrounded by fields of rolling green hills, this house was the perfect place to relax on the patio with glasses of wine and plates of pasta. Sonia and Rosario were excellent hosts and their shop (on the premises) was filled with their company’s pasta as well as sweet goodies like biscotti. Highly recommend!"
Tuscan style house, independent, panoramic swimming pool, whirlpool, wi fi.
Volterra Countryside House
Living area

Volterra Countryside House

9.6 out of 10, Exceptional, (14)
"Lots of room on 3 floors very close to all the sites"
Volterra Countryside House
GIULIA -1 Bedroom Country House in Monteriggioni - Siena
Interior

GIULIA -1 Bedroom Country House in Monteriggioni - Siena

10.0 out of 10, Exceptional, (2)
"Ha sido una estancia maravillosa. El lugar estupendo. =)"
GIULIA -1 Bedroom Country House in Monteriggioni - Siena
LUXURY COTTAGE WITH POOL & BREATHTAKING VIEW - NEXT TO A GOLF COURSE (FRANTOIO)
Pool

LUXURY COTTAGE WITH POOL & BREATHTAKING VIEW - NEXT TO A GOLF COURSE (FRANTOIO)

10.0 out of 10, Exceptional, (42)
"The accommodations were perfect for the 4 of us. The location was just what we were looking for, out in the country, beautiful land as far as the eye could see! "
LUXURY COTTAGE WITH POOL & BREATHTAKING VIEW - NEXT TO A GOLF COURSE (FRANTOIO)
Belvilla by OYO San Francesco Uno
Holiday Home Exterior [summer]

Belvilla by OYO San Francesco Uno

10.0 out of 10, Exceptional, (12)
"Wir hatten als Familie einen super Urlaub 😊 Das Haus und das Anwesen sind traumhaft gelegen eine Ruheoase. Schöner Ausgangspunkt um die Toskana zu entdecken. Riccardo ist ein toller Gastgeber und wir würden sehr gerne wiederkommen. 5 Sterne plus für dieses Anwesen"
Belvilla by OYO San Francesco Uno
House in a typical village in the heart of Chianti
Exterior

House in a typical village in the heart of Chianti

9.4 out of 10, Exceptional, (34)
"It's a great home base to start exploring the region. Two wineries are very close by, and Florence is an easy drive away. The traditional way the house is built keeps it nice and cold during the day. We loved it!"
House in a typical village in the heart of Chianti
LUXURY COTTAGE WITH POOL & BREATHTAKING VIEW - NEXT TO A GOLF COURSE (PENDOLINO)
Pool

LUXURY COTTAGE WITH POOL & BREATHTAKING VIEW - NEXT TO A GOLF COURSE (PENDOLINO)

9.8 out of 10, Exceptional, (47)
"It was amazing. House is beautiful and very clean with a gorgeous view. Sara and family were very helpful to us. "
LUXURY COTTAGE WITH POOL & BREATHTAKING VIEW - NEXT TO A GOLF COURSE (PENDOLINO)
Le Macine, a wonderful ancient restored watermill with Pool
Property grounds

Le Macine, a wonderful ancient restored watermill with Pool

9.6 out of 10, Exceptional, (74)
"House was so cute, owner was there when we arrived and was very responsive to any questions. Great location to many of the surrounding towns."
Le Macine, a wonderful ancient restored watermill with Pool
Tuscan house in an ancient village near San Gimignano - Il Fienile
Natural bio pool with a spectacular view

Tuscan house in an ancient village near San Gimignano - Il Fienile

9.8 out of 10, Exceptional, (50)
"Excellent and quick contact with property owner. She was very responsive when I had to make very rapid arrangements (less than 72 hours) after a different VRBO didn't work out. Upon our arrival, Roberto (the property manager - lovely gentleman - very prompt and responsive), helped us to understand the property and it's layout. We felt well-prepared and faced no difficulties during our stay. Roberto speaks Italian and English and we speak mostly English with just enough Italian to be...
Tuscan house in an ancient village near San Gimignano - Il Fienile
Glicini 1, your holiday home in Chianti just 30 minutes from Florence and Siena
Pool

Glicini 1, your holiday home in Chianti just 30 minutes from Florence and Siena

10.0 out of 10, Exceptional, (49)
"We've been going to Italy for the last 15 years. This place was clean, conveniently located and perfect for a couple that need a quiet break. And the views of the surrounding hills were spectacular. We will be back, if we're lucky."
Glicini 1, your holiday home in Chianti just 30 minutes from Florence and Siena
House with pool in residence, near San Gimignano
Pool

House with pool in residence, near San Gimignano

9.2 out of 10, Wonderful, (26)
"Great location, comfortable property with everything we needed. Perfect as a base for exploring Tuscany. The pool was great for unwinding after a day on the road and the patio, comfortable and peaceful. We will be back, thank you Fabio."
House with pool in residence, near San Gimignano
LUXURY COTTAGE WITH POOL & BREATHTAKING VIEW - NEXT TO A GOLF COURSE (MORAIOLO)
Pool

LUXURY COTTAGE WITH POOL & BREATHTAKING VIEW - NEXT TO A GOLF COURSE (MORAIOLO)

10.0 out of 10, Exceptional, (34)
"You couldn’t possibly ask for anything better than this Villa! It is clean, rustic, authentic, and the VIEWS are amazing! We didn’t have weather that allowed us to enjoy the pool but it was nice. Simply amazing!"
LUXURY COTTAGE WITH POOL & BREATHTAKING VIEW - NEXT TO A GOLF COURSE (MORAIOLO)
Info House
Exterior

Info House

10.0 out of 10, Exceptional, (11)
"Giovanni was an amazing host. He even gave us a welcoming gift of a bottle of wine and apples. I had such an incredible time just relaxing in the peace and quiet and getting some writing done. I would recommend this spot to anyone who is interested in doing the same."
Info House
detached villa with private pool and garden
Pool

detached villa with private pool and garden

9.0 out of 10, Wonderful, (18)
"We loved this property- very well equipped, lovely pool and great views. And, only a few minutes walk into the village with lovely bars restaurants and shops. A perfect location. The only thing that might cause an issue for some ( not for us) , is that the third bedroom is a mezzanine floor within the second bedroom with a very steep staircase. The only access to the bathroom from these rooms is either through the main bedroom or through the patio door and around the outside of the property. ...
detached villa with private pool and garden
Two-room WIFI and swimming pool.
Pool

Two-room WIFI and swimming pool.

8.6 out of 10, Excellent, (4)
"Sehr schöne Unterkunft, kann ich weiter empfehlen."
Two-room WIFI and swimming pool.
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.
Don't see what you're looking for?
See all available properties in Castel San Gimignano
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Castel San Gimignano

Il Battistero Siena - Residenza d'Epoca
Room

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (142)
"The service at this hotel was impeccable. We were running late for our wine tasting but they were still SO accommodating! The rooms were beautiful and the view from the hotel are amazing. It was super accessible to everything. Also, the parking options were great - highly recommend. They're so responsive through texting and it was great to have this level of service. Highly rec! "
The price is AED 418
AED 469 total
includes taxes & fees
26 Nov - 27 Nov
Il Battistero Siena - Residenza d'Epoca
panoramica casa con piscina privata
Pool

panoramica casa con piscina privata

7.6 out of 10, Good, (8)
"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....
panoramica casa con piscina privata
ApartHotel Anghel
Room

ApartHotel Anghel

8.2 out of 10, Very Good, (305)
"Nice place, quiet and clean!"
The price is AED 288
AED 327 total
includes taxes & fees
15 Dec - 16 Dec
ApartHotel Anghel
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.