Castel San Gimignano Vacation Rentals

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Nov 23 - Nov 24
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Nov 24 - Nov 25
Next weekend
Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7

Vacation Rentals in Castel San Gimignano

Outdoor pool, pool umbrellas, sun loungers
Chianti Village Morrocco

Chianti Village Morrocco

3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (108)
"Front desk was very helpful and very comfortable room. "
United States
Chris
$70 nightly
The price is $80
Dec 24 - Dec 25
Total with taxes and fees
Chianti Village Morrocco
Lobby lounge
ApartHotel Anghel

ApartHotel Anghel

Siena
8.4 out of 10, Very Good, (331)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
ApartHotel Anghel
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Siena City Centre
9.6 out of 10, Exceptional, (190)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Exterior
Farmhouse in the heart of the real chiantishire

Farmhouse in the heart of the real chiantishire

Castellina in Chianti
10.0 out of 10, Exceptional, (147)
"We loved our stay! The Farmhouse is really lovely and the view out the back is exceptional. We enjoyed a lot of home cooked meals with the most stunning view. Daniele was amazing to communicate with as well. Definitely hope to be back one day! "
Australia
Rebekah T.
Farmhouse in the heart of the real chiantishire
Grand Apartment with Garden | Private kitchen | Full-size fridge, microwave, oven, stovetop
Regis Condo

Regis Condo

Siena City Centre
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
Regis Condo
Royal Apartment | View from room
Tuscasì Aparthotel

Tuscasì Aparthotel

Sovicille
9.0 out of 10, Wonderful, (24)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
$58 nightly
The price is $67
Nov 28 - Nov 29
Total with taxes and fees
Tuscasì Aparthotel
2 bars/lounges
Camping Boschetto Di Piemma

Camping Boschetto Di Piemma

3.0 star property
San Gimignano
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
Outdoor dining
Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills

Siena
9.6 out of 10, Exceptional, (75)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
United States
Jessica P.
Villa with large garden in the Chianti hills
Panoramic Suite, City View | View from room
Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi

Siena City Centre
9.6 out of 10, Exceptional, (116)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
$163 nightly
The price is $184
Nov 26 - Nov 27
Total with taxes and fees
Residenza d'Epoca Palazzo Borghesi
Exterior
Camping Siena Colleverde

Camping Siena Colleverde

3.0 star property
Scacciapensieri
8.2 out of 10, Very Good, (159)
"Safe, great proximity to Siena without being too close, nice pool."
United States
Martha
Camping Siena Colleverde
Outdoor pool
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

San Gimignano
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
Property grounds
"Casa di Leo" Bright And Romantic House Surrounded by Medieval Walls and Pool

"Casa di Leo" Bright And Romantic House Surrounded by Medieval Walls and Pool

Belforte
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
Pool
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi

Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi

Montespertoli
9.4 out of 10, Exceptional, (66)
"Check in smoothHost helpfulBeds comfortable.Perfect for a 2 week vacation for 21 family members.Close to major tourist attractions.Pool area very frequently used,the kids loved it.Evenings spent talking in the court yard were lovely.Chef Loradena's cooking class at the house in the industrial kitchen was a hit with all.P"
United States
Elisabeth R.
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi
Outdoor dining
san gimignano apartment in historical center, courtyard and fast free wifi

san gimignano apartment in historical center, courtyard and fast free wifi

San Gimignano City Centre
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.
$170 nightly
The price is $176
Dec 2 - Dec 3
Total with taxes and fees
san gimignano apartment in historical center, courtyard and fast free wifi
Exterior
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Castellina in Chianti
10.0 out of 10, Exceptional, (64)
"We had a company retreat at this amazing location. Everyone was in love with the place and the facilities!"
Netherlands
Jochem G.
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Pool
Le Macine, a wonderful ancient restored watermill with Pool

Le Macine, a wonderful ancient restored watermill with Pool

Volterra
9.6 out of 10, Exceptional, (82)
"A lovely stay, good quality air con in bedrooms, Alex is a great host. Make sure you go to one of the meals he hosts because the food was divine. Good location to Volterra, property is right next to a road but gated. "
United Kingdom
Anna W.
Le Macine, a wonderful ancient restored watermill with Pool
Outdoor pool
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!

Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!

Siena
10.0 out of 10, Exceptional, (9)
"Fabulous place to stay with a big group of family and friends. Very easy walk to town and the beautiful treasures of Siena."
United Kingdom
Marc K.
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Pool
panoramica casa con piscina privata

panoramica casa con piscina privata

siena
7.0 out of 10, Good, (10)
"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....
United Kingdom
Olivier B.
$173 nightly
The price is $173
Dec 1 - Dec 2
Total with taxes and fees
panoramica casa con piscina privata
Interior detail
Castello di Montegufoni

Castello di Montegufoni

Montespertoli
8.0 out of 10, Very Good, (31)
"This was a stunning castle to stay in. The frescoed ceilings were gorgeous. Loved every minute that we were there. The staff were wonderful. The only thing i would recommend is to add a vending machine and maybe to offer pastries in thr morning. "
United States
Cheryl
Castello di Montegufoni
A heated pool
Holiday house with private pool and fenced garden

Holiday house with private pool and fenced garden

Volterra
10.0 out of 10, Exceptional, (63)
"it was a great holiday, with a beautiful house, beautiful view and a very friendly welcome from Jurgen."
Netherlands
frank l.
Holiday house with private pool and fenced garden
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 Castel San Gimignano Hotel Reviews

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"The Grand Hotel Continental in Siena is a rare gem,elegant, inviting, and steeped in history. From the beautifully preserved interiors to the warm, attentive staff, every detail makes you feel genuinely cared for. Its central location is unbeatable, placing Siena’s most charming sights just steps away. A perfect blend of luxury and authentic Tuscan character, this hotel transforms a stay in Siena into something truly unforgettable. The foods were yummy took! "
Betty 4-night trip
Posted 3 days ago
Grand Hotel Continental Siena – Starhotels Collezione

Find out more about Castel San Gimignano

Everything you need to know about Castel San Gimignano vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Castel San Gimignano vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Castel San Gimignano vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castel San Gimignano vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castel San Gimignano. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Castel San Gimignano in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $67 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Castel San Gimignano rentals

At Expedia, we put the best Castel San Gimignano vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Castel San Gimignano rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Castel San Gimignano vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castel San Gimignano. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Can I find a vacation rental in Castel San Gimignano?

Yes, we have vacation rentals close to top local attractions in Castel San Gimignano, or you can select a more secluded option if you're looking for a relaxing stay. Castel San Gimignano is known for its coffeehouses and local tours. Make sure you have time to check out the wineries while you're in the area.

What are some of the best vacation rentals in Castel San Gimignano?

Villa with large garden in the Chianti hills: This vacation home rental outside of Castel San Gimignano is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

How many vacation rentals will I find in Castel San Gimignano?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Castel San Gimignano stay.

What can I see and do in Castel San Gimignano?

Explore the area and family-friendly sights such as Chianti Observatory, or get out into nature at a spot like Sentierelsa Trail. In the larger area, you’ll find Sovestro in Poggio Winery and Piazza della Cisterna.

What are vacation rentals like in Castel San Gimignano?

Vacation rentals are privately owned accommodations you can book for several days or more in Castel San Gimignano. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family gatherings.