Castel San Gimignano Vacation Rentals

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Nov 15 - Nov 16
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Vacation Rentals in Castel San Gimignano

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
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)
"Really enjoyed our short stay. The studio has all we needed, and we were given ine with a wraparound balcony with views of the stunning countryside!"
United Kingdom
Heike
$71 nightly
The price is $81
Dec 16 - Dec 17
Total with taxes and fees
Chianti Village Morrocco
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Siena City Centre
9.6 out of 10, Exceptional, (188)
"Staff was very nice and helpful."
United States
Steven
$155 nightly
The price is $175
Nov 16 - Nov 17
Total with taxes and fees
Il Battistero Siena - Residenza d'Epoca
2 bars/lounges
Camping Boschetto Di Piemma

Camping Boschetto Di Piemma

3.0 star property
San Gimignano
8.8 out of 10, Excellent, (85)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveler
Camping Boschetto Di Piemma
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, (146)
"Everything was perfect: thank you"
United Kingdom
Richard D.
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
$72 nightly
The price is $83
Nov 16 - Nov 17
Total with taxes and fees
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
$67 nightly
The price is $77
Dec 10 - Dec 11
Total with taxes and fees
Tuscasì Aparthotel
Exterior
Camping Siena Colleverde

Camping Siena Colleverde

3.0 star property
Scacciapensieri
8.2 out of 10, Very Good, (159)
"Quiet. Rooms are adequate. Parking is easy. On-site dining is good. Short walk to bus transport "
Australia
Robert
Camping Siena Colleverde
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)
"Adrianna was very helpful. And her home was comfortable for our family of four,. The garden was beautiful and we ate outdoors every meal. The pool was clean, yet well loved. Thanks for a great stay in a perfect location to see the surrounds of Tuscany."
Australia
Fiona F.
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, (115)
"Great location in Siena!"
United States
Sherry
$160 nightly
The price is $181
Nov 16 - Nov 17
Total with taxes and fees
Residenza d'Epoca Palazzo Borghesi
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)
"The Leoni Villa is the perfect spot for a family vacation. There were 14 of us from 2 years old to 65 years old and we all had a great time! The rooms are great as well as the grounds which offers lemon, plum and olive trees. The Villa also has a spectacular pool with great views. Marco the caretaker was wonderful and helped us with anything we needed."
United States
Cynthia B.
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)
"Amazing place with great location "
Canada
ANGELA C.
$186 nightly
The price is $192
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)
"This was a trip we soon won't forget and we will 100% be back to visit. We <3 Isola Serena!!"
United States
Ashley M.
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Outdoor pool, an infinity pool
Beautiful apartment in San Gimignano - RoccaiaCasa'70

Beautiful apartment in San Gimignano - RoccaiaCasa'70

San Gimignano
9.8 out of 10, Exceptional, (48)
"Quiet place to stay"
United States
mark e.
Beautiful apartment in San Gimignano - RoccaiaCasa'70
Interior detail
Castello di Montegufoni

Castello di Montegufoni

Montespertoli
8.0 out of 10, Very Good, (31)
"Advertised as a stay in castle, given an apartment outside the castle at the car park! Last night of stay and the next morning No hot water! No cleaning for 7 days, no change of the sheets or towels. Tree cutting at 8am. Apartment smells like damp. Cleaners while cleaning other apartments talking loudly like they were arguing. The outside look it is amazing, beautiful scenery!"
United Kingdom
Liridon
Castello di Montegufoni
Outdoor dining
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany

Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany

Siena
10.0 out of 10, Exceptional, (107)
"Beautiful home, beautiful views. "
United States
James D.
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany
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)
"This property exceeded our expectation and was fantastic. Juergen and Gabi were the best hosts anyone could hope to have when staying abroad. Every recommendation for food, touring or wine tasting was absolutely spot on. We will be back and have already been recommending to our friends and family. "
United States
Todd L.
Holiday house with private pool and fenced garden
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)
"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."
United States
Susan A.
Le Macine, a wonderful ancient restored watermill with 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.
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Top Castel San Gimignano Hotel Reviews

La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"It was a totally delightful experience. Our needs were taken care of, the Breakfast delicious and the meals at their restaurant superb. It was a perfect place to rest, relax and see Siena. "
Janice 3-night trip
Posted 3 days ago
La Certosa di Pontignano

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 $77 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.

Explore a world of travel with Expedia

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?

Casa Vacanze Le Case: This vacation home rental outside Castel San Gimignano offers an outdoor pool, a terrace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities like a stovetop and kitchenware can make your vacation run smoothly. You and your friends and family can relax into your vacation with amenities like a garden.

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

With 6 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.