Val d'Elsa Vacation Rentals

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Vacation Rentals in Val d'Elsa

Property grounds
Yellow House Country Villa in Chianti Classico
10.0 out of 10, Exceptional, (89)
"A beautiful house for nature lovers , we had everything we needed for our stay. The owner was very friendly and helpful. We really enjoyed our time there . The road to the house was a little bit rough , it could be difficult with a small car . Stefano Grazie per tutti!"
Yellow House Country Villa in Chianti Classico
Outdoor pool
Villa with pool, 4 rooms en suite, Wi-Fi, walking distance from San Gimignano
10.0 out of 10, Exceptional, (83)
"AMAZING! GORGEOUS! SPACIOUS! SPOTLESS! CHARMING! VIEWS SECOND-TO-NONE! CONVENIENT! Everything we could have hoped for and more booking a villa sight unseen! Alessandro - the owner - could not possibly have been more accommodating! From beginning to end, he was responsive, kind, bending over backwards to accommodate our needs. The spacious bedrooms with en suite bathrooms were perfect for 5 sisters to have their own space after a day of sightseeing! We flew into Florence, rented a vehicle and...
Villa with pool, 4 rooms en suite, Wi-Fi, walking distance from San Gimignano
Outdoor pool
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.
10.0 out of 10, Exceptional, (107)
"Great villa and property that was fantastic for our group of 12, including 6 children between ages 5 and 11. So much for them to do with the open spaces, various games, pool, etc. I’ve stayed in Italy with my family three times now and I think this was the best villa and location for driving to many of the great Tuscan cities."
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.
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Pool
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
10.0 out of 10, Exceptional, (30)
"We had a magical stay at Villa Sarah. The home is beautiful and the views look like paintings. Communication could not have been easier but it’s above and beyond your typical VRBO. Their team arranged for a driver (the fabulous Sonia!), an incredible chef, and wine tours. Sonia even got my son in to see her eye doctor one afternoon. Every recommendation the owners made was spot on. I can’t wait to return!"
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
View from property
Enchanting Tuscany Vacation Rental in Medieval Fortress Town Panoramic Views
10.0 out of 10, Exceptional, (90)
"This was a wonderful hamlet with beautiful buildings, views, and quiet. The host, Cindy, was super helpful and very quick to respond to emails. She gave very good directions to the home and how to check in. The home was clean and comfortable for my husband and me. Highly recommend taking cooking class as well. Great location to visit many small towns and wineries."
Enchanting Tuscany Vacation Rental in Medieval Fortress Town Panoramic Views
Outdoor pool
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
10.0 out of 10, Exceptional, (66)
"This was the most remarkable place with a short 10 minute drive to San GiMignano. The accommodations were outstanding. So clean and had everything we needed. The views of SanG and the towers was so unreal. The grounds were surrounded by wine and olive vineyards that were picturesque beyond words. There was a wine tasting vineyard within a 5 minute walk. We also had Allesandro book a professional chef come in to cook a 5 course dinner. Absolutely the best. We originally wanted to stay within the...
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Property grounds
House in enchanting hill location surrounded by vineyards and olive groves
10.0 out of 10, Exceptional, (31)
"We wanted to stay someplace in quiet beautiful Tuscany and this property was located perfectly. The house is a guest house and the main house is near. It is perfectly and remotely located with the most beautiful views! The patio and outdoors are so beautiful and rustic. It is a drive to do anything but so many little towns and villas to visit. Note, the bedroom is a loft with a sturdy steps but low ceiling."
House in enchanting hill location surrounded by vineyards and olive groves
Outdoor pool
- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
10.0 out of 10, Exceptional, (90)
"Stayed here for a week with my husband, daughter, son in law and 5 year old granddaughter. The views from every window were spectacular!! Clean with a fully stocked kitchen, comfortable beds and great outdoor seating area with a brick outdoor bbq. We had our first breakfast prepared for us by the family that lives in the bottom portion of the villa and served at the outdoor seating area overlooking vineyards and olive groves while the rooster was crowing. What a way to start our week!! By the...
- Top Location - Villa in San Gimignano, Top View, 4 DBL En-Suite, Pool, A. C, WiFi
Outdoor pool
BRUNELLO - Cozy cottage located in a peaceful & panoramic position in Tuscany
10.0 out of 10, Exceptional, (51)
"This is a great property with loveku views and a great welcome. Loved our stay and will be going back."
BRUNELLO - Cozy cottage located in a peaceful & panoramic position in Tuscany
Indoor pool, outdoor pool
Stunning Villa: 24 guests, private SwimmingPool
10.0 out of 10, Exceptional, (23)
"We were a group of 22 celebrating a birthday. We spent a wonderful week exploring Tuscany and relaxing at the villa. Fabio was a wonderful host - very responsive and always happy to assist with arrangements or answer questions. The property is vast with many beautiful spaces to relax and cook. I highly recommend it!"
Stunning Villa: 24 guests, private SwimmingPool
Outdoor pool
Entire Tuscan farmhouse with private pool between Siena and Florence
10.0 out of 10, Exceptional, (3)
"We had a wonderful visit to the area and loved the home and property. The check-in and departure was very easy. We had many questions before our arrival and every time we received a prompt reply"
Entire Tuscan farmhouse with private pool between Siena and Florence
The house is located in the heart of Tuscany, in the historic center of San Gimignano.
10.0 out of 10, Exceptional, (11)
"Lots of space. Relaxed. Great home base from which to explore. We went to Volterra for a day. Recommendable. San Gimignano is a great place to visit. Driving wasnt a problem."
The house is located in the heart of Tuscany, in the historic center of San Gimignano.
Property grounds
Red House -- Country villa in Chianti Classico
9.8 out of 10, Exceptional, (101)
"The little red house is a wonderful place to completely relax and enjoy the Tusan/Chianti countryside. Very secluded and quiet. Easy access to dining options. Our host, Stefano, was very helpful and replied quickly to any questions."
Red House -- Country villa in Chianti Classico
Outdoor pool
Cottage with private enclosed garden and panoramic pool, 1 km from the village
9.8 out of 10, Exceptional, (30)
"The property is very well maintained and very nicely finished. The interior is very nicely finished including a full kitchen with dishwasher and two nicely finished complete baths. We enjoyed sitting outside on the patio for breakfast. This was our second stay at Podere Monte because we liked it so much the first time. We have visited Italy many times and have stayed from Lake Como and Venice in the north to Amalfi in the south, and this is our favorite area. Casole and surroundings are very...
Cottage with private enclosed garden and panoramic pool, 1 km from the village
Pool
San Gimignano - Panoramic garden and beautiful pool!
9.8 out of 10, Exceptional, (34)
"Close to tourist places and easy to travel to sites. The hosts were the best and the cooking class and food was incredible!! It is peaceful and the views are beautiful. I would recommend to others but note the house is aging and needs refresh, the air conditioners did not work well, but is authentic in many ways."
San Gimignano - Panoramic garden and beautiful pool!
Outdoor pool, an infinity pool
Beautiful apartment in San Gimignano - RoccaiaCasa'70
9.8 out of 10, Exceptional, (30)
"Everything you need for a quiet, comfortable, scenic stay in the Tuscan countryside. Nestled among grape vines and olive trees, Rita's home is the perfect place from which to launch day trips to San Gimignano, Siena and Florence, or just for relaxing. Comfortable beds, nice patio and porch with a great view of San Gimingano on a hill to the west. She has a well-equipped kitchen and if you need a supermarket, it is only 10 minutes down the road in Poggibonsi. We also enjoyed a hands-on cooking...
Beautiful apartment in San Gimignano - RoccaiaCasa'70
Outdoor pool
VILLA CAROL LUXURY five minutes from San Gimignano, Private Pool A/C WI-FI
9.8 out of 10, Exceptional, (74)
"This villa is an outstanding property. The location is central to the best areas in the Tuscan region The hosts are wonderful I would highly recommend"
VILLA CAROL LUXURY five minutes from San Gimignano, Private Pool A/C WI-FI
Property grounds
Holiday Home 'La Loggia di Giulia' with Private Terrace, Whirlpool and Garden
9.8 out of 10, Exceptional, (6)
"Beautiful view"
Holiday Home 'La Loggia di Giulia' with Private Terrace, Whirlpool and Garden
Interior
HISTORICAL RESIDENCE CHIANTI private swimming pool 30 km from FLORENCE
9.8 out of 10, Exceptional, (25)
"Beautiful property and old world charm. Perfectly located and lovely hosts."
HISTORICAL RESIDENCE CHIANTI private swimming pool 30 km from FLORENCE
Superior Double Room Single Use, 1 Queen Bed, Balcony, Hill View | View from room
Palazzo Pacini
9.6 out of 10, Exceptional, (70)
"The bedroom was small but had a lovely view from the bathroom window and balcony. Breakfast was delicious and staff were friendly. It was disappointing that the room was hot and stuffy even with air-conditioning on (temp 24.5 degrees). We opened the balcony doors which helped however let insects in. It was also disappointing for the price that parking was a few minutes walk from property. "
The price is CA $202
CA $225 total
includes taxes & fees
May 25 - May 26
Palazzo Pacini
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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.

Val dElsa Vacation Rental Travel Info

Other types of properties in Val d'Elsa you may be interested in

Aerial view
Hotel Casolare Le Terre Rosse
3.0 star property
9.2 out of 10, Wonderful, (373)
"Feels like a home"
The price is CA $212
CA $239 total
includes taxes & fees
Jun 12 - Jun 13
Hotel Casolare Le Terre Rosse
View from room
La Cisterna
3.0 star property
9.0 out of 10, Wonderful, (524)
"Great location"
The price is CA $148
CA $169 total
includes taxes & fees
Jun 17 - Jun 18
La Cisterna
3 outdoor pools, open 9:00 AM to 7:00 PM, pool umbrellas, sun loungers
Poderi Arcangelo
8.8 out of 10, Excellent, (227)
"Stunning property with the most incredible breathtaking views. Note that the property is very remote therefore you will need a car to get to it and a car to get from each building on the property. It would be useful to know that dinner is only served at 8pm and there is not really any food or drinks available in between so would be good to come stocked with supplies."
The price is CA $336
CA $375 total
includes taxes & fees
May 31 - Jun 1
Poderi Arcangelo
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Val d'Elsa. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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