Val d'Elsa Vacation Rentals

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Vacation Rentals in Val d'Elsa

Camping Boschetto Di Piemma
3.0 star property
9.0 out of 10, Wonderful, (58)
"Nice quiet spot in the woods but very close to San Gimignano. Very clean. Comfortable beds. They don’t provide towels or soaps, but that is clear up front. You can rent towels if you want and they sell soap/ shampoo in the office. "
The price is CA $70
CA $79 total
includes taxes & fees
Jun 3 - Jun 4
Camping Boschetto Di Piemma
Castello Del Nero - Podere San Filippo
10.0 out of 10, Exceptional, (33)
"Beautiful property at a scenic and peaceful location. We stayed in a 2 bedroom apartment which had 2 bathrooms, a real bonus! We appreciated the pool and the deckchairs scattered around the grounds of the property. There were many restaurant choices within 10 min drive from the property. Things we did not like: 1. We asked reception for towels for the pool and were told to use those in our room. We saw the same receptionist delivering pool towels to another party moments later. 2. We were...
The price is CA $1,148
CA $1,266 total
includes taxes & fees
May 31 - Jun 1
Castello Del Nero - Podere San Filippo
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 $203
CA $226 total
includes taxes & fees
Jun 10 - Jun 11
Palazzo Pacini
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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
Villa San Filippo
4.0 star property
8.6 out of 10, Excellent, (34)
"Conveniently situated between Florence and Siena in the heart of the Chianti region with stunning views. Friendly relaxed hosts who provide a substantial breakfast. Beautiful large swimming pool to cool off at the end of the day."
The price is CA $202
CA $228 total
includes taxes & fees
May 31 - Jun 1
Villa San Filippo
Lovely converted barn with enclosed garden and private pool
9.6 out of 10, Exceptional, (50)
"We had a lovely stay in a converted barn with pool. Very rustic but quiet and close to all the places we wanted to visit. We had a car"
Lovely converted barn with enclosed garden and private 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
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
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.
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
9.6 out of 10, Exceptional, (47)
"This villa is a dream. You really feel like you’re in a Disney castle in the home and in the little village! Our hosts were so easy to communicate with and so patient with us as we arrived much later than planned. They even went to great lengths to try and help us find food upon arrival because our kids were starving. It’s a fantastic location if you plan to take day trips all over Tuscany. It was nice to be centrally located so we could head out to Florence, San Gimignano, Lucca, and Pisa and...
Tuscany Luxury Spacious Villa Private Pool Wi-Fi free near Siena Family Frendly
Enchanting Tuscany Vacation Rental in Medieval Fortress Town Panoramic Views
10.0 out of 10, Exceptional, (92)
"The apartment is as advertised –a renovated unit in the historic town. It is spacious and stocked with many essentials to make your stay more convenient. There are two great restaurants a stone’s throw away – one making wood oven pizzas and the other doing traditional local Italian food. There are two cafes a short walk away for your morning espresso with amazing deli sandwiches and pastries and a small Coop grocery store within 15 minute walk. The town is in the heart of Chianti between Sienna...
Enchanting Tuscany Vacation Rental in Medieval Fortress Town Panoramic Views
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
10.0 out of 10, Exceptional, (31)
"Wonderful Villa, very scenic and quiet. Caterina wonderful to work with."
Villa Sarah Luxury Villa a San Gimignano 5 room en suite swimming pool spa
House in enchanting hill location surrounded by vineyards and olive groves
10.0 out of 10, Exceptional, (32)
"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
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
9.8 out of 10, Exceptional, (69)
"If you've got an image in your head of the Tuscan countryside, you will not be disappointed. The views from this property could star in a tourism campaign. The house is extremely comfortable and each room has a private, ensuite bathroom. The outdoor areas are wonderful for al fresco dinners and watching the sunset with an Aperol Spritz in hand. Our host, Alessandro, is well organized and has anticipated every need and every question -- from restaurant recommendations to wine tastings."
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
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
Info House
9.8 out of 10, Exceptional, (6)
"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
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
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!
"Sunflower 4" Romantic for two
9.2 out of 10, Wonderful, (22)
"The property is very beautiful and rustic-it is off a gravel road so a car is needed, but it is not far from a supermarket and restaurants. The pool was delightful after a long hot day exploring the region, and the property was very large and perfect for multiple evening strolls. Stelio and Rossella were extremely friendly, accommodating, and helpful hosts. We were even greeted by one of the chickens and their dog! Stelio arranged a wine tasting with one of his friends, which was delightful. The...
"Sunflower 4" Romantic for two
Authentic country house originally a convent, dates back to around the year 1000
9.6 out of 10, Exceptional, (44)
"Host was very accommodating. Facility was excellent. Location is very good for day trips to Siena,Volterra and Pisa. Our grandson really enjoyed the pool."
Authentic country house originally a convent, dates back to around the year 1000
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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

Hotel Ristorante Alcide
4.0 star property
8.0 out of 10, Very good, (362)
"Good"
The price is CA $96
CA $111 total
includes taxes & fees
Jun 9 - Jun 10
Hotel Ristorante Alcide
Hotel Casolare Le Terre Rosse
3.0 star property
9.2 out of 10, Wonderful, (374)
"Feels like a home"
The price is CA $220
CA $247 total
includes taxes & fees
Jun 12 - Jun 13
Hotel Casolare Le Terre Rosse
Poderi Arcangelo
8.8 out of 10, Excellent, (233)
"Beautiful location. Very nice room with a lovely view. Dinner was good value, food wholesome and nice. Convivial atmosphere which was nice but service at dinner needed to be a little more professional and pleasant. Breakfast was good but would have liked a better selection of breads and meats and hot eggs."
The price is CA $216
CA $243 total
includes taxes & fees
Jun 5 - Jun 6
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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