
Luxury rentals in Province of Siena
Find and book unique accommodations on Airbnb
Top-rated luxury vacation rentals in Province of Siena
Guests agree: these stays are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Province of Siena luxury vacation rentals
Other great luxury vacation rentals in Province of Siena
Luxe

Villa in Buonconvento
5 out of 5 average rating, 6 reviewsPodere Maiano
AnthonyRating, 5 stars26 months ago
Villa di Montesoli was an amazing experience for our entire multigenerational family. Our group consisted of 9 adults and 4 children including an 18 month infant. Pietro and the entire staff were beyond accommodating to all of us the entire week. The accommodations were fantastic with plenty of space for the entire family, with bonus spa room (hot tub, sauna and pool table). Outdoors we enjoyed family bocce. We were not in season to use the pool but it would be ideal for a summer stay. The location of the Villa is perfect for a memorable Tuscan vacation. The property expands many acres with fantastic views of hills and valleys within Val d’Orcia. We were able to visit Pienza, Montalcino, Montepulciano, Cortona, Siena and even Florenece from the Villa, in addition to a local farm, olive oil producer and wineries for tastings/tours all within our 7 day stay. We took advantage of breakfast and dinner each day at the Villa and the house cooks Giovanna and Daniela were wonderful and the food was amazing- true home cooked italian meals. They were also helpful shopping on our behalf at the local COOP for anything that we may require during the stay. We also enjoyed a fun and delicious pizza night with Ciro at the Villa - he was awesome. Pietro was very attentive during our stay and also had great communication prior to our trip. If you are looking for a true Tuscan experience, in an ideal location with a fabulous host look no further than Villa di Montesoli.
Luxe

Villa in Radicondoli
Dimora storica San Lorenzo a Montalbano
RonniRating, 5 stars1 month ago
Perfect stay in the beautiful Tuscan countryside! The Villa is newly renovated and impeccably decorated. Each bedroom has its own bathroom, all beautifully decorated with very comfortable beds. The kitchen is enormous and well equipped to entertain a large group. The pool and garden are truly gorgeous, facing out into the countryside for a fabulous view. Finally, our hosts were amazing, They provided us with tons of recommendations, arranged for a local chef and even got us into a winery for a last minute tasting. I cannot recommend this property and the Villa Med hosts enough! We will be reaching out to them for our next trip!
Luxe
Villa in Sarteano
Rosenzia
MatthewRating, 5 stars10 months ago
Poggio Mori has to be seen to be believed. It is truly spectacular. The pictures make it look good, but the reality is something entirely better even than that. We visited with friends and family, and could not have had a better time. Wow.
Luxe

Home in Gaiole in Chianti
Timeless Elegance: 16th-Century Tuscan Farmhouse
JodyRating, 5 stars2 months ago
Loved the home and the staff was amazing!
Luxe

Villa in San Gimignano
Villa Iris Tenuta Melograni
JulieRating, 5 stars25 months ago
Fabulous location and gorgeous grounds. Very well maintained also with lovely owners
Luxe

Home in Buonconvento
Villa di Montesoli
Laurel LeeRating, 5 stars2 weeks ago
This is the greatest place on earth. It is more beautiful than the pictures even show. Every room is truly enormous and so beautifully designed. The view from every room is a dream - and from the outdoor dining and lounge area just heaven. We couldn’t stop saying it doesn’t look real. We were here on a work retreat from NYC and there is so much room for everyone to have privacy. It’s also more luxury than I even realized with really nice huge brand new bathrooms. The host helped us with everything and every recommendation was excellent. We hired the local chefs that were recommended and they were perfect - pizza in the outdoor pizza oven, delicious pasta and meats from local nonnas. Some of us came by the train from Florence and it was so easy into Buonconvento. Others drove (beautiful!!) and others took the recommended driver who took us at all hours to Rome and Florence airports - use him he’s great. The food at the local town is so good and easy to get to. Magical!!
Luxe

Villa in Buonconvento
Borgo Finocchieto
Luxe

Villa in Sarteano
Aiola
Destinations to explore
- Rentals with a fire pit Province of Siena
- Tiny house rentals Province of Siena
- Smoking-friendly rentals Province of Siena
- Rentals with a fireplace Province of Siena
- Rentals with pools Province of Siena
- Villa rentals Province of Siena
- Townhouse rentals Province of Siena
- Barn rentals Province of Siena
- Loft rentals Province of Siena
- Bed and breakfasts Province of Siena
- Rentals with breakfast Province of Siena
- Castle rentals Province of Siena
- Condo rentals Province of Siena
- Rentals with outdoor seating Province of Siena
- Serviced apartment rentals Province of Siena
- Private suite rentals Province of Siena
- Guesthouse rentals Province of Siena
- Cottage rentals Province of Siena
- Rentals with a hot tub Province of Siena
- Rentals with a kayak Province of Siena
- Fitness-friendly rentals Province of Siena
- Vacation home rentals Province of Siena
- Rentals with an EV charger Province of Siena
- Apartment rentals Province of Siena
- Nature eco lodge rentals Province of Siena
- Rentals with a washer and dryer Province of Siena
- Rentals with a balcony Province of Siena
- Rentals with lake access Province of Siena
- Rentals with a sauna Province of Siena
- Rentals with a home theater Province of Siena
- Rentals with a patio Province of Siena
- Rentals with an accessible height bed Province of Siena
- Kid-friendly rentals Province of Siena
- Pet-friendly rentals Province of Siena
- Waterfront rentals Province of Siena
- Hotel rentals Province of Siena
- House rentals Province of Siena
- Boutique hotel rentals Province of Siena
- Family-friendly rentals Province of Siena
- Farmstay rentals Province of Siena
- Luxury rentals Tuscany
- Luxury rentals Italy
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Lake Trasimeno
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Basilica of Santa Maria Novella
- Mugello Circuit
- Cala Violina
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Kite Beach Fiumara
- Marina di Grosseto beach
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Cavallino Matto
- Teatro Verdi
- Palazzo Vecchio
- Things to do Province of Siena
- Art and culture Province of Siena
- Tours Province of Siena
- Sightseeing Province of Siena
- Food and drink Province of Siena
- Nature and outdoors Province of Siena
- Things to do Tuscany
- Wellness Tuscany
- Tours Tuscany
- Art and culture Tuscany
- Entertainment Tuscany
- Nature and outdoors Tuscany
- Sports activities Tuscany
- Sightseeing Tuscany
- Food and drink Tuscany
- Things to do Italy
- Nature and outdoors Italy
- Food and drink Italy
- Entertainment Italy
- Wellness Italy
- Tours Italy
- Sightseeing Italy
- Sports activities Italy
- Art and culture Italy
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes