Lupompesi vacation rentals

We found 513 vacation rentals — enter your dates for availability

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August 2025

September 2025

Discover a selection of vacation rentals in Lupompesi that are perfect for your trip. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include a garden and pool. Whatever you're looking for, you'll find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Lupompesi

Showing deals for:Nov 7 - Nov 14

Exceptional

(14 reviews)

Mulino della Solaia, Arceno Rentals Club, Luxury Villa in Tuscany, pool, wifi

Monticiano, Toscana

15% off

includes taxes & fees

Exceptional

(19 reviews)

FARMH. PODERE CUNINA 25 KM SUD SIENA / MONTALCINO PRENDENDO LEZIONI DI CUCINA

Buonconvento

10% off

includes taxes & fees

Exceptional

(59 reviews)

Chic Tuscan apartment pool spectacular view modern comfort wifi air conditioning

Sovicille, Provincia di Siena

10% off

includes taxes & fees

Exceptional

(21 reviews)

FARMH. PODERE CUNINA 25 KM SUD SIENA DI FRONTE AL MONTALCINO PRENDENDO CUCINE DI CUCINA

Buonconvento

10% off

includes taxes & fees

Exceptional

(14 reviews)

FARMH. PODERE CUNINA 25 KM SUD SIENA DAVANTI AL MONTALCINO TENENDO CUCINE CLAS

Buonconvento

10% off

includes taxes & fees

Exceptional

(152 reviews)

Antica fattoria 25 km a Siena di fronte a Montalcino con piscina / lezione di cucina

Buonconvento, Siena

10% off

includes taxes & fees

Exceptional

(54 reviews)

Prestigious apartment infinity pool breathtaking view wifi and air conditioning

Sovicille, Provincia di Siena

33% off

includes taxes & fees

Exceptional

(30 reviews)

FARMH. PODERE CUNINA 25 KM SUD SIENA DI FRONTE AL MONTALCINO PRENDENDO LEZIONI DI CUCINA

Buonconvento

7% off

includes taxes & fees

Exceptional

(36 reviews)

FARMH. PODERE CUNINA 25 KM SUD SIENA DI FRONTE AL MONTALCINO PRENDENDO CUCINE DI CUCINA

Buonconvento

10% off

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Lupompesi

Bosco della Spina

Sleeps 2 · 1 bedroom

Water, Plant, Sky, Building, Swimming Pool, Azure, Tree, Shade, Outdoor Furniture, Grass

Stunning private villa for 4 people with WIFI, A/C, pool, TV, terrace and parking

Sleeps 4 · 2 bedrooms · 1 bathroom

Top rated rentals - Lupompesi

Stunning

Stunning views, quiet, lush gardens. Amenities pool, washer

Kylene M.

Stayed May 2025

Premier Host

A visit of Tuscany

Property is perfectly located. We wanted to have a good overview of Tuscany..... and we got it...We spent the first day in Siena and then we visited : Volterra , Montepulciano, Montalcino and the same day we had wine tasting at Castiglion del Bosco winery, then Cortona, Monteregionni, San Ginignano and we spent the last day in PienzaNothing wrong about the house. We loved everything about Tuscany........and mostly the winethe house is cozy, clean and in a very quiet environment !

Yves G.

Stayed Apr 2025

Premier Host

Our Trip to Tuscany

The picture of the farmhouse doesn't do the location justice after you see it in person.. it's a spectacular view! We arrived on a beautiful sunny day and were warmly welcomed by our hosts. After getting a quick tour of where we would be staying for the next week, we were pleasantly surprised by the kind gesture of homemade olive oil and wine left for us to have. Thank you! The location of this property is perfect for visiting the Tuscany countryside. Not only did we visit Siena on a few occasions, we also did day trips to Montepulciano, Cortona, Piensa and San Gimigagno. Our hosts gave us our space but also took time to answer our questions and make us feel welcome. We especially loved our conversations about all the delicious fruit they had growing in their yard! We will miss waking up to "Rusty" the rooster and seeing the chickens, rabbits and cats each day. Thank you for sharing your lovely home with the world.. this was the type of vacation we were hoping to have! Arrivederci Todd, Joy & Pauline

Todd M.

Stayed Oct 2024

Premier Host

Like living in a painting!

I can’t say enough about what a magical place Macchione is! It exceeded our expectations in every way. Every inch of the villa has been meticulously restored and decorated impeccably. The view is stunning and there was plenty of room for the 12 of us (6 adults and 6 kids) with room to spare. Cally was an incredible host, providing all sorts of helpful information leading up to our stay, and was always available to answer questions. We spent lots of time in the pool and playing ping pong and enjoyed day trips to Buonconvento and Siena. It was an unforgettable experience and we would love to return!

Kim P.

Stayed Jun 2024

Amazing property!

We had an absolutely amazing stay in Tuscany! The property is even more spectacular than the photos, a truly relaxing holiday! The apartment was so historic, yet with modern conveniences, really exceptional and we would highly recommend to anyone! The owners are wonderful and very accessible anytime. Pool, grounds and area are second to none, can’t imagine a more exceptional property in Tuscany!

Patrick Q.

Stayed Jun 2024

Amazing location

Fell in love with this Tuscan paradise. Views for miles, peaceful, easy to get to. Host was a pleasure to deal with and very responsive to questions or concerns. We will definitely aim to stay here again to explore more of Tuscany

Angele L.

Stayed May 2024

Premier Host

Perfect Apartment

We stayed in 7 difference locations while visiting Italy, and found this apartment in Siena to be the best. The apartment was very comfortable, nicely decorated, and had everything that we needed to make our stay enjoyable. Cristina, Claudio, and Beatrice were all very helpful throughout the booking and check-in process, as well as during our stay. Bus stops are very handy, as they are located just outside the front door. I would highly recommend booking this property.

Brenda M.

Stayed Oct 2023

Casa Bella

Our host was lovely and very accommodating and even got us a ride to the train station. We didn't have a car so we took advantage of the bus system and went on adventures. There is a bakery and a wee grocery. Great coffee. All in all we enjoyed our stay.

Deborah O.

Stayed Jun 2023

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value

Find out more about Lupompesi

The beautiful area of Lupompesi awaits your stay

The countryside and other outdoor surroundings create an inviting atmosphere in Lupompesi. Travelers appreciate the restaurants in this scenic city. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Lupompesi

Do you want to find top things to see and do in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Lupompesi a one-of-a-kind vacation spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

Castiglion del Bosco Winery (6.8 mi / 10.9 km)
Terme Petriolo (8.3 mi / 13.3 km)
Siena Circuit (10.2 mi / 16.4 km)
Tenuta Greppo Franco Biondi Santi (10.8 mi / 17.4 km)
San Giovanni Terme Rapolano (12.6 mi / 20.3 km)
Castello Banfi (13.5 mi / 21.8 km)

Exploring the natural landscape of Lupompesi

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Lupompesi is a great place to get outside. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city center:

I Canaloni del Torrente Farma (12 mi / 19.3 km)
Horti Leonini (13.7 mi / 22 km)
Terme Antica Querciolaia (13.7 mi / 22.1 km)
Val di Chiana (22.8 mi / 36.7 km)
Val di Merse (8.1 mi / 13 km)
Enoteca Italiana (10.6 mi / 17.1 km)

How to get to and around Lupompesi

The nearest airport is in Florence Airport, Peretola (FLR), located 44.2 mi (71.2 km) from the city center.

Frequently asked questions

How much does it cost to rent a vacation rental in Lupompesi?

The average price for a vacation rental in Lupompesi depends on a number of factors, like length of stay, property type and season. Whether you're in search of a sprawling villa with lots of bedrooms or a cozy cabin for just you and the kids, just add your travel dates to find stays with unbeatable value.

How much does it cost to rent a beach house in Lupompesi?

The average price for a vacation rental close to the beach in Lupompesi will depend on when you'll be there and the type and size of property you're looking for. Find prices quickly and easily on Vrbo by entering your preferred travel dates and destination. Then use our filters to pick the number of bedrooms and amenities important to you, like WiFi, air conditioning and a pool.

What are the top attractions for families in Lupompesi?

Castello di Montepescini will keep the kids busy during your Lupompesi break. This family-friendly attraction is close to the center.

How old do you have to be to rent a vacation rental in Lupompesi?

We recommend checking with the Lupompesi vacation property you'd like on Vrbo as the age limit varies. However, typically it's 16, 18 or 21.

How long can I rent a vacation rental in Lupompesi for?

The length of time you can rent a vacation rental in Lupompesi differs according to the property. Just enter your preferred travel dates to view a list of options offering extended stays. With tons of creature comforts such as kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to find a terrific place to call your home away from home in Lupompesi.