Villa del Monte Vacation Rentals

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Vacation Rentals in Villa del Monte

Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas
Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo

4.0 star property
Florence
8.2 out of 10, Very Good, (226)
"The property is perfect if you’re looking for a place to relax and have the most wonderful views of Tuscany area, the staff, Andrea was really helpful and kind. It’s better if you rent a car to get there, by bus you’ll have to walk a lot. But the place is totally worth it,"
United States
Jorge
$60 nightly
The price is $83
Dec 13 - Dec 14
Total with taxes and fees
Fattoria il Milione Agriturismo
Aerial view
Relais Villa Olmo

Relais Villa Olmo

Impruneta
9.4 out of 10, Exceptional, (227)
"This is a beautiful Villa with a stunning views. Rooms were large and very clean and the location was wonderful. It was close to Florence and ideal for exploring Tuscany. Restaurant offered delicious buffet breakfast and many other wonderful local dishes for lunch and dinner. I would highly recommend this Villa and would love to stay here again."
United States
Ewa
Relais Villa Olmo
Cribs/infant beds, bed sheets
hu Firenze Certosa camping in town

hu Firenze Certosa camping in town

Impruneta
8.0 out of 10, Very Good, (57)
"Wonderful staff and great amenities!"
Canada
Chenjin
hu Firenze Certosa camping in town
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)
"Front desk was very helpful and very comfortable room. "
United States
Chris
$66 nightly
The price is $75
Dec 12 - Dec 13
Total with taxes and fees
Chianti Village Morrocco
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, (148)
"We loved our stay! The Farmhouse is really lovely and the view out the back is exceptional. We enjoyed a lot of home cooked meals with the most stunning view. Daniele was amazing to communicate with as well. Definitely hope to be back one day! "
Australia
Rebekah T.
Farmhouse in the heart of the real chiantishire
Outdoor pool
CHRISTMAS OFFER!10% DISCOUNT! Charming Villa Torre in Chianti, 8ensuite bedrooms

CHRISTMAS OFFER!10% DISCOUNT! Charming Villa Torre in Chianti, 8ensuite bedrooms

San Casciano in Val di Pesa
10.0 out of 10, Exceptional, (124)
"Excellent property Great bedrooms and eating area"
United Kingdom
douglas f.
CHRISTMAS OFFER!10% DISCOUNT! Charming Villa Torre in Chianti, 8ensuite bedrooms
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)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
United States
Jessica P.
Villa with large garden in the Chianti hills
2 bars/lounges
Camping Boschetto Di Piemma

Camping Boschetto Di Piemma

3.0 star property
San Gimignano
8.8 out of 10, Excellent, (85)
"The mobile homes were a great alternative when Via Francigena hostels were full. Friendly people, swimming pool was wonderful , and an easy walk back and forth to San Gimignano."
United States
Martha
Camping Boschetto Di Piemma
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
Outdoor dining
Villa with concierge service & heated pool at 20 minute from Florence center

Villa with concierge service & heated pool at 20 minute from Florence center

impruneta
10.0 out of 10, Exceptional, (105)
"The Villa and grounds are absolutely beautiful! Caterina and her family members were the most gracious hosts. They could not do enough to make sure we had a "once in a lifetime" multi-generational family trip and truly made us feel like part of their family during our stay. We loved every second of our time in Tuscany and would highly recommend this amazing property."
United States
Charles S.
$1,557 nightly
The price is $1,562
Jan 5 - Jan 6, 2026
Total with taxes and fees
Villa with concierge service & heated pool at 20 minute from Florence center
Outdoor dining
PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION

Ruffoli
9.8 out of 10, Exceptional, (59)
"This is the most special place I’ve ever been. It’s breathtakingly beautiful. The house itself it’s stunning but the outside terrace and pool area is a dream. I will absolutely come back here again if I get the chance. The host was very helpful, communicative and kind."
United States
Alexandra E.
PICTURESQUE VIEWS OLIVE VINEYARDS EAT DRINK PURE RECREATION
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)
"Check in smoothHost helpfulBeds comfortable.Perfect for a 2 week vacation for 21 family members.Close to major tourist attractions.Pool area very frequently used,the kids loved it.Evenings spent talking in the court yard were lovely.Chef Loradena's cooking class at the house in the industrial kitchen was a hit with all.P"
United States
Elisabeth R.
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi
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)
"Gorgeous property - we had a wonderful stay "
United Kingdom
Michelle D.
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Exterior detail
La Casa di Ines

La Casa di Ines

San Gimignano City Centre
9.6 out of 10, Exceptional, (7)
"Love this town. Location is great "
United States
William
$76 nightly
The price is $90
Dec 19 - Dec 20
Total with taxes and fees
La Casa di Ines
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)
"Great experience in a medieval villa converted to apartments. We were there for one night and enjoyed it very much!"
United States
Matthew E.
$149 nightly
The price is $155
Jan 7 - Jan 8, 2026
Total with taxes and fees
san gimignano apartment in historical center, courtyard and fast free wifi
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)
"it was a great holiday, with a beautiful house, beautiful view and a very friendly welcome from Jurgen."
Netherlands
frank 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)
"Clean and comfortable stay with lovely garden and pool, overall a great experience"
United Kingdom
Daniel A.
Le Macine, a wonderful ancient restored watermill with Pool
Pool
Your panoramic house in Tuscany between vineyards and olive groves.

Your panoramic house in Tuscany between vineyards and olive groves.

Barberino Val d'Elsa
9.8 out of 10, Exceptional, (43)
"The property was absolutely charming. It really had that homey, Italian, Tuscan charm about it. The kids and my husband loved it too. I wish I had planned for more days there. We didn’t have time to partake in the cooking class or truffle hunting, but I guess that just leaves a reason to come back. The location was great too because it’s in the country away from the busy cities, but a close enough drive to all the various Tuscan sites.The owners were very nice and spoke good enough English....
United States
Gwen L.
Your panoramic house in Tuscany between vineyards and olive groves.
Seasonal outdoor pool, pool umbrellas, sun loungers
Castello Del Nero - Podere San Filippo

Castello Del Nero - Podere San Filippo

Barberino Tavarnelle
9.8 out of 10, Exceptional, (38)
"Much nicer stay then the rooms at the Como"
United States
Anonymous traveler
Castello Del Nero - Podere San Filippo
Terrace/patio
Country House & Spa - Inside Nature with panoramic views, Art Surrounded

Country House & Spa - Inside Nature with panoramic views, Art Surrounded

Volterra
9.8 out of 10, Exceptional, (65)
"Villanovia is as wonderful as it looks online. Marco and Laura are exceptional hosts and took care of us with kindness and made sure our every need was well taken care - we had a lovely stay! Thank you Marco and Laura!"
United States
Sarah R.
Country House & Spa - Inside Nature with panoramic views, Art Surrounded
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 Villa del Monte Hotel Reviews

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

10/10 Excellent
"The hotel and services exceeded my expectations."
Vili 2-night trip
Posted 6 days ago
Hotel Borgo di Cortefreda Relais

Find out more about Villa del Monte

Everything you need to know about Villa del Monte 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 Villa del Monte 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 Villa del Monte vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Villa del Monte vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Villa del Monte. 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 Villa del Monte 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 $75 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 Villa del Monte rentals

At Expedia, we put the best Villa del Monte 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 Villa del Monte 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 Villa del Monte vacation.

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Frequently asked questions

Can I find vacation rentals in Villa del Monte?

Yes, we have vacation rentals close to well known sights in Villa del Monte, or you can select a secluded option if you're looking for relaxation.

What's the top vacation rental in Villa del Monte?

Farmhouse in the heart of the real chiantishire: Visitors like this Villa del Monte vacation home rental. It is located in a rural location and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Villa del Monte?

Explore the area and family-friendly sights such as Chianti Observatory, or get out into nature at a spot like Sentierelsa Trail. Casa del Boccaccio and Tenuta Torciano Winery are a couple of places you'll find in the larger area.

What are vacation rentals like in Villa del Monte?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Villa del Monte. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for small groups.