Villa del Monte Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Villa del Monte vacation rentals

Outdoor pool, sun loungers
Borgo San Giusto

Borgo San Giusto

Borgo San Giusto
Empoli
9.4 out of 10, Exceptional, (38)
"The hotel stay was great."
United Kingdom
Jonathan
The price is ￥15,389
￥17,478 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Borgo San Giusto
Property grounds
B&B Il Moscondoro

B&B Il Moscondoro

B&B Il Moscondoro
Montopoli in Val d'Arno
8.0 out of 10, Very Good, (8)
"B&b nella campagna toscana, esperienza piacevole, il plus è il silezio totale che ha accompagnato il mio sonno"
Italy
Davide
The price is ￥15,028
￥16,531 total
includes taxes & fees
Dec 27 - Dec 28
B&B Il Moscondoro
Comfort Room | Premium bedding, free WiFi
Room Rent Morrona

Room Rent Morrona

Room Rent Morrona
Terricciola
9.0 out of 10, Wonderful, (6)
"Ottima struttura "
Italy
Marzia
Room Rent Morrona
Exterior detail
La Casa di Ines

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
The price is ￥12,173
￥14,309 total
includes taxes & fees
Jan 8 - Jan 9, 2026
La Casa di Ines
Full-size fridge, oven, stovetop, espresso maker
Rocca Palazzaccio

Rocca Palazzaccio

Rocca Palazzaccio
3.0 star property
Impruneta
9.0 out of 10, Wonderful, (14)
"A lovely stay at this property with our 2 year old.The apartment had everything we needed and communication with the host was very good There are steep hills to access the property by car or foot so bear that in mind but we managed fine with a pram and a car its just worth noting Handy to have laundry facilities on site aswell. There is a coop just a few minutes down the road Lovely views and a clean pool which was perfect for our little one to use and toys there that he could play in the...
United Kingdom
Lauren
Rocca Palazzaccio
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas
Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo
4.0 star property
Florence
8.4 out of 10, Very Good, (229)
"We stayed two days with kids. Perfect resort feeling, enjoyed sun rising, perfect ample amount of healthy and fresh breakfast, very welcoming and friendly helpful staff, room are spacious and clean, and cozy remote control heating options, washrooms are very clean and water is always hot. "
Canada
Manjeet
The price is ￥9,369
￥12,877 total
includes taxes & fees
Dec 26 - Dec 27
Fattoria il Milione Agriturismo
Property amenity
Antica Pieve B&B

Antica Pieve B&B

Antica Pieve B&B
Barberino Tavarnelle
9.4 out of 10, Exceptional, (14)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
The price is ￥14,193
￥20,021 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Antica Pieve B&B
Exterior detail
Villa il Fedino

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
The price is ￥22,002
￥24,937 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Villa il Fedino
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, sun loungers
Lebbiano Residence Bio Resort

Lebbiano Residence Bio Resort

Lebbiano Residence Bio Resort
3.0 star property
Scandicci
9.4 out of 10, Exceptional, (23)
"Vicino a Firenze e quindi alle principali via di scambi, ma in una tranquillità disarmante. Il silenzio è parte integrante della struttura, ma sia chiaro assolutamente positivo. La struttura è ubicata in una zona veramente bella e le stanze sono confortevoli, comode e con la possibilità di cucinare. Infine fatevi coccolare dalla colazione servita in compagnia di uno stupendo gattone rosso e dalla bella Camilla. ;-)"
Italy
Matteo
The price is ￥23,073
￥29,972 total
includes taxes & fees
Jan 16 - Jan 17, 2026
Lebbiano Residence Bio Resort
Outdoor pool, pool umbrellas, sun loungers
Chianti Village Morrocco

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
Chianti Village Morrocco
Terrace/patio
B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (82)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is ￥18,654
￥21,254 total
includes taxes & fees
Dec 26 - Dec 27
B&B La Fonte del Machiavelli
Breakfast, lunch, dinner served; Regional cuisine
La Locanda di Pietracupa

La Locanda di Pietracupa

La Locanda di Pietracupa
Barberino Tavarnelle
9.4 out of 10, Exceptional, (35)
"Great place, wonderful restaurant"
Germany
Isabell
La Locanda di Pietracupa
Seasonal outdoor pool, open 8 AM to 8 PM, pool umbrellas, sun loungers
Tenuta Sant'Ilario

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (33)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
Tenuta Sant'Ilario
Beach
La Casina between sea and culture: relaxation and history.

La Casina between sea and culture: relaxation and history.

La Casina between sea and culture: relaxation and history.
Montecatini Val di Cecina
10.0 out of 10, Exceptional, (1)
"Wij hebben genoten van ons onderkomen. Attente host die na onze vraag welk koffiezetapparaat er aanwezig was (klein Italiaans app) een bonen koffiemachine neergezet, super lief. We hadden alleen een kleine badkamer, maar dat was minder erg. Verder toplocatie. Het enige wat ze misschien uit hun advertentie kunnen halen is -dicht bij zee-. TIP….. Maak leuke foto’s van jullie mooie kleine dorpje."
Netherlands
Jolanda B.
The price is ￥12,490
￥20,021 total
includes taxes & fees
Jan 10 - Jan 11, 2026
La Casina between sea and culture: relaxation and history.
Garden
Fullino Nero

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (49)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is ￥15,979
￥18,312 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Fullino Nero
Property entrance
Affittacamere a 20 minuti da Firenze

Affittacamere a 20 minuti da Firenze

Affittacamere a 20 minuti da Firenze
Empoli
8.2 out of 10, Very Good, (19)
"Very basic lodgings - simple but good location between Florence & Pisa. Breakfast place right underneath the rooms made breakfast convenient. Parking was super simple & across the street, which is rare in Italy. "
United States
Scott
The price is ￥15,356
￥17,442 total
includes taxes & fees
Dec 29 - Dec 30
Affittacamere a 20 minuti da Firenze
Exterior
Sportland

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland
Breakfast, lunch, dinner served; garden views
Marignolle Relais and Charme

Marignolle Relais and Charme

Marignolle Relais and Charme
Florence
9.2 out of 10, Wonderful, (90)
"I stayed here June 2025 and was most delighted in the property and staff. They were incredibly kind and accommodating and the property is beautiful. Would stay here again!"
Canada
Shelley
Marignolle Relais and Charme
Exterior
appartamenti la piazzetta

appartamenti la piazzetta

appartamenti la piazzetta
Signa
10.0 out of 10, Exceptional, (3)
"Molto carina e curata nel dettaglio gli appartamenti grandi e luminosi. La pulizia ottima e i gestori veramente molto gentili. Posizione strategica a pochi minuti da Firenze e aeroporto. "
Italy
valeria
The price is ￥16,465
￥18,478 total
includes taxes & fees
Jan 8 - Jan 9, 2026
appartamenti la piazzetta
Balcony
Palazzo al Torrione 2

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (107)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is ￥14,816
￥21,824 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Palazzo al Torrione 2
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 San Luigi

Hotel Borgo San Luigi

10/10 Excellent
"Beautiful location with clean rooms and wonderful staff. Really enjoyed the breakfast too! Recommended! "
Allyson 3-night trip
Posted 3 weeks ago
Hotel Borgo San Luigi

Find out more about Villa del Monte

Search for holiday rentals in Villa del Monte on Expedia! You can easily find your home rentals, villas, holiday apartments in Villa del Monte using one of the methods below:

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Look no further and take a look at our great range of rental properties in Villa del Monte!

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?

Villa with large garden in the Chianti hills: Visitors like this Villa del Monte vacation home rental. It is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

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.