Villa del Monte Vacation Rentals

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Oct 22 - Oct 23
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Oct 24 - Oct 26
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Oct 31 - Nov 2

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
8.2 out of 10, Very Good, (223)
"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
$93 nightly
The price is $119
Oct 23 - Oct 24
Total with taxes and fees
Fattoria il Milione Agriturismo
2 bedrooms, cribs/infant beds, bed sheets
hu Firenze Certosa camping in town
hu Firenze Certosa camping in town
8.0 out of 10, Very Good, (50)
"Wonderful staff and great amenities!"
Canada
Chenjin
hu Firenze Certosa camping in town
Aerial view
Relais Villa Olmo
Relais Villa Olmo
9.4 out of 10, Exceptional, (226)
"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
$153 nightly
The price is $172
Nov 12 - Nov 13
Total with taxes and fees
Relais Villa Olmo
2 bars/lounges
Camping Boschetto Di Piemma
Camping Boschetto Di Piemma
3.0 star property
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
$54 nightly
The price is $63
Oct 28 - Oct 29
Total with taxes and fees
Camping Boschetto Di Piemma
Outdoor pool, pool umbrellas, sun loungers
Chianti Village Morrocco
Chianti Village Morrocco
3.0 star property
8.6 out of 10, Excellent, (105)
"Front desk was very helpful and very comfortable room. "
United States
Chris
$73 nightly
The price is $83
Nov 3 - Nov 4
Total with taxes and fees
Chianti Village Morrocco
Exterior
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
10.0 out of 10, Exceptional, (64)
"We had a company retreat at this amazing location. Everyone was in love with the place and the facilities!"
Netherlands
Jochem G.
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Outdoor dining
Villa with large garden in the Chianti hills
Villa with large garden in the Chianti hills
9.6 out of 10, Exceptional, (73)
"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
Full-size fridge, oven, stovetop, espresso maker
Rocca Palazzaccio
Rocca Palazzaccio
3.0 star property
9.0 out of 10, Wonderful, (13)
"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
$74 nightly
The price is $85
Oct 29 - Oct 30
Total with taxes and fees
Rocca Palazzaccio
Interior
Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.
Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.
9.0 out of 10, Wonderful, (23)
"excellent"
United States
David S W.
Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.
Exterior detail
La Casa di Ines
La Casa di Ines
9.6 out of 10, Exceptional, (5)
"Amazing property and family ! "
Canada
Mary
$77 nightly
The price is $90
Oct 23 - Oct 24
Total with taxes and fees
La Casa di Ines
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
10.0 out of 10, Exceptional, (104)
"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
Exterior
Farmhouse in the heart of the real chiantishire
Farmhouse in the heart of the real chiantishire
10.0 out of 10, Exceptional, (143)
"What a view! This location was all that we were hoping for. Thank you! "
United States
Alyson F.
Farmhouse in the heart of the real chiantishire
Sauna, hot tub, steam room, Turkish bath, body treatments, aromatherapy
Castellare di Tonda Resort & Spa
Castellare di Tonda Resort & Spa
8.0 out of 10, Very Good, (49)
"Mini Club, Traktorfahrten, Essen"
Germany
Marco
$86 nightly
The price is $96
Oct 26 - Oct 27
Total with taxes and fees
Castellare di Tonda Resort & Spa
Outdoor pool, an infinity pool
Beautiful apartment in San Gimignano - RoccaiaCasa'70
Beautiful apartment in San Gimignano - RoccaiaCasa'70
9.8 out of 10, Exceptional, (47)
"We really enjoyed our stay. It was in a very quiet, out of the way picturesque place. Our host was great - had everything we needed and very helpful and great communication. Would definitely recommend and would stay here again. "
Canada
Danielle H.
Beautiful apartment in San Gimignano - RoccaiaCasa'70
Family Apartment | Living area | TV
appartamenti la piazzetta
appartamenti la piazzetta
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
$89 nightly
The price is $100
Oct 23 - Oct 24
Total with taxes and fees
appartamenti la piazzetta
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
10.0 out of 10, Exceptional, (105)
"One of the best hosts and most special homes I’ve ever stayed in. There was this feeling like everything you’ve been dreaming about while planning a trip- it’s all here. Cozy, peaceful, thoughtful in every detail. What really stayed with me though was how kind and supportive the host was the entire time. That kind of care isn’t common, and it honestly made a big difference. Just grateful."
Canada
Andrew B.
$1,589 nightly
The price is $1,594
Nov 3 - Nov 4
Total with taxes and fees
Villa with concierge service & heated pool at 20 minute from Florence center
Outdoor pool
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
10.0 out of 10, Exceptional, (123)
"We spent 2 weeks in this beautiful villa with close access to Florence and the easy trains of Italy. Bea and Jacapo were wonderful hosts and meals at the villa were delicious. The pool was a great relief at the end of warm and busy traveling days. We highly recommend this beautiful villa. "
United States
Jennifer R.
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.
A heated pool
Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl
Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl
10.0 out of 10, Exceptional, (42)
"We celebrated our 25th wedding anniversary with friends. It was a beautiful property with the most amazing views. This family owned and operated property was well taken care of. The service was exceptional."
United States
Melissa M.
Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl
Seasonal outdoor pool, pool umbrellas, sun loungers
Castello Del Nero - Podere San Filippo
Castello Del Nero - Podere San Filippo
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
Interior detail
Castello di Montegufoni
Castello di Montegufoni
8.2 out of 10, Very Good, (30)
"This was a stunning castle to stay in. The frescoed ceilings were gorgeous. Loved every minute that we were there. The staff were wonderful. The only thing i would recommend is to add a vending machine and maybe to offer pastries in thr morning. "
United States
Cheryl
Castello di Montegufoni
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

Boccioleto Resort&Spa

Boccioleto Resort&Spa

10/10 Excellent
"The staff was incredibly kind and accommodating. Our flight was delayed but they were very accommodating and held a table for us in the restaurant. They also made sure we had everything we needed. The room was a bit dated but the bed was comfortable. "
Rose 1-night trip
Posted 3 days ago
Boccioleto Resort&Spa

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 $63 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.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Villa del Monte. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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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?

Agriturismo La Ferrozzola: You might want to consider this vacation home rental near Villa del Monte, which offers a terrace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and kitchenware. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.