Default HTG hotel image

Penna Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Penna vacation rentals

Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

Borgo di Erboli

Borgo di Erboli
Cavriglia
$116 nightly
The price is $130
Jul 16 - Jul 17
Total with taxes and fees
Borgo di Erboli
Lobby

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (24 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
$168 nightly
The price is $185
Jul 19 - Jul 20
Total with taxes and fees
Villa Cassia di Baccano
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (70 reviews)
"This was our second stay. The property is beautiful and our room was lovely. The breakfast was one of the best on our trip in Italy."
Canada
Dr Anne
$165 nightly
The price is $191
Jul 20 - Jul 21
Total with taxes and fees
Villa Curina Resort
Interior

Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Barberino Tavarnelle
10.0 out of 10, Exceptional, (12 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
$203 nightly
The price is $208
Jul 13 - Jul 14
Total with taxes and fees
Chianti Craft House Badia a Passignano
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (29 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
$93 nightly
The price is $107
Jul 14 - Jul 15
Total with taxes and fees
DormiVeglia B&B
Spa

2 Cuori e 1 Yurta Glamping in Toscana

2 Cuori e 1 Yurta Glamping in Toscana
Asciano
$291 nightly
The price is $327
Jul 16 - Jul 17
Total with taxes and fees
2 Cuori e 1 Yurta Glamping in Toscana
Exterior

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (36 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
$171 nightly
The price is $188
Jul 19 - Jul 20
Total with taxes and fees
Villa di Sotto
Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (24 reviews)
"Such a beautiful place to stay! The cottage was amazing, very spacious and clean. The grounds themselves were picturesque, was well above our expectations and the host was very welcoming and accommodating."
United Kingdom
Sasha
$346 nightly
The price is $390
Jul 13 - Jul 14
Total with taxes and fees
Borgo Argenina
Lounge

Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
$92 nightly
The price is $106
Jul 28 - Jul 29
Total with taxes and fees
Mariani Bed & Breakfast
Property grounds

LE BOTTI FIORENTINE

LE BOTTI FIORENTINE
Reggello
$156 nightly
The price is $178
Jul 27 - Jul 28
Total with taxes and fees
LE BOTTI FIORENTINE
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers

iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (38 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
$118 nightly
The price is $136
Jul 13 - Jul 14
Total with taxes and fees
iConic Wellness Resort
Outdoor dining

Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
$122 nightly
The price is $122
Jul 13 - Jul 14
Total with taxes and fees
Dolce Casa 2 by Tiny Away
1 bedroom, WiFi, bed sheets

Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
$129 nightly
The price is $129
Jul 13 - Jul 14
Total with taxes and fees
Dolce Casa 1 by Tiny Away
Family Apartment, 2 Bedrooms, Hill View, Tower | View from room

Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci
Pergine Valdarno
9.6 out of 10, Exceptional, (5 reviews)
"We absolutely loved our stay at this hotel. The suite was perfect and the restaurant had probably the best food I have had in Tuscany. We definitely plan to stay there again."
United States
Gregory
$174 nightly
The price is $195
Jul 14 - Jul 15
Total with taxes and fees
Casa Vacanze Le Fornaci
Exterior

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (324 reviews)
"We all loved this place. It is conveniently close to Florence or Sienna so you can take a day trips if you get bored but there are plenty of activities on site. We wished we have reserved more days to stay but we will do that next year."
United States
Kalinka
$87 nightly
The price is $99
Jul 14 - Jul 15
Total with taxes and fees
Hu Norcenni Girasole Village
Property entrance

Palazzo Tarlati Residenza d'Epoca

Palazzo Tarlati Residenza d'Epoca
Civitella in Val di Chiana
8.0 out of 10, Very Good, (3 reviews)
"Small family-owned inn located in center of Civitella in Val di Chiana. Room was comfortable and included all we needed. It was cold upon check-in which the co-owner tried to remedy with a space heater. It took a while. The room warmed up after the first night. The other co-owner kindly offered me our first night complimentary. (Thank you again.). The breakfast was simple and included fruit, juice, yogurt, sliced cheese and cold cut, packages sweets, tea, coffee and water. The owners were...
United States
Marco
$125 nightly
The price is $137
Jul 13 - Jul 14
Total with taxes and fees
Palazzo Tarlati Residenza d'Epoca
Outdoor dining

Deluxe room Cartazucchero in the heart of Arezzo

Deluxe room Cartazucchero in the heart of Arezzo
Arezzo Centro Storico
10.0 out of 10, Exceptional, (3 reviews)
"From all the places we stayed during our 13-day trip to Italy, this was by far our favorite. Fabio was incredibly communicative and friendly right from the start, sending us clear instructions on how to get there. He greeted us at the door with such warmth that it truly felt like we were staying with family. The room was spotless, beautifully decorated, and generously stocked with water, cookies, pastries, and other treats. It had the comfort and attention to detail of a hotel, yet the warmth of...
United States
Hector
$88 nightly
The price is $96
Jul 15 - Jul 16
Total with taxes and fees
Deluxe room Cartazucchero in the heart of Arezzo
Outdoor dining

Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
$304 nightly
The price is $308
Jul 14 - Jul 15
Total with taxes and fees
Casa Marisa in Castellina in Chianti
Lunch and dinner served

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (43 reviews)
"Beautiful historic fortress / castle with tastefully updated rooms, great amenities that maintains the old character "
Canada
Ariel
$234 nightly
The price is $262
Jul 13 - Jul 14
Total with taxes and fees
Castello di Gargonza
Outdoor dining

House with views of the Chianti

House with views of the Chianti
impruneta
10.0 out of 10, Exceptional, (4 reviews)
"My wife and I stayed here for our honeymoon and have already talked about returning here for an anniversary. This house was clean, charming and located in a beautiful area. The views from the property are stunning."
United States
Chase B.
$287 nightly
The price is $291
Jul 17 - Jul 18
Total with taxes and fees
House with views of the Chianti
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Penna Hotel Reviews

Palagina la cascina

Palagina la cascina

10/10 Excellent
"We enjoyed our stay at Palagina SO MUCH! I wanted to add another night but our schedule didn't allow. The room had an amazing view to wake up to each morning, it was clean, the pool was awesome (especially the shallow kids section) The grounds and property were absolutely beautiful. We had a rough and stressful day and getting to Palagina really made everything better. It was also great that restaurants and food options were within a 10 minute drive. If we ever get to visit Tuscany again I would absolutely come back."
Vannarith 2-night trip
Posted 8 hours ago
Palagina la cascina

Find out more about Penna

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

Penna vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Penna. 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 Penna 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 $74 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 Penna rentals

At Expedia, we put the best Penna 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 Penna 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 Penna 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 Penna. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Penna?

Yes, we offer vacation rentals near the most popular local attractions in Penna, or you can choose a more secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Penna?

Borgo Argiano: Visitors like this Penna vacation home rental. It is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and an electric kettle. You can relax into your vacation with a garden and a library.

How many vacation rentals are there in Penna?

Choose from 3 Expedia vacation rentals in Penna for a memorable vacation.

What can I see and do in Penna?

While exploring the area, visit family-friendly sights like Borgo di Vescine - Tenute di Castelvecchi, or get outside and enjoy nature at Piazza Guido Monaco. San Pietro a Gropina and Croce del Pratomagno are a couple of places you'll find in the larger area.

What are vacation rentals like in Penna?

Vacation rentals are privately owned accommodations you can reserve for a short or long stay in Penna. Vacation rentals feature extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.