A mountainous landscape with terraced fields, a winding road, and a village with traditional buildings.

Pennabilli Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Pennabilli vacation rentals

A modern kitchen with a central island, a dining area with a long table, and a chandelier.

1. Elegance and relaxation in an exclusive ground floor apartment flooded with light.

Elegance and relaxation in an exclusive ground floor apartment flooded with light.
Carpegna
$148 nightly
The price is $148
Sep 3 - Sep 4
Total with taxes and fees
Elegance and relaxation in an exclusive ground floor apartment flooded with light.

2. Cozy nest in the heart of Sassocorvaro, terrace with breathtaking views.

Cozy nest in the heart of Sassocorvaro, terrace with breathtaking views.
Sassocorvaro
$139 nightly
The price is $139
Sep 5 - Sep 6
Total with taxes and fees
Cozy nest in the heart of Sassocorvaro, terrace with breathtaking views.
A modern living room with a white sofa, a coffee table, and a TV mounted on the wall. There is a plant on the coffee table and a small shelf with decorative items.

3. Gio's Hygge Nest

Gio's Hygge Nest
Montegrimano
$113 nightly
The price is $113
Sep 27 - Sep 28
Total with taxes and fees
Gio's Hygge Nest
Two wine glasses on a table with a view of greenery and hills in the background.

4. Holiday Apartment "Relax And Apartment" with Mountain View, Private Terrace & Wi-Fi

Holiday Apartment "Relax And Apartment" with Mountain View, Private Terrace & Wi-Fi
Sant'Agata Feltria
$276 nightly
The price is $276
Oct 1 - Oct 2
Total with taxes and fees
Holiday Apartment "Relax And Apartment" with Mountain View, Private Terrace & Wi-Fi
A wooden chair facing a scenic view of rolling hills and a mountain range under a clear sky.

5. Beautiful self-catering flat for rent in the country

Beautiful self-catering flat for rent in the country
URBANIA
9.2 out of 10, Wonderful, (37 reviews)
"We had an excellent time in this lovely, cosy and fully equipped accommodation. The host was extraordinarily kind and helpful so we felt welcome and at home."
Germany
Joerg G.
$133 nightly
The price is $133
Sep 1 - Sep 2
Total with taxes and fees
Beautiful self-catering flat for rent in the country
A table set outdoors with a view of mountains, including a basket of pastries, cups of coffee, and a bottle of water.

6. Locanda del Viandante

Locanda del Viandante
Anghiari
9.0 out of 10, Wonderful, (6 reviews)
"客室は清潔で、とても可愛いかったです。宿泊場所からの眺望は感動します。 朝食が人生でベスト朝食でした！"
Japan
Tatsuya
$126 nightly
The price is $139
Sep 1 - Sep 2
Total with taxes and fees
Locanda del Viandante
An open-air bedroom with a bed, a table with a vase, and a chair.

7. Bubble room

Bubble room
Castelci
$430 nightly
The price is $430
Sep 29 - Sep 30
Total with taxes and fees
Bubble room
A bedroom with a bed, bedside tables, a nightstand, a wall-mounted air conditioner, and a door leading to a bathroom.

8. Casa Gioia - Relaxation between Riccione, Rimini, and San Marino

Casa Gioia - Relaxation between Riccione, Rimini, and San Marino
Emilia-Romagna
10.0 out of 10, Exceptional, (2 reviews)
"We enjoyed our stay very much! It is in a peaceful location that is very quiet and beautiful. We stayed for three weeks and it became like our home. The apartment was clean and as described. We would stay there again!"
United States
Chad B.
$198 nightly
The price is $198
Sep 7 - Sep 8
Total with taxes and fees
Casa Gioia - Relaxation between Riccione, Rimini, and San Marino
A bedroom with a stone wall, a bed, a wardrobe, a balcony with chairs, and a view of buildings.

9. Le Terrazze sul Fiume

Le Terrazze sul Fiume
Santa Sofia
$90 nightly
The price is $99
Oct 1 - Oct 2
Total with taxes and fees
Le Terrazze sul Fiume

10. Apartment in the Historic Village of Verucchio

Apartment in the Historic Village of Verucchio
Verucchio
$337 nightly
The price is $353
Sep 1 - Sep 2
Total with taxes and fees
Apartment in the Historic Village of Verucchio
A building entrance with a stone wall, a wooden pergola, and a potted plant.

11. Chic Apartment with Outdoor Serenity

Chic Apartment with Outdoor Serenity
San Sepolcro
10.0 out of 10, Exceptional, (10 reviews)
"Close to town center and the garden was great for morning coffee. Kitchen had everything needed for quick meals."
United States
Anonymous traveler
$140 nightly
The price is $140
Sep 21 - Sep 22
Total with taxes and fees
Chic Apartment with Outdoor Serenity
A stone building with a pool, surrounded by trees and outdoor seating.

12. -2 / 3-seater garage with private garden, swimming pool, park and spa

-2 / 3-seater garage with private garden, swimming pool, park and spa
sansepolcro (arezzo)
9.6 out of 10, Exceptional, (4 reviews)
"Es waren traumhafte Tage. So extrem ruhig ..... Richtig entspannend. Alles da zur Selbstversorgung an Küchenutensilien. Alles sehr sauber. Der Besitzer sehr freundlich und bemüht. Wir fahren nächstes Jahr wieder hin ..... Aber länger. Sehr empfehlenswert"
Austria
Margit H.
$178 nightly
The price is $178
Sep 1 - Sep 2
Total with taxes and fees
-2 / 3-seater garage with private garden, swimming pool, park and spa

13. La Nocina

La Nocina
Santa Sofia
$192 nightly
The price is $211
Sep 1 - Sep 2
Total with taxes and fees
La Nocina
A café with a counter labeled 'Joy' and a variety of food items displayed in a glass case.

14. Charming Apartment in Historic Bagno di Romagna

Charming Apartment in Historic Bagno di Romagna
Bagno di Romagna
Charming Apartment in Historic Bagno di Romagna
A courtyard with stone buildings, arched doorways, and outdoor seating.

15. B&B Corte dei Turchi

B&B Corte dei Turchi
Longiano
9.2 out of 10, Wonderful, (17 reviews)
"Great location and good quality restaurants."
United Kingdom
Murat
$118 nightly
The price is $130
Sep 7 - Sep 8
Total with taxes and fees
B&B Corte dei Turchi
A rooftop terrace with a red building, a paved walkway, and a view of a forested hill.

16. Residence Città Ideale

Residence Città Ideale
Urbino
7.4 out of 10, Good, (6 reviews)
$67 nightly
The price is $80
Sep 13 - Sep 14
Total with taxes and fees
Residence Città Ideale
A stone building with a wooden door, surrounded by lush greenery and a clear sky.

17. farmhouse calcinaia on the lake APARTMENT BARN 4/6 PLACES SWIMMING POOL park sp

farmhouse calcinaia on the lake APARTMENT BARN 4/6 PLACES SWIMMING POOL park sp
arezzo
10.0 out of 10, Exceptional, (1 review)
"Immerso nella natura con alloggio spazioso e completo di tutto. Perfetta organizzione e comunicazione da parte di Francesco chi ci ha dato anche utili consigli sul da farsi e vedere nei paraggi. Consigliato!"
Italy
Riccardo B.
$251 nightly
The price is $251
Sep 1 - Sep 2
Total with taxes and fees
farmhouse calcinaia on the lake APARTMENT BARN 4/6 PLACES SWIMMING POOL park sp
A swimming pool with wooden deck, white lounge chairs, and umbrellas.

18. Room 'Resort Villa Paola - Camera Tordo' with Sea View, Wi-Fi and Air Conditioning

Room 'Resort Villa Paola - Camera Tordo' with Sea View, Wi-Fi and Air Conditioning
Longiano
$214 nightly
The price is $214
Sep 7 - Sep 8
Total with taxes and fees
Room 'Resort Villa Paola - Camera Tordo' with Sea View, Wi-Fi and Air Conditioning
A table set outdoors with a view of a vineyard and a distant landscape.

19. the SERVITU 'apartment 4/6 places, swimming pool, spa park

the SERVITU 'apartment 4/6 places, swimming pool, spa park
arezzo
$271 nightly
The price is $271
Sep 1 - Sep 2
Total with taxes and fees
the SERVITU 'apartment 4/6 places, swimming pool, spa park
A rustic outdoor dining area with wooden tables and chairs, hanging birdcages, and a view of greenery.

20. Beb 1416 Room with Shared Terrace, Shared Garden, and Wi-Fi

Beb 1416 Room with Shared Terrace, Shared Garden, and Wi-Fi
ANGHIARI
10.0 out of 10, Exceptional, (1 review)
"I greatly enjoyed my stay at this beautiful and unique apartment. It was captivatingly decorated with antiques and appointed with all needed amenities. the hosts were charming and helpful, and made every effort to make me feel at home and my stay comfortable. If I had the time, I believe a longer stay would have been quite pleasant."
United States
Andrew P.
$108 nightly
The price is $112
Sep 9 - Sep 10
Total with taxes and fees
Beb 1416 Room with Shared Terrace, Shared Garden, and Wi-Fi
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 Pennabilli Hotel Reviews

Hotel Aria

Hotel Aria

10/10 Excellent
"Everything was perfect"
Adam 3-night trip
Posted 4 hours ago
Hotel Aria

Find out more about Pennabilli

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

Pennabilli vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pennabilli. 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 Pennabilli 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 $45 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 Pennabilli rentals

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

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Pennabilli?

Yes, there are vacation rentals in Pennabilli close to Orto dei Frutti Dimenticati, or you can choose a more secluded option if you want a relaxing stay. Pennabilli is known for its cathedral and seaside. Make sure you have time to check out the art and temples during your trip.

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

Holiday Home in Tuscany with Private Garden: This vacation home rental outside of Pennabilli 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 fridge, a stovetop, and a microwave.

How many vacation rentals will I find in Pennabilli?

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

What’s there to see and do in Pennabilli?

Orto dei Frutti Dimenticati and Valle del Marecchia are a couple of scenic spots to enjoy the outdoors, whereas Mateureka Museum of Calculation is one of the cultural attractions. Porta San Francesco and Chiesa del Santuario della Madonna delle Grazie are a couple of places you'll find in the larger area.

What’s a vacation rental in Pennabilli like?

Vacation rentals are privately owned properties where you can stay for a couple of days or more in Pennabilli. Vacation rentals feature extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family trips.