Trappola Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Trappola vacation rentals

Lobby lounge
Villa Cassia di Baccano

Villa Cassia di Baccano

Loro Ciuffenna
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
$142 nightly
The price is $157
Jan 8 - Jan 9, 2026
Total with taxes and fees
Villa Cassia di Baccano
Front of property
L' Eroico

L' Eroico

Gaiole in Chianti
10.0 out of 10, Exceptional, (12)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
L' Eroico
Classic Double or Twin Room, 1 Double Bed | Premium bedding, down comforters, pillowtop beds, minibar
THE MONNA LISA RESORT

THE MONNA LISA RESORT

Arezzo
9.6 out of 10, Exceptional, (8)
"Massimiliano was a great host, but we were the only guests and the restaurant was closed. The hotel was basically unmanaged. It should not have been listed as a hotel. "
United States
Bart
$120 nightly
The price is $140
Dec 19 - Dec 20
Total with taxes and fees
THE MONNA LISA RESORT
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
Villa La Ginestra

Villa La Ginestra

Subbiano
9.6 out of 10, Exceptional, (5)
"Le charme de l'endroit, l'attention de l'hôte, le confort, le déjeuner delicieux."
Canada
Philippe
Villa La Ginestra
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Relais Villa Belvedere

Relais Villa Belvedere

Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (70)
"Very nice place"
United States
Maria
$95 nightly
The price is $107
Dec 10 - Dec 11
Total with taxes and fees
Relais Villa Belvedere
Balcony
Cameracaffè Centro

Cameracaffè Centro

Arezzo Centro Storico
8.6 out of 10, Excellent, (179)
"Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. "
United States
Keith
$79 nightly
The price is $94
Dec 15 - Dec 16
Total with taxes and fees
Cameracaffè Centro
Apartment, 2 Bedrooms | Premium bedding, down comforters, in-room safe, blackout drapes
Terre di Baccio

Terre di Baccio

Greve in Chianti
9.8 out of 10, Exceptional, (71)
"Great hotel in a beautiful location with fantastic staff. "
United Kingdom
Mark
$253 nightly
The price is $283
Dec 27 - Dec 28
Total with taxes and fees
Terre di Baccio
View from room
The Florence Hills Resort & Wellness

The Florence Hills Resort & Wellness

Pelago
8.8 out of 10, Excellent, (175)
"Great stay would recommend "
United Kingdom
Luan
$67 nightly
The price is $81
Dec 17 - Dec 18
Total with taxes and fees
The Florence Hills Resort & Wellness
Terrace/patio
Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci

Pergine Valdarno
9.4 out of 10, Exceptional, (3)
"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
$131 nightly
The price is $148
Jan 3 - Jan 4, 2026
Total with taxes and fees
Casa Vacanze Le Fornaci
View from property
Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna
9.8 out of 10, Exceptional, (35)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
$164 nightly
The price is $180
Dec 10 - Dec 11
Total with taxes and fees
Relais Villa Belpoggio - Residenza d'Epoca
Exterior
B&B da Ronald...a Pian del Papa

B&B da Ronald...a Pian del Papa

Pratovecchio Stia
8.0 out of 10, Very Good, (11)
"La struttura è facilmente raggiungibile. Supersilenziosa e in una zona tranquilla, con un fantastico panorama. Proprietari gentilissimi!"
Italy
Tatiana
B&B da Ronald...a Pian del Papa
Outdoor pool, sun loungers
Rocca di Castagnoli

Rocca di Castagnoli

Gaiole in Chianti
9.2 out of 10, Wonderful, (28)
"It was wonderful to stay in a castle in Tuscany no less Every person we met was attentive and kind We were staying near friends and didn’t hang around the grounds much or use the pool but everything seemed well kept It’s really a place to retreat to eat at and sleep at which served our purpose well "
Canada
Shingo
$238 nightly
The price is $271
Jan 1 - Jan 2, 2026
Total with taxes and fees
Rocca di Castagnoli
Outdoor dining
Gallo Nero apartment 2/4 people close to the center of Greve in Chianti

Gallo Nero apartment 2/4 people close to the center of Greve in Chianti

Greve in Chianti
$166 nightly
The price is $171
Dec 10 - Dec 11
Total with taxes and fees
Gallo Nero apartment 2/4 people close to the center of Greve in Chianti
Lunch, dinner served; Italian cuisine, garden views
Locanda del Viandante

Locanda del Viandante

Anghiari
9.0 out of 10, Wonderful, (6)
"Smuk beliggenhed - meget autentisk på den gode måde"
Denmark
tina
$143 nightly
The price is $157
Dec 11 - Dec 12
Total with taxes and fees
Locanda del Viandante
1 bedroom, iron/ironing board, free WiFi, bed sheets
Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Arezzo Centro Storico
10.0 out of 10, Exceptional, (1)
" La casa pulitissima è molto bella, l’host molto disponibile e gentile, risponde sempre e anche subito. La posizione ottimale per fare il giro dei mercatini e di tutta la città. Consigliatissima "
Italy
Maria Gemma
$185 nightly
The price is $185
Jan 4 - Jan 5, 2026
Total with taxes and fees
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Interior
Chianti dreaming in Radda-3 independent bedrooms with private bathroom and TV

Chianti dreaming in Radda-3 independent bedrooms with private bathroom and TV

Toscana
10.0 out of 10, Exceptional, (1)
"The apartment was perfect for what we needed. It was very clean and very comfortable. The beds were comfortable and the bathrooms were quite roomy and even had a place for your shampoo and soap in the shower. "
United States
Wendy T.
$320 nightly
The price is $320
Dec 10 - Dec 11
Total with taxes and fees
Chianti dreaming in Radda-3 independent bedrooms with private bathroom and TV
Property grounds
GUELFI 6, apartment in the heart of the historic center of POPPI casentino

GUELFI 6, apartment in the heart of the historic center of POPPI casentino

Poppi
$161 nightly
The price is $165
Dec 10 - Dec 11
Total with taxes and fees
GUELFI 6, apartment in the heart of the historic center of POPPI casentino
Balcony
Antella Residence

Antella Residence

Bagno a Ripoli
8.8 out of 10, Excellent, (6)
"Appartamento grande e pulito. Comodo. Fornito di ogni confort. La titolare è gentile e disponibile (al checkout però abbiamo provato a chiamarla per consegnare le chiavi ma non ha risposto nessuno è abbiamo dovuto lasciarle sul bancone della reception chiusa). Struttura silenziosa. Un po' di rumore dalla caldaia e dai termosifoni ma niente di insopportabile. La mattina abbiamo sentito un po' di rumori dovuti ad altri ospiti poco civili. Ad ogni modo, è un ottimo posto per alloggiare e girare nei...
Italy
Nunzia
$133 nightly
The price is $147
Dec 10 - Dec 11
Total with taxes and fees
Antella Residence
Classic Room, Valley View | Living area
Suite 50

Suite 50

Pontassieve
$87 nightly
The price is $99
Jan 8 - Jan 9, 2026
Total with taxes and fees
Suite 50
Exterior
Residence Casprini da Omero

Residence Casprini da Omero

Greve in Chianti
Residence Casprini da Omero
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 Trappola Hotel Reviews

A Point Arezzo Park Hotel

A Point Arezzo Park Hotel

6/10 Okay
"The room was in quite poor condition. There was only lukewarm water, the heating was noisy, the tv didn’t work, the lights over the bed flashed and the toilet seat was loose. It was a very stylish hotel but it just needs some maintenance. The breakfast was very good and the bed was comfortable "
Zena 1-night trip
Posted 1 month ago
A Point Arezzo Park Hotel

Find out more about Trappola

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

Trappola vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Trappola. 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 Trappola 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 $81 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 Trappola rentals

At Expedia, we put the best Trappola 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 Trappola 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 Trappola 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 Trappola. 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

Can I find vacation rentals in Trappola?

Yes, there are vacation rentals close to well known local attractions in Trappola, or you can go with a more secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals that Trappola has to offer?

Romantic house in the middle of the Chianti vineyards in the heart of Tuscany.: This vacation home rental near Trappola is located in a rural location and has an outdoor pool, 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 Trappola?

Explore the area and family-friendly sights such as Poppi Zoo, or get out into nature at a spot like Piazza Guido Monaco. In the larger area, you’ll find Croce del Pratomagno and Mulino Ad Acqua.

What are vacation rentals like in Trappola?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Trappola. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for family trips.