A vineyard with rows of grapevines, rolling hills, and distant buildings.

Poggibonsi Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Poggibonsi vacation rentals

An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

1. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (103 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is NT$4,557
NT$5,086 total
includes taxes & fees
Oct 27 - Oct 28
Palazzo Pacini
A narrow street with stone buildings, a tower, and an archway.

2. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
10.0 out of 10, Exceptional, (1 review)
"Fantastic all around experience. The rooms were beautiful and clean and this unique mix of rustic modern Italian styling. Located right in the heart of the old city made it very easy to walk everywhere. The service was fantastic, I was able to message the team and within a minute I got the help and had my questions answered. I’d definitely stay there again."
Canada
Bradley
The price is NT$3,436
NT$3,963 total
includes taxes & fees
Nov 3 - Nov 4
Materia Rooms San Gimignano
A reception desk with the word "SPORTLAND" prominently displayed.

3. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is NT$1,573
NT$1,804 total
includes taxes & fees
Oct 26 - Oct 27
Sportland
A table with breakfast items and a view of rolling hills.

4. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (121 reviews)
"Superb property. Nice and quiet atmosphere. We enjoyed a lot. Definitely will come again."
United States
Nirav
The price is NT$2,767
NT$3,117 total
includes taxes & fees
Oct 26 - Oct 27
Chianti Village Morrocco
An open wooden door leading to an outdoor patio with a table and chairs.

5. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is NT$2,980
NT$4,373 total
includes taxes & fees
Nov 2 - Nov 3
Palazzo al Torrione 2
A view from a window overlooking a rural landscape with fields and a distant mountain range.

6. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (67 reviews)
"Francesco, our host, is so nice and welcoming. We had the beat stay and our room had the most fantastic view. Excellent breakfast, place was super clean and quiet. We highly recommend."
Canada
Caroline
The price is NT$4,447
NT$5,074 total
includes taxes & fees
Oct 26 - Oct 27
B&B Palazzo Tortoli
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

7. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (91 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveler
The price is NT$1,733
NT$2,016 total
includes taxes & fees
Oct 26 - Oct 27
Camping Boschetto Di Piemma
A stone building with a wooden table and chairs, a stone wall, and a door leading to an interior space.

8. Teranga in Chianti - Parking & Garden 3 BR

Teranga in Chianti - Parking & Garden 3 BR
Tavarnelle Val di Pesa
The price is NT$3,154
NT$12,745 total
includes taxes & fees
Nov 3 - Nov 4
Teranga in Chianti - Parking & Garden 3 BR
A building with a wooden door, windows with shutters, and flower boxes.

9. Donna Nobile

Donna Nobile
San Gimignano City Centre
8.2 out of 10, Very good, (168 reviews)
"Very easy checkin, friendly staff. Loved the kitchen area!"
Canada
Treena
The price is NT$2,590
NT$3,031 total
includes taxes & fees
Nov 1 - Nov 2
Donna Nobile
A patio with wicker furniture and potted plants, overlooking a scenic landscape.

10. Affittacamere Le Ginestre

Affittacamere Le Ginestre
San Gimignano City Centre
7.8 out of 10, Good, (6 reviews)
"Spacious. Clean. Quite. Air conditioned. Comfort. The View. The best. "
United States
Jorge
The price is NT$3,436
NT$3,962 total
includes taxes & fees
Oct 27 - Oct 28
Affittacamere Le Ginestre
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

11. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very good, (3 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is NT$6,048
NT$6,762 total
includes taxes & fees
Oct 26 - Oct 27
Villa Montecastello
A neatly made bed with a metal frame, two bedside tables with lamps, a wooden door, and a textured ceiling.

12. IL VECCHIO CONVENTO

IL VECCHIO CONVENTO
San Gimignano City Centre
4.0 out of 10, (3 reviews)
"Unterkunft konnte wegen Wasserschaden nicht bezogen werden. Vermieter hat nicht geholfen eine Alternative zu finden…"
Germany
Bodo
The price is NT$4,781
NT$5,441 total
includes taxes & fees
Oct 26 - Oct 27
IL VECCHIO CONVENTO
A neatly made bed with a metal frame, two bedside tables with lamps, a wooden door, and a textured ceiling.

13. Charming San Gimignano Apartment With City Views

Charming San Gimignano Apartment With City Views
San Gimignano City Centre
The price is NT$8,608
NT$12,671 total
includes taxes & fees
Nov 6 - Nov 7
Charming San Gimignano Apartment With City Views
A terrace with outdoor seating, a view of the city, and a clock tower in the background.

14. Palazzo Alfieri Residenza d’epoca - Place of Charme

Palazzo Alfieri Residenza d’epoca - Place of Charme
Historic Centre of Florence
9.2 out of 10, Wonderful, (861 reviews)
"The staff are amazing & the location is great"
United Kingdom
Helen Jane
The price is NT$6,861
NT$8,059 total
includes taxes & fees
Nov 20 - Nov 21
Palazzo Alfieri Residenza d’epoca - Place of Charme
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

15. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (81 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is NT$8,844
NT$9,875 total
includes taxes & fees
Nov 6 - Nov 7
Terre di Baccio
A historic building with ornate iron gates, potted plants, and a visible staircase leading to an upper floor.

16. Signoria Collection

Signoria Collection
Historic Centre of Florence
9.8 out of 10, Exceptional, (18 reviews)
"Room was always clean. Location is amazing."
Canada
Doug
The price is NT$5,319
NT$6,289 total
includes taxes & fees
Nov 24 - Nov 25
Signoria Collection
A villa with a swimming pool, outdoor seating, and a tennis court.

17. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (81 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is NT$4,769
NT$5,392 total
includes taxes & fees
Oct 26 - Oct 27
Villa Curina Resort
An arched entrance with a lantern above, flanked by two potted plants.

18. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (108 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is NT$5,789
NT$6,514 total
includes taxes & fees
Nov 23 - Nov 24
Villa il Fedino
A modern bedroom with a large bed, a desk with chairs, and a bathroom visible through an open door.

19. Palazzo Mannaioni Suites

Palazzo Mannaioni Suites
4.0 star property
Historic Centre of Florence
9.2 out of 10, Wonderful, (1,195 reviews)
"We had a good stay! It’s a great location"
Canada
Heather
The price is NT$3,856
NT$4,752 total
includes taxes & fees
Nov 9 - Nov 10
Palazzo Mannaioni Suites
A bathroom with a window view of a historic building and a tiled roof.

20. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (495 reviews)
"Very friendly staff and great location close to the center of town. Breakfast was a nice touch and just what we needed to start the day. Would recommend!"
United States
Jacob
The price is NT$3,267
NT$3,740 total
includes taxes & fees
Nov 2 - Nov 3
Siena Vip
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 Poggibonsi Hotel Reviews

Villa Lecchi Hotel Wellness

Villa Lecchi Hotel Wellness

10/10 Excellent
"The view is awesome, the restaurant is very good, the pool is fabulous, the room is perfect, the price is very correct as well"
Sebastien 1-night trip
Posted 9 days ago
Villa Lecchi Hotel Wellness

Find out more about Poggibonsi

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

  • View our selection of featured holiday rentals in Poggibonsi
  • Use the map to find apartments and other holiday homes in the Poggibonsi neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Poggibonsi while they last

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

Frequently asked questions

Can I find vacation rentals in Poggibonsi?

Yes, we have vacation rentals close to popular sights in Poggibonsi, or you can select a more secluded option if you want a relaxing place to stay. Poggibonsi is known for its wineries and seafood restaurants.

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

Villa La Stella - Casa per Ferie: This vacation home rental near Poggibonsi is located near the airport and has a garden, a library, and air-conditioning to put you at ease in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Poggibonsi?

Expedia has 6 vacation rentals for your stay in Poggibonsi.

What’s there to see and do in Poggibonsi?

Cultural attractions include Archeodromo di Poggibonsi, whereas Alta Val d'Elsa River Park is a spot to enjoy nature. Other places in town to visit include Collegiata di Santa Maria Assunta Museum and Poggio Imperiale Fortress.

What’s a vacation rental in Poggibonsi like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Poggibonsi. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for a small group gathering.