A historic castle on a hill surrounded by lush greenery.

Certaldo Vacation Rentals

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Our top choices for Certaldo vacation rentals

1. Borgo Antico Residence

Borgo Antico Residence
Certaldo Alto
10.0 out of 10, Exceptional, (3 reviews)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
The price is CA $92
CA $146 total
includes taxes & fees
Oct 16 - Oct 17
Borgo Antico Residence

2. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (121 reviews)
"It’s seen its best day a while ago. Basic necessities for an overnight, but I wouldn’t choose it again."
United States
Winonah
The price is CA $103
CA $117 total
includes taxes & fees
Oct 13 - Oct 14
Chianti Village Morrocco

3. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (113 reviews)
"They were very helpful to me when I arrived. I difficulty accessing there messages to me. They put me at ease"
United States
Angela
The price is CA $151
CA $214 total
includes taxes & fees
Oct 2 - Oct 3
Palazzo al Torrione 2

4. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (65 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is CA $177
CA $202 total
includes taxes & fees
Oct 21 - Oct 22
B&B Palazzo Tortoli

5. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (102 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is CA $174
CA $195 total
includes taxes & fees
Nov 1 - Nov 2
Palazzo Pacini

6. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (105 reviews)
"Tha parking was easy on the property. It was within walking distance to the villages with shops, restaurants and cafes. The best part was the staff. The owners were incredibly helpful, friendly and made you feel like family. Breakfast outside was lovely overlooking the hills of Tuscany. We met many people and had lovely conversations with other travelers during breakfast. A gem in Tuscany."
United States
Lori
The price is CA $298
CA $334 total
includes taxes & fees
Oct 6 - Oct 7
Villa il Fedino

7. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (89 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveller
The price is CA $67
CA $79 total
includes taxes & fees
Oct 5 - Oct 6
Camping Boschetto Di Piemma

8. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (86 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is CA $193
CA $221 total
includes taxes & fees
Oct 13 - Oct 14
Antico Borgo il Cardino

9. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (268 reviews)
"Very friendly and clean."
United States
Mohamed
The price is CA $198
CA $223 total
includes taxes & fees
Oct 21 - Oct 22
Relais Villa Olmo

10. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (39 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is CA $226
CA $255 total
includes taxes & fees
Oct 6 - Oct 7
La Locanda di Pietracupa

11. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very good, (108 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
The price is CA $61
CA $72 total
includes taxes & fees
Oct 12 - Oct 13
hu Firenze Certosa camping in town

12. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (80 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 CA $409
CA $457 total
includes taxes & fees
Oct 16 - Oct 17
Terre di Baccio

13. Mamo Florence - Le Farine Della Signoria Apartments

Mamo Florence - Le Farine Della Signoria Apartments
Historic Centre of Florence
8.8 out of 10, Excellent, (11 reviews)
"Great host, amazing location!"
United States
raxshaaz
The price is CA $189
CA $331 total
includes taxes & fees
Oct 28 - Oct 29
Mamo Florence - Le Farine Della Signoria Apartments

14. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (27 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is CA $304
CA $348 total
includes taxes & fees
Oct 5 - Oct 6
Borgo Argenina

15. Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1,742 reviews)
"Love this place, came back twice. Literally had all you need . The shuttle downtown is amazing, exploring with families can be chaotic this helped. The pool gets a bit crowded during peak season but still worth a visit."
United States
Ama
The price is CA $89
CA $109 total
includes taxes & fees
Oct 26 - Oct 27
Hu Firenze Camping In Town

16. Villa La Stella - Casa per Ferie

Villa La Stella - Casa per Ferie
Le Cure
8.6 out of 10, Excellent, (256 reviews)
"The location and staff were decent. It’s an older property that could use some upgrades."
Canada
Connor
The price is CA $177
CA $207 total
includes taxes & fees
Nov 1 - Nov 2
Villa La Stella - Casa per Ferie

17. La Torre Del Cestello

La Torre Del Cestello
Historic Centre of Florence
9.2 out of 10, Wonderful, (334 reviews)
"Great location easy to park car with car service they offer"
United States
Joanna
The price is CA $169
CA $208 total
includes taxes & fees
Nov 1 - Nov 2
La Torre Del Cestello

18. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (98 reviews)
"Everything was very clean and modern, working perfect. We didn’t meet anyone from the staff. And it would be nice if they leave some bottle of water for each room. We like the place a lot. People have to consider that it is outside Siena walls and it’s a pretty steep and long distance walk"
United States
María
The price is CA $95
CA $111 total
includes taxes & fees
Oct 20 - Oct 21
Domus il Palio B&B

19. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (484 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
The price is CA $140
CA $161 total
includes taxes & fees
Nov 1 - Nov 2
Siena Vip

20. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (211 reviews)
"We enjoyed our stay very much. Staff was very friendly and offered great advise on places to eat. The rooms had great charm to them. We were delighted with our selection of where to stay."
United States
Enrique
The price is CA $162
CA $184 total
includes taxes & fees
Oct 31 - Nov 1
B&B Il Corso
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 Certaldo Hotel Reviews

Find out more about Certaldo

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Certaldo. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Certaldo?

Yes, we have vacation rentals close to well known sights in Certaldo, or you can go with a more remote option if you're looking for relaxation. Nature enthusiasts will enjoy the gardens and countryside in Certaldo. Make sure you have time to check out the festivals while you're in the area.

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

Villa La Stella - Casa per Ferie: This vacation home rental near Certaldo 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 Certaldo?

Choose from 9 Expedia vacation rentals in Certaldo for a memorable vacation.

What’s there to see and do in Certaldo?

Enjoy the area's cultural attractions such as Museum of Sacred Art, or get outdoors into nature at a spot like Boboli Gardens. Other popular places to visit in the area include Piazza di Santa Maria Novella and Piazza del Duomo.

What’s a vacation rental in Certaldo like?

A vacation rental is a private property you can book for a few weeks or just a few days in Certaldo. Vacation rentals feature extras such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a small group gathering.