Val d'Elsa Vacation Rentals from $55: Search Short-Term Rentals

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Our top choices for Val d'Elsa vacation rentals

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

1. Palazzo Pacini

Colle di Val d'Elsa

John

$126 nightly

Oct 27 - Oct 28

Total with taxes and fees

A narrow street with stone buildings, a tower, and an archway.

2. Materia Rooms San Gimignano

San Gimignano City Centre

Bradley

$114 nightly

Oct 5 - Oct 6

Total with taxes and fees

An open wooden door leading to an outdoor patio with a table and chairs.

3. Palazzo al Torrione 2

San Gimignano City Centre

Angela

$133 nightly

Oct 27 - Oct 28

Total with taxes and fees

A reception desk with the word "SPORTLAND" prominently displayed.

4. Sportland

Colle di Val d'Elsa

Giorgio

$40 nightly

Oct 18 - Oct 19

Total with taxes and fees

An interior with stone walls, wooden doors, and a bar area with stools and bottles.

5. Borgo Il Poggiaccio

Sovicille

Louie

$161 nightly

Sep 29 - Sep 30

Total with taxes and fees

A view from a window overlooking a rural landscape with fields and a distant mountain range.

6. B&B Palazzo Tortoli

San Gimignano City Centre

Harold

$130 nightly

Oct 18 - Oct 19

Total with taxes and fees

A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

7. Riserva di Fizzano Residence

Castellina in Chianti

Janet

$171 nightly

Oct 4 - Oct 5

Total with taxes and fees

A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

8. Villa Montecastello

Monteriggioni

Alvaro

$158 nightly

Sep 28 - Sep 29

Total with taxes and fees

A narrow alleyway with brick walls, wooden barrels, and potted plants.

9. San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

San Gimignano City Centre

Marilyn H.

$167 nightly

Sep 29 - Sep 30

Total with taxes and fees

A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

10. Camping Boschetto Di Piemma

San Gimignano

Anonymous traveler

$47 nightly

Oct 4 - Oct 5

Total with taxes and fees

A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

11. Villa San Filippo

Barberino Val d'Elsa

Nadia

$88 nightly

Oct 27 - Oct 28

Total with taxes and fees

A stone courtyard with a bench, potted plants, and a building in the background.

12. Casa di Campagna in Toscana

Sovicille

Sally

$107 nightly

Oct 27 - Oct 28

Total with taxes and fees

A stone building with outdoor seating and a view of the countryside.

13. Antico Borgo Poggiarello

Monteriggioni

James Bakley

$160 nightly

Oct 17 - Oct 18

Total with taxes and fees

A narrow cobblestone street with historic buildings, a chain-link fence, and a wooden door with a number plaque.

14. Colle di Val d'Elsa - Siena - Apt Pink - B

Colle di Val d'Elsa

"The host is excellent. Perfect English and Italian. Thoughtful and great communication. Parking instructions were accurate. The apartment was beautiful and the bed was comfortable. The apartment is walkable to dining and shopping. The street is steep and the nearby medievale hill town is steeper. While we loved walking up to the hill town everyday, we liked the variety of dining and shopping near the apartment."

Tamara C.

$152 nightly

Oct 11 - Oct 12

Total with taxes and fees

A stone-walled room with a wooden desk, a chair, a TV, and a large window with curtains.

15. Tenuta Sant'Ilario

Gambassi Terme

Sergio

$103 nightly

Oct 21 - Oct 22

Total with taxes and fees

A patio with wicker furniture and potted plants, overlooking a scenic landscape.

16. Affittacamere Le Ginestre

San Gimignano City Centre

Jorge

$95 nightly

Oct 18 - Oct 19

Total with taxes and fees

An outdoor cafe area with tables and chairs, a red awning, and buildings with signs in the background.

17. DomuS Miniato

San Miniato

Thomas

$92 nightly

Oct 11 - Oct 12

Total with taxes and fees

A vineyard with a stone building, a metal gate, and purple plants in the foreground.

18. Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!

San Gimignano City Centre

William

$251 nightly

Sep 28 - Sep 29

Total with taxes and fees

A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

19. Borgo Antico Residence

Certaldo Alto

jane

$91 nightly

Oct 11 - Oct 12

Total with taxes and fees

20. Residence Arianna

Sovicille

Violeta

$124 nightly

Oct 4 - Oct 5

Total with taxes and fees

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Top Val d'Elsa Hotel Reviews

Villa Sabolini

8/10 Good

"Beautiful 14th century villa in the Tuscan hills with very pretty pool and restaurant areas, and very helpful and friendly staff. The food was hearty and enjoyable, but not the highest standard, even compared to restaurants in the area. It's in a great location for exploring Florence, Chianti region and Siena. The room we used (superior garden view) was good, very interesting features due to the age of the property, with a stunning view. However, it was not very cosy for spending time in and the A/C struggled as well. Overall we were very happy with our choice and had a great stay!"

Hotel Palazzo San Lorenzo & SPA

8/10 Good

"I can’t fault the hotel in general, but honestly, it felt a bit soulless. We stayed at the sister hotel Relais Della Rovere earlier in the week and loved it. It felt warm, authentic and welcoming. The bar was by reception and constantly had people in it and all areas of the hotel were charming, whereas the Palazzo San Lorenzo, while impressive looking, lacked character inside despite being an old palace and in an area of architectural beauty/interest. As you are up the top of the old town, although there are some nice restaurants, they all keep strange opening hours/ days and on a Monday there is nowhere in walking distance to get lunch and limited options for dinner on a Sunday. That would have been fine if the hotel had food options, but they only do breakfast (which is very nice ) and then dinner for two hours in the evening. We were expecting Caffe San Lorenzo to do food, but we never saw it open and apparently they don’t do food despite it stating they do on the website. Maybe it’s off season for them, but the website doesn’t give opening times or say what days the restaurant/ caffe Lorenzo are closed. You get two small bottles of water in the fridge in the room daily, but there is nowhere to get any other bottled drinks throughout the day or around the pool unless you drive down to the main town to a supermarket. Whilst a decent hotel, we wanted somewhere to relax and not have to venture far to eat and drink after a busy week previously, this didn’t tick that box for us"

Hotel Da Vinci

8/10 Good

"Compared with hotels in Asia, the amenities here are relatively basic, as slippers, toothbrushes, and toothpaste are not provided. My only other observation is that the bathroom is not completely sealed off from the room, unlike what you typically find in hotels in Asia. As a result, sounds from the bathroom can be heard quite clearly in the room, which can be slightly uncomfortable. Also the position where the shower head located is not ideal. I wet the whole floor on my first shower!"

Residenza d'Epoca Palazzo Buonaccorsi

10/10 Excellent

"It was a unique experience staying in an old medieval building with a beautiful view of the towers of San Gimignano. The bathroom was a little small, but the room itself was quite spacious. I do wish the bedding had been a little cleaner. The host welcomed us warmly, and the town was absolutely beautiful. It is definitely a place I would love to visit again."

Find out more about Val d'Elsa

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

Val d'Elsa vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Val d'Elsa. 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 Val d'Elsa 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 $55 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 Val d'Elsa rentals

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

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Our top choices for Val d'Elsa vacation rentals

1. Palazzo Pacini

2. Materia Rooms San Gimignano

3. Palazzo al Torrione 2

4. Sportland

5. Borgo Il Poggiaccio

6. B&B Palazzo Tortoli

7. Riserva di Fizzano Residence

8. Villa Montecastello

9. San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

10. Camping Boschetto Di Piemma

11. Villa San Filippo

12. Casa di Campagna in Toscana

13. Antico Borgo Poggiarello

14. Colle di Val d'Elsa - Siena - Apt Pink - B

15. Tenuta Sant'Ilario

16. Affittacamere Le Ginestre

17. DomuS Miniato

18. Welcome "Casa San Gimi" your perfect base for exploring the wonders of Tuscany!

19. Borgo Antico Residence

20. Residence Arianna

Find vacation rentals that suit your style

Top Val d'Elsa Hotel Reviews

Villa Sabolini

Find out more about Val d'Elsa

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