Val d'Elsa Vacation Rentals from $59: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Val d'Elsa vacation rentals

Deluxe Apartment, 1 Bedroom | Minibar, in-room safe, laptop workspace, soundproofing

Borgo San Giusto

Empoli

Paul

$96 nightly

Apr 19 - Apr 20

Total with taxes and fees

Riserva di Fizzano Residence

Castellina in Chianti

Eileen

$207 nightly

May 13 - May 14

Total with taxes and fees

Antico Borgo Poggiarello

Monteriggioni

James Bakley

$178 nightly

May 7 - May 8

Total with taxes and fees

Affittacamere a 20 minuti da Firenze

Empoli

Scott

$75 nightly

Apr 19 - Apr 20

Total with taxes and fees

Deluxe Room, Patio | Frette Italian sheets, premium bedding, minibar, in-room safe

Tenuta Sant'Ilario

Gambassi Terme

Ilaria

$122 nightly

Apr 20 - Apr 21

Total with taxes and fees

Borgo Il Poggiaccio

Sovicille

Dean

$221 nightly

May 13 - May 14

Total with taxes and fees

"A Casa di Franca Villa con piscina"

Gambassi Terme

"Pros: La estancia en la casa fue muy bonita. Estaba cerca de Florencia, Siena, Sant Gimigano, etc. Viajamos toda la familia y los propietarios fueron muy acogedores. La piscina es un sitio perfecto para relajarse y bañarse después de ver la Toscana. Nuestros hijos y sobrinos jugaron porque tenían de todo. La casa muy equipada y limpia con televisión en todas las habitaciones. Los propietarios además nos ayudaron con un pequeño contratiempo que tuvimos. Nos sentimos como en casa, muchas...

Anonymous traveler

$1,453 nightly

Apr 25 - Apr 26

Total with taxes and fees

Casa di Campagna in Toscana

Sovicille

Alasdair

$102 nightly

Apr 21 - Apr 22

Total with taxes and fees

Romantic Double Room, 1 Bedroom, Non Smoking | View from room

B&B Palazzo Tortoli

San Gimignano City Centre

April

$143 nightly

Apr 19 - Apr 20

Total with taxes and fees

Palazzo Pacini

Colle di Val d'Elsa

John

$116 nightly

Apr 26 - Apr 27

Total with taxes and fees

Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Monteriggioni

$173 nightly

Apr 19 - Apr 20

Total with taxes and fees

Sportland

Colle di Val d'Elsa

Giorgio

$52 nightly

May 17 - May 18

Total with taxes and fees

Antica Pieve B&B

Barberino Tavarnelle

Jessica

$150 nightly

May 19 - May 20

Total with taxes and fees

Palazzo al Torrione 2

San Gimignano City Centre

Angel

$136 nightly

Apr 23 - Apr 24

Total with taxes and fees

APART. OF CHARM, AIR CONDITIONING, FENCED POOL IN THE HEART OF CHIANTI-FLORENCE

MONTERIGGIONI

"We absolutely loved Marcella & Enzo’s property. The pool was exactly what we needed to relax after a busy and hot few days in Rome & Venice. Just a 10 min drive from the train station. The home is set up very nicely with the 2 bedrooms and 2 bathrooms. We loved meeting the donkeys, having a quiet place to relax along with modern conveniences like a washing machine. We were treated like family. We hope to return in the future. Huge thank you! Breathtaking views. The cottage was picture perfect. "

Anonymous traveler

$487 nightly

Apr 19 - Apr 20

Total with taxes and fees

Seasonal outdoor pool, pool umbrellas, sun loungers

Villa San Filippo

Barberino Tavarnelle

Andrew

$86 nightly

Apr 21 - Apr 22

Total with taxes and fees

Casa Vacanze Le Case

San Gimignano

Jackie

$103 nightly

May 5 - May 6

Total with taxes and fees

Donna Nobile

San Gimignano City Centre

Treena

$93 nightly

Apr 19 - Apr 20

Total with taxes and fees

Apartment "Tenuta Acquabona - Entire Country House" with Pool

Gambassi Terme

$2,406 nightly

Apr 20 - Apr 21

Total with taxes and fees

Borgo Antico Residence

Certaldo Alto

jane

$113 nightly

Apr 27 - Apr 28

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Villas

Private vacation homes

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Val d'Elsa Hotel Reviews

Villa Petriolo

10/10 Excellent

"If you enjoy peace, tranquillity, the Italian countryside, and an ethos that embraces sustainability (without any compromise on a luxury experience) then this is your spirit home away from home. The facility and surrounding countryside is stunning. The staff are exceptional, friendly and knowledgeable about the produce and the experience on offer. The food was outstanding in both the restaurants, and the fact that all produce used in the restaurants is sourced from no more than 20 miles away (although most is self produced on the property) is testament to the outstanding chefs working there. The pool was beautiful, the rooms were luxurious without being over the top. The bed was incredibly comfortable, the shower was great and the whole complex was always spotlessly clean. I cannot speak highly enough about this little piece of heaven on earth. If you like partying this isn’t the place for you. But if you are looking for a place to wind down and enjoy the peace and some beautiful food, then you won’t be able to help but love it here. "

Poderi Arcangelo

4/10 Poor

"Below expectations for the price – nice location but disappointing experience We stayed for three nights in early April as a couple. During the same trip, we stayed in other agriturismos in a similar price range, and this one unfortunately did not compare well in terms of value and overall experience. The location near San Gimignano is very nice, with pleasant countryside views. However, the service and overall guest experience felt quite limited. Key issues: • Breakfast (€20 pp): limited and inconsistent selection (e.g. stale croissants, very basic fruit unless requested, no plain yogurt, eggs gone cold) • Short breakfast window (until 10:00), creating a rush with slow replenishment • Staff appeared very stretched, resulting in a lack of welcome and a tense atmosphere • Accommodation: annex building requires driving to the main property for meals; not very convenient • Kitchen available but guests asked not to use it • Dinner: fixed menu with no choice; food was good but simple; service felt canteen-like and not particularly atmospheric • Other points: • Pool remained covered despite warm weather • No takeaway breakfast offered for early departure (despite we paid for it) • Complimentary wine (Expedia Gold benefit) only offered at check-out, hence not able to enjoy it) Positives: • Nice setting and views • Comfortable bed • Good house wine Overall: While the property itself is pleasant, it felt more like the hotel prioritise their convenience. "

Hotel Palazzo San Lorenzo & SPA

10/10 Excellent

"Parking is tricky, but we found a free parking lot close by. Check-in was easy and Livia was a gem full of helpful tips and resources. Check out - the front desk guy wasn’t very helpful. We paid the city tax in cash and wanted our change in coins - just a few coins to use in town- very much needed in Italy and he wasn’t willing to provide coins or even break a ten. He offered no assistance. Overall the room, spa and property is nice. No restaurant during off season, but the breakfast provided was excellent."

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 $59 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.

Explore a world of travel with Expedia

Expedia's Latest Trends

Hotels

Flights

Cars

Packages

General

Val d'Elsa Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Val d'Elsa vacation rentals

Borgo San Giusto

Riserva di Fizzano Residence

Antico Borgo Poggiarello

Affittacamere a 20 minuti da Firenze

Tenuta Sant'Ilario

Borgo Il Poggiaccio

"A Casa di Franca Villa con piscina"

Casa di Campagna in Toscana

B&B Palazzo Tortoli

Palazzo Pacini

Villa Montecastello

Sportland

Antica Pieve B&B

Palazzo al Torrione 2

APART. OF CHARM, AIR CONDITIONING, FENCED POOL IN THE HEART OF CHIANTI-FLORENCE

Villa San Filippo

Casa Vacanze Le Case

Donna Nobile

Apartment "Tenuta Acquabona - Entire Country House" with Pool

Borgo Antico Residence

Find vacation rentals that suit your style

Top Val d'Elsa Hotel Reviews

Villa Petriolo

Find out more about Val d'Elsa

Explore a world of travel with Expedia

Trending destinations on Expedia.com

Expedia's Latest Trends

Go further with the Expedia app