House holiday rentals in Guardistallo

4.97 out of 5 average rating, 194 reviews

An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.

Home in Simignano

Casa al Gianni - The Simignano Barn

Transformed from a historic barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living area, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this little slice of paradise!

FamilyValueAccuracy

5.0 out of 5 average rating, 117 reviews

A stone house is positioned on a hillside overlooking the deep blue sea. Lush green terrain surrounds the structure, and a large umbrella provides shade near the entrance. The coastline and distant boats can be seen in the background under a clear sky.

Home in Rio Marina

Captain's House | Monte Grosso, Elba

The Casa del Capitano is located on the top of Monte Grosso in the National park of the tuscan archipelago. The location is unique on the island and from here you have a fantastic view of the city of Portoferraio, Piombino, Corsica, Capraia and Gorgona. The house was restored during a project lasting several years, in close collaboration with the National Park and was designed to be self-sufficient and ecological. Here you use purely the energy of the sun, without having to renounce luxury.

LocationValueNearby

4.93 out of 5 average rating, 201 reviews

The rustic stone house features a facade adorned with climbing greenery, offering a blend of natural beauty and architectural charm. Large wooden doors open onto a welcoming terrace, which is surrounded by greenery, providing a serene outdoor space for relaxation.

Home in Volterra

Collina Power

Collina is an ancient stone farmhouse, the house is surrounded by fields and olive groves. It has a large garden with swimming pool and a terrace where you can have pleasant lunches and dinners. A barbecue and garden furniture are available. The road to get to the house in the last stretch is not paved and is therefore not suitable for sports cars or particularly low ones. The route lends itself to pleasant walks during the day, while at night we recommend using a car because it is not lit.

ValueFamilyAccuracy

4.96 out of 5 average rating, 137 reviews

Home in Montescudaio

Open space surrounded by nature

Casa Namaste is a small stone cottage with well-kept interiors 1 km from the medieval village of Montescudaio. The house is completely surrounded by woods and centuries-old oaks. 150 meters away flows the Cecina river. In the 5000 square meter garden there is a natural spring with a large stone tub to cool off and an outdoor hot shower surrounded by greenery. We have a Vodafone adsl line with download 33 and upload 1.4. Smart TV and air conditioning are also available starting this spring

LocationFamilyAccuracy

5.0 out of 5 average rating, 232 reviews

An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.

Home in Gambassi Terme

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

FamilyValueAir conditioning

5.0 out of 5 average rating, 69 reviews

An outdoor seating area is showcased on a sunlit terrace, featuring a small wooden table surrounded by colorful chairs. A terracotta pot filled with vibrant red flowers adds a touch of color against the rustic stone wall of the structure.

Home in Casale Marittimo

Countryside-panoramic sea Casale Marittimo Tuscany

Small apartment immersed in the tranquility of the Tuscan countryside. Ten minutes from the Etruscan Coast. Sea view. To spend a stay in the name of privacy and relaxation, but with all the attractions of the area just a short walk from here. I welcome your furry friend,JUST ONE and SMALL. From here many hiking trails and bike paths start to discover the evocative landscapes. Great typical restaurants, and wineries.!!! Enjoy your stay! Tourist tax is payable at check-out.

FamilyLocationWalkability

Home in Montecatini Val di Cecina

The open living area showcases a warm orange sofa against a white wall, complemented by a rustic stone feature and a spiral staircase. A dining table is set with light-colored wooden chairs, while decor pieces add character to the space.

La Casina dei Caci

This house offers, for those who love nature, a landscape that extends from the wooded hills to the sea where we can admire a splendid sunset. For those who love to take walks or go cycling, there are itineraries to follow, rest assured. This accommodation is about 5 km from the centre of Montecatini Val di Cecina, of which 3 km of paved road and 2 km of dirt road. From 1 January 2026, a tourist tax of 1.50 euros per person per night to be paid on site.

LocationFamilyHeating

4.88 out of 5 average rating, 213 reviews

Home in Barberino Tavarnelle

Nada Home

3 comfortable, fully air-conditioned double bedrooms, each with its own private bathroom, in the heart of Chianti, ideally located between Florence, Siena and San Gimignano. A welcoming, well-kept home in the peaceful Tuscan countryside. Fully equipped kitchen with dishwasher, oven and bar area, plus a laundry room with washing machine and dryer. Private garden for your exclusive use with a private hydromassage pool, heated in winter upon request 🌷

LocationFamilyOutdoor spaces

4.87 out of 5 average rating, 215 reviews

5.0 out of 5 average rating, 21 reviews

The tranquil salt-water pool reflects the colors of the sunset, creating a serene atmosphere. Lush landscapes surround the pool area, with silhouettes of trees and hills visible in the background. A patio set can be seen nearby, suggesting a space for relaxation.

Home in Chianni

The Cottage to relax and enjoy

Detached country house – for exclusive use – in stone and glass from the 18th century; ideal for 4 people. The spacious wooden terrace at the house with a large dining table invites you to socialize. On the terrace by the saltwater pool (10m x 5m, depth 1.4m-2.4m), you can relax on the sun loungers and deckchairs. Large property with olive and fruit trees, completely self-sufficient accommodation thanks to photovoltaics. (CIN IT050012C29N4AT4OD)

ValueLocationCondition

4.93 out of 5 average rating, 122 reviews

A rustic villa features large glass panels that offer views of the surrounding greenery. The spacious outdoor patio area is equipped with a dining set and lounge chairs. Towering trees and well-maintained grass frame the property under a bright blue sky, enhancing the serene countryside setting.

Home in San Miniato

Lovely house in a scenic and paiceful location

This beautiful house is nestled in a quiet and panoramic location, making it the perfect spot to get away from it all. With three bedrooms, three bathrooms, and room for up to six guests, this is the perfect place for a group of friends or a large family to call home while exploring Tuscany. Spend your days hiking the picturesque landscape, wandering through charming villages, or simply relaxing in the lovely gardens of the house.

LocationFamilyLong stay

Home in Rosignano Marittimo

A terrace overlooking the coastline is equipped with a large umbrella, sun loungers, and a small pool. The rocky coastline and clear blue water are visible, while lush greenery frames the outdoor area, creating a serene environment for relaxation.

Frontemare house with exclusive sea access

Casa Frontemare is a completely renovated property with direct access to the sea, from which you can enjoy a panoramic view of the sea, the Tuscan islands and wonderful sunsets. It is a perfect place for those who love a relaxing and private vacation. The proximity to the Tuscan art cities and the small typical villages means that it is also possible to discover new places and discover the flavors of Italian cuisine.

FamilyValueLong stay

4.95 out of 5 average rating, 107 reviews

4.96 out of 5 average rating, 144 reviews

A winding driveway is lined with tall cypress trees on either side. The green landscape stretches into the distance, revealing rolling hills and a distant rustic building surrounded by nature, creating a serene and inviting setting.

Home in Montaione

Cercis - La Palmierina

The apartment is part of a completely fenced estate of 60 hectares of unspoiled nature: more than 1000 olive trees, countless cypresses and fragrant forests create an idyllic environment for those seeking tranquility and silence. The Palmierina estate is near Castelfalfi (a true jewel of medieval architecture) and close to Florence (50 Km), Siena (50 Km), and Pisa (50 Km). There are two golf courses nearby.

LocationValueShared spaces

Popular amenities for Guardistallo house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in San Filippo a Ponzano

The image showcases a refreshing pool surrounded by lounge chairs and umbrellas, enhancing the outdoor relaxation area. The pool is framed by lush greenery and a stone wall, with the charming rustic house visible in the background under a clear blue sky.

Infinity pool in Chianti 1

LocationFamilyShared spaces

5.0 out of 5 average rating, 140 reviews

4.93 out of 5 average rating, 162 reviews

A shaded outdoor dining area features a large table surrounded by several chairs, nestled under a pergola with lush greenery. The shared swimming pool glistens in the background, framed by terracotta tiles and scenic views of the Tuscan landscape.

Home in San Miniato

Private villa/swimming pool in Tuscany

FamilyLocationAccuracy

4.95 out of 5 average rating, 200 reviews

A cozy bedroom is highlighted with a floral wallpaper featuring vibrant colors. A bedside table made of wood stands beside a spacious bed dressed in pink bedding. A modern lamp provides warm lighting, enhancing the inviting details of the room.

Home in Pievescola

Borgo Ripostena – No. 8 Casa Vecchia

ValueFamilyHospitality

Home in Barberino Val d'Elsa

The image captures a scenic view of a well-maintained garden featuring a private pool and a barbecue area. The stone structure is adorned with a tiled roof, framed by lush greenery and rolling hills in the background. Soft clouds add to the tranquil atmosphere.

Ancient Barn in Chianti with Pool

ValueLocationCheckout

4.89 out of 5 average rating, 125 reviews

4.84 out of 5 average rating, 148 reviews

A charming house is framed by lush greenery, with several trees dotting the manicured lawn. The exterior features warm tones, complemented by a covered porch area. Various plants provide a natural ambiance, enhancing the serene outdoor space.

Home in Montespertoli

I Limoni Apartment in Tuscany

ValueLocationCheck-in

4.88 out of 5 average rating, 34 reviews

Home in Lajatico

Margherita: Tuscany views, Pool & Walk to Village

LocationFamilyComfort

4.99 out of 5 average rating, 69 reviews

A scenic view showcases rolling green hills of Tuscany, dotted with olive trees and distant houses. The pool area, adorned with a lounge chair and shaded by a white umbrella, invites relaxation. The blue sky is streaked with soft clouds, enhancing the tranquil landscape.

Home in Morrona

Villino Isotta (exclusive private villa)

LocationValueLong stay

5.0 out of 5 average rating, 21 reviews

An aerial view captures the traditional Tuscan farmhouse surrounded by lush green hills and fields. The property features a newly constructed infinity pool and a tranquil pond, set against a backdrop of rolling countryside under a clear blue sky.

Home in Volterra

Charming Tuscan Villa with pool

LocationFamilyNearby

Weekly house rentals

Home in Barberino Tavarnelle

beautiful farmhouse in the Chianti region with panoramic garden

FamilyLocationIndoor spaces

4.96 out of 5 average rating, 47 reviews

4.94 out of 5 average rating, 35 reviews

A charming countryside house features a light-colored façade and green shutters. A welcoming porch area is equipped with a simple bench. The surrounding landscape showcases lush greenery and blue skies, creating a serene atmosphere.

Home in Bibbona

House with view of olive trees, 10 minutes from the sea

FamilyLocationWi-Fi

4.88 out of 5 average rating, 26 reviews

Home in Cecina

[10 min from the sea] Apartment with garden + Jacuzzi

FamilyLocationCheck-in

Home in Castagneto Carducci

The outdoor patio features a spacious lounge area, adorned with comfortable seating and illuminated by soft lighting. Stone walls and wooden beams create a rustic charm. Sheer curtains gently billow in the evening breeze, enhancing the inviting atmosphere of the space.

Villa Siloral a jewel in the Etruscan Coast

LocationValueHospitality

4.89 out of 5 average rating, 18 reviews

5.0 out of 5 average rating, 16 reviews

Home in Florence

Villa Agnese · Pool · Duomo View · Parking

FamilyValuePool

5.0 out of 5 average rating, 4 reviews

Home in Capannori

Tuscan Villa with Private Pool & Countryside Views

FamilyLocationComfort

4.86 out of 5 average rating, 14 reviews

Home in Riparbella

special offer 15-20 september elegant house. AC

FamilyLocationNearby

Home in Marina di Bibbona

The exterior of a two-story apartment is framed by lush greenery and tall trees. A covered patio area features outdoor seating and is adorned with colorful flowers. Light filters through the trees, creating a serene environment.

Allegra apartment Tombolino beach

FamilyLocationPets

4.88 out of 5 average rating, 8 reviews

Private house rentals

5.0 out of 5 average rating, 28 reviews

The pool area is softly illuminated by garden lights, creating a serene atmosphere in the evening. Surrounding olive trees and tall cypress trees provide a natural backdrop, while blooming flowers add a touch of color. The pool's turquoise water invites relaxation.

Home in Certaldo

Casa La Selva

FamilyLocationCleanliness

Home in Barberino Tavarnelle

Relaxing Tuscan Country Home with Beautiful Views

LocationFamilyKitchen

5.0 out of 5 average rating, 86 reviews

5.0 out of 5 average rating, 6 reviews

A serene swimming pool is framed by a well-maintained garden, offering a view of rolling hills and lush vegetation. Five umbrella shades stand closed beside the pool, which is surrounded by stone pavers and vibrant greenery, inviting relaxation and tranquility.

Home in Chianni

Podere La Sterza The barn

FamilyLocationIndoor spaces

5.0 out of 5 average rating, 46 reviews

A charming pathway leads through an arched structure adorned with greenery. Brick paving and vibrant plants line the sides, while light filters in, creating a serene ambiance. The narrow lane continues beyond the arch, inviting exploration of the surrounding area.

Home in Lajatico

Stylish Gem in Historic Lajatico

LocationValueView

Home in Montecatini Val di Cecina

Romantic Tuscan Town house with Breathtaking Views

ValueLocationDecor

4.9 out of 5 average rating, 21 reviews