Vacation rentals with a pool in Guardistallo

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient family-run property from the 1600s located in the beautiful hills of Chianti in Tuscany, with the possibility of arranging a private shuttle and local experiences directly with our family. The apartment is available for 2 adults with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with incomparable sunsets.

Value · Family · EV charging

In the Tuscan countryside, Podere I Luoghi with swimming pool Ap1

In an old 19th-century farm, a lovely apartment surrounded by the greenery of the Tuscan countryside, on a hill with a beautiful sea view. It has 3 double bedrooms with a private bathroom, an equipped kitchen, a dining room and an outdoor area ideal for outdoor dining and relaxation. Seasonal swimming pool from June to September. Just 12 km from the sea, perfect for visiting villages such as Bolgheri, Castagneto Carducci, Montescudaio and Volterra, among hills, vineyards and authentic flavors.

Location · Cleanliness · Condition

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

Location · Value · Nearby

Villa Gourmet Food, Pizza, Chef, Pool and Nature

Villa Gourmet Typical farmhouse in the heart of Tuscany with 6 bedrooms that can comfortably accommodate up to 14 guests. - Exclusive saltwater infinity pool - Gourmet cuisine - Large garden with private parking - Two Free Charging Station (3,75 KW) - Veranda with table and Weber barbecue by the pool - Children's play area and table tennis - Football pitch - Home Restaurant service available - Cooking class and pizza workshop using a wood-fired oven - Shuttle Services

Value · Location · Air conditioning

Torre dei Belforti

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Family · Value · Hiking

Villino Isotta (exclusive private villa)

Located in the “wine city” (so named for its numerous vineyards and wineries), VILLINO ISOTTA (the name of the house) is perfect for COUPLES, FRIENDS, FAMILIES, OR GROUPS (SLEEPS 16) WITH AN EXCLUSIVE OUTDOOR POOL AND HOT TUB! Relax and enjoy the colors and scents of Tuscany in this quiet home where time seems to have stopped! VIEW OF RARE BEAUTY! We are located in a strategic position, in the center between Florence and Pisa, between Siena and Lucca!

Family · Location · Breakfast

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)

Value · Family · Breakfast

Ai Massi Annamaria Farmhouse (three-room apartment 57sqm)

Apartment (three-room apartment of 57 sqm, sleeps 4) with sea view, located on the SECOND FLOOR of the farmhouse, entrance on the west side. It has a kitchen (equipped with a fridge, dishwasher, induction stove, microwave, kettle, toaster, immersion blender and Moka coffee maker), a living room (TV and Wi-Fi), two bedrooms with double bed and bathroom. The property has an eco-friendly swimming pool and overlooks the Etruscan Coast countryside.

Family · Value · Decor

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.

Location · Value · Hospitality

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.

Value · Family · Sleep quality

Charming Tuscan Villa with pool

Nestled on a panoramic hill and located just 3.8 km from the historic city of Volterra, Podere Casalino is easily accessible via a paved road and has private parking onsite. This traditional Tuscan farmhouse is set in the Volterra countryside, and was completely restored and preserved 25 years ago and updated again in late 2024. A new kitchen has been installed in Spring 2025.

Location · Family · Parking

Mimosa: Scenic Tuscany Stay, Pool & Walk to town

Welcome to La Lunaria di Lajatico, an elegant residence in the Tuscan hills, just a 7-minute walk from the village of Lajatico, hometown of Andrea Bocelli. With two pools, panoramic terraces overlooking rolling hills, olive groves, BBQ, and full modern comfort, it offers four rustic-chic apartments—ideal for families, couples, or groups seeking authentic Tuscany close to town.

Value · Family · Outdoor spaces