
Holiday rentals with a pool in Guardistallo
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Top-rated rentals with a pool in Guardistallo
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Il Cubetto -Sea Studio: sense of peace and freedom
Our little place, Il Cubetto, inaugurated with the 2020 season, stands in full Tuscan country and is particularly distinctive because of its absolute exclusivity: only two studio apartments within our 7000 sqm of garden planted with many fruit trees, with great attention to any detail. Our guests, a maximum of two per studio apartment, have the use of a salt-water infinity swimming pool overlooking the valley. Depending on the car they drive, they can park next to the cottage or beside the road.

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

Il Frantoio (Hydromassage + Fireplace)
✨ Rifugio romantico nel cuore della Toscana — perfetto in ogni stagione 🍂 Benvenuti a Palazzo Riccardi, uno storico edificio nel suggestivo borgo di Rivalto, dove l’autenticità toscana incontra il design moderno. Lasciati conquistare dal camino a legna, dal bagno con vasca idromassaggio e da un’atmosfera calda e avvolgente. Ideale per coppie in cerca di relax e charme, questo appartamento è un nido perfetto in ogni stagione ma è in autunno e inverno che diventa davvero magico 💫

Belforti Tower
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.

Apartment in Agriturismo with pool and great view
L'appartamento, facente parte di un agriturismo è arredato in stile tipico , tutto interamente rinnovato , composto da camera matrimoniale, cucina , bagno e divano letto doppio nella cucina; situato nel centro della Toscana è un ottimo punto di partenza per poter visitare la regione; a 20 minuti da San Gimignano e 35 da Firenze. E' adatto ad una coppia o ad una famiglia con figli piccoli avendo come soluzione per la terza e la quarta persona un unico divano letto matrimoniale.

In the Tuscan green, Podere I Places with swimming pool Ap2
Lovely apartment immersed in the greenery of the Tuscan countryside, with 2 bedrooms (double and single), bathroom, livable kitchen and outdoor space. Seasonal outdoor pool (June-September). Located on a hill with sea views, ideal for hiking or cycling. Environmental Guide Service Available. 12 km from the beaches of Bibbona and Cecina, 45 min from Baratti. Perfect for visiting Bolgheri, Castagneto Carducci, Volterra, San Gimignano, Pisa, Florence and Lucca.

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 IT050012C2LZ3CHRNQ)
Historic charm with modern comfort, Tuscany
Charming Retreat for Two, 15 Minutes from Vinci Escape to a cozy hideaway perfect for couples seeking relaxation and comfort. Enjoy a private garden and a shared travertine pool with stunning views of the Tuscan countryside—especially magical at sunset. Ideal for romantic, slow-paced weekly stays. We live on the property with discretion and are happy to assist if needed. A car is required to reach the house.

sea view villa with private infinity pool
RENTALS ONLY FROM SATURDAY TO SATURDAY. The house is located within our farm, surrounded by forest is distance from the village of Castagneto Carducci only 3.5 km. Its unique location offers a wonderful view of the sea and the country, ensuring a pleasant tranquility, away from the heat and noise of the country.

Tenuta Chiudendone in Tuscany
Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Countryside Dream farm in Tuscany
Great place in the middle of Tuscan Hills, you will be surrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.
Popular amenities for Guardistallo rentals with a pool
House rentals with a pool

Infinity pool in Chianti area

Cercis - La Palmierina

Ancient Barn in Chianti with Pool

Private villa/swimming pool in Tuscany

Antico Borgo Ripostena – n. 5 Garage

Iris Residence "Casa vista mare-giardino-piscina"

Collina Power

Nada Home
Condo rentals with a pool

„Toscana Amore Mio“, stunning view, 18min Volterra

Stone House in Chianti with pool and parking

Adalberto Apartment inside the Manor of Fulignano

Vintage apartment with swimming pool in Chianti

New, bright, cozy Florence apartment with view

Manuela apartment with pool in farmhouse

La Casetta

Locanda degli Alberi - Cherry Tree
Home rentals with a private pool

Cinzia by Interhome

Tuscan Villa Featured Conde Nast Best Villas Italy

Stone House with Exclusive Pool Codilungo in Chianti

Costacce by Interhome

Aurora by Interhome

Il Pezzo Farm by Interhome

Farmhouse , pool, 13 px. Lucca 10km

The Barn by Interhome
When is the best time to visit Guardistallo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $316 NZD | $266 NZD | $276 NZD | $244 NZD | $227 NZD | $266 NZD | $318 NZD | $377 NZD | $261 NZD | $188 NZD | $289 NZD | $321 NZD |
| Avg. temp | 7°C | 8°C | 10°C | 13°C | 17°C | 21°C | 24°C | 24°C | 21°C | 17°C | 12°C | 8°C |
Quick stats about holiday rentals with a pool in Guardistallo

Total holiday rentals
Explore 130 holiday rentals in Guardistallo

Nightly prices starting at
Guardistallo holiday rentals start at $101 NZD per night before taxes and fees

Verified guest reviews
Over 890 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
110 of Guardistallo holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Guardistallo rentals

4.6 Average rating
Guardistallo stays receive an average rating of 4.6 out of 5 from guests
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- Elba
- Santa Maria Novella
- Piazza della Signoria
- Mercato Centrale
- Ponte Vecchio
- Santa Maria Novella
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Salvatore Ferragamo Museum
- Cathedral of Santa Maria del Fiore
- Marina di Cecina
- Del Chianti
- Siena Cathedral
- Porta Elisa
- Basilica of Santa Maria Novella
- Spiagge Bianche
- Piazza dei Cavalieri
- Cala Violina
- Gorgona
- Piazza del Duomo (Pisa)
- Uffizi Gallery
- Piazzale Michelangelo
- Fortezza da Basso
- Piazza della Repubblica




