
Vacation rentals with a pool in Siena
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Quick stats about vacation rentals with a pool in Siena

Total vacation rentals
Explore 100 vacation rentals in Siena

Nightly prices starting at
Siena vacation rentals start at G$14,609 GYD per night before taxes and fees

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Over 2,070 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
90 of Siena vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Siena rentals

4.7 Average rating
Siena stays receive an average rating of 4.7 out of 5 from guests
Top-rated rentals with a pool in Siena
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni è un antica proprietà del 1600 a gestione familiare situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare navetta privata e esperienze locali direttamente con la nostra famiglia . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello e vigneti con tramonti unici.

Palazzo Monaci - Piscina nelle crete Senesi
Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

Tuscan cottage with an heavenly view
Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.

Relax e charme tra le colline del chianti
Bellissima colonica in pietra, indipendente, immersa tra gli olivi e le colline del Chianti, con giardino privato e piscina panoramica. Piano terra con ampi saloni, antico camino e forno a legna, soggiorno luminoso e cucina full optional. Al primo piano tre suites composte da camera, studio e bagno privato. Accesso tramite cancello e strada bianca in proprietà privata a soli 500 metri dal paese di Strada in Chianti. Ideale per quiete e relax. Location strategica per visitare la Toscana.

Stone House with Exclusive Pool Codilungo in Chianti
Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.

Podere La Castellina - N°1 COTTAGE
Cottage indipendente in pietre e mattoni all'interno del "Podere la Castellina" (ex convento 13° secolo), nel magnifico parco naturale della Montagnola Senese. Il cottage può ospitare comodamente 5 persone e comprende: - ampio soggiorno con tv e camino - cucina abitabile con forno - camera matrimoniale - camera con tre letti singoli - bagno con doccia A disposizione degli ospiti piscina panoramica, solarium e terrazza con vista mozzafiato, dotata di forno a legna e barbecue.

Private Chianti Cottage, Garden & Vineyard Views
Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Villa Capanna, Private Pool, Breathtaking Views
Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.

A Big Dream in a Little Tower.
The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.
Popular amenities for Siena rentals with a pool
House rentals with a pool

Casina in campagna Podere Scorno con piscina

Infinity pool in Chianti 1

Cercis - La Palmierina

Ancient Barn in Chianti with Pool

SuiteLouise.pool, Hot Tub,homeGym & private Garden

Explore Chianti from a Charming Stone House

Agriturismo Casa Giulia di Sopra

Country House in the Crete Senesi
Condo rentals with a pool

Appartamento Loggiato 3 in toscana vicino Siena

Adalberto Apartment inside the Manor of Fulignano

Scenic Stilish Country

Residenza Vintage con Piscina nel Chianti

Poggiolieto Suite - on hills 10' from city center

Manuela appartamento con piscina in agriturismo

Charming Residence Castello di Orgiale near Siena

Agriturismo Poggio Bonelli, 4 people apartment
Home rentals with a private pool

Villa il Palagio nelle campagne toscane

Suite Casa Luigi con piscina esclusiva

Esplora la natura al centro di Vigneti Chianti

TREEhouse/casaBARTHEL
Historic villa x8 with exclusive pool
When is the best time to visit Siena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$54,679 GYD | G$59,479 GYD | G$55,305 GYD | G$55,722 GYD | G$60,731 GYD | G$67,409 GYD | G$61,566 GYD | G$54,261 GYD | G$57,601 GYD | G$53,844 GYD | G$48,209 GYD | G$48,835 GYD |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°C |
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- Lake Trasimeno
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- Ponte Vecchio
- Basilica of Santa Maria Novella
- Mugello Circuit
- Parco Regionale Della Maremma
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- Stazione Santa Maria Novella
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- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Gulf of Baratti
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- Parco delle Cascine
- Piazza della Repubblica
- Del Chianti
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- Pitti Palace
- Boboli's Garden
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- Museums Italy
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- Dining Italy
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- Galleries Italy
- Tours Italy
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