
Vacation rentals with a pool in Montalcino
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Montalcino

Nightly prices starting at
Montalcino vacation rentals start at $90 per night before taxes and fees

Verified guest reviews
Over 20 verified reviews to help you choose

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

4.9 Average rating
Montalcino stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated rentals with a pool in Montalcino
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

EcoLodge – modernes Design in ruhiger Panoramalage
Die EcoLodge, modern, ökologisch, komfortabel, liegt mitten in der Natur in einer friedlichen, fruchtbaren Kulturlandschaft am Monte Amiata in der stillen Südtoskana. Sie gehört zu einem alten Bauernhaus mit viel Platz, wunderschöner Aussicht, vielen alten Obst-, Marroni-, Olivenbäumen und unserem Weinberg. Es ist ein idealer Standort. Von hier aus können Sie weltberühmte Sehenswürdigkeiten erkunden, viel unternehmen und abseits der Touristenströme die Ruhe des toskanischen Landlebens genießen.
FamilyValueBiking

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.
FamilyValueCondition

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.
LocationValueCondition

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.
ValueFamilyCheck-in

Villa a Montepulciano con Piscina
The Villa "I Girasoli" is part of the holiday farm "Il Serraglio" which covers 17 hectares. The Villa has a total area of 220 square meters that includes two bedrooms, two bathrooms, a large living room with an antique fireplace. Free WiFi. Direct access to the pool (which can be used by our other guests too) * 2 AirCon units: 1 per bedroom * * Pool open from April to November. Circular warm pool, (36C/97F) from April 1 to October 31. Pool is shared with other guests of our property. *
ValueLocationWalkability

Rural Tuscany | Family farmstay with restaurant
Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.
ValueLocationPool

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.
FamilyLocationAmenities

Appartamento Mimosa - Poggio al Vento
Private apartment in a farmhouse from the 1600s. The same consists of kitchen, double bedroom and bathroom. It has everything you need for a pleasant stay. From the terrace, the breathtaking view, overlooking Mount Amiata, Rocca D'Orcia an ancient fortress and the Castle of Ripa D'Orcia. The swimming pool overlooks the Montalcino side. We are an organic farm, we produce high quality wine and oil. We offer, for a fee, tastings of our red wines. Winery tour etc
FamilyValuePool

Casa Crociani - Amazing Pool & Free Parking
Just 4.7 km from Montepulciano (7 minutes by car), this house is located in a quiet position surrounded by greenery, with a splendid view of the Tuscan hills. The property is equipped with all the necessary amenities to ensure a pleasant stay, perfect for relaxing weekends or vacations. You can relax on the private patio, in the outdoor gardens, or spend unforgettable moments by the pool, enjoying the peace and beauty of the surrounding landscape.
LocationValueHiking

Appaloosa - Apartment for couples and families
Appaloosa apartment accommodates 4–5 guests and offers air conditioning, Wi-Fi and direct access to the panoramic swimming pool. Ideal for couples or families looking for a relaxing stay in the Tuscan countryside. On the ground floor there is a kitchen, living area, a twin bedroom and a bathroom with shower. Upstairs, reached by a spiral staircase, is the double bedroom with an additional single chair bed.
FamilyValueBiking

Castel Brunello - 2 doublebed rooms + terrace
Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.
FamilyValueIndoor spaces

Appartamento bilocale classic
Soggiornate in uno dei nostri tre appartamenti bilocali classici, composti da una camera matrimoniale, bagno privato, soggiorno con divano letto e con attrezzature (forno microonde, bollitore, lavello e mini frigo). Avrete la colazione e la possibilità di fare una visita in vigna con degustazione classica in cantina.
LocationValueHospitality
Popular amenities for Montalcino rentals with a pool
House rentals with a pool

Infinity pool in Chianti 1
ValueLocationSleep quality

Private Chianti Cottage, Garden & Vineyard Views
FamilyLocationBackyard

Vineyards Paradise
FamilyLocationBathroom

Borgo Ripostena – n. 5 Rimessa
ValueLocationAmenities

Traditional stone house in Tuscany
FamilyValueDecor

Agriturismo Casa Giulia di Sopra
LocationFamilyAmenities

Country House in the Crete Senesi
LocationValueKitchen

House Rigomagno Siena
FamilyLocationGrill
Condo rentals with a pool

Appartamento Loggiato 3 in toscana vicino Siena
FamilyLocationBathroom

Agriturismo Poggio Bonelli, 2 people apartment
FamilyLocationNearby

Cottage romantico in Toscana piscina e giardino
LocationOutdoor spacesDecor

Casa Granaio | Ground floor 1-bedroom apartment (2
LocationValueCheckout

House between Firenze, Arezzo, chianti e Siena
FamilyValuePets

Manuela appartamento con piscina in agriturismo
FamilyLocationKitchen

Charming Residence Castello di Orgiale near Siena
LocationFamilyAir conditioning

La Casetta
FamilyLocationLong stay
Home rentals with a private pool

Wp Relais Borgo Vignalunga
FamilyLocationDecor

Stone House with Exclusive Pool Codilungo in Chianti
FamilyValueWalkability

Villa Pergo is an ancient charming country villa
LocationFamilyCleanliness

Esplora la natura al centro di Vigneti Chianti
FamilyLocationAmenities

Villa il Palagio nelle campagne toscane
FamilyValueAccess

Podere Molinaccio-Luxury Tuscan-style Eco Villa
FamilyLocationPool

Suite Casa Luigi con piscina esclusiva
LocationFamilyAccuracy

Bliss out in Historic Farmhouse on Organic Wine Estate with Tennis and Pool
LocationFamilyIndoor spaces
Destinations to explore
- Apartment rentals Montalcino
- Pet-friendly rentals Montalcino
- Villa rentals Montalcino
- Luxury rentals Montalcino
- Rentals with a hot tub Montalcino
- Hotel rooms Montalcino
- Bed and breakfasts Montalcino
- Cottage rentals Montalcino
- House rentals Montalcino
- Farmstay rentals Montalcino
- Rentals with a sauna Montalcino
- Condo rentals Montalcino
- Vacation home rentals Montalcino
- Family-friendly rentals Montalcino
- Rentals with breakfast Montalcino
- Rentals with pools Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Lake Trasimeno
- Lake Bolsena
- Parco Regionale Della Maremma
- Cala Violina
- Feniglia
- Gulf of Baratti
- Del Chianti
- Centro Storico Orvieto
- Cascate del Mulino
- Mount Amiata
- La Scarzuola
- Avignonesi Winery Fattoria Le Capezzine
- CavallinoMatto
- Antinori nel Chianti Classico
- Vulci
- Siena Cathedral
- Val di Chiana
- Palazzo Pubblico
- Terme San Filippo
- Valdichiana Outlet Village
- Ugolino Golf Club
- Rimigliano Natural Park
- Casa Barthel
- Riserva Naturale Diaccia Botrona
- Things to do Montalcino
- Food and drink Montalcino
- Things to do Siena
- Sightseeing Siena
- Art workshops Siena
- Tastings Siena
- Art and culture Siena
- Entertainment Siena
- Museums Siena
- Dining Siena
- Food tours Siena
- Cultural tours Siena
- Outdoors Siena
- Landmarks Siena
- Nature and outdoors Siena
- Wildlife Siena
- Food and drink Siena
- Cooking Siena
- Tours Siena
- Sports activities Siena
- Things to do Tuscany
- Water sports Tuscany
- Flying Tuscany
- Cooking Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Sports activities Tuscany
- Tours Tuscany
- Wildlife Tuscany
- Landmarks Tuscany
- Entertainment Tuscany
- Workouts Tuscany
- Tastings Tuscany
- Galleries Tuscany
- Food and drink Tuscany
- Outdoors Tuscany
- Food tours Tuscany
- Dining Tuscany
- Sightseeing Tuscany
- Museums Tuscany
- Performances Tuscany
- Shopping and fashion Tuscany
- Art workshops Tuscany
- Cultural tours Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Food and drink Italy
- Food tours Italy
- Cooking Italy
- Flying Italy
- Cultural tours Italy
- Wellness Italy
- Art and culture Italy
- Nature and outdoors Italy
- Tastings Italy
- Wildlife Italy
- Landmarks Italy
- Sports activities Italy
- Museums Italy
- Performances Italy
- Art workshops Italy
- Dining Italy
- Sightseeing Italy
- Galleries Italy
- Tours Italy
- Outdoors Italy
- Architecture Italy
- Water sports Italy
- Entertainment Italy
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes







