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

Total vacation rentals
Explore 20 vacation rentals in Montaione

Nightly prices starting at
Montaione vacation rentals start at ﺩ.ﺇ 331 per night before taxes and fees

Verified guest reviews
Over 140 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Montaione vacation rentals include wi-fi access

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

4.8 Average rating
Montaione stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated rentals with a pool in Montaione
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Infinity pool in Chianti 1
Our house is a part of a stone farmhouse completely independent from the rest of the adjacent property. Arranged on three floors, on the ground floor there is a large entrance hall, a large living room with fireplace, a bedroom with 1 double bed and a bathroom with window. On the first floor there are two bedrooms (2 +2 beds) with a bathroom with window. In the basement, at garden level, there is the kitchen and the dining room. From the kitchen you access the outside where you will find an area for outdoor dining with a large dining table under a pergola. You then go down towards the garden with barbecue area.
ValueLocationBackyard
5.0 out of 5 average rating, 143 reviews
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.
LocationFamilyIndoor spaces
5.0 out of 5 average rating, 352 reviews
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.
FamilyValueDecor
4.98 out of 5 average rating, 218 reviews
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
FamilyLocationDecor
4.98 out of 5 average rating, 127 reviews
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.
ValueFamilyComfort
4.98 out of 5 average rating, 107 reviews
Tenuta Collerucci | Casa Poeta
Tenuta Collerucci is a charming farmhouse located in the heart of the Tuscan countryside, just 4 km from the Etruscan town of Montaione in the Valdelsa area. Set on a beautiful hill, the estate is surrounded by vineyards and olive groves, offering stunning panoramic views of the Tuscan landscape. The farmhouse features four rustic-style apartments and a delightful swimming pool, making it an ideal retreat for relaxation and enjoying the region’s natural beauty.
FamilyLocationAmenities
4.79 out of 5 average rating, 102 reviews
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.
ValueLocationBackyard
4.99 out of 5 average rating, 481 reviews
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.
LocationFamilyAccuracy
4.93 out of 5 average rating, 124 reviews
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.
LocationFamilyCondition
4.96 out of 5 average rating, 147 reviews
Countryside Cottage With View - Le Papere apt
The cottage is part of a charming traditional Tuscan farmhouse, built in stone and situated in one of the most beautiful areas of Tuscany. A lovely garden surrounds the house and has magnificent views of the medieval town with its famous towers. Warm and cozy atmosphere that makes you feel instantly at home. For those who wish to live the experience of the Tuscan countryside as it is lived by the locals.
LocationValueNearby
4.88 out of 5 average rating, 139 reviews
Countryside Dream farm in Tuscany
Have you ever dreamed of experiencing the rolling hills of Tuacany ? This is a berautiful organic farm 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.
FamilyLocationOutdoor spaces
4.98 out of 5 average rating, 201 reviews
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.
ValueFamilyBathroom
4.95 out of 5 average rating, 222 reviewsPopular amenities for Montaione rentals with a pool
House rentals with a pool

Frontemare house with exclusive sea access
LocationValueAccess
4.96 out of 5 average rating, 112 reviews
SuiteLouise.pool, Hot Tub,homeGym & private Garden
LocationFamilyCondition
4.91 out of 5 average rating, 128 reviews
Relaxation and charm in the Chianti hills
ValueFamilyCheck-in
4.99 out of 5 average rating, 115 reviews
Private villa/swimming pool in Tuscany
LocationFamilyWalkability
4.93 out of 5 average rating, 165 reviews
Open space surrounded by nature
FamilyValueCondition
4.96 out of 5 average rating, 137 reviews
Casa Giulia di Sopra Farmhouse
FamilyLocationCheck-in
4.95 out of 5 average rating, 107 reviews
I Limoni Apartment in Tuscany
LocationValueDecor
4.85 out of 5 average rating, 151 reviews
Borgo Ripostena – n. 9 Frantoio
ValueLocationQuiet
4.94 out of 5 average rating, 118 reviewsCondo rentals with a pool

La Casetta
FamilyLocationBathroom
4.93 out of 5 average rating, 197 reviews
Casa Luna-Splendida overlooking the pool and Tuscan nature
ValueLocationCheck-in
4.97 out of 5 average rating, 151 reviews
Adalberto Apartment inside the Manor of Fulignano
LocationFamilyEV charging
4.95 out of 5 average rating, 152 reviews
Apt. Panzanello-Panzano in Chianti
FamilyValueCheck-in
4.96 out of 5 average rating, 282 reviews
Scenic Stilish Country
LocationFamilyHiking
4.88 out of 5 average rating, 137 reviews
Bel Canto Lari, exclusive, rural, Tuscan retreat
FamilyLocationQuiet
4.97 out of 5 average rating, 105 reviews
Vintage Residence with Pool in Chianti
FamilyValueCondition
4.96 out of 5 average rating, 149 reviews
Poggiolieto Studio - on hills 10' from city center
ValueFamilyHospitality
4.85 out of 5 average rating, 214 reviewsHome rentals with a private pool

TREEhouse/casaBARTHEL
LocationFamilySleep quality
4.88 out of 5 average rating, 821 reviews
Farmhouse , pool, 13 px. Lucca 10km
LocationFamilyCondition
4.99 out of 5 average rating, 148 reviews
Casa Luigi Suite with exclusive pool
FamilyLocationWifi
4.95 out of 5 average rating, 122 reviews
Luxe Estate nr Florence. Vineyard, Pool, Privacy
FamilyLocationGetting around
4.97 out of 5 average rating, 73 reviews
Villa Fonteintanata Ground floor
FamilyLocationBathroom
4.8 out of 5 average rating, 76 reviewsHistoric villa x8 with exclusive pool
LocationFamilyAir conditioning
4.87 out of 5 average rating, 46 reviewsDestinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Cala Violina
- Mercato Centrale
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mugello Circuit
- Spiagge Bianche
- Pisa Centrale Railway Station
- Fortezza da Basso
- Uffizi Gallery
- Gulf of Baratti
- Piazza della Repubblica
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Parco delle Cascine
- Piazza della Signoria
- Val di Luce
- Pitti Palace





