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Holiday rentals with a pool in Trequanda

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Trequanda

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Top Guest favourite
Aerial view of the agriturismo surrounded by lush green hills and fields. The property includes a swimming pool, framed by rows of tall cypress trees that create a natural boundary. The rural landscape extends into the distance, illustrating the serene environment.
Condo in Asciano
4.92 out of 5 average rating, 177 reviews

Loggiato 3 apartment in Tuscany near Siena

The Loggiato 3 apartment for 2 people is located in the Santa Lucia farmhouse (FARMHOUSE DIVIDED INTO 7 APARTMENTS) in the Crete Senesi near Siena and is located on the first floor with a private table in front of the windows of the loggia. Composed of a double bedroom (two single beds joined together), a bathroom and a living room with a functional kitchen. It is equipped with a wood stove. Outdoor space with table and chairs available on the ground floor. AIR CONDITIONING in the room is PAID according to consumption.

Guest favourite
A spacious outdoor pool is surrounded by neatly arranged lounge chairs and framed by lush greenery and tall cypress trees. The inviting blue water reflects the clear sky and the structure of the residence sits elegantly in the background.
Home in Asciano
4.96 out of 5 average rating, 113 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Guest favourite
The exterior of a rustic stone villa features a large, multi-level structure with a sloping roof and a shaded terrace. Comfortable seating areas with sun loungers are positioned on the grassy lawn, surrounded by low greenery and tall trees, under a clear blue sky.
Home in Sinalunga
4.93 out of 5 average rating, 14 reviews

Perfect Large Family Villa in Tuscany

*** New in Summer 2025*** Il Corniolo is our 'happy place' - a charming rural Tuscan villa with modern features and a simple family-friendly design, perfect for you & friends. Near the bustling tourist towns of Montelpulciano & Pienza, Il Corniolo is your home-from-home; a haven of countryside calm with lovely pool & hilltop views overlooking the olive groves & vineyards in L' Amorosa valley. Our home-away-from-home is a spacious, well-appointed luxury villa for you to come & make memories in.

Top Guest favourite
The exterior of the villa is framed by lush greenery and tall trees, with a stone pathway leading to the entrance. The structure features traditional architecture, characterized by stone walls and wooden accents, set against a backdrop of rolling hills and a blue sky with scattered clouds.
Villa in Montepulciano
4.97 out of 5 average rating, 116 reviews

Wine Experience Villa in Montepulciano

🏡 Villa Talosa è immersa nei vigneti della Fattoria della Talosa, storica azienda vitivinicola di Montepulciano produttrice di Vino Nobile. Un luogo autentico, ideale per rilassarsi con la magia della campagna toscana e una vista incantevole da ogni finestra. A soli 1,5 km dal centro storico, raggiungibile anche a piedi, potrete visitare la nostra Cantina Storica del 1500 sotto Piazza Grande: un’esperienza unica tra storia, passione per il vino. Riscaldamento e aria condizionata sono inclusi.

Top Guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano
4.97 out of 5 average rating, 204 reviews

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.

Top Guest favourite
A breathtaking view of the sunrise over misty hills is captured, with soft light illuminating the landscape. Underneath, a spacious garden is visible, featuring a few lounge chairs and canopies, while vibrant greenery enhances the serene outdoor space.
Townhouse in Montalcino
5 out of 5 average rating, 30 reviews

Podere Ampella House with a Beautiful View

Newly restored peaceful charming townhouse in the the famous Val d'Orcia in the heart of Tuscany , The property sits on a gentle hill in a small hamlet offering stunning panoramic views and sunsets. Whether you visit with family, or friends, this house is perfect for offering ample private garden and a common pool, never crowed. The hamlet is just a short drive from the nearby beautiful towns and villages allowing easy access to explore the Tuscan sceneries, cultural and culinary delights.

Top Guest favourite
The exterior of a charming farmhouse is visible, featuring stone walls adorned with climbing greenery. Large windows reflect natural light and overlook the landscaped garden. A gravel path leads to the entrance, surrounded by greenery and trees under a clear blue sky.
Home in Rigomagno
4.96 out of 5 average rating, 114 reviews

House Rigomagno Siena

Apartment with beamed ceilings and terracotta floors, this apartment is set in a 19th-century farmhouse located in the hills of Siena in Rigomagno Toscana. From the solarium next to the swimming pool in the middle of the olive trees, you can admire the panorama of the Sienese hills and the medieval village of Rigomagno ... all this characterizes the ideal holiday for couples or families who want to relax. Solarium, garden, terrace, swimming pool are exclusively for guests of the apartment.

Top Guest favourite
A large, rectangular swimming pool is set within a green lawn, surrounded by tall trees and blooming shrubs. Sun loungers are placed around the pool, providing a space for relaxation. The lush Tuscan countryside stretches into the distance under a clear blue sky.
Villa in Montepulciano
4.95 out of 5 average rating, 154 reviews

A paradise in Montepulciano...

Villa Il Cubo is a full centralized air conditioned private house with large private swimming pool placed in the best garden spot for incredible views on the countryside around. Decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point. Supermarkets, restaurants, grocery stores, wineries are just a few minutes away. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY!!!!!!

Guest favourite
A rustic stone building is surrounded by lush greenery, featuring a staircase leading to a welcoming entrance. Outdoor seating areas are positioned under shaded trees, inviting relaxation. Flower pots add a touch of color to the serene courtyard setting.
Apartment in San Quirico d'Orcia
4.8 out of 5 average rating, 220 reviews

Studio (2+1) in Val d'Orcia - Tuscany

A few steps from the historic center of medieval San Quirico d'Orcia and just 100 meters from the supermarket, a stay made of silence and the quiet passage of time, of days with a relaxing and regenerating atmosphere characteristic of the lifestyle in Val d'Orcia. The Taste of Tranquility is guaranteed by a 5000 sqm park that offers lawns and shady trees suitable for reading or simple relaxation. Ideal for a stay with an "antique" flavor", combined with all modern comforts.

Top Guest favourite
The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.
Castle in Ferrano
4.99 out of 5 average rating, 210 reviews

The Castle of Ferrano - Castle in Tuscany

Try the experience to stay in a real Castle! Il Castello di Ferrano offers to his hosts the chance of doing an unforgettable experiece:you will be the only guests in the castle and everythig will be for you (private pool from June to September, gardens ecc.)Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Top Guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 446 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.

Guest favourite
A spacious living area features terracotta flooring and a rustic wooden ceiling with exposed beams. A cozy fireplace serves as a focal point, surrounded by stone. A bright orange sofa complements the warm tones, while a small wooden table sits on a patterned rug, adorned with a flower arrangement.
Apartment in Montisi
4.92 out of 5 average rating, 24 reviews

Apartment in historic house with pool and view

"I Girasoli" is part of the historic house "Borgo La Grancia", located in a spectacular area of the Tuscan countryside. It is composed of a very large and bright living room with a sofa bed, kitchen, a double bedroom and a bathroom with shower. The apartment is elegantly furnished with Tuscan terracotta floors, beams and period furniture. It has a gorgeous view of the gardens, the pool area and the valley.

Popular amenities for Trequanda rentals with a pool

When is the best time to visit Trequanda?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$540 NZD$547 NZD$517 NZD$566 NZD$535 NZD$528 NZD$641 NZD$644 NZD$599 NZD$481 NZD$477 NZD$526 NZD
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Quick stats about holiday rentals with a pool in Trequanda

  • Total holiday rentals

    Explore 230 holiday rentals in Trequanda

  • Nightly prices starting at

    Trequanda holiday rentals start at $104 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,290 verified reviews to help you choose

  • Family-friendly holiday rentals

    150 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 150 rentals that welcome pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    230 of Trequanda holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Trequanda rentals

  • 4.8 Average rating

    Trequanda stays are highly rated by guests—averaging 4.8 out of 5!

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