
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.

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.

The Eagle and the Olive Tree
At Aquila e l'Ulivo, an ancient renovated farmhouse from the 1200s, you will not only find all the necessary comforts for a wonderful stay, but you will also experience the thrill of feeling free and immersed in the unspoiled nature of Val D'Orcia. Here you'll have the opportunity to walk with the two falcons Ayga and Sayen and interact with the eagles, and why not sip an excellent aperitif by the pool. We are waiting for you in our world, made up of animals, relaxation, nature and even a touch of Magic.

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.

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.

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.

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.

Wp Relais Borgo Vignalunga
Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.

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.

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.

A paradise in Montepulciano...
Villa Il Cubo has a large private park and swimming pool and marvellous views on the Tuscan countryside. It is fully air-conditioned and the decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point at a moderate extra contribution. Supermarkets, restaurants, grocery stores, wineries are just a few minutes away. IN JULY AND AUGUST LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY.

Tuscany View - Villa Arianna
This beautiful villa, which can accommodate up to ten (10) people, will provide an unparalleled Tuscan experience. While positioned perfectly to allow easy access to the most beautiful towns and villages of southern/central Tuscany (such as Arezzo, Florence, Siena, Cortona, Montepulciano) and northern Umbria (such as Perugia, Orvieto, Assisi); you’ll find this villa offers complete privacy as well as a sense of peace and tranquility to all who visit.

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.
Popular amenities for Trequanda rentals with a pool
House rentals with a pool

Infinity pool in Chianti area

Italian Internal

Cottage surrounded by nature

Cercis - La Palmierina

Private villa/swimming pool in Tuscany

Il Vecchio Mulino

Explore Chianti from a Charming Stone House

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
Apartment rentals with a pool

Loggiato 3 apartment in Tuscany near Siena

Chianti La Pruneta, Michelangelo apartment.

Fattoria Lornano Winery- villa ''Trebbiano''

💜 "Gaia" at Podere Le Fontanelle

Spinosa Apartment in Podere Capraia

House between Firenze, Arezzo, chianti e Siena

Vintage Residence with Swimming Pool in Chianti

Poggiolieto Suite - on hills 10' from city center
Home rentals with a private pool

Stone House with Exclusive Pool Codilungo in Chianti

Villa Pergo is an ancient charming country villa

Casa Clotilde by Interhome

Historic home with exclusive pool

Charming villa in the Chianti hills

Podere Molinaccio - Luxury Tuscan-style Eco Villa

Villa il Palagio in the Tuscan countryside

Casa Luigi Suite with exclusive pool
When is the best time to visit Trequanda?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £229 | £232 | £220 | £240 | £227 | £224 | £272 | £274 | £255 | £243 | £236 | £260 |
| 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 |
Quick stats about holiday rentals with a pool in Trequanda

Total holiday rentals
Explore 270 holiday rentals in Trequanda

Nightly prices starting at
Trequanda holiday rentals start at £67 per night before taxes and fees

Verified guest reviews
Over 2,300 verified reviews to help you choose

Family-friendly holiday rentals
190 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 190 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
260 of Trequanda holiday rentals include wifi access

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

4.7 Average rating
Trequanda stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Rentals with a firepit Trequanda
- Rentals with a fireplace Trequanda
- Farm stay rentals Trequanda
- Rentals with a patio Trequanda
- Pet-friendly rentals Trequanda
- Smoking-friendly rentals Trequanda
- Villa rentals Trequanda
- Family-friendly rentals Trequanda
- Rentals with a hot tub Trequanda
- Apartment rentals Trequanda
- Flat rentals Trequanda
- Rentals with a washing machine and dryer Trequanda
- Rentals with breakfast Trequanda
- Bed and breakfasts Trequanda
- House rentals Trequanda
- Rentals with outdoor seating Trequanda
- Rentals with pools Siena
- Rentals with pools Tuscany
- Rentals with pools Italy
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Strozzi Palace
- Santa Maria Novella
- Basilica Di San Miniato A Monte
- Lake Trasimeno
- Ponte Vecchio
- Lake Bolsena
- Basilica of Santa Maria Novella
- Del Chianti
- Cascate del Mulino
- Eremo Di Camaldoli
- Mercato Centrale
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Piazzale Michelangelo
- Pitti Palace
- Parco delle Cascine
- Palazzo Vecchio
- Boboli's Garden
- Basilica of St Francis
- Avignonesi Winery Fattoria Le Capezzine
- Stadio Artemio Franchi




