
Holiday rentals with a pool in Trequanda
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Top-rated rentals with a pool in Trequanda
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House rentals with a pool

Interno Italiano
What a wonderful experience! The description of the home was excelled by the reality. It was very clean and tastefully decorated — Anna has an eye for design and art. the three bedrooms easily accommodated us. The large patio with its charming table and vine screened roof was a charming place to enjoy our morning cappuccino. the home is situated in a agricultural community built in 1788, situated in extensive vineyards. The buildings have been thoroughly renovated into a series of private homes. The community contained renters like us, but also young communities and older retirees. We had a chance to get to know people in the neighborhood, who were uniformly friendly. the AirBnB is about 25 minutes away from Arezzo by car. The best place to park we found was in the short term parking at the train station. From there it was just a short walk to the Old Town. Anna was a wonderful and charming host. We recommend this property highly!

StageROOM03 -Chianti Idillic Country living
We loved the villa. It was private and had an incredible setting. Ivan was very responsive and incredibly helpful in suggesting restaurants and other activities. The only issue we had was finding the unit when we arrived. It was a little confusing at first to find our way to the villa.

A Charming House in Asciano - Siena
Very nice place with a great view, very quiet and relaxing. The apartment was clean and cozy. The only inconvenience were the squeaky doors.

Vineyards Paradise
Our stay at Piero’s home was the highlight of our family’s three week Italy trip! It is one of the most beautiful homes we have stayed at and the spectacular vineyards, gardens, and pool really added something special. We plan to definitely return/stay again! Thank you Piero for sharing your special home!

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
Ilonka & Rob were wonderful hosts & the house was stellar. We thoroughly enjoyed our stay - it was incredibly quiet & peaceful - away from the hustle & bustle yet close enough to enjoy several surrounding towns & villages as day trips or for evening dinners. Their home is charming, super clean, & stocked with everything we could possibly need. They even shared fresh fruits & vegetables from their personal garden which we incorporated into our meals when we cooked at home. We enjoyed some nice walks through the mountainside which offer beautiful views & solitude. (Thanks to our hosts for recommending!) We hope to be back when it is cooler - but we did enjoy the pool during the hot afternoons. Until then, we are grateful to have found this gem & for the kindness extended to us by Ilonka & Rob. They answered all our questions, provided helpful recommendations, & were generous with their time - available when needed & happy to socialize but always respecting guest privacy.

Paluffo Torre House
Perfect location - could not select a more beautiful setting. Il Paluffo manages to feel luxurious and green as well as rustic with modern comforts all at the same time. The location is stunning - pictures do not do it justice. Il Paluffo is tastefully decorated, intimate with lots of amenities, and unique offerings. There was a cooking class offered while we were there! This is a truly unique and magical place, the perfect Tuscany experience.

Antico Borgo Ripostena – n. 8 Casa Vecchia
This place is something else! The views, the pool, the houses, the interior - it’s something else. We stayed with our 18 month old and had such a happy time - surrounded by nature in such gorgeous accommodation and a kiddy kitchen / toys which were perfect for Otis. It’s simply beautiful and Martina is so helpful - highly recommend with a family or groups of friends for a zen and unique time. Close to lots of gorgeous places and Martina has wonderful recommendations. Only watch out is the 2km dirt track road to get to the location but it’s 100% worth it and quite fun! Enjoy - we can’t wait to come back :)

Gaiole in Chianti Poggio Casabianca
Valeria und Simone haben eine super schöne und saubere Wohnung! Wir haben uns von Anfang an sehr wohlgefühlt. Die Wohnung bietet einen super Ausgangspunkt für zahlreiche Wanderungen und Ausflüge. Während unseres Aufenthaltes haben wir immer gute Tipps und Ratschläge von den beiden bekommen. Unser Hund hat sich auch sehr wohlgefühlt und da das Grundstück komplett eingezäunt ist, konnte er sich frei bewegen. Wir würden jederzeit wiederkommen. Es war eine unglaublich schöne Zeit!
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment
Lovely stay in this rural location. Comfortable, scenic, friendly hosts! Nice pool!! Clean and everything we needed! Massimo made us feel as comfortable as possible down to the details!! We loved Iris the dog too (and we think she loved us!) Recommend the meal which helped make my wife’s birthday very special.

Appartamento Loggiato 3 in toscana vicino Siena
We hebben een onvergetelijke 14 dagen doorgebracht op deze droomplek. Het huis is prachtig gelegen op een heuvel met 360 graden kilometers ver schitterend uitzicht. Het is goed bereikbaar en centraal gelegen zodat vele bekende plekken in Toscane goed bereikbaar zijn. Het appartement heeft alles wat je nodig hebt om te koken, zelfs is er een Bialetti Moka koffiezetter aanwezig voor de liefhebber maar ook een gewoon koffiezetapparaat. De Coop supermarkt en bakker zijn binnen 15 minuten rijden te vinden. Anna, Francesca en hun team houden alles op en top schoon, ze zijn goed bereikbaar en spreken goed Engels. Ook hun moeder komt dagelijks langs om te controleren af alles in orde is. Bij het zwembad is het heerlijk vertoeven met een uitzicht waar je nooit genoeg van krijgt. Alles is uitstekend geregeld, iedereen heeft zijn eigen plekken buiten. Een top plek!

La Foresteria | Casa Granaio
This place is even more beautiful than the photos show! We are travelling round Italy for our honeymoon and this has been our highlight. From the amazing grounds to the incredible food at the little restaurant it’s all been perfect. Thank you Marian for excellent communication and being so accommodating. What a fantastic place - Grazie!!

VILLA LE PERGOLE - Florence
Anna was a fantastic host, who treated us with the upmost respect and kindness. While her place is a bit difficult to find at first, once you're there, you're in one of the most beautiful scenes we've seen during our time in Italy. Also, it was close enough that we were still early able to travel into Florence each day we were there. Anna was so nice in providing us with breakfast each morning, which included apricot jam from her fruit trees and homemade bread. We would recommend this spot for anyone looking for a quiet place to stay outside of the busy city.

House between Firenze, Arezzo, chianti e Siena
Nous avons été de suite sous le charme de cette propriété. Tout ici compose l'image qu'on peut se faire de la belle campagne Toscane. Tout en haut de la colline surplombant la vallée, la vue y est splendide et romantique. La propriété a été renovée avec le confort d'aujourd'hui tout en conservant son âme d'autrefois. On s'y sent de suite bien, l'energie est bienfaisante, la nature, les animaux, tout est en harmonie! L'accueil, la cuisine d'Oscar, la superbe piscine, la terrasse ombragée, les petits-dejeuners copieux fait maison! C'est plus qu'un coup de coeur, cet endroit est une pépite! Nous reviendrons!

Relaxation and peace in the countryside Cortona G
We spend 10 days at Emanuele’s place. His wife and he were very nice to us and we felt like part of the family. Recommendation and insights about surrounding towns were top notch and we got to know authentic Tuscan cuisine and every one of them was amazing. The location itself is perfect to relax (pool) and bring the chaos of city life behind. We were also invited by our host to a typical Italian party and we felt very welcome and enjoyed great food and incredible company at the party. We are grateful for the amazing experiences and would highly recommend the place. Thank you very much Angela & Emanuele ❤️

La Casetta
Können wir absolut empfehlen ! Ist alles so wie im Text beschrieben und auf den Foto´s zu sehen. Liegt ca 2 km außerhalb vom total schnuckeligen Örtchen Casole de Elsa. Von Andrea + Barbara gab´s alle nötigen Infos zur Anreise und viele tolle Tipps vor Ort, immer mit den dazugehörigen Links. Zum Beispiel verzögerte sich unsere Anreise verkehrsbedingt auf ca. 22:15 Uhr. War kein Problem, wir standen in Kontakt und als wir ankamen, hat uns Andrea persönlich in Empfang genommen. Und wenn wir während unseres Aufenthaltes eine Frage hatten, kam immer sehr zügig eine Antwort. (Wo man in Siena am Besten parken kann, wie gelangt man am Besten nach Florenz, ...)

Villa Falco-Cignella Resort Apartments in Tuscany
Très bel endroit, au calme absolu avec très belle vue sur le lac trasimeno. Jolie piscine et restaurant agréable. Personnel très gentil et professionnel.
Home rentals with a private pool

Tuscan Villa Featured Conde Nast Best Villas Italy
This 500 year old house is ideally situated in Tuscany and the Chianti region. It is a perfect place for day trips to other towns, for wine, tasting excursions, and for visiting Florence. The idyllic setting gives you a sense of country life in Italy, and the views from the patio and house are stunning. There are spectacular wineries within 5 to 10 minutes of the house. We found the house very comfortable and enjoyed our stay very very much. Rose and Pier couldn’t have been more helpful in planning our stay and excursions. We found through them fabulous restaurants, and wineries that we would not have discovered on our own. They were also incredibly responsive when we had questions. Our only confusion about the house was that the listing showed three bathrooms, but one was in the laundry room in a separate building . Just something to know. Thank you to Rose for a lovely vacation ! It was the perfect place to explore Tuscany from!

Stone House with Exclusive Pool Codilungo in Chianti
We can't imagine a more beautiful place to stay while we visited Chianti! The location is absolutely heavenly, and Emanuela's home is stunning. Everything was so comfortable, and our family particularly loved spending time outside and enjoying the pool. It's conveniently located for several Tuscan day trips, and there are many amazing wineries nearby. And the icing on the cake were Emanuela and Giovanni, who went above and beyond in helping us throughout our trip - from recommendations and help with reservations to having a few food items and coffee stocked for our first day's breakfast. Easily the best hosts we've ever enjoyed in our years staying in Airbnbs!

Esplora la natura al centro di Vigneti Chianti
Staying at Agrigreen La Lama was hands down the best Airbnb experience I’ve ever had. From the moment we arrived, Rita welcomed us with such warmth and hospitality that we felt at home. The property is peaceful, beautifully maintained, and full of charm—surrounded by nature and the kind of quiet that soothes the soul. One of the most memorable parts of our stay was getting to cook in Rita’s own home, which she generously opened to us. It was such a unique and personal experience that made us feel truly connected to the space and the spirit of the farm. If you’re looking for a place to slow down, feel grounded, and enjoy genuine hospitality, Rita’s space is an absolute gem. I’m already looking forward to the day I can return.

Historic home with exclusive pool
Wir (7 Freundinnen) haben den Aufenthalt in der Villa sehr genossen! Das Haus, vor allem der Vorgarten und der Pool, sind wunderbar. Maria ist super! Sie hat uns sehr viele Tipps zur Umgebung zugesendet (auch die notwendigen Sachen, wie Einkaufsmöglichkeiten). Zudem wurden wir mit einem sehr feinen Kuchen überrascht und wenn man etwas brauchte, kam sehr schnell eine Antwort. Die Villa ist gut ausgestattet und die Umgebung wunderschön. Parkplätze hat es genügend. Einzig die Schlaglöcher und der Zugang zur Villa sind etwas herausfordernd - jedoch machbar!

Angeli by Interhome
We are one big family (15 people- adults and children). We booked the villa for 1 week and we had a wonderful time. The inside is beautiful, very spacious and well maintained. The kitchen is well equipped and there is a big dinning table enough for everybody to seat at. There is a big living room, TV room and a decorated library. The rooms are also spacious and each one has its own bathroom. One negative is that the villa doesn't have air condition. However, when we stayed the weather was chilly and there was no need for cooling/heating. The garden is massive. There is a big swimming pool with furniture to relax around it. Although the water was still very cold, the children did not skip the fun of swimming. There is outdoor cooking area near the pool with a big grill. We used it few times to barbiqu. There was also enough space for us to park 4 cars. The hostess and the owner were great. We received a quick response to any question or request. This villa is a great choice. ⭐️⭐️⭐️⭐️

Aurora by Interhome
Wir hatten eine schöne Woche in dieser Unterkunft. Insbesondere der Außenbereich war traumhaft! Danke und gerne wieder!

Villa di charme sulle colline del Chianti
We stayed in the villa for 3 weeks with my family (2 young kids) and it was absolutely perfect!!! Francesca was an incredible host, fantastic communication. The house itself was beautiful, clean and the pool was just magic. Close to Florence and all the wonderful towns nearby, we can’t recommend this place enough. Would stay again without hesitation.

Podere Molinaccio-Luxury Tuscan-style Eco Villa
Absolutely amazing stay at this villa. Pool was perfect, villa was stunning, AC was much appreciated in the 90 degree heat, and the host was one of the very best ever! She was as our personal concierge helping set up a private chef, olive oil and wine tasting, truffle hunting and more. We spent a week and could have stayed longer there is so much to explore in Umbria and Tuscany and we absolutely loved it!
Quick stats about holiday rentals with a pool in Trequanda
Total rentals
220 properties
Nightly prices starting at
$132 NZD before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
150 properties are a good fit for families
Pet-friendly rentals
150 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace
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- Santa Maria Novella
- Duomo di Firenze
- Lake Trasimeno
- Lake Bolsena
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Mercato Centrale
- Kite Beach Fiumara
- Marina di Grosseto beach
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Cala Di Forno
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- The Boboli Gardens
- Tenuta Le Velette
- Teatro Verdi