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Holiday rentals with a pool in Tuscan Archipelago

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Tuscan Archipelago

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

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Top guest favourite
An outdoor patio area features rustic stone walls adorned with potted flowers. A wooden dining set is positioned on a brick surface, with a traditional tile-roof structure in the background. Decorative elements include hanging plant pots and a wooden beam, contributing to the inviting setting.
Home in Chiusdino
5 out of 5 average rating, 46 reviews

Il Camino: cosy & artfully inspired country house

In the heart of Tuscany you find the estate Tirisondola. Located on the private top of a panoramic hill near the medieval town Chiusdino, it offers uninterrupted views over Tuscan forests, hills & olive groves. Relaxing calm environment, with the spirit of art & history, and ideally situated near the great cultural Tuscan centers and the sea. Il Camino is one of 3 individual and lovely Tuscan country houses, fully equipped with kitchen/living room, bed room, bath room, galleries and terrace.

Top guest favourite
Flat in Caminino
4.91 out of 5 average rating, 183 reviews

Pieve di Caminino Historic Farm

Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

Top guest favourite
Apartment in Valpiana
5 out of 5 average rating, 45 reviews

Piscina a sfioro vista bosco, mare a pochi minuti

Vivi la Toscana autentica tra mare e campagna! A 10 km da Follonica e Massa Marittima, il nostro agriturismo Casetta Valmora offre appartamenti con patio privato, Wi-Fi, aria condizionata e colazione su richiesta, immersi in uliveti e boschi, ideali per coppie e famiglie. Da Maggio 2026 sarà disponibile la nuova piscina a sfioro panoramica con vista sul bosco, per momenti di puro relax. Nei dintorni scopri borghi medievali, Cala Violina, percorsi bike, golf (due campi a 15 km) e prodotti locali.

Guest favourite
A charming stone cottage is surrounded by lush greenery and tall trees. Two white lounge chairs are positioned on the manicured lawn, accompanied by a small round table. A sun umbrella offers shade, while large windows reflect natural light, showcasing the inviting interior.
Home in Montescudaio
4.96 out of 5 average rating, 122 reviews

Open space immerso nella natura

Casa namaste è un piccolo casolare in pietra con interni curatissimi a 1 km dal borgo medievale di Montescudaio La casa è completamente circondata da bosco e querce secolari a 150 metri scorre il fiume Cecina nel giardino di 5000 metri quadrati c'è una sorgente naturale con una grande vasca in pietra per rinfrescarsi e una doccia calda esterna immersa nel verde..abbiamo una linea adsl Vodafone con download 33 e upload 1.4..da questa primavera è inoltre disponibile smart TV e climatizzatore

Top guest favourite
A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.
Villa in Montecatini Val di Cecina
4.99 out of 5 average rating, 129 reviews

Torre dei Belforti

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Guest favourite
An aerial view captures the serene layout of the estate, surrounded by lush greenery and rolling hills. The inviting pool is situated centrally, accompanied by sun loungers. Stone buildings harmonize with the natural landscape, reflecting the tranquil beauty of the Montagnola Senese.
Holiday home in Sovicille
4.97 out of 5 average rating, 150 reviews

Podere La Castellina - N°1 COTTAGE

Cottage indipendente in pietre e mattoni all'interno del "Podere la Castellina" (ex convento 13° secolo), nel magnifico parco naturale della Montagnola Senese. Il cottage può ospitare comodamente 5 persone e comprende: - ampio soggiorno con tv e camino - cucina abitabile con forno - camera matrimoniale - camera con tre letti singoli - bagno con doccia A disposizione degli ospiti piscina panoramica, solarium e terrazza con vista mozzafiato, dotata di forno a legna e barbecue.

Top guest favourite
A sunny pool area is surrounded by lush greenery, featuring a rectangular swimming pool with a sunlit patio. Several green and white umbrellas provide shade over lounge chairs, inviting guests to relax in the outdoor space.
Apartment in Casole D'Elsa
4.97 out of 5 average rating, 105 reviews

Manuela appartamento con piscina in agriturismo

Sarete ospitati in un appartamento situato al primo piano ,con ingresso indipendente e vi si accede salendo 17 scalini .E' composto da una cucina/ soggiorno con caminetto, su cui si affacciano tutte le altre stanze . Ha due camere, una matrimoniale e una con 2 letti singoli , un bagno con doccia zanzariere alle finestre. Prima di entrare c'è piccolo balcone condiviso con l'appartamento GIRASOLI. Il riscaldamento deve essere richiesto all'arrivo costo Euro 20,00 al giorno

Guest favourite
A modern villa is showcased, featuring large glass windows and a spacious terrace. A swimming pool extends from the building, reflecting the surrounding greenery. Outdoor seating is arranged near the pool, providing an area for relaxation and enjoyment of the natural setting.
Holiday home in Morcone
5 out of 5 average rating, 5 reviews

Villa privata con piscina - Moddissi Charme

Lussuosa villa con piscina, circondata dal verde a soli pochi minuti dalla spiaggia di Morcone. Zona notte confortevole offre ben 3 camere da letto matrimoniale e una con letti singoli, ognuno dotato di bagno privato completo, tv e aria condizionata. Nella zona giorno è presente un'ampia cucina attrezzata, tavolo da pranzo con zona relax e smart tv; da qui accesso alla terrazza esterna ideale per gustare un ottimo aperitivo al tramonto. Posto auto

Guest favourite
An aerial view captures the expansive countryside, characterized by lush greenery and rolling hills. The property features stone buildings nestled among trees, with a swimming pool visible in the foreground and fields stretching into the distance, offering a serene landscape.
Farm stay in Sovicille
4.94 out of 5 average rating, 127 reviews

Agriturismo La Villa - Il Ciliegio, Pool & Garden

We are pleased to welcome you to our Cherry Tree House, the last newly renovated jewel of the Agriturismo La Villa. Located on second floor, built among the rocks of the typical Senese countryside, our new home will be ready to lull you into all kinds of comforts: free wifi, swimming pool, barbecue area, air conditioning, smart TV. private parking, wood and private garden, just 40 steps away, overlooking our lavender and olive grove.

Top guest favourite
A rustic stone building is set against a backdrop of rolling green hills and olive trees. A shaded pergola is visible in the foreground, offering a space to relax and enjoy the scenic views of the Tuscan countryside.
Farm stay in Radicondoli
5 out of 5 average rating, 21 reviews

Il melograno, Podere il Giglio

Podere il Giglio is a small farmhouse surrounded by 3 hectares of olive trees, it enjoys a lovely view . At guests' disposal there is an indipendent house 'il melograno', that can accommodate 4 people: living room with fireplace, kitchen, 2 bathrooms with shower and 2 bedrooms. Outdoor and a private gazebo. In the Podere there is a 5mt x 10 mt pool.

Top guest favourite
A solitary tree stands prominently in the foreground, framed against a vast landscape. Below, the coastline stretches toward the horizon, with the sea shimmering in the distance. The view includes a charming town nestled among the lush greenery of the surrounding hills.
Farm stay in Castagneto Carducci
4.99 out of 5 average rating, 114 reviews

sea view villa with private infinity pool

RENTALS ONLY FROM SATURDAY TO SATURDAY. The house is located within our farm, surrounded by forest is distance from the village of Castagneto Carducci only 3.5 km. Its unique location offers a wonderful view of the sea and the country, ensuring a pleasant tranquility, away from the heat and noise of the country.

Top guest favourite
A cozy bedroom is highlighted with a floral wallpaper featuring vibrant colors. A bedside table made of wood stands beside a spacious bed dressed in pink bedding. A modern lamp provides warm lighting, enhancing the inviting details of the room.
Home in Pievescola
4.95 out of 5 average rating, 192 reviews

Antico Borgo Ripostena – n. 8 Casa Vecchia

Charming cottage in the heart of Tuscany on a peaceful property surrounded by 5 hectares of private gardens and forest. The apartment has stunning views over San Gimignano and the Chianti Hills. One of the two bedrooms has air conditioning.

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