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Holiday rentals with a pool in Tolentino

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Tolentino

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

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Guest favourite
Villa
5 out of 5 average rating, 8 reviews

Villa Ermelinda · Ville Carborello Weddings

Villa Ermelinda is a private 16th-century villa set among the rolling hills of Le Marche, ideal for intimate weddings, destination weddings and exclusive stays. It offers exclusive use, a panoramic pool, gardens, a big terrace and beautiful spaces for symbolic ceremonies, poolside aperitifs and dinners under the stars. Hosting up to 18 guests, it also works perfectly with nearby Villa Nasca & Villa Adele, just a few minutes away, for larger wedding groups and unforgettable wedding weekends.

Top guest favourite
The Villa is set among olive trees, featuring a tranquil saltwater pool surrounded by lounge chairs. A stone terrace offers shaded seating, and the rustic building showcases large windows and natural materials. The expansive grounds create an inviting space for relaxation and leisure.
Home in Spello
5 out of 5 average rating, 15 reviews

Villa degli Olivi

Nestled among the ancient olive trees, Villa degli Olivi offers a haven of serenity and sophistication and is a short stroll into the cobblestoned paths of Spello along a flat, tree lined lane. This recently renovated Villa offers modern luxury while maintaining its Italian roots. Offering 4 bedrooms, 3 full baths and the possibility for 2 additional guests with a sleeper sofa. A cozy studio apartment with full kitchen, bathroom, laundry and sleeper sofa is also available for an additional cost.

Guest favourite
A spacious living area is highlighted by exposed wooden beams and a stone accent wall. A white sofa is positioned around a brick fireplace, with a cozy nook containing cushions. A television sits on a wooden stand, enhancing the room's relaxed atmosphere.
Farm stay
4.96 out of 5 average rating, 89 reviews

La dolce Visciola

La dolce Visciola si trova tra le verdi colline marchigiane e si affaccia su uno splendido panorama che va dalle campagne fino al mare. Luogo ideale per chi ama rilassarsi immerso nella natura. Per chi vuole ricaricare le energie rimanendo in Agriturismo troverete un ampio giardino con piscina, bocciodromo e barbecue. Inoltre, per chi lo desidera, potrete degustare alcune delizie locali della nostra azienda agricola, per vivere appieno il vostro soggiorno nelle Marche attraverso tutti i sensi.

Top guest favourite
The Sferisterio theater is highlighted by its grand brick colonnade, illuminated against a dusk sky. The curved structure features multiple seating levels with historic elements and a vibrant atmosphere, showcasing an audience gathered in anticipation of the evening performance.
Flat
4.94 out of 5 average rating, 34 reviews

Opera & Nature Lovers Loft Suite 30 mins 2 Opera

Located in the heart of Le Marche—ranked 2nd in Lonely Planet's 2020 list of "The Top 20 Regions in the World to Visit"—this sunny apartment offers the perfect base to relax or explore. Just 30 minutes from the world-renowned open-air opera venue, the Sferisterio in Macerata, and within an hour to mountains, lakes, and the sea. Discover ancient hilltop towns, nature reserves, outdoor markets, health spas, and scenic hiking, biking, and riding trails. 5 mins’ drive to the village of Mogliano.

Top guest favourite
A serene pool area is featured, with crystal-clear water reflecting the surrounding greenery. The rustic stone buildings in the background are framed by lush trees, while comfortable seating arrangements invite relaxation under the sun.
Casa particular
4.91 out of 5 average rating, 22 reviews

M'illumino d'immenso

Goditi una vacanza diversa e. rigenera corpo e mente. Portati dei libri da leggere sotto i gelsi . Percorri cammini in mezzo alla natura respirando aria sana e percorrendo kilometri di campagna con coltivazioni bio mentre osservi il paesaggio dove la natura ha saputo creare dei quadri. Rilassati con tutta la famiglia vivendo giornate con altro spirito ed altra attenzione a chi ti è vicino, in un alloggio dove la serenità l'atmosfera e la natura rendono tutto meravigliosamente unico.

Guest favourite
An aerial view of the villa is presented, showcasing the surrounding green landscape with trees and a well-maintained garden. The rectangular swimming pool is visible, framed by wooden decking, creating an inviting outdoor space adjacent to the pink-hued villa.
Villa
5 out of 5 average rating, 26 reviews

Elegante villa con piscina immersa nel verde

Villa Regno offre una vacanza di relax in un'atmosfera elegante. Immersa in un parco panoramico di 5000m con ulivi, noci, vigna, piscina e area BBQ. Gli interni spaziosi, accoglienti e luminosi sono ricercati in ogni dettaglio: ampio salone, 1 cucina attrezzata, 4 camere matrimoniali, 1 doppia e 2 bagni, uno con vasca idromassaggio. La sua posizione vicino al mare e ai Monti Sibillini offre svago, avventura e cultura. Vi accoglieremo nella vostra lingua: inglese, arabo, francese e spagnolo!

Guest favourite
An aerial view of the luxurious pool area showcases a sparkling turquoise pool surrounded by comfortable loungers and umbrellas. Lush greenery complements the elegant setting, providing a serene and inviting outdoor space for relaxation.
Holiday home
5 out of 5 average rating, 6 reviews

Junior Suite Sole | Pool + Hill View

Independent Junior Suite in the hills of Le Marche, designed for guests seeking privacy, nature, and a slower pace, without giving up comfort and attention to detail A studio apartment with private entrance, kitchen, bathroom, and private garden. French-size canopy bed for an intimate and cosy stay Shared panoramic swimming pool (max 8 guests) and organic breakfast prepared fresh every morning included. Ideal for couples, friends or solo travellers looking for a peaceful countryside stay

Superhost
A serene swimming pool is situated on a deck, featuring clear turquoise water under a bright sky. An umbrella provides shade beside chaise lounges. Scenic hills and mountains stretch into the distance, creating a picturesque backdrop of nature.
Home
5 out of 5 average rating, 4 reviews

GrazieSole Agriturismo casa intera in esclusiva

The GrazieSole farmhouse is a newly renovated 1900s farmhouse, in a characteristic style with original stone walls, exposed bricks and ceilings with wooden beams, it has a 12-metre swimming pool with breathtaking views and a wide panorama that extends from the Sibillini Mountains to the adjacent hillside villages. It is located in open countryside one kilometer from the center of the village of Penna S. Giovanni, in a sunny and quiet position, surrounded by a garden and large green spaces.

Top guest favourite
The living area features a blend of comfortable seating with a brown leather sofa and wooden dining furniture. A round table with green chairs is positioned near large glass doors, allowing natural light to enter the space. Bookshelves line one wall, adding a functional touch.
Home
4.97 out of 5 average rating, 74 reviews

Il Casale di Laura

Il casale in mattoni antichi sorge in prossimità del centro storico. Si sviluppa su due piani. Il primo piano composto da ampio salone, cucina e un bagno e il secondo piano composto da 3 stanze da letto arredate e confortevoli , 2 bagni, il tutto ad uso esclusivo degli ospiti. Vi è il giardino e un uliveto di 70 ulivi. Il casale si trova inoltre a 10 km dal mare. È presente una bella piscina per rilassarsi 😍 Questo e’ l’annuncio ufficiale in cui chiedere info. Struttura Dog-friendly 😉😉

Top guest favourite
Aerial view of the villa surrounded by lush vineyards and olive groves. The spacious garden features manicured landscaping and a private pool. The villa, with a terracotta roof and warm exterior, is situated amidst tranquil countryside, offering scenic views of the surrounding hills.
Villa
5 out of 5 average rating, 30 reviews

Scappo in Umbria, Mevania Villa

The villa is surrounded by the Sagrantino hills, a few steps from the medieval village of Bevagna, located in the center of Umbria, few miles away to Assisi. The strategic location allows you to easily reach the most enchanting locations such as Perugia, Spoleto, Montefalco, Foligno, Gubbio, Spello, Trevi, Campello Sul Clitunno, Rasiglia, Norcia, Todi, Rome, Florence and many others. You will find yourself in a unique place, immersed in an enchanting paradise of peace and tranquility.

Guest favourite
An aerial view showcases the agriturismo's rustic stone buildings surrounded by greenery. A blue swimming pool is located in the garden, complemented by sun loungers. The landscape features open fields and scattered trees, creating a serene outdoor space.
Flat
5 out of 5 average rating, 7 reviews

Agriturismo Elisei appartamento piscina sauna spa

Sei alla ricerca di un luogo tranquillo, rilassante, immerso nella natura e lontano dal caos? Vuoi scoprire il fascino del Parco Nazionale dei Monti Sibillini e suoi borghi? Scegli l’Agriturismo Elisei, piccolo e per poche persone, permette ad ognuno degli ospiti di avere tanto spazio all’aperto. L’Agriturismo dispone di un ampio giardino con piscina, oltre ad un area benessere con sauna e spa. CIN: IT043021B5CETGSYCI

Guest favourite
A private villa is set amidst lush greenery, showcasing a panoramic saltwater pool nestled in the garden. Surrounding olive trees and vibrant shrubs enhance the serene landscape, while the charming stone farmhouse stands invitingly behind, offering a harmonious blend of nature and architecture.
Villa
5 out of 5 average rating, 5 reviews

Casa Antonio - Private Pool, Air conditioning

Casa Antonio is a private villa with pool in Le Marche region, in the small borgo of Mogliano. Surrounded by green hilly scenery, with a fine view over the Sibillini mountains, it is the perfect combination of peace and simplicity, the ideal place to savour the traditional flavours of Le Marche countryside, far from the frenetic rhythms of the city.

Popular amenities for Tolentino rentals with a pool

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Quick stats about holiday rentals with a pool in Tolentino

  • Total holiday rentals

    Explore 50 holiday rentals in Tolentino

  • Nightly prices starting at

    Tolentino holiday rentals start at £67 per night before taxes and fees

  • Verified guest reviews

    Over 350 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    50 of Tolentino holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Tolentino rentals

  • 4.9 Average rating

    Tolentino stays are highly rated by guests – averaging 4.9 out of 5!

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