Some info has been automatically translated. Show original language
Airbnb your place

Holiday rentals with a pool in Tolentino

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Tolentino

  • Total holiday rentals

    Explore 40 holiday rentals in Tolentino

  • Nightly prices starting at

    Tolentino holiday rentals start at $170 NZD per night before taxes and fees

  • Verified guest reviews

    Over 290 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Tolentino holiday rentals include Wi-Fi 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!

Top-rated rentals with a pool in Tolentino

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

1 of 1 pages1 / 1
Top 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 in Cingoli

The sweet Visciola

La Dolce Visciola is located among the green hills of the Marche region and overlooks a splendid panorama that stretches from the countryside to the sea. Ideal place for those who love to relax surrounded by nature. For those who want to recharge their batteries while staying at the farmhouse, you will find a large garden with swimming pool, bocce ball court and barbecue. In addition, for those who wish, you can taste some local delicacies from our farm, to fully experience your stay in the Marche through all the senses.

4.96 out of 5 average rating, 96 reviews
Superhost
Villa in Castelraimondo

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.

4.82 out of 5 average rating, 11 reviews
Superhost
The property showcases a panoramic view of the surrounding hills, featuring a luxurious swimming pool at the center, surrounded by sun loungers. Two separate suites are visible, framed by lush greenery and well-maintained gardens, providing a serene outdoor space for relaxation.
Cottage in Casagatti

Casa Janna Cottage | Pool + 2 Suites

A two-storey countryside house in the Marche hills, hosted by locals and shaped by food, nature, and a slow rhythm. A boutique stay with seasonal organic breakfast included. The house sleeps up to 4 guests and is fully independent, with living area, kitchen and 2 bedrooms. Private garden with dining and a premium two-person hammock. Shared pool for a small number of guests only (max 8 in tot) surrounded by rolling hills. Ideal for couples, friends or families seeking calm and a refined stay.

5.0 out of 5 average rating, 4 reviews
Top Guest favourite
A wooden pool is set within a landscaped area, featuring clear water and steps for entry. Relaxing lounge chairs are positioned nearby on the sun-drenched outdoor space, with greenery framing the scene. An umbrella offers shade, enhancing the tranquil outdoor environment.
Home in Cingoli

Farmhouse with garden and pool for exclusive use of wifi

Casale Nonno Dario is a typical Marche countryside home nestled in the hills of the Balcone delle Marche and a strategic position to enjoy the surrounding beauty from the sea to the mountains It is located in the hamlet of Castelletta and includes a living area with a lounge, kitchen and fireplace. Bathroom with shower. Sleeping area with 3 double bedrooms and the possibility of adding a crib and a cot. Large outdoor garden with swimming pool, umbrella, barbecue Free parking on the property.

5.0 out of 5 average rating, 54 reviews
Guest favourite
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 in Penna San Giovanni

GrazieSole Agriturismo exclusive whole house

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.

5.0 out of 5 average rating, 8 reviews
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 in Matelica

I light up with immense

Enjoy a different vacation and regenerate your body and mind. Bring books to read under the mulberry trees. Walk through nature, breathing healthy air and traveling kilometers of countryside with organic crops while observing the landscape where nature has been able to create paintings. Relax with the whole family, living days with a different spirit and more attention to those close to you, in accommodation where serenity, atmosphere and nature make everything wonderfully unique.

4.9 out of 5 average rating, 30 reviews
Guest favourite
Vibrant sunflowers bloom in the foreground, creating a lively scene against the rolling hills of Le Marche. A rustic stone building is positioned amidst lush greenery, while the expansive landscape showcases fields and distant towns under a clear blue sky.
Apartment in Mogliano

Experience Authentic Italian Village Life

Located in the heart of Le Marche, ranked 2nd in Lonely Planet’s 2020 list of “Top 20 Regions in the World to Visit.” This spacious apartment and garden offer the perfect base to relax or explore. Within 40 mins’ drive of mountains, lakes, and the sea, with many ancient hilltop towns nearby. Just 5 mins from Mogliano, where you’ll find everything you need for your stay. Nature reserves, outdoor markets, health spas, hiking, biking, and riding trails are all within easy reach.

4.98 out of 5 average rating, 45 reviews
Guest favourite
An indoor wellness area features a heated hydromassage minipool for six, surrounded by wide glass panels that provide views of the lush outdoor landscape and an inviting blue swimming pool beyond. Natural wood beams enhance the room's warm aesthetic.
Apartment in Gualdo

Elisei Farmhouse – Attic, Pool, Sauna, Spa

Are you looking for a quiet, relaxing place, surrounded by nature and away from the hustle and bustle? Do you want to discover the charm of the Monti Sibillini National Park and its villages? Choose the Elisei Farmhouse, small and for a few people, allowing each of the guests to have plenty of outdoor space. The farmhouse has a large garden with swimming pool, as well as a wellness area with sauna and spa. CIN (National Identification Code): IT043021B5CETGSYCI

5.0 out of 5 average rating, 7 reviews
Top Guest favourite
An infinity pool is set against a backdrop of rolling fields and olive trees. Two shaded umbrellas provide coverage over several lounge chairs positioned on a stone patio. Colorful flowers line the edge of the pool area, contributing to the serene outdoor environment.
Condo in Potenza Picena

Casa Leccino (house with a view)

Welcome to the beautiful Marche countryside just minutes by car from the beaches of the Adriatic Riviera. The large 120 sqm apartment, equipped with air conditioning, is an ideal base for a quiet stay by the sea or to discover the extraordinary historical/landscape and food and wine richness of the Marche region. Infinity swimming pool overlooking the olive grove, outdoor furniture, barbecue and patio shared with other guests of the property.

4.99 out of 5 average rating, 71 reviews
Top Guest favourite
A serene outdoor area is shown, featuring a rectangular pool surrounded by lush green grass. Sun loungers and umbrellas are positioned alongside the pool, under a clear blue sky. Rolling hills and trees frame the background, creating a peaceful natural setting.
Apartment in Sant'Elpidio a Mare

La Ponderosa Couple

Exclusive apartment in a typical Marche farmhouse, completely renovated with swimming pool. A perfect location surrounded by nature where you can enjoy relaxation just 12 km from the nightlife of Civitanova Marche and 8 km from the sea of Porto Sant'Elpidio. The apartment consists of a living room with kitchen, 2 double bedrooms and 1 twin bedroom that can be converted into a double bedroom.

4.97 out of 5 average rating, 34 reviews
Top Guest favourite
Villa in Sant'Angelo in Pontano

Villa in the Sibillini Mountains, Pool & Privacy

Private pool villa in Sant’Angelo in Pontano, among the rolling hills of Marche at the foot of the Sibillini Mountains. Sleeps up to 8 with 4 double bedrooms, all with en-suite bathrooms (3 upstairs + 1 in a separate annex), Wi-Fi and air conditioning. Large shaded porch for outdoor dining, lounge corners, and an outdoor BBQ/oven area. Great base for the Sibillini Park and Lake Fiastra.

5.0 out of 5 average rating, 5 reviews
Top Guest favourite
A modern salt-water pool is set against a backdrop of rolling hills, surrounded by a stone terrace. The tranquil water reflects the blue sky and scattered clouds, creating a serene outdoor space that emphasizes the natural landscape.
Home in Belvedere Ostrense

Casa Raggia

Welcome to your oasis of tranquility! This beautiful modern wooden semi-detached house, nestled in the countryside, is the ideal retreat for those who want to relax in nature without sacrificing comfort and design. Built with natural and eco-sustainable materials, the house is furnished with taste and attention to detail, offering a cozy, bright, and contemporary environment.

5.0 out of 5 average rating, 15 reviews

Popular amenities for Tolentino rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top Guest favourite
A two-story independent house is depicted, surrounded by trees and flowering plants. A gravel pathway leads to the entrance, with outdoor seating visible on the side. The property is situated against a backdrop of rolling hills, enhancing its natural setting.
Home in Corinaldo

For those who love tranquility!

4.97 out of 5 average rating, 187 reviews
Guest favourite
A gravel driveway leads to a charming two-story villa surrounded by lush greenery. The building features a mixture of stone and brick walls, framed by large windows with red shutters. Sunlight filters through the trees, creating a serene atmosphere.
Home in Serra

villa Strada

4.94 out of 5 average rating, 35 reviews
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 in Montecosaro

Laura's Country House

4.97 out of 5 average rating, 74 reviews
Guest favourite
A shaded outdoor seating area features wooden furniture, including a sofa and table. Soft, flowing curtains frame the space, providing a gentle breeze. A bottle and glasses are placed on the table, with a scenic green landscape visible in the background.
Home in Treia

Stay in nature: Casa Kikenda Relais

4.98 out of 5 average rating, 43 reviews
Guest favourite
A tranquil salt-water pool is surrounded by lush gardens filled with blooming flowers. Lounge chairs are positioned along the poolside, offering views of rolling hills under a clear blue sky, enhancing the serene atmosphere of the outdoor space.
Home in Falerone

Farm house with exclusive access to the pool

4.89 out of 5 average rating, 18 reviews
Top Guest favourite
A serene view of the villa surrounded by lush greenery, featuring stone walls partially covered with vines. Tall cypress trees rise in the background, while a gravel path leads up to the entrance of the villa. The blue sky is dotted with fluffy white clouds.
Home in Trevi

Hidden Gem in the Heart of Umbria

4.99 out of 5 average rating, 71 reviews
Superhost
Home in Montegranaro

Breath of Nature

4.91 out of 5 average rating, 11 reviews
Superhost
Home in Fermo

The House in the Garden

4.75 out of 5 average rating, 16 reviews

Condo rentals with a pool

Superhost
Condo in Arcevia

Luxury Apartment with pool - Villa the Stable

5.0 out of 5 average rating, 3 reviews
Superhost
An outdoor dining area is set under a rustic stone shelter with a wooden beam ceiling. A wooden table with matching chairs is arranged, accompanied by decorative plants. The backdrop features a lush green landscape, enhancing the inviting atmosphere of the space.
Condo in Spoleto

Casa del Melograno in Pianciano

4.7 out of 5 average rating, 10 reviews
Guest favourite
A historic villa is shown surrounded by lush green landscapes, with an inviting swimming pool in the foreground. The exterior features stone walls and multiple windows, while sun loungers are positioned beside the pool, offering a serene outdoor space.
Condo in Potenza Picena

Historic Residence Santa Cassella 7

5.0 out of 5 average rating, 8 reviews
Superhost
An outdoor pool area presents a long, rectangular swimming pool, surrounded by sun loungers and umbrellas. Scenic hills and greenery are visible in the background, creating a serene atmosphere ideal for relaxation.
Condo in Sant'Elpidio a Mare

Gli Ulivi apartment with pool

4.76 out of 5 average rating, 21 reviews
Guest favourite
A large swimming pool is surrounded by lush greenery, reflecting the sunlight and trees above. Comfortable seating is visible behind the pool, offering a serene area for relaxation among the olive trees.
Condo in Mogliano

Tranquil apartment with pool

4.87 out of 5 average rating, 39 reviews
Guest favourite
Condo in Recanati

Dependance Alla Luna with pool

5.0 out of 5 average rating, 6 reviews
Guest favourite
A contemporary two-story building is situated among well-maintained greenery. The structure features balconies on the upper level, while a stone pathway leads up to the entrance. Lush bushes provide privacy, and the clear blue sky enhances the serene environment.
Condo in Marcelli

Charming one-bedroom apartment, in a resort with a pool

4.94 out of 5 average rating, 63 reviews
Guest favourite
A large swimming pool is framed by lush olive trees and sun loungers. A shaded seating area with a wooden roof offers a cozy retreat, while the surrounding hills provide a scenic backdrop of green and rolling landscapes.
Condo in Morano Madonnuccia

L'Artista - Apartment for 6 Colle Mura

5.0 out of 5 average rating, 9 reviews

Other holiday rentals with a pool

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 in Mogliano

Casa Antonio - Private Pool, Air conditioning

5.0 out of 5 average rating, 5 reviews
Top Guest favourite
The image captures a serene sunset over a private pool, with lush green grass surrounding the area. Sunlight casts a warm glow on the villa's exterior, highlighting large windows that reflect the fading daylight. Trees and hills are visible in the background, enhancing the peaceful setting.
Villa in Servigliano

Villa with exclusive private, heated pool

4.97 out of 5 average rating, 34 reviews
Top Guest favourite
A standalone house features a stone exterior with a terracotta-red accent wall. Surrounding greenery and a gravel pathway lead to the entrance. Soft sunlight highlights the distant trees, contributing to a serene outdoor environment.
Apartment in Recanati

D'In Su la Vetta Apartment: with pool

5.0 out of 5 average rating, 38 reviews
Guest favourite
A scenic view of a countryside landscape is presented, featuring a gentle hillside covered in tall grass and plants. In the background, a soft-colored house is visible against the deep blue sea, surrounded by lush greenery and trees under a clear sky.
Holiday home in Altidona

The house on the Adriatic

4.94 out of 5 average rating, 18 reviews
Guest favourite
An outdoor terrace offers a panoramic view of the surrounding landscape, with mountains in the distance and the city below. A wooden slatted roof provides shading, while a potted plant adds a touch of greenery to the outdoor seating area.
Apartment in Ascoli Piceno

L'Attico Sul Fiume center home

4.91 out of 5 average rating, 199 reviews
Top Guest favourite
A swimming pool is surrounded by well-maintained greenery and shrubs, offering views of the rolling hills in the distance. The calm blue water reflects the sky and clouds, creating a serene outdoor space for relaxation.
Home in Colmurano

Casa Moscatel - rural idyll, stunning panorama

5.0 out of 5 average rating, 14 reviews
Guest favourite
A restored farmhouse is showcased, featuring a stone pathway leading to a private pool. Several chaise lounge chairs are arranged by the poolside, complementing the expansive green lawn and picturesque countryside views in the background.
Home in Tolentino

Casa Pace e Gioia - private pool & amazing views

4.9 out of 5 average rating, 20 reviews
Villa in Convento

Villa Torre Anna: Historic Tower, Swimming Pool, and Jacuzzi

4.75 out of 5 average rating, 4 reviews

When is the best time to visit Tolentino?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$255 NZD$239 NZD$243 NZD$361 NZD$414 NZD$406 NZD$394 NZD$370 NZD$278 NZD$246 NZD$246 NZD$268 NZD
Avg. temp5°C5°C9°C12°C17°C21°C24°C24°C19°C14°C9°C6°C

Destinations to explore