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Vacation rentals with a pool in Tolentino

Find and book unique homes with a pool on Airbnb

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Popular amenities for Tolentino rentals with a pool

House rentals with a pool

Top guest favorite
Home in Corinaldo
4.97 out of 5 average rating, 133 reviews

For those who love tranquility!

Nearshore Development ltdRating, 5 stars1 day ago
Massimo and his father Giordano are great hosts. Giordano reminds me of my father. Full of life and love of good wine. we have stayed at the villa before and as always we had a great time. the view of the surrounding hills, full of trees and farmland is stunning. everything is calm and beautiful. Corinaldo is close and walkable, with great places to eat and a pleasure to walk around. the new garden area with the swimming pool is great to relax. I had my first swimming of 2025 and the sunbathed in complete tranquility. the house itself is large and furnished with the old style (when furniture was an art). The villa is situated at a great spot and can be used as a base to discover the surrounding villages. only one hour from Ancona and the beautiful old town with all the places to visit. We plan to be back every year during our European trip.
Superhost
Home in San Giovanni
4.8 out of 5 average rating, 20 reviews

Pool house, relax in the olive trees garden

Anne-CRating, 5 stars8 months ago
Maria Teresa and her son were great tips for catering, as for visits to villages (but there are also plenty of museums to visit), the sublime hikes to do in this area... in short, great tips. Unfortunately over a week we couldn't visit everything but we caught our eyes already:) it would have taken us more than a week on site. The welcome, just like our departure will have been very warm with Maria Teresa who we thank very much for allowing us to discover this beautiful region! The house is secluded and at night there is a masterful calm, this house is ideal for relaxing and refreshing. The house complies with the photos of the site, the olive grove is sublime. No light pollution at night either, a real joy. In short, only beautiful images printed in our retinas. We had a great stay. Thanks again and maybe see you next time:)
Top guest favorite
Home in Petrignano
5 out of 5 average rating, 31 reviews

Casolare Famiglia Grande Assisi. Families and friends

MarcoRating, 5 stars1 week ago
Fantastic place, very nice house we stayed comfortably in 7 with 3 bathrooms among other things there are no problems… clean tidy and very spacious house. The playroom was very much liked, especially by my 4-year-old daughter, who would have stayed there all the time instead of coming around with us. Beautiful outdoor garden, with lots of games much loved by children and everything you need to eat and grill and in fact we took advantage of it. The hosts are extremely kind and helpful both with regard to the house and the advice they gave us about the surroundings to visit. If I had to go back there, we'd definitely like to go back to this house. Amazing!
Guest favorite
Home in San Marco di Montefalco
4.94 out of 5 average rating, 51 reviews

Tower - Fonte Sala Agritourism

IainRating, 5 stars3 weeks ago
Wow! What an incredible property. We loved our time staying at ‘the tower’. It is a beautiful setting among the olives and vines on a hilltop. The surrounding area is beautiful and it’s an easy walk to local vineyards and restaurants. Only one caveat: the WiFi is very weak and not suitable for video calls.
Superhost
Home in Assisi
4.8 out of 5 average rating, 83 reviews

House with garden and private pool

ChrisRating, 5 stars3 weeks ago
Daiana’s place is clean and spacious and in a lovely location. The beds and sofa were very comfortable and Daiana was very responsive and helpful. And flexible with check out. The house could do with a few more basic items which Daiana provided when requested. We were attending an event at the nearby castle so it was as an ideal location. The pool however was still closed for the winter so worth checking in advance.
Guest favorite
Home in Quadrelli
5 out of 5 average rating, 6 reviews

Magical Umbrian Villa with pool!

Jan-WillemRating, 5 stars10 months ago
We had a wonderful time at Christiane's location! What a beautiful place! Thank you so much!
Guest favorite
Home in Canavaccio
4.97 out of 5 average rating, 72 reviews

Calbertone family and bike holidays Urbino

FabrizioRating, 5 stars1 week ago
We stayed in 13 at Angelo's house, for the weekend of June 2. The house is very beautiful, in a quiet area, it is very spacious both inside and outside, with a patio and a garden that offer a beautiful view. The pool, being above ground, is not very large but absolutely functional for cooling off while enjoying the garden, and it was very much used by the 5 girls of the group who had a great time! Angelo was always available and kind to us, a great host!
Guest favorite
Home in Montalto delle Marche
4.94 out of 5 average rating, 34 reviews

Mini apartment with pool Villa Cerqueto

PeterRating, 5 stars5 days ago
We received a very warm welcome from the family. The apartment was well-equipped with everything we needed, and the outdoor area was perfect for relaxation. Our host, Pia, surprised us several times with freshly baked cakes, eggs from their own chickens, and even an aperitivo by the pool. The garage features a 6–7 kW charger for electric cars, which is a major plus for this area and accommodation. I’d totally recommend staying at the accommodation in this area.

Condo rentals with a pool

Superhost
Condo in Gubbio
4.9 out of 5 average rating, 10 reviews

Querceto farmhouse with pool in Umbria

HosseinRating, 5 stars1 month ago
Giuseppe and family are WONDERFUL hosts. made us feel right at home. beautiful property and beautiful location. can't wait to be back!
Superhost
Condo in Ancona
4.88 out of 5 average rating, 32 reviews

House Fuà

PaulaRating, 5 stars1 week ago
Danielle was super friendly and responsive and if you like to cook the kitchen is very well equiped.
Guest favorite
Condo in Senigallia
5 out of 5 average rating, 20 reviews

Casa Beatrice

AndreyRating, 5 stars9 months ago
Michele’s apartments are one of the best i’ve ever been to! It was super-clean and cosy where you can feel yourself like home, a lot of space and we fell in love with balcony! You feel it is not just a flat to rent, but really somebody’s home, and it is fantastic! All what you can need is provided and even more! Washing and dishwashing machines, ironboard and iron, air conditioner etc. Location is just perfect - close to the sea and old city, but not in the touristic area, rather residential, but you can reach center in 20 minutes on foot. Parking slots always were available next to the building or 2-3 mins walk (in September). Michele and Beatrice are very communicative and reply to all the questions promptly. We loved staying at Casa Beatrice and if we come again - we will stay there! I highly recommend Casa Beatrice to everyone coming to Senigallia!
Superhost
Condo in Pilonico Paterno
4.8 out of 5 average rating, 15 reviews

"La Collina di Pilonico" Farmhouse -Magnolia-

StefanoRating, 5 stars9 months ago
very nice location... reachable in terms of the tourist towns Assisi, Perugia,Spello, Gubbio,Orvieto. we highly recommend it for those who want to spend a weekend in absolute tranquility not to mention the pool at your complete disposal. highly recommend for those who want to have a wonderful weekend Thank you again we will consider in case we want to come back.
Superhost
Condo in Porto San Giorgio
4.84 out of 5 average rating, 25 reviews

On the waterfront, climate, parking, WiFi, bikes

AndreaRating, 5 stars7 months ago
Angela and her husband were very kind, the house is close to the beach, pleasant even out of season
Superhost
Condo in Colli al Metauro
4.9 out of 5 average rating, 10 reviews

Serafini Home 20 20km from the sea by Yohome

PeterRating, 5 stars9 months ago
We had a great stay. Fantastic location, Katia was proactive and helpful throughout. Arrival instructions were clear, but I missed a step - response was speedy sending me photos to show me what to do. House bigger than we expected. Very quiet, good facilities and as described. Shared swimming pool, but it was big, well maintained and never crowded. Would thoroughly recommend.
Guest favorite
Condo in Genga
4.95 out of 5 average rating, 22 reviews

Al Borgo delle Rondini

SimonRating, 5 stars9 months ago
Laura and Alessandro are great hosts, very kind, warm and helpful. The apartment is just like the photos and description. Absolutely quiet, with great views. My kids especially loved the pool.
Guest favorite
Condo in Serra De' Conti
4.94 out of 5 average rating, 95 reviews

Casa Bertina

LuciaRating, 5 stars9 months ago
Short but intense stay, a real shame not to have stayed longer than the three days we had available. The place is lovely, beautiful view, cottage in great condition, top swimming pool. We were not well, very well, even more. The apartment matches the host's description, clean and with everything available. Super pool, practically at our exclusive disposal. Mr. Lino and his wife are reserved, discreet but always ready and helpful. We left a piece of our heart. Congratulations, we hope to return. Thank you Mr. Lino and wife, you have allowed our vacation to end with a memory that we will always carry with us. Lucia & Family

Home rentals with a private pool

Home in Massa Martana
4.83 out of 5 average rating, 6 reviews

The Dance by Interhome

MilaRating, 5 stars13 months ago
Wow. Just wow. This is paradise on earth, and I wish I would never go home. The house and surroundings are just more stunning than any picture can show. Kids friendly, family friendly, stunning surroundings, near great restaurants, and supermarkets. The hosts are very responsive, and they have a maintenance person fixing everything you need. I will definitely come back with my family. Very, very, very recommendable.
Home in Roseto degli Abruzzi

Serrani by Interhome

CarlottaRating, 5 stars46 months ago
Great location, new and clean house, one person stays to sleep in an area next door during the accommodation. Comfortable for sea and the center of the country.
Home in Auditore
4.55 out of 5 average rating, 11 reviews

Green Wellness House by Interhome

GrzegorzRating, 5 stars12 months ago
Super home with many amenities Very good location, in the city of Casinina there is everything you need (shops, restaurants , cafes) It takes 35 minutes to get to the beaches, Forli airport just over an hour around beautiful mountains and walking areas
Home in Assisi

La Mora by Interhome

LiamRating, 5 stars1 month ago
great stay
Guest favorite
Home in Bevagna
4.91 out of 5 average rating, 33 reviews

La Letizia by Interhome

FernandaRating, 5 stars1 month ago
Location with a wonderful view of Assisi and the region, especially Mount Subasio. The host was very attentive and always willing to answer our questions. The property was very organized and equipped, so it met all our needs. i recommend it.
Home in Tortoreto
4.75 out of 5 average rating, 4 reviews

Fonte del Ceppo 1 by Interhome

ElisaRating, 5 stars10 months ago
A house completely surrounded by greenery, totally available and with a pool included, which has made our stay really special. Privacy is total. Lovely veranda dinners. Excellent communication with the owner, who takes care of the daily maintenance of the pool in a very discreet way. The beaches of Tortoreto, great for children, are about an 8-minute drive on an easily accessible road. Highly recommended.
Home in Montone di Mosciano Sant'Angelo
5 out of 5 average rating, 3 reviews

Fonte del Ceppo 2 by Interhome

LisaRating, 5 stars8 months ago
Very nice apartment! A lot of space, peaceful and well equipped kitchen.
Home in Massa Martana

Centuries-old olive tree by Interhome

FabrizioRating, 5 stars58 months ago
Great home to relax with family and/or friends

Quick stats about vacation rentals with a pool in Tolentino

  • Total rentals

    50 properties

  • Nightly prices starting at

    ﺩ.ﺇ220 before taxes and fees

  • Total number of reviews

    290 reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Italy
  3. Marche
  4. Province of Macerata
  5. Tolentino
  6. Rentals with pools