
Vacation rentals with a pool in Tolentino
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Tolentino

Total vacation rentals
Explore 40 vacation rentals in Tolentino

Nightly prices starting at
Tolentino vacation rentals start at G$20,922 GYD per night before taxes and fees

Verified guest reviews
Over 290 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Tolentino vacation 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.

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.
LocationFamilyBreakfast

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.
LocationFamilyAccuracy

Cottage Casa Janna | 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.
LocationFamilyHospitality

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.
FamilyValueBathroom

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.
LocationFamilyGrill

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.
FamilyLocationOutdoor spaces

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.
LocationFamilyAccuracy

Casale Biancopecora, Casa Cerqua
Apartment Casa Cerqua of 100 sq. meters finely furnished, we recovered all the old materials of the house in the recent renovation adapting the old farmhouse to the latest earthquake regulations. The decor is a right mix of modern and ancient, elegant but functional. Outside there is a large private area available for guests, with shaded dining area and private barbecue. Complete the property with a 12x4.5 pool with shaded porch available for guests to enjoy.
FamilyLocationSleep quality

Hillside chalet in stone and wood.
At the foot of Mount San Vicino, on a beautiful hill 420 meters above sea level, in complete tranquility and easily accessible, you can enjoy a beautiful 360-degree view, from the Sibillini Mountains to the Gola della Rossa. Easily reachable in 15 minutes Fabriano, in 20 minutes the beautiful caves of Frasassi, in 30 minutes Gubbio and in 60 minutes Senigallia or the Bay of Conero, in 20 minutes the ducal city of Camerino.
ValueLocationAmenities

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.
LocationFamilyWifi

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.
LocationFamilyBathroom

Country House with Pool and Garden
Country house with swimming pool and garden - The farmhouse with swimming pool is located in the countryside with well-kept and completely renovated furnishings, for a relaxing vacation 5 km from the Fiastra Abbey Nature Reserve, 30 km from the entrance to the Monti Sibillini Park, 30 km from the Adriatic Sea and 60 km from the Conero Riviera.
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Popular amenities for Tolentino rentals with a pool
House rentals with a pool

Laura's Country House
LocationFamilyBreakfast

Casa Raggia
LocationFamilyDecor

villa Strada
LocationFamilyHot tub

Breath of Nature
LocationFamilyLaundry

Hidden Gem in the Heart of Umbria
FamilyLocationNearby

Farm house with exclusive access to the pool
LocationBathroomComfort

The House in the Garden
FamilyLocationBeach

La Casetta - Entire house 5 minutes from the center.
LocationFamilyGetting around
Condo rentals with a pool

Casa Leccino (house with a view)
FamilyLocationIndoor spaces

Luxury Apartment with pool - Villa the Stable
PoolComfortDecor

Historic Residence 7
LocationViewCondition

Casa del Melograno in Pianciano
FamilyLocationDecor

Tranquil apartment with pool
FamilyLocationOutdoor spaces

Gli Ulivi apartment with pool
LocationFamilyGetting around

L'Artista - Apartment for 6 Colle Mura
LocationFamilyOutdoor spaces

Charming one-bedroom apartment, in a resort with a pool
ValueLocationAccuracy
Other vacation rentals with a pool

Agriturismo Elisei – apartment, pool, sauna, spa
LocationFamilyComfort

Villa with exclusive private, heated pool
FamilyLocationGrill

D'In Su la Vetta apartment with pool
FamilyValueGrill

House with pool, 1st floor, Villa Cerqueto
LocationFamilyAccuracy

Villa Giulia, a stunning farmhouse in the Marche.
FamilyLocationBathroom

L'Attico Sul Fiume center home
ValueFamilyCheckout

Casa Pace e Gioia - private pool & amazing views
LocationFamilyHospitality

Casa Moscatel - rural idyll, stunning panorama
LocationFamilyPets
When is the best time to visit Tolentino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,383 GYD | G$29,500 GYD | G$29,919 GYD | G$44,564 GYD | G$51,050 GYD | G$50,004 GYD | G$48,539 GYD | G$45,610 GYD | G$34,312 GYD | G$30,337 GYD | G$30,337 GYD | G$33,057 GYD |
| Avg. temp | 5°C | 5°C | 9°C | 12°C | 17°C | 21°C | 24°C | 24°C | 19°C | 14°C | 9°C | 6°C |
Destinations to explore
- Riviera del Conero
- Senigallia Beach
- Basilica of St Francis
- Frasassi Caves
- Sibillini Mountains National Park
- Spiaggia Urbani
- Sibillini Mountains
- Furlo Gorge Nature Reserve
- Shrine of the Holy House
- Sirolo
- Mount Subasio
- Tennis Riviera Del Conero
- Gola del Furlo
- Rocca Roveresca
- Spiaggia della Torre
- Fonti Del Clitunno
- Rocca Maggiore
- Spoleto Cathedral
- Cattedrale di San Rufino
- Lame Rosse
- Eremo delle Carceri
- National Gallery
- Basilica di Santa Maria degli Angeli
- Etruscan Well





