
Holiday rentals with a pool in Apennine Mountains
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Apennine Mountains
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Relaxation and charm in the Chianti hills
Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful Chianti hills in Tuscany, with the possibility of organising a shuttle service and exclusive experiences tailored to your needs. The apartment is available for 2 adults with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle, hills and vineyards with unique sunsets.

The Eagle and the Olive Tree
At Aquila e l'Ulivo, an ancient renovated farmhouse from the 1200s, you will not only find all the necessary comforts for a wonderful stay, but you will also experience the thrill of feeling free and immersed in the unspoiled nature of Val D'Orcia. Here you'll have the opportunity to walk with the two falcons Ayga and Sayen and interact with the eagles, and why not sip an excellent aperitif by the pool. We are waiting for you in our world, made up of animals, relaxation, nature and even a touch of Magic.

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Exclusive 10 Acre Estate w/ Pool & Olive Grove!
Enchanting, exclusive 10acres estate on a hill, memorable sunsets; large pool framed by lavender&rosemary, open year-round. New air conditioning, Starlink internet. Very private&peaceful 2 floors, 4bedrooms, 4baths, jacuzzibathtub, 55inch smartTV, well-equipped kitchen, porch & pergola for alfresco dining, Weber barbecue, pizza oven, olive grove, fireplace; 20 min. to Orvieto,Todi,Amelia; 10 minutes drive to train station to Rome/Florence, 5min drive to shops in town. Grounds/pool caretaker

Tuscan cottage with an heavenly view
Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

The house among olive trees
A cottage made up of stone and timber built on two storeys, with a large living room, glass window, a couch for two people and a bathroom with sauna; on the second storey there is a double bedroom. Outdoors, there is a large garden with a porch equipped with BBQ and a wooden table. The site is located on the pleasant hills between Bellegra and Olevano Romano. We have currently added two beds, set up in a wonderful Indian teepe available for two extra guests in addition to the four ones.

Rural Tuscany | Family farmstay with restaurant
Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

Belforti Tower
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.

The Castle of Ferrano - Castle in Tuscany
Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment. Turquoise: https://www.airbnb.com/rooms/plus/9430389.

Spectacular and Cozy Loft w/Terrace, near Termini
This one of a kind rustic yet elegant loft is full with details in wood, metal and stone, all handmade by Giulio, his owner. The fabulous terrace will take your breath away. How about some coffee with your slippers on while contemplating the Colosseum or watching the sun go down behind the Vatican shadow from the hut tub? Located minutes away from Termini Station but still a peaceful home. The access to the appartment is made by stairs. Breakfast it's on us!
Popular amenities for Apennine Mountains rentals with a pool
House rentals with a pool

Cottage surrounded by nature

Private Chianti Cottage, Garden & Vineyard Views

Infinity pool in Chianti area

Cercis - La Palmierina

Vineyards Paradise

Villa degli Olivi

Borgo Ripostena – no. 8 Casa Vecchia

Stone residence between the sea, mountains and swimming pool.
Apartment rentals with a pool

Farmhouse near Florence - Loggia

Vintage Residence with Swimming Pool in Chianti

The Painter's House

A dream home with a pool near Piazza del Popolo

Ginestra: Private Pool Overlooking Florence

Poggiolieto Suite - on hills 10' from city center

Garden & SPA -FlorArt Boutique Apartment

Casaletto 210 B1 Villa with pool and parking
Home rentals with a private pool

Stone House with Exclusive Pool Codilungo in Chianti

Villa Pergo is an ancient charming country villa
Historic villa x8 with exclusive pool

Luxurious Villa with Panoramic Terrace and Private Pool

Agriturismo Henni panoramic pool sauna and jacuzzi

Villa il Palagio in the Tuscan countryside

Casa Luigi Suite with exclusive pool
Wp Relais Villa Vignalunga
Destinations to explore
- Nature eco lodge rentals Apennine Mountains
- Treehouse rentals Apennine Mountains
- Cave rentals Apennine Mountains
- Bed and breakfasts Apennine Mountains
- Private suite rentals Apennine Mountains
- Rentals with beach access Apennine Mountains
- Pet-friendly rentals Apennine Mountains
- Resort rentals Apennine Mountains
- Villa rentals Apennine Mountains
- Tower rentals Apennine Mountains
- Flat rentals Apennine Mountains
- Serviced apartment rentals Apennine Mountains
- Campsite rentals Apennine Mountains
- Dome rentals Apennine Mountains
- Apartment rentals Apennine Mountains
- Hotel rooms Apennine Mountains
- Yurt rentals Apennine Mountains
- Guest house rentals Apennine Mountains
- Rentals with a fireplace Apennine Mountains
- Rentals with an EV charger Apennine Mountains
- Fitness-friendly rentals Apennine Mountains
- Rentals with an accessible-height bed Apennine Mountains
- House rentals Apennine Mountains
- Rentals with a washing machine and dryer Apennine Mountains
- Rentals with a kayak Apennine Mountains
- Houseboat rentals Apennine Mountains
- Rentals with a patio Apennine Mountains
- Chalet rentals Apennine Mountains
- Rentals with a firepit Apennine Mountains
- Beachfront rentals Apennine Mountains
- Luxury rentals Apennine Mountains
- Earth house rentals Apennine Mountains
- Rentals with breakfast Apennine Mountains
- Cottage rentals Apennine Mountains
- Boat rentals Apennine Mountains
- Rentals with a balcony Apennine Mountains
- Hut rentals Apennine Mountains
- Smoking-friendly rentals Apennine Mountains
- Shepherd’s hut rentals Apennine Mountains
- Family-friendly rentals Apennine Mountains
- Rentals with outdoor seating Apennine Mountains
- Island rentals Apennine Mountains
- Rentals with a sauna Apennine Mountains
- Ski-in/ski-out rentals Apennine Mountains
- Bungalow rentals Apennine Mountains
- Boutique hotels Apennine Mountains
- Tent rentals Apennine Mountains
- Rentals with a cinema Apennine Mountains
- Loft rentals Apennine Mountains
- Holiday home rentals Apennine Mountains
- Hostel rentals Apennine Mountains
- Townhouse rentals Apennine Mountains
- Rentals with an accessible-height toilet Apennine Mountains
- Cabin rentals Apennine Mountains
- Farm stay rentals Apennine Mountains
- Aparthotel rentals Apennine Mountains
- Tiny house rentals Apennine Mountains
- Barn rentals Apennine Mountains
- Castle rentals Apennine Mountains
- Rentals with a hot tub Apennine Mountains
- Rentals with lake access Apennine Mountains
- Rentals with a soaking bathtub Apennine Mountains
- Motorhome rentals Apennine Mountains
- Waterfront rentals Apennine Mountains
- Rentals with pools Italy
- Things to do Apennine Mountains
- Entertainment Apennine Mountains
- Wellness Apennine Mountains
- Nature and outdoors Apennine Mountains
- Sports activities Apennine Mountains
- Sightseeing Apennine Mountains
- Art and culture Apennine Mountains
- Tours Apennine Mountains
- Food and drink Apennine Mountains
- Things to do Italy
- Tours Italy
- Entertainment Italy
- Food and drink Italy
- Wellness Italy
- Art and culture Italy
- Nature and outdoors Italy
- Sports activities Italy
- Sightseeing Italy





