By Wyndham Vacation Rentals
Shortlist

Italy

Holiday cottages in Italy provide the perfect opportunity to relax, explore and enjoy a slice of “La Dolce Vita”. The fact that Italy offers such a taste of the sweet life should come as no surprise. After all, there are few other holiday destinations that present such a welcome mix of warm climate, fantastic cuisine, fascinating heritage and stunning scenery, so it’s hardly surprising to find that many of our customers return to Italian cottages year after year.

Rome was famously not built in a day, so we’d suggest a holiday cottage in the region if you want to make the most of your time there! Alongside its iconic attractions – the Colosseum, Trevi Fountain, Forum, Vatican and more – you’ll find something of interest on every street of Italy’s wonderful capital city. It’s also been said that it’s impossible to have a bad meal in Rome. This is something that our previous holidays – not to mention our waistlines – can attest to. If you fancy exploring the birthplace of Italy’s celebrated culture then we wouldn’t hesitate to recommend a holiday cottage in Florence. Birthplace of the Rennaissance, and home to one of the world’s most famous Davids, it’s a region filled with fascinating history and unrivalled beauty. Venice’s network of alleys and waterways has been delighting visitors for years, and it still offers one of the definitive Italian holiday experiences. If you fancy something a little more tranquil then Italy’s rural landscape offers patchwork hills, sparkling blue waters and golden sands aplenty. Tuscany may be one of its most celebrated destinations, but neighbouring Umbria is equally attractive with great food and drink, a fascinating history and a wonderfully relaxed pace of life. Italy’s south offers plenty of opportunities to relax and unwind in the sun. Explore Sicily and enjoy a beautifully diverse array of attractions within a stunning landscape that offers some of Italy’s finest beaches. Capri and the Amalfi coast also offer some of the best beach locations to make the most of your time on your Italian holiday.

With so many activities, and such a diverse landscape, Italy is a fantastic holiday playground with a wealth of options for all ages. Uncovering the country’s history, culture and heritage is one of the most popular ways to enjoy your time there, but if you’d prefer to relax by the pool then we’re sure you’ll be equally satisfied. Beach breaks are equally popular for those with Italian holiday cottages and the country boasts some of the most spectacular shoreline you could wish for. Basically, however you choose to spend your time in Italy you’re guaranteed a wonderfully memorable holiday.

If you’re ready to begin your exploration take a look at our featured holiday cottages in Italy today.
588 cottages are available
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  • Woodland View

    Capolona

    Grade
    3
    2
    1
    1
    Ref: ITA705

    An ideal base for guests who want to spend a nice holiday in their own littlel paradise. This beautiful Italian property is set in a quiet hillside position, located about 1km above Capolona /Subbiano. The living room boasts an open fireplace and leads out to the covered terrace. Guests are spoilt for choice with outdoor spaces to relax in with another terrace situated on the rear side of the house, and the grounds include a large natural plot with various romantic seats, as well as a barbecue under the shade of tall trees. Your four-legged friend can join you on your holidays too. Capolona offers all amenities including shops, restaurants, bars and a tennis court. Visit castles and borghi of the Casentino region or travel to Arezzo only 15km away.

    All on ground floor: Living/dining room. Kitchen. 2 bedrooms: 1 double, 1 single. Bathroom with shower attachment and toilet.

    Open fire in living room. CH. Cot. DVD. Stereo/CD. Gas/elec cooker. M/wave. W/machine. T/dryer. D/washer. Garden with terrace and furniture. BBQ. Parking (2 cars).

    • Distance to Capolona 1km
    • Nearest facilities 600m
    • Distance to airport 80km

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  • Il Focolare

    San Gimignano

    Grade
    3
    2
    1
    1
    Ref: ITN155

    Located near the beautiful medieval town of San Gimignano is this beautiful estate consisting of two buildings, which were divided into 9 apartments. Accessed by a rough track, the facility is located in a peaceful setting in an elevated location, with views of the surrounding hills and vineyards. The owner conveniently lives on-site, and guests to this holiday apartment have access to the lovely grounds, shared outdoor swimming pool and barbecue area. The world-famous walled town of San Gimignano is just a short drive away and Siena is just 35km away.

    External stairs to entrance. All on first floor: Living/dining room/kitchen. 2 bedrooms: 1 double, 1 single. Bathroom with toilet.

    Open fire in kitchen. CH. Satellite TV. Gas cooker. Shared w/machine. Wi-fi. Shared grounds with furniture. Shared BBQ. Parking. Shared outdoor swimming pool (98m²), open May-Sep. No smoking. NB: Drops in grounds.

    • Distance to San Gimignano 4.5km
    • Nearest facilities 3km
    • Nearest airport Florence

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  • Ginestra 1

    Castelnuovo D’Elsa

    Grade
    3
    2
    1
    2
    Ref: TV092

    Surrounded by vineyards & olive groves

    A beautiful wine and olive producing estate lying in a wonderful 300 hectare estate of vineyards and olive groves, woodland and lakes, at the heart of which lies an ancient castle and its traditional farmhouses, with origins dating back 1000 years. In this charming natural setting, discerning guests are welcomed to a selection of perfectly kept holiday apartments situated in the old castle. Restored in keeping with their Tuscan traditions, the comfortable properties are attractively furnished. An excellent location for excursions, guests can visit San Gimignano, San Miniato, Certaldo and Vinci, as well as day trips to Lucca, Pisa, Volterra, Siena and Florence. By request, you can visit the deep cellars of the old villa. An excellent location for excursions, guests can visit San Gimignano, San Miniato, Certaldo and Vinci, as well as day trips to Lucca, Pisa, Volterra, Siena and Florence. By request, you can visit the deep cellars of the old villa.

    All on first floor: Living/dining room/kitchen. 2 bedrooms: 1 double, 1 single. 2 shower rooms with toilet.

    CH. Satellite TV. Gas cooker. M/wave. Shared laundry. Shared garden and furniture. Parking (1 car). Shared swimming pool (5 x 8m; depth 0.5-2m), open mid May-Sep. Pet free of charge. NB: Steps and slopes in grounds.

    Distance to Castelnuovo 3km

    • Distance to Lucca 50km
    • Distance to Forte di Marmi beach 55km
    • Nearest facilities 3km
    • Nearest airport Pisa

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  • Sangiovese 2

    San Donato in Poggio

    Grade
    3
    2
    0
    1
    Ref: ITC623

    This ground floor holiday apartment forms part of an ancient farmhouse in the Chianti hills with 5 other properties (ITC638, ITC617, ITC637, ITC631 and ITC635). Surrounded by vineyards and olive trees, it has been carefully decorated and furnished. The architectonic characteristics that have made this corner of Tuscany famous throughout the world have been conserved through the stone walls, windows and arches of the loggias. The property benefits its own terrace with barbecue and furniture, as well as from beautiful views of the countryside and shared use of the outdoor swimming pool. Completely fenced-in and made even more beautiful by blooming plants, the property includes a pretty lawn with garden furniture. Ideal location for exploring Florence and Siena.

    Step to entrance: All on ground floor: Living/dining room/kitchen. 2 bedrooms: 1 double, 1 single. Shower room with toilet.

    CH. Cot on request. Gas/elec cooker. W/machine. Terrace and furniture. Shared garden. Shared BBQs. Parking (1 car). Shared outdoor swimming pool (18m x 8m), open mid May-mid Sep.

    • Distance to San Donato in Poggio 1.5km
    • Distance to Florence 20km
    • Nearest facilities 1.5km
    • Nearest airport Florence

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  • San Giustino

    San Giustino

    Grade
    3
    2
    0
    1
    Ref: ITA205

    These 2, well-appointed apartments share panoramic views over to Valdarno and towards the Chianti Hills. Baciano Apartment (ITA206) boasts a ground floor position whilst Apartment Piccolo (ITA205) is on the first floor, although access is gained via 2 steps from the side of the property. There is a private outdoor area with garden furniture for each apartment. The barbecue, large outdoor swimming pool with sun terraces, a common room and 10km² of grounds are shared with 3 apartments. Wine, olive oil and local specialities are available on site. San Giustino is 2km. This is an ideal base for exploring the area with Chianti 30km, Florence 70km, Siena 50km and Arezzo 25km, all within easy reach.

    2 steps to entrance. All on first floor: Living/dining room/kitchen. 2 bedrooms: 1 double, 1 single. Shower room with bidet and toilet.

    CH. Satellite TV. Gas/electric cooker. Internet connection. Lawned garden with terrace, sitting-out are and furniture. Shared BBQ. Shared grounds. Parking (1 car). Shared outdoor swimming pool (162m² open mid May-Sep). NB: Slopes and drops in grounds.

    • Distance to San Giustino 2km
    • Distance to Arezzo 20km
    • Nearest facilities 2km
    • Nearest airport Florence

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  • Gardenia

    Greve in Chianti

    Grade
    4
    2
    0
    1
    Ref: ITC143

    Located in a beautiful stone farmhouse, this delightful holiday apartment has been renovated, yet keeping its typical building characteristics. The lovely apartments are among olive trees and vineyards, and the farm produces excellent wines, as well as olive oil, grappa and brandy, which guests can taste and purchase if they wish to. The wonderful Querceto Castle is close by, one of the most beautiful places in the Chianti area, where the wine cellars can be visited on request. The 12 apartments enjoy shared use of the outdoor swimming pool.

    All on first floor: Living/dining room/kitchen. 2 double bedrooms. Shower room with toilet.

    Satellite TV. Gas/electric cooker. Tel. Shared grounds with furniture. Parking (2 cars). Shared outdoor swimming pool (98m², open May-Sep).

    • Distance to Firenze 30km
    • Nearest facilities 2km
    • Nearest airport Florence

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  • Picche

    Volterra

    Grade
    4
    2
    0
    1
    Ref: ITN654

    This lovely renovated small country house is set in the green hills of central Tuscany, 16km from San Gimignano and is located near the nature reserve of Monte Nero. It benefs from an open-plan lounge/kitchen, a double bedroom, twin bedroom, bathroom with shower and a sunny veranda with furniture, and is in an ideal location for hiking and al fresco dining with several picnic areas in the vicinity. The gravel road that leads to the property is part of a historic salt road that connected Volterra to San Gimignano, and was also connected to the main road Via Francigena. Centrally located for the beach resorts on the Tyrrhenian coast and visiting the main tourist towns of Tuscany, with panoramic view of hills and forests. Easily reached are the towns of Volterra 10km, and San Gimignano 16km away.

    All on ground floor: Living/dining room/kitchen. 2 bedrooms: 1 double, 1 twin. Shower room with bidet and toilet. Most rooms with sloping, beamed ceilings. Tiled floors throughout.

    CH. Cot. H/chair. Satellite TV. Gas/electric cooker. D/washer. Lawned garden with terrace and furniture. BBQ. Parking (2 cars). NB: Step to terrace.

    • Distance to Volterra 10km
    • Distance to beach 42km
    • Nearest facilities 3km
    • Nearest airport Florence

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  • Paladino 2

    San Martino in Colle, Lucca

    Grade
    4
    2
    1
    1
    Ref: ITL190

    This wondeful property, accessed via a rough track, is part of an old farm that has been divided into a total of four holiday apartments. It provides accommodation on two levels, with access via a separate entrance. The property has its own private outdoor space which is equipped with tables and chairs, a BBQ, sun loungers, deck chairs and parasols for your relaxation under the sun. There is an open-air swimming pool just 2km away and the sandy beachs are 45km distant. There is much to see and do in the city of Lucca, 12km.

    Ground floor: Living room. Dining room/kitchen. First floor: 2 bedrooms: 1 double, 1 twin. Shower room with toilet.

    CH. Cot. H/chair. Satellite TV. Gas/elec cooker. Shared w/machine. Internet connection. Shared lawned garden with furniture. BBQ. Parking (2 cars). Pet free of charge.

    • Distance to Lucca 12km
    • Nearest facilities 2km
    • Distance to beach 45km
    • Nearest airport Pisa

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  • Villa I Due Golfi

    Sant’Agnello

    Grade
    4
    2
    0
    2
    Ref: IKS152

    This beautiful, semi-detached holiday house is located only 3km from Sorrento and has a large terrace and outdoor seating area overlooking the Gulf of Naples and Positano, which offers a breathtaking panorama by day and romantically lit sky at night. Both bedrooms have direct access to the terrace. The discreet owners live on site and are on hand if you need any help or advice during your stay. The location is ideal for a relaxing stay, and while you are there visit the Sorrento Peninsula with its typical villages such as Positano and then dive into the crystal clear waters of the sea. Make sure you visit the protected coastal park of Punta Campanella, which is a 30 minutes’drive away. In Castellammare di Stabia, 20km, you can take the funicular to go up on Mount Faito (1092m), and the views from the top are definitely worth the hike.

    All on ground floor: Living/dining room/kitchen with French doors. 2 double bedrooms both with French doors. Bathroom with bidet and toilet. Shower room with bidet and toilet. Tiled floors throughout.

    Open fire in living room. CH. Cot. Satellite TV. Gas cooker. M/wave. W/machine. Fridge. Wi-fi. Garden and furniture. Terrace. BBQ.

    • Distance to Sorrento 3km
    • Distance to beach 2.5km
    • Nearest facilities 100m
    • Nearest airport Naples

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  • Casa Terzorio

    Santo Stefano al Mare

    Grade
    4
    2
    1
    2
    Ref: ILL505

    Lovely attic apartment with a seaside view, a few minutes from Santo Stefano al Mare in Liguria. The accommodation is on the second and third floors and has two terraces with furniture for outdoor dining and to enjoy the surrounding views. The apartment offers a bathroom with Jacuzzi bath, ideal for those relaxing moments. This is the ideal starting point to visit the gorgeous beaches of the Riviera dei Fiori with its characteristic towns such as Sanremo, 17km, and Porto Maurizio, 14km, or to discover hamlets such as Borgio Verezzi, 65km, with its caves, listed as one of the most beautiful villages of Italy. Triora is 37km away, known as the town of witches, the fashionable Alassio, 43km, with its narrow lanes called ’budelli’, the Hanbury Botanic Gardens, 44km, with typical red rocks, and the whole of the Côte d’Azur in France, and Menton, 50km away, are all easily reached and worth visiting. Or why not try out part of the longest coastal cycle path in Europe, 20km, connecting Sanremo to San Lorenzo al Mare.

    Living room with sofa bed and French doors/dining room/kitchen. 2 bedrooms: 1 double, 1 single. Bathroom with toilet. Shower room with toilet.

    CH. Gas/electric cooker. M/wave. W/machine. D/washer. Wi-fi. Two terraces with furniture. BBQ. Parking (1 car). No smoking. NB: Turning stone stairs (no handrail). Low ceilings on third floor.

    • Distance to Santo Stefano al Mare 1km
    • Distance to beach 1km
    • Nearest facilities 1km
    • Nearest airport Genoa

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  • Il Frantoio

    Loro Ciuffenna

    Grade
    4
    2
    0
    1
    Ref: ITA353

    This pretty, terraced house has been comfortably and traditionally furnished to provide the ideal holiday base for guests to relax and explore the local area. Situated in the hills in the town of Loro Ciuffenna, the property benefits from a private above-ground swimming pool and a sun terrace with furniture, ideal for dining al fresco. This accommodation provides the ideal start point for day trips to Florence, Siena, Arezzo and Chianti, as well as for trekking in the mountains of Pratomagno. The popular town of Arezzo is just 30km away.

    Ground floor: Living/dining room/kitchen. First floor: 2 bedrooms: 1 double, 1 twin. Shower room with bidet and toilet. Sloping ceilings throughout first floor.

    Open fire in living room. CH. Cot on request. Gas/elec cooker. W/machine. Terrace. Shared outdoor furniture. Parking (1 car). Shared outdoor above ground swimming pool (36m²), open mid June-mid Sep. NB: Steps to pool.

    • Distance to Montevarchi 13km
    • Distance to Arezzo 30km
    • Nearest facilities 1.5km
    • Nearest airport Siena

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  • Sangiovese 5

    San Donato in Poggio

    Grade
    4
    2
    0
    1
    Ref: ITC637

    This first floor holiday apartment forms part of an ancient farmhouse in the Chianti hills with 5 other properties (ITC638, ITC617, ITC623, ITC631 and ITC635). Surrounded by vineyards and olive trees, it has been carefully decorated and furnished. The architectonic characteristics that have made this corner of Tuscany famous throughout the world have been conserved through the stone walls, windows and arches of the loggias. The property benefits from beautiful views of the countryside and shared use of the outdoor swimming pool. Completely fenced-in and made even more beautiful by blooming plants, the property includes a pretty lawn with garden furniture. Ideal location for exploring Florence and Siena.

    All on first floor: Living/dining room/kitchen. 2 bedrooms: 1 double, 1 twin. Shower room with toilet.

    CH. Cot on request. Cooker. W/machine. Shared garden and furniture. Shared BBQs. Parking (1 car). Shared outdoor swimming pool (18m x 8m), open mid May-mid Sep.

    • Distance to San Donato in Poggio 1.5km
    • Distance to Florence 20km
    • Nearest facilities 1.5km
    • Nearest airport Florence

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