50 Best Vacation Rentals in Province of Ascoli Piceno - Holiday Lettings - Cabins

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San Benedetto Del Tronto
68 properties
Ascoli Piceno
30 properties
Grottammare
30 properties
Cupra Marittima
16 properties
Ripatransone
14 properties
Offida
12 properties
Montefiore dell'Aso
11 properties
Montalto delle Marche
11 properties
Montedinove
10 properties
Monteprandone
6 properties
Carassai
5 properties

Province of Ascoli Piceno

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579 Vacation rentals

23

San Benedetto Del Tronto Vacation home rental

Province of Ascoli Piceno / San Benedetto Del Tronto

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.9 mi
  • Child friendly
House with separate entrance, multilevel (internal staircase): ground floor, kitchen / living room + bathroom (shower and toilet); first floor, bedroom (bed) + Balcony; second floor, bedroom (bed). …see more

from $75 / night

$521 / week

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Responds fast!
avg. 3 hours 2 minutes

from $75 / night

13

Vacation apartment in San Benedetto Del Tronto

Province of Ascoli Piceno / San Benedetto Del Tronto

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
The Regent Suite is the fourth apartment that we have the top floor of a building of new construction (year 2011) with a lift and it is certainly the most beautiful because it has 2 large terraces where you can dine and have a living room for gardens . The apartment sle …see more

from $87 / night

$744 - $2,169 / week

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from $87 / night

(2) Excellent 

16

Vacation condo rental

Province of Ascoli Piceno / San Benedetto Del Tronto

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
La SUITE TIFFANY è il più piccolo dei ns appartamenti misurando infatti 75mq ma sempre con sei posti letto; è ubicato all'ultimo piano di una palazzina, dotata di ascensore, di nuovissima costruzione in prima fila mare sul lato sud ed ovest dell'edificio, cioè sul retro …see more

from $87 / night

$558 - $1,549 / week

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from $87 / night

12

Vacation apartment in Cupra Marittima

Province of Ascoli Piceno / Cupra Marittima

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Air conditioning
In the city center of maritime cupra 20 meters from the beach, we rent nice loft consisting of living room with sofa bed, bedroom, bedroom, bathroom with shower tub, LCD TV in every room, washing machine, air-conditioned to accommodate Max 4/5 people ADSL available incl …see more

from $88 / night

$620 / week

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from $88 / night

(1) Excellent 

9

Vacation apartment in San Benedetto Del Tronto

Province of Ascoli Piceno / San Benedetto Del Tronto

1 5 7 nights min

  • 1 bedroom
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Esclusivo appartamento situato in zona centralissima sull'isola pedonale di San Benedetto del Tronto. Con una passeggiata di max 150 metri, attraverso un parco di palme e pini secolari, si raggiunge il primo stabilimento balneare. L'unità immobiliare, di nuovissima ulti …see more

from $107 / night

$744 / week

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from $107 / night

(2) Very Good 

11

Grottammare Vacation apartment rental

Province of Ascoli Piceno / Grottammare

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Tina's House is a pretty new apartment, in a building of only three floors, a lift to 250 mt, from the seafront in Grottammare (AP). Close to the A14 motorway exit and a range of services such as, Tobacconist, pharmacy, bus stop, bar and shopping mall, in addition to a …see more

from $100 / night

$769 - $892 / week

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from $100 / night

(2) Very Good 

26

Vacation apartment in Montefiore dell'Aso

Province of Ascoli Piceno / Montefiore dell'Aso

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 11 mi
  • Swimming pool
  • Child friendly
Villa Rosa Bianca is a beautiful restored `casale' set in a tranquil location, yet only 12km from the sea and safe bathing areas of Pedaso, and 4km from Montefiore Dell'Aso, famous for its `infiorata' when the streets are covered with pictures made from flowers. Apartm …see more

from $86 / night

$572 - $915 / week

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avg. 1 hour 1 minutes

from $86 / night

(4) Excellent 

17

Apartment rental in San Benedetto Del Tronto

Province of Ascoli Piceno / San Benedetto Del Tronto

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
Esclusivo appartamento situato in zona centralissima sull'isola pedonale di San Benedetto del Tronto. Con una passeggiata di max 150 metri, attraverso un parco di palme e pini secolari, si raggiunge il primo stabilimento balneare. L'unità immobiliare, di nuovissima ulti …see more

from $124 / night

$868 / week

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from $124 / night

(2) Excellent 

19

San Benedetto Del Tronto Vacation apartment rental

Province of Ascoli Piceno / San Benedetto Del Tronto

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Child friendly
MaVip is a recently built tourist town located in San Benedetto del Tronto (AP) a few steps from the sea and the Riviera delle Palme. The residence is situated in a quiet and well served area where you can easily reach all the necessary services to make your holiday mor …see more

from $71 / night

$496 - $1,115 / week

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Responds fast!
avg. 2 hours 25 minutes

from $71 / night

(5) Very Good 

10

Vacation b&b in Cupra Marittima

Province of Ascoli Piceno / Cupra Marittima

8 16 1 night min

  • 8 bedrooms
  • Sleeps 16
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
Casa per ferie Maria Immacolata Cupra Marittima, where you can spend unforgettable days, if you are interested in a vacation for body and spirit, in the charming territory of Cupra Marittima where is located our hotel. Waiting for the warm welcome, all the comforts of …see more

from $56 / night

$391 / week

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from $56 / night

14

Vacation studio in San Benedetto Del Tronto

Province of Ascoli Piceno / San Benedetto Del Tronto

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
Confortevole e funzionale monolocale di ca 25 mq, situato al primo piano in uno stabile di pregio nel cuore della città e che si affaccia sulla centralissima Rotonda Giorgini. Posizionato nell’isola pedonale tra le vie dei negozi di San Benedetto del Tronto ed a due pas …see more

from $50 / night

$347 / week

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from $50 / night

(1) Excellent 

19

Vacation condo rental

Province of Ascoli Piceno / San Benedetto Del Tronto

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
The HORTENSIA is a bright apartment situated on the top floor of a building with elevator, recently built in the front row and a wonderful sea view. The apartment is approximately 87mq. Upon entering we find a wide and bright living room with kitchenette with all applia …see more

from $87 / night

$620 - $1,859 / week

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from $87 / night

4

Vacation townhouse in Ascoli Piceno

Province of Ascoli Piceno / Ascoli Piceno

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden
Apartment in Ascoli Piceno, Parignano, mq. 100, floor ideal for short business stays, summer vacation, holidays or weekends throughout the year. Located in a small building in via Nazario Sauro, 19/A in a central area of the city very peaceful and quiet. It consists of …see more

from $100 / night

$372 / week

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from $100 / night

(1) Excellent 

14

Vacation apartment in Grottammare

Province of Ascoli Piceno / Grottammare

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
Dear / or welcome / o and thank you for the interest shown so far to Our House of Holidays. In 2004, after a 'careful renovation of the entire private residence, our family decided to open to guests three of the five apartments available, making it a small vacation home …see more

from $75 / night

$372 - $1,016 / week

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avg. 3 hours 21 minutes

from $75 / night

6

Vacation home with swimming pool in Montefiore dell'Aso

Province of Ascoli Piceno / Montefiore dell'Aso

5 20 1 night min

  • 5 bedrooms
  • Sleeps 20
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Set in its own garden with free pool, Casa Vacanze Patrizia is just 10 km from the Marche coast and its beaches, and offers studios with kitchenettes and Wi-Fi hotspot. The apartments have a living / dining room with fully equipped kitchenette, bathroom, private entranc …see more

from $87 / night

$607 / week

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from $87 / night

(1) Excellent 

14

Vacation apartment in San Benedetto Del Tronto

Province of Ascoli Piceno / San Benedetto Del Tronto

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
La Rotonda sul Mare is a comfortable and contemporary 90m2 apartment. Perfect for couples or family who want to enjoy a relaxing holiday by the sea. Sleeps 5 adults and child under 3 in travel cot. The apartment is in a small and quiet building without a lift, but with …see more

from $91 / night

$637 / week

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Responds fast!
avg. 1 hour 37 minutes

from $91 / night

(2) Very Good 

11

San Benedetto Del Tronto Vacation apartment rental

Province of Ascoli Piceno / San Benedetto Del Tronto

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Una colorata vacanza con Nemo e Dory! Luminoso bilocale a pochissimi passi dal mare. Composto da soggiorno/cucina con divano letto, una camera matrimoniale, bagno e un ampio terrazzo perfetto per mangiare fuori nelle calde serate estive. La cucina è attrezzata di …see more

from $87 / night

$434 - $1,215 / week

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Responds fast!
avg. 3 hours 19 minutes

from $87 / night

(5) Excellent 

17

San Benedetto Del Tronto Vacation apartment rental

Province of Ascoli Piceno / San Benedetto Del Tronto

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
A lovely apartment with all comforts, ideal to spend your summer holidays by the sea in San Benedetto del Tronto (Ascoli Piceno in the province of Marche--Italy) or even for a period of residence or work in the city. Completely renovated in 2015, it is on the first floo …see more

from $72 / night

$496 - $930 / week

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Responds fast!
avg. 2 hours 25 minutes

from $72 / night

(1) Very Good 

20

Hotel apartment rental in Grottammare

Province of Ascoli Piceno / Grottammare

46 50 7 nights min

  • 46 bedrooms
  • Sleeps 50
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
The residential complex for Dimora di Mare vacation, new construction, and the first year of life, Grottammare, beautiful town of the famous Riviera delle Palme, in the province of Ascoli Piceno in Marche.In strategic location, our apartments are just 400 m away from th …see more

from $186 / night

$1,301 - $1,735 / week

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from $186 / night

(2) Excellent 

10

Vacation townhouse in Porto d'Ascoli

San Benedetto Del Tronto / Porto d'Ascoli

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Comfortable and cozy apartment on the beach of the famous Riviera delle Palme. Living room with kitchenette, sofa bed, double bedroom, bathroom and two balconies with breathtaking views of the beautiful waterfront. And 'possible to use the fully equipped kitchen to prep …see more

from $100 / night

$397 - $1,289 / week

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Responds fast!
avg. 3 hours 19 minutes

from $100 / night

13

Porto d'Ascoli Vacation condo rental

San Benedetto Del Tronto / Porto d'Ascoli

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
Apartment located in San Benedetto del Tronto, in the front row with a splendid sea view from the terrace. The apartment is new and well decorated. It has a double bedroom with four-poster bed and a bedroom with two single beds that through a sliding door can be transfo …see more

from $93 / night

$558 / week

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from $93 / night

18

Vacation apartment in San Benedetto Del Tronto

Province of Ascoli Piceno / San Benedetto Del Tronto

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Appartamento di ca. 70mq al piano terra situato in una tranquilla e storica via della città a due passi dall'isola pedonale ed a ca. di 10 minuti di cammino dalla spiaggia.  Arredato con stile e completo di tutti i comfort, dispone di un'ampia sala con due divani e tel …see more

from $62 / night

$434 - $1,413 / week

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Responds fast!
avg. 3 hours 31 minutes

from $62 / night

(1) Very Good 

20

San Benedetto Del Tronto Vacation apartment rental

Province of Ascoli Piceno / San Benedetto Del Tronto

3 4 7 nights min

  • 3 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The “Contea dei Ciliegi” (cherry county) country house is situated on the lush hill behind Pedaso, a small picturesque seaside resort by the Adriatic sea, belonging to the province district of Fermo, in the Marches region. The whole Marches region preserves a wide cultu …see more

from $84 / night

$583 - $1,301 / week

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from $84 / night

20

Vacation townhouse in Comunanza

Province of Ascoli Piceno / Comunanza

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Pet friendly
The Red Mulberry is a farm that offers mini apartments immersed in the Marche countryside straddling the provinces of Fermo and Ascoli. The apartments have one double bedroom (with possibility to add a bed), a bathroom with shower and a small kitchen. The apartments hav …see more

from $75 / night

$434 / week

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from $75 / night

(6) Excellent 

24

Vacation apartment in Montefiore dell'Aso

Province of Ascoli Piceno / Montefiore dell'Aso

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Swimming pool
Villa Rosa Bianca is a beautiful restored `casale' set in a tranquil location, yet only 12km from the sea and safe bathing areas, and 3km from Montefiore Dell'Aso, famous for its `infiorata' when the streets are covered with pictures made from flowers. Apartment Adriati …see more

from $71 / night

$459 - $645 / week

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Responds fast!
avg. 1 hour 1 minutes

from $71 / night

(4) Excellent 

10

Townhouse rental in Massignano with golf nearby

Province of Ascoli Piceno / Massignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly
Experience the beauty of staying in the heart of the medieval old town! Hill House at 6 km from the sea in the medieval historic center behind the Torre Civica. Streets, the spiazzetti frame to the bel paese. Open a window and a breathtaking view on the hills and sea co …see more

from $25 / night

$174 / week

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from $25 / night

(1) Very Good 

21

Farmhouse accommodation in Massignano

Province of Ascoli Piceno / Massignano

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Nearest beach 4 mi
  • Child friendly
  • Pet friendly
The farm is a typical Marche country house recently restored in full respect of the tradition of the place, is intended for the accommodation only, it consists of 2 independent units, surrounded by an olive grove and overlooking the sea. And 'it situated in the territor …see more

from $48 / night

$335 - $536 / week

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from $48 / night

(6) Excellent 

27

Vacation apartment in Offida

Province of Ascoli Piceno / Offida

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 15 mi
  • Child friendly
  • Car not necessary
"Abode of small lace makers" in the historical center of Offida, one of the most beautiful towns in Italy. It 'a small attic of a former bishop's palace of the fifteenth century. The dwelling consists of a living room with kitchenette, double bedroom, bathroom with show …see more

from $62 / night

$409 / week

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from $62 / night

12

Vacation b&b in Cupra Marittima

Province of Ascoli Piceno / Cupra Marittima

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Suitable for children age 5+
The B&B is on the first floor of a portion of eighteenth-century villa surrounded by greenery, with a separate entrance, just 500 metres from the sea where there are chalet, sandy beaches with free or equipped with seaside restaurants, some in the Convention. The sea ha …see more

from $199 / night

$1,363 / week

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from $199 / night

14

Vacation apartment in Grottammare

Province of Ascoli Piceno / Grottammare

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Pet friendly
Dear / or welcome / o and thank you for the interest shown so far to Our House of Holidays. In 2004, after a 'careful renovation of the entire private residence, our family decided to open to guests three of the five apartments available, making it a small vacation home …see more

from $62 / night

$310 - $954 / week

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Responds fast!
avg. 3 hours 21 minutes

from $62 / night

(8) Excellent 

29

Apartment accommodation in San Benedetto Del Tronto

Province of Ascoli Piceno / San Benedetto Del Tronto

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
A delightful apartment with all comforts, ideal to spend your summer holidays by the sea in San Benedetto del Tronto (in the province of Ascoli Piceno Marche -Italy) or even for a period of residence or work in the city. Completely renovated in 2015, is on the first fl …see more

from $100 / night

$682 - $1,239 / week

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Responds fast!
avg. 2 hours 45 minutes

from $100 / night

10

Grottammare Vacation apartment rental

Province of Ascoli Piceno / Grottammare

3 9 3 nights min

  • 3 bedrooms
  • Sleeps 9
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
On the ground floor of a country house set in an olive grove overlooking the Adriatic. The apartment has a large paved outdoor area and a lawn with fruit trees and olive trees, overlooking the harbour of San Benedetto del Tronto and, on clear days, the massive of the Gr …see more

from $112 / night

$781 - $911 / week

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from $112 / night

(1) Very Good 

10

Vacation b&b in Ripatransone

Province of Ascoli Piceno / Ripatransone

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The Marche farmhouse Laetitia is a completely refurbished, located between the hills, yet only minutes from the sea. Here you can enjoy a splendid view and relaxation, just a few km from malls, points of interest, culinary walks and everything the Piceno has to offer. …see more

from $137 / night

$954 / week

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Responds fast!
avg. 2 hours 58 minutes

from $137 / night

(1) Excellent 

21

Vacation b&b in Roccafluvione

Province of Ascoli Piceno / Roccafluvione

4 6 1 night min

  • 4 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
Il B&B si trova in ROCCAFLUVIONE (AP) terra del pregiato Tartufo Nero vicino al "PARCO DEI MONTI SIBILLINI" in uno degli angoli più tranquilli della "COLLINA MARCHIGIANA" Le stanze sono graziose,ospitali e comode, cosi composte 1 CAMERA Matrimoniale + un Bagno con fine …see more

from $25 / night

$174 / week

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Responds fast!
avg. 3 hours 37 minutes

from $25 / night

(1) Excellent 

11

Grottammare Vacation apartment rental

Province of Ascoli Piceno / Grottammare

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
New apartment near the sea, carefully tended and with 2 fabulous balconies that overlook the coast. The "The Shell" apartment is unique with an incredible sea view. Located in the pedestrian area of ​​Groton, Pearl of the Adriatic, there is no need even to cross the str …see more

from $124 / night

$521 - $1,425 / week

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from $124 / night

26

San Benedetto Del Tronto Vacation apartment accommodation

Province of Ascoli Piceno / San Benedetto Del Tronto

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0.6 mi
  • Child friendly
  • Car not necessary
RENT Cute and equipped 90 sqm apartment just 600 meters from the Sea. An environment Elegant and Comfortable Ideal for Families or Couples for a holiday of relaxation and of Tranquility. It is home to Max 6 people. The apartment is on the third floor and consists of a l …see more

from $62 / night

$558 - $1,177 / week

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from $62 / night

8

Vacation townhouse in Ascoli Piceno

Province of Ascoli Piceno / Ascoli Piceno

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Nearest beach 25 mi
  • Ask about children
  • Car not necessary
Charming apartment in the historic centre of Ascoli Piceno where relax in complete privacy. Resting on a 200 ' Tower, the alcove was restored, leaving the walls of travertine, retaining the wooden plank and terracotta floors, authentic furniture and antique textiles. A …see more

from $75 / night

$496 / week

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from $75 / night

21

Apartment accommodation in Grottammare

Province of Ascoli Piceno / Grottammare

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Pet friendly
new apartment just steps from downtown and the beach with a large terrace overlooking the sea third floor 2 bedrooms, 2 bathrooms large living room with fireplace, kitchen, living room with sofa bed. Very well maintained furnishings. Washing machine, dishwasher, wifi, a …see more

from $100 / night

$459 - $1,239 / week

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Responds fast!
avg. 3 hours 41 minutes

from $100 / night

(4) Excellent 

19

Vacation apartment in San Benedetto Del Tronto

Province of Ascoli Piceno / San Benedetto Del Tronto

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
A delightful apartment with all comforts, ideal to spend your summer holidays by the sea in San Benedetto del Tronto (in the province of Ascoli Piceno Marche -Italy) or even for a period of residence or work in the city. Completely renovated in 2015, is on the first fl …see more

from $81 / night

$558 - $1,053 / week

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Responds fast!
avg. 2 hours 25 minutes

from $81 / night

(1) Excellent 

18

Vacation apartment in Grottammare

Province of Ascoli Piceno / Grottammare

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
FOR STAYS OF 3 WEEKS APPLY FOR DISCOUNTED QUOTE. The apartment has been restored in its interior, in March 2017 and has an area of ​​approximately 40 m²; It has ceilings over 3 meters high, thick walls, shuttered windows and shutters with adjustable blades and is rented …see more

from $45 / night

$248 / week

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Responds fast!
avg. 1 hour 5 minutes

from $45 / night