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

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672 Vacation rentals

(7) Excellent 

25

Villa accommodation in Carassai with swimming pool

Province of Ascoli Piceno / Carassai

4 9 1 night min

  • 4 bedrooms
  • sleeps 9
  • 1 night min
  • Nearest beach 5 mi
  • Swimming pool
  • Child friendly
A well furnished villa with a private swimming pool and stunning views. Peaceful and relaxing surroundings where you can while away the hours around the pool or from the beautiful terrace, eating and drinking the local produce whilst admiring the wonderful surroundings …see more

from $265 / night

$1,854 / week

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from $265 / night

(5) Excellent 

27

Vacation apartment in Montefiore dell'Aso

Province of Ascoli Piceno / Montefiore dell'Aso

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • 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, and 3km from Montefiore Dell'Aso, famous for its `infiorata' when the streets are covered with pictures made from flowers. Apartment Sibilli …see more

from $122 / night

$818 - $1,474 / week

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avg. 1 hour 0 minutes

from $122 / night

(11) Excellent 

21

Ortezzano Vacation b&b rental

Province of Ascoli Piceno / Ortezzano

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Nearest beach 20 mi
  • Swimming pool
  • Child friendly
At a very Sunny and panoramic place nice B&B whit Familyroom,dubbelrooms and appartments. Right between the olivetrees and Vineyard. The familyroom has a Double room whit private bathroom and very large privet roofterras, Whit wonderfull view at the sibilian mountains …see more

from $85 / night

$588 / week

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from $85 / night

(1) Excellent 

5

Vacation villa rental

Province of Ascoli Piceno / Monteprandone

3 7 7 nights min

  • 3 bedrooms
  • sleeps 7
  • 7 nights min
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly
VILLA MATILDA MONTEPRANDONE ELEGANT VILLA IN HILL AREA OF THE CITY OF MONTEPRANDONE, VIEWS OF THE SEA AND MOUNTAINS EAST-SOUTH-WEST, WITH POOL, GARDEN AND PRIVATE PARKING. It DEVELOPS ON THREE LEVELS: GROUND FLOOR, WITH LARGE WINDOWS overlooking the WIDE PORCH WITH DIRE …see more

from $392 / night

$2,611 / week

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from $392 / night

7

Monteprandone Vacation villa rental

Province of Ascoli Piceno / Monteprandone

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
Elegante villa in collina, vista panoramica dal mare ai monti, piscina,grande giardino e ampio parcheggio privato. tre camere matrimoniali con possibilità di aggiungere letto singolo e/o culla, 2 bagni con vasca e doccia, 2 bagni di servizio, salotto e salone con vetrat …see more

from $392 / night

$1,828 - $3,447 / week

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from $392 / night

22

Vacation apartment with shared pool in Appignano del Tronto

Province of Ascoli Piceno / Appignano del Tronto

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Nearest beach 25 mi
  • Swimming pool
  • Child friendly
Apartment ' VISTA MARE ' is located on the East side of the villa. In the morning sun you can here on your private terrace or enjoy your breakfast under the covered Gazebo. You have a great view over the rolling hills and the typical ' typical and beautiful Calanghi for …see more

from $164 / night

$1,143 / week

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from $164 / night

(3) Very Good 

20

Vacation villa in Grottammare

Province of Ascoli Piceno / Grottammare

2 6 5 nights min

  • 2 bedrooms
  • sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Apartment in villa renovated in 2014 of approximately 200 sqm on the ground floor with large private fenced garden, 1 bedroom, 1 double room, sofa bed in living room, 2 bathrooms, one with bath, kitchen, dining room with wood burning fireplace, large living room with TV …see more

from $104 / night

$718 - $865 / week

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from $104 / night

(1) Excellent 

16

Ascoli Piceno ski b&b to rent.

Province of Ascoli Piceno / Ascoli Piceno

2 9 1 night min

  • 2 bedrooms
  • sleeps 9
  • 1 night min
  • Beach/lakeside relaxation
  • Ski
  • Child friendly
Our B&B is located in an area surrounded by peaceful countryside, in an area rich in historical, architectural and cultural, in a place with a spectacular view of the hills. The Nightingale is a charming and elegant building, an ancient building where the echoes of the …see more

from $72 / night

$392 / week

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Responds fast!
avg. 3 hours 59 minutes

from $72 / night

(11) Excellent 

19

Vacation apartment with swimming pool in Offida

Province of Ascoli Piceno / Offida

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool
The apartment is part of a large Liberty listed villa, dating back to the 15th century and recently restored with the help of local artisans to a high standard, set within extensive private grounds. The apartment is completely private and self-contained, with its own e …see more

from $157 / night

$1,045 - $1,828 / week

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from $157 / night

13

Vacation apartment in Ripatransone

Province of Ascoli Piceno / Ripatransone

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Our Apartments 3 comfortable apartments each with its own terrace overlooking the sea or panoramic mountain views. Just a few hundred meters from the Rotweinstrasse the brands The wellness oasis Nestled in 5,000 square meters Mediterranean, partly subtropical garden "Il …see more

from $92 / night

$640 / week

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from $92 / night

(3) Very Good 

26

Vacation apartment in Montefiore dell'Aso

Province of Ascoli Piceno / Montefiore dell'Aso

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • 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 $90 / night

$602 / week

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avg. 1 hour 0 minutes

from $90 / night

(6) Excellent 

3

Vacation b&b rental

Province of Ascoli Piceno / Colli Del Tronto

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 15 mi
  • Child friendly
  • Air conditioning
Mellon è un edificio rurale risalente agli inizi del ‘900, profondamente ristrutturato nel corso del 2015 all’insegna della sostenibilità. L’efficientamento energetico, l’ampio impiego del legno per solai e coperture, l’edificio interamente alimentato dall’energia elett …see more

from $98 / night

$686 / week

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from $98 / night

4

Condo rental in Carassai

Province of Ascoli Piceno / Carassai

2 3 1 night min

  • 2 bedrooms
  • sleeps 3
  • 1 night min
  • Child friendly
  • Ask about pets
The property is located in Carassai at 400mt from the historical centre, very close to the main roads. The apartment is fully furnished with precious finishes in a total white style, is situated on the ground floor and have large balconies. There are 2 bedrooms one doub …see more

from $92 / night

$588 / week

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from $92 / 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
  • Nearest beach 0.18 mi
  • 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 $168 / night

$1,175 / week

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avg. 3 hours 3 minutes

from $168 / night

(1) Excellent 

31

Vacation condo in San Benedetto Del Tronto

Province of Ascoli Piceno / San Benedetto Del Tronto

2 3 min stay varies

  • 2 bedrooms
  • sleeps 3
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Attic recently renovated with new furniture, new floors, new windows, energy-efficient windows, armored door. Independent heating and air conditioning, in the master bedroom. It is located in a building on the third floor without elevator in a residential area. I leave …see more

from $50 / night

$348 / week

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avg. 3 hours 26 minutes

from $50 / night

(2) Very Good 

25

Montalto delle Marche Vacation home rental

Province of Ascoli Piceno / Montalto delle Marche

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 25 mi
  • Child friendly
Structure farm nestled in the green hills in the background of the Apennines and a few kilometers from the Adriatic coast. A large garden and swimming pool will be a beautiful setting for your holiday in the Marche. The old stone farmhouse, beautifully restored, consist …see more

from $85 / night

$588 - $869 / week

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from $85 / night

32

Vacation apartment with swimming pool in Montalto delle Marche

Province of Ascoli Piceno / Montalto delle Marche

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Nearest beach 23 mi
  • Swimming pool
  • Child friendly
The Apartment of flowers is located in the heart of the Marche region of Italy, located 20 minutes from the beaches of the Adriatic and the Apennine mountains, so you can spend the day at the beach and the evening in the country. We offer a comfortable holiday fo …see more

from $178 / night

$457 / week

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from $178 / 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 $59 / night

$413 / week

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Responds fast!
avg. 3 hours 48 minutes

from $59 / 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 $105 / night

$849 - $1,959 / week

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avg. 3 hours 59 minutes

from $105 / night

4

Vacation home in Montefiore dell'Aso

Province of Ascoli Piceno / Montefiore dell'Aso

3 5 7 nights min

  • 3 bedrooms
  • sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary
This elegant home in the center of a lovely medieval village is my home for part of the year. The renovation of this gem is complete, with a gourmet kitchen, formal dining room, two complete all new bathrooms, and comfortable bedrooms. Two living rooms, one a former m …see more

from $85 / night

$590 / week

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from $85 / night

(1) Very Good 

14

Townhouse rental in San Benedetto Del Tronto

Province of Ascoli Piceno / San Benedetto Del Tronto

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Two-roomed apartment situated near by sea at Porto d'ascoli about 500 m from the seafront. The apartment is part of a newly built complex with shops and activities on the ground floor. Composed of a living-room/kitchenette, hallway, bathroom with shower and double bedro …see more

from $79 / night

$457 / week

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avg. 32 minutes

from $79 / night

(1) Excellent 

18

Vacation apartment in Grottammare

Province of Ascoli Piceno / Grottammare

1 4 14 nights min

  • 1 bedroom
  • sleeps 4
  • 14 nights min
  • 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 $38 / night

$261 / week

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Responds fast!
avg. 1 hour 46 minutes

from $38 / 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 $105 / night

$784 - $2,370 / week

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avg. 3 hours 59 minutes

from $105 / night

(2) Excellent 

19

Porto d'Ascoli Vacation apartment rental

San Benedetto Del Tronto / Porto d'Ascoli

1 5 3 nights min

  • 1 bedroom
  • sleeps 5
  • 3 nights min
  • Child friendly
  • Pet friendly
House of Irma is a structure suitable for families for long or short periods of holidays by the sea, convenient to walk to the beach and central to all the services of banks, restaurants pubs and supermarkets. Just 5min drive from the motorway exit, the Irma House offer …see more

from $72 / night

$457 / week

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from $72 / night

(8) Excellent 

13

B&b rental in Monteprandone

Province of Ascoli Piceno / Monteprandone

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Ask about children
  • Pet friendly
The b & b 5 Colli is surrounded by the rolling hills of Piceno, a warm and welcoming simple opportunity to relax in complete serenity. The b & b 5 hills has an orchard, a vegetable garden and an olive grove, for breakfast homemade cakes are prepared exclusively with nat …see more

from $46 / night

$320 - $457 / week

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Responds fast!
avg. 1 hour 11 minutes

from $46 / night

(1) Excellent 

7

Cupra Marittima Vacation apartment rental

Province of Ascoli Piceno / Cupra Marittima

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Residence Marano is a lovely newly built property located in the town of Cupra Marittima, just 500 mt. the fine white beach and on the slopes of the old medieval village of Marano, from which you can enjoy the enchanting view towards the sea and the medieval family. The …see more

from $84 / night

$588 - $1,502 / week

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from $84 / night

(2) Very Good 

12

Vacation apartment in Grottammare

Province of Ascoli Piceno / Grottammare

1 4 14 nights min

  • 1 bedroom
  • sleeps 4
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Ask about children
FOR STAYS OF 3 WEEKS DISCOUNTED ASK FOR QUOTATION. The apartment, about 40 m², on the first floor of a small building; It has ceilings over 3 meters high, thick walls in the kitchen and bathroom windows with blinds and shutters. And 'in vacation rental estive.E' compris …see more

from $38 / night

$261 / week

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Responds fast!
avg. 1 hour 46 minutes

from $38 / night

(15) Excellent 

26

Vacation home in Ripatransone

Province of Ascoli Piceno / Ripatransone

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
In the heart of the Marches vineyards, on the road of DOC Rosso Piceno is the Dimora Country Tenuta Cocci Grifoni. The building, once the home of the family owners, enjoys a panoramic view of the nearby medieval villages of Ripatransone and Offida and lies halfway betwe …see more

from $163 / night

$1,136 / week

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from $163 / night

(1) Excellent 

14

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
  • 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 $118 / night

$825 / week

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Responds fast!
avg. 1 hour 37 minutes

from $118 / night

31

Vacation home with swimming pool in Montalto delle Marche

Province of Ascoli Piceno / Montalto delle Marche

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 24 mi
  • Swimming pool
  • Child friendly
Your holiday house is situated in beautiful open countryside 250 metres above sea-level, only 20 minutes from the beaches of the Adriatic and 20 minutes from the splendid Appenine mountains. La Dependence is a detached farm cottage approximately 80 square metres …see more

from $92 / night

$640 / week

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from $92 / night

(1) Excellent 

18

Townhouse rental in Grottammare

Province of Ascoli Piceno / Grottammare

1 4 14 nights min

  • 1 bedroom
  • sleeps 4
  • 14 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
ASK ESTIMATE DISCOUNTED FOR STAYS OVER 20 DAYS. Notice for SUMMER 2017: outside the building there is a scaffolding construction. But there are NO jobs in progress and the scaffold itself is only present in front of the kitchen window and allows you to close the shutter …see more

from $66 / night

$407 / week

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Responds fast!
avg. 1 hour 46 minutes

from $66 / night

(10) 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 $105 / night

$718 - $1,241 / week

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Responds fast!
avg. 2 hours 43 minutes

from $105 / night

(1) Excellent 

8

Vacation apartment in Ascoli Piceno

Province of Ascoli Piceno / Ascoli Piceno

5 5 1 night min

  • 5 bedrooms
  • sleeps 5
  • 1 night min
  • Child friendly
The Bed and Breakfast "La culla dei Sabini" is located in the historic city center, just steps from the Renaissance Piazza del Popolo. Staying here means to live in independence and comfort, the charm of Ascoli Piceno. The B & B is an open space with a mezzanine floor a …see more

from $66 / night

$315 - $1,048 / week

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from $66 / night

(2) Excellent 

25

Vacation cottage in Ascoli Piceno

Province of Ascoli Piceno / Ascoli Piceno

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 36 mi
  • Child friendly
La Casetta is a self-contained single storey stone cottage situated on the side of Monte Piselli with views down over Ascoli Piceno and the Tronto valley right the way down to the Adriatic coast. Comprising three bedrooms, a family bathroom, a large lounge/dining room/k …see more

from $118 / night

$745 - $1,175 / week

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from $118 / night

7

Townhouse rental in Cupra Marittima

Province of Ascoli Piceno / Cupra Marittima

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Air conditioning
Charming attic apartment surrounded by greenery, in a villa with Park and sea views, with double bedroom and bathroom with bath and Cork, in open-space with air conditioning: kitchen area, equipped with comforts and small peninsula for breakfast, dining area and sitting …see more

from $131 / night

$849 / week

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from $131 / night

(1) Excellent 

13

Apartment rental in Cupra Marittima

Province of Ascoli Piceno / Cupra Marittima

3 5 7 nights min

  • 3 bedrooms
  • sleeps 5
  • 7 nights min
  • Child friendly
  • Pet friendly
Residence Marano is a lovely newly built property located in the town of Cupra Marittima, just 500 mt. the fine white beach and on the slopes of the old medieval village of Marano, from which you can enjoy the enchanting view towards the sea and the medieval family. The …see more

from $85 / night

$591 - $1,510 / week

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from $85 / night

(7) Excellent 

27

Vacation apartment in Offida

Province of Ascoli Piceno / Offida

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • 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 $79 / night

$431 / week

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from $79 / night

6

Vacation apartment in Porto d'Ascoli

San Benedetto Del Tronto / Porto d'Ascoli

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Nearest beach 0.18 mi
  • Child friendly
  • Air conditioning
RESIDENCE NEAR THE SEA, THREE KM FROM THE CENTER, IN FRONT OF CYCLE PATH IN SUMMER FROM JUNE TO META 'September ALL-INCLUSIVE CONSUMPTION AND AIR CONDITIONING BEACH CLOTHES AND BIKE. NEARBY RESTAURANTS MINIMARKET CINEMA PARK-CHILDREN. CHALET ON THE BEACH WITH ANIMATION. …see more

from $234 / night

$1,632 / week

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Responds fast!
avg. 3 hours 3 minutes

from $234 / night

(3) Very Good 

20

Ascoli Piceno Vacation b&b rental

Province of Ascoli Piceno / Ascoli Piceno

2 7 1 night min

  • 2 bedrooms
  • sleeps 7
  • 1 night min
  • Nearest beach 30 mi
  • Child friendly
the special feature of this villa, of which we possess a large apartment two floors with a total of 150 square meters, is being totally immersed in the greenery and quiet, with the convenience of a reserved parking space, without taking sides, the Center more than a 3-m …see more

from $66 / night

$392 / week

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from $66 / night

21

Vacation apartment in Cupra Marittima

Province of Ascoli Piceno / Cupra Marittima

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 0.2 mi
  • Child friendly
  • Pet friendly
La villa in questione , sita a Cupra Marittima in Via Rossini n.12 , è di complessivi circa 370metri quadri è composta da un piano terra con relativo accesso di ingresso indipendente e da un primo piano con relativo accesso di ingresso indipendente .Tale villa dista cir …see more

from $71 / night

$523 / week

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from $71 / night

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