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

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San Benedetto Del Tronto
76 properties
Grottammare
34 properties
Ascoli Piceno
32 properties
Cupra Marittima
15 properties
Ripatransone
15 properties
Offida
15 properties
Montalto delle Marche
12 properties
Montefiore dell'Aso
11 properties
Montedinove
11 properties
Acquaviva Picena
7 properties
Cossignano
7 properties
Monteprandone
6 properties
Carassai
6 properties

Province of Ascoli Piceno

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678 Vacation rentals

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 $82 / night

$696 - $2,029 / week

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Responds fast!
avg. 3 hours 24 minutes

from $82 / night

(1) Excellent 

27

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 $70 / night

$488 - $773 / week

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from $70 / 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 $146 / night

$1,016 / week

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from $146 / night

15

San Benedetto Del Tronto Vacation apartment rental

Province of Ascoli Piceno / San Benedetto Del Tronto

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
A few steps from the sea and close to all amenities of downtown San Benedetto del Tronto! Ideal apartment to spend the summer holidays to 300 mt from the sea. Brand new, renovated in 2017. With 6 beds is ideal for large families or 2 families with children. Its main fea …see more

from $83 / night

$465 - $1,104 / week

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Responds fast!
avg. 2 hours 17 minutes

from $83 / night

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 $349 / night

$1,626 - $2,903 / week

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from $349 / night

23

San Benedetto Del Tronto Vacation home 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 0.9 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 $70 / night

$488 / week

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Responds fast!
avg. 3 hours 54 minutes

from $70 / 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 $58 / night

$279 - $929 / week

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from $58 / night

(1) Excellent 

9

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
  • 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 $128 / night

$697 - $1,103 / week

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from $128 / 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 $81 / night

$536 - $857 / week

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Responds fast!
avg. 58 minutes

from $81 / 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 $83 / night

$581 / week

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from $83 / 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 $82 / night

$569 / week

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from $82 / night

17

Vacation home in Offida

Province of Ascoli Piceno / Offida

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 17 mi
  • Child friendly
House townhouse in Offida, in one of the most beautiful towns in Italy, in the historic center. We prepare two rooms with a shared bathroom for guests, a breakfast room with adjoining a small library. Panoramic terrace on the roofs of Offida. A 17 km from the Adriatic c …see more

from $41 / night

$285 / week

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from $41 / 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 $41 / night

$285 - $407 / week

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Responds fast!
avg. 51 minutes

from $41 / 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 $93 / night

$430 - $1,162 / week

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Responds fast!
avg. 3 hours 45 minutes

from $93 / night

19

Vacation apartment in San Benedetto Del Tronto

Province of Ascoli Piceno / San Benedetto Del Tronto

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
Central apartment with balcony breathtaking view on the 1st floor in a prestigious building restructured. Unique location for services and shops, with the beach just 200 meters, has 4 beds and is equipped with every comfort. Master's, comfortable and functional apartmen …see more

from $82 / night

$569 / week

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from $82 / 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 $68 / night

$407 - $871 / week

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Responds fast!
avg. 2 hours 17 minutes

from $68 / night

(3) Very Good 

23

Vacation townhouse in Montalto delle Marche

Province of Ascoli Piceno / Montalto delle Marche

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Suitable for children age 5+
  • Ask about pets
Beautiful views all around and a sense of living history. Le Marche is a stunningly beautiful region of Italy on the eastern side of the country on the Adriatic coast. Inland, the breathtaking mountains form a pastoral idyll with rolling hills and striking hillto …see more

from $51 / night

$348 / week

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Responds fast!
avg. 34 minutes

from $51 / 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 $87 / night

$605 / week

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Responds fast!
avg. 1 hour 37 minutes

from $87 / night

(1) Excellent 

8

Ascoli Piceno Vacation studio rental

Province of Ascoli Piceno / Ascoli Piceno

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 32 mi
  • Child friendly
  • Car not necessary
With its privileged location between the Duomo and the Baptistery, in the old palace Former Episcopal Seminary in 1600, the studio can accommodate 2 guests and is equipped with kitchen, air conditioning, washer-dryer. The studio apartment on the third floor with lift, …see more

from $53 / night

$337 / week

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from $53 / night

(1) Excellent 

11

Grottammare Vacation apartment rental

Province of Ascoli Piceno / Grottammare

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Elegant, new, welcoming near the sea and in the center and with a breathtaking view! The apartment "The Lighthouse" has an incredible view of the sea. Located in one of the most beautiful villas of the pedestrian area of ​​Groton, Pearl of the Adriatic, a step away from …see more

from $117 / night

$523 - $1,459 / week

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from $117 / 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 $93 / night

$638 - $1,160 / week

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Responds fast!
avg. 2 hours 17 minutes

from $93 / night

9

B&b accommodation in San Benedetto Del Tronto

Province of Ascoli Piceno / San Benedetto Del Tronto

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
The structure consists of two maisonettes in a liberty-style building in the historical centre of San Benedetto del Tronto, a stone's throw from the pedestrian area and close to the shopping streets. The waterfront area and easily accessible on foot in under 10 minutes. …see more

from $70 / night

$487 - $1,461 / week

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Responds fast!
avg. 3 hours 11 minutes

from $70 / night

(2) Very Good 

26

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
  • Nearest beach 0.1 mi
  • Child friendly
Elegant apartment with sea view, fully furnished and air conditioned, located in the second row on the sea. The beach is accessible on foot (100m from the beach) and all structures located on the Adriatic coast (the Riviera). Free parking and supermarket within walking …see more

from $47 / night

$233 - $871 / week

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Responds fast!
avg. 3 hours 42 minutes

from $47 / night

(1) Very Good 

15

San Benedetto Del Tronto Vacation apartment rental

Province of Ascoli Piceno / San Benedetto Del Tronto

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
SAN BENEDETTO DEL TRONTO (AP). Location Porto d'Ascoli and served in quiet, street of Via del Mare about 700 meters from the beach. apartment rent for short periods, 92 square meters for up to 6 people, on the ground floor: entrance hall, living room with sofa bed, kitc …see more

from $53 / night

$348 - $777 / week

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from $53 / night

8

Vacation apartment in Grottammare

Province of Ascoli Piceno / Grottammare

1 6 7 nights min

  • 1 bedroom
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
The apartment is located in a comfortable and quiet residential area. Guests can also take advantage during your stay of a large garden. This property caters to those who want to spend their holidays not far from the sea in complete relaxation. The beach is accessible b …see more

from $42 / night

$291 - $929 / week

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from $42 / night

(5) 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 $200 / night

$1,395 / week

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from $200 / 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 $92 / night

$639 - $769 / week

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from $92 / 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 $130 / night

$906 / week

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Responds fast!
avg. 3 hours 26 minutes

from $130 / night

13

Vacation apartment rental

Province of Ascoli Piceno / Grottammare

2 4 13 nights min

  • 2 bedrooms
  • Sleeps 4
  • 13 nights min
  • Nearest beach 0.15 mi
  • Child friendly
  • Car not necessary
The apartment, about 50 m², has high ceilings and large windows with shutters and is located on the ground floor of a 6-storey building (the windows do not face the county road but on a private road); It is accessed via private entrance (shared with Pineta and Gigi) and …see more

from $41 / night

$285 / week

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from $41 / 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 $117 / night

$813 / week

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from $117 / 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 $76 / night

$523 - $1,324 / week

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Responds fast!
avg. 2 hours 18 minutes

from $76 / night

22

Vacation apartment in Cupra Marittima

Province of Ascoli Piceno / Cupra Marittima

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
Apartment 145 sqm. Complete with all amenities can accommodate up to 6 adult guests and 2 children. Consisting of 3 bedrooms, 2 bathrooms; large living room with veranda overlooking the sea; kitchen, terrace and garage. Located on the first floor, opposite the pedestria …see more

from $117 / night

$1,162 - $1,742 / week

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from $117 / night

(2) Excellent 

27

Offida Vacation villa rental

Province of Ascoli Piceno / Offida

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 15 mi
  • Swimming pool
  • Child friendly
Villa Carlo is a large luxury Villa among olives trees and wineyards with private heated swimming pool (13 x 4 mts), glass house in the garden with spa and hot tube (jacuzzi up to 6 people), sauna (up to 6 people). Nature, quiet, wonderful view. Free organic wine & ol …see more

from $465 / night

$2,903 - $5,110 / week

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from $465 / night

4

Cupra Marittima Vacation apartment rental

Province of Ascoli Piceno / Cupra Marittima

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Private garden
very large apartment in a small building about 100m from the sea and close to all the other services the first floor ocean side in quiet spacious with parking spaces reserved Le Marche our region with major sites of historical importance, artistic, religious, landscape …see more

from $67 / night

$464 - $1,160 / week

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from $67 / night

(7) 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 $58 / night

$384 / week

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from $58 / night

(1) Excellent 

12

Apartment rental in Grottammare

Province of Ascoli Piceno / Grottammare

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Wonderful apartment on the sea! The apartment "L'Ancora" is a brand new, elegant apartment conveniently placed. Located in the pedestrian area of ​​Groton, downtown and along the seafront. Bars, supermarkets, restaurants, excellent bars and pizzerias, shops ... It's all …see more

from $93 / night

$465 - $1,208 / week

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from $93 / 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 $63 / night

$465 / week

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Responds fast!
avg. 2 hours 48 minutes

from $63 / night

(1) Excellent 

12

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 0.2 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 $41 / night

$232 / week

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Responds fast!
avg. 1 hour 44 minutes

from $41 / 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 $70 / night

$407 / week

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Responds fast!
avg. 35 minutes

from $70 / 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 $105 / night

$732 - $854 / week

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from $105 / night