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38 Holiday apartments & homes for a holiday with pool in Ascoli Piceno & surrounding area

Casa Lilith
Casa Lilith
Casa Lilith
Casa Lilith
Casa Lilith
Casa Lilith
Casa Lilith
Casa Lilith
Casa Lilith
Casa Lilith
Casa Lilith
Casa Lilith
Casa Lilith
Casa Lilith
Casa Lilith
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Monteprandone

Casa Lilith

9 guests
230 m2
4 bedrooms

Villa with pool and outbuilding in a secluded location 7km to long sandy beach of San Benedetto. 4 bedrooms 3 bathrooms, Panoramic view.

from 285 / night
prices from 286€ per night
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Villa Greta
Villa Greta
Villa Greta
Villa Greta
Villa Greta
Villa Greta
Villa Greta
Villa Greta
Villa Greta
Villa Greta
Villa Greta
Villa Greta
Villa Greta
Villa Greta
Villa Greta
San Benedetto del Tronto

Villa Greta

9 guests
250 m2
4 bedrooms

Private villa with pool and jacuzzi located in Monte Giberto in Le Marche, just 20 km from the beaches of Porto San Giorgio. Wi-Fi, air conditioning and a large garden are present.

from 298 / night
prices from 299€ per night
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10%
Villa Ambra
Villa Ambra
Villa Ambra
Villa Ambra
Villa Ambra
Villa Ambra
Villa Ambra
Villa Ambra
Villa Ambra
Villa Ambra
Villa Ambra
Villa Ambra
Villa Ambra
Villa Ambra
Villa Ambra
Ripatransone

Villa Ambra

14 guests
370 m2
7 bedrooms

Elegant villa with a private pool and spacious, comfortable rooms, only 10 minutes from the beaches of Grottammare

Free cancellation

10% Promotion 04/29/2026 - 05/22/2026

from 443 / night
prices from 443€ per night
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15%
Villa dei Limoni
Villa dei Limoni
Villa dei Limoni
Villa dei Limoni
Villa dei Limoni
Villa dei Limoni
Villa dei Limoni
Villa dei Limoni
Villa dei Limoni
Villa dei Limoni
Villa dei Limoni
Villa dei Limoni
Villa dei Limoni
Villa dei Limoni
Villa dei Limoni
Ripatransone

Villa dei Limoni

13 guests
360 m2
6 bedrooms

Villa dei Limoni is a roomy villa with pool in the hills of Ripatransone, just 15 minutes from the Adriatic sea.

Free cancellation

15% Promotion 05/02/2026 - 10/16/2026

from 470 / night
prices from 471€ per night
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10%
Villa La Fonte
Villa La Fonte
Villa La Fonte
Villa La Fonte
Villa La Fonte
Villa La Fonte
Villa La Fonte
Villa La Fonte
Villa La Fonte
Villa La Fonte
Villa La Fonte
Villa La Fonte
Villa La Fonte
Villa La Fonte
Villa La Fonte
Ripatransone

Villa La Fonte

18 guests
400 m2
7 bedrooms

Wonderful villa with pool perfect for families and groups of friends, lovely sea views, just few kilometers from the beautiful beaches of Grottammare and San Benedetto del Tronto.

Free cancellation

10% Promotion 04/29/2026 - 05/22/2026

from 375 / night
5.0
prices from 375€ per night
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Villa delle Rose
Villa delle Rose
Villa delle Rose
Villa delle Rose
Villa delle Rose
Villa delle Rose
Villa delle Rose
Villa delle Rose
Villa delle Rose
Villa delle Rose
Villa delle Rose
Villa delle Rose
Villa delle Rose
Villa delle Rose
Villa delle Rose
Montalto delle Marche

Villa delle Rose

16 guests
350 m2
7 bedrooms

Villa with panoramic pool in the hills of the Piceno, just 20 minutes from the beaches of Cupra Marittima, up to 16 people, ideal for families with children.

Free cancellation
from 330 / night
5.0
prices from 330€ per night
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10%
Villa Montefiore
Villa Montefiore
Villa Montefiore
Villa Montefiore
Villa Montefiore
Villa Montefiore
Villa Montefiore
Villa Montefiore
Villa Montefiore
Villa Montefiore
Villa Montefiore
Villa Montefiore
Villa Montefiore
Villa Montefiore
Villa Montefiore
Montefiore dell'Aso

Villa Montefiore

14 guests
200 m2
8 bedrooms

Beautiful and spacious villa with private pool and large garden, located in Montefiore dell'Aso, just a few kilometres from the Adriatic coast.

Free cancellation

10% Promotion 04/29/2026 - 05/22/2026

from 396 / night
prices from 396€ per night
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15%
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
6 guests
32 m2
3 bedrooms

15% Promotion 05/23/2026 - 09/20/2026

from 218 / night
4.5
prices from 218€ per night
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15%
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
4 guests
32 m2
2 bedrooms

15% Promotion 05/23/2026 - 09/20/2026

from 173 / night
4.4
prices from 173€ per night
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15%
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
Porto Sant'Elpidio
Holiday flat family holiday Porto Sant'Elpidio
4 guests
42 m2
2 bedrooms

15% Promotion 05/23/2026 - 09/20/2026

from 122 / night
4.5
prices from 122€ per night
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15%
Villa Anna Maria
Villa Anna Maria
Villa Anna Maria
Villa Anna Maria
Villa Anna Maria
Villa Anna Maria
Villa Anna Maria
Villa Anna Maria
Villa Anna Maria
Villa Anna Maria
Villa Anna Maria
Villa Anna Maria
Villa Anna Maria
Villa Anna Maria
Villa Anna Maria
Monteprandone

Villa Anna Maria

15 guests
700 m2
7 bedrooms

Elegant villa with pool near Monteprandone, in the South of Le Marche, just 15 minutes from the beach of San Benedetto del Tronto

Free cancellation

15% Promotion 08/01/2026 - 08/28/2026

from 400 / night
prices from 400€ per night
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5%
Villa Lerant
Villa Lerant
Villa Lerant
Villa Lerant
Villa Lerant
Villa Lerant
Villa Lerant
Villa Lerant
Villa Lerant
Villa Lerant
Villa Lerant
Villa Lerant
Villa Lerant
Villa Lerant
Villa Lerant
Acquaviva Picena

Villa Lerant

9 guests
160 m2
4 bedrooms

Wonderful villa in the hills with heated pool, wellness area and air conditioning, just 10 minutes from the beach of San Benedetto del Tronto

Free cancellation

5% Promotion 04/29/2026 - 10/02/2026

from 471 / night
prices from 472€ per night
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15%
Villa Torre
Villa Torre
Villa Torre
Villa Torre
Villa Torre
Villa Torre
Villa Torre
Villa Torre
Villa Torre
Villa Torre
Villa Torre
Villa Torre
Villa Torre
Villa Torre
Villa Torre
Ripatransone

Villa Torre

12 guests
240 m2
5 bedrooms

Villa with heated pool with 4 hydro-massage seats, air conditioning, wellness area with sauna and whirlpool bathtub, stunning panoramic view, just 10 minutes from the sea

Free cancellation

15% Promotion 04/29/2026 - 05/22/2026

from 286 / night
prices from 286€ per night
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Il Vecchio Acero - Girasole
Il Vecchio Acero - Girasole
Il Vecchio Acero - Girasole
Il Vecchio Acero - Girasole
Il Vecchio Acero - Girasole
Il Vecchio Acero - Girasole
Il Vecchio Acero - Girasole
Il Vecchio Acero - Girasole
Il Vecchio Acero - Girasole
Il Vecchio Acero - Girasole
Il Vecchio Acero - Girasole
Il Vecchio Acero - Girasole
Il Vecchio Acero - Girasole
Il Vecchio Acero - Girasole
Il Vecchio Acero - Girasole
Montalto delle Marche

Il Vecchio Acero - Girasole

5 guests
80 m2
2 bedrooms

Agriturismo surrounded in the green hills of the Apennines in the background and a few kilometers from the Adriatic coast

from 140 / night
prices from 140€ per night
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Serene Escape, Ascoli Piceno
Serene Escape, Ascoli Piceno
Serene Escape, Ascoli Piceno
Serene Escape, Ascoli Piceno
Serene Escape, Ascoli Piceno
Serene Escape, Ascoli Piceno
Serene Escape, Ascoli Piceno
Serene Escape, Ascoli Piceno
Serene Escape, Ascoli Piceno
Serene Escape, Ascoli Piceno
Serene Escape, Ascoli Piceno
Serene Escape, Ascoli Piceno
Serene Escape, Ascoli Piceno
Serene Escape, Ascoli Piceno
Serene Escape, Ascoli Piceno
Ascoli Piceno
Serene Escape, Ascoli Piceno
4 guests
85 m2
2 bedrooms

On the 1st floor: (Living room(TV, fireplace, seating area), Kitchen(dining table, stove, electric kettle, coffee machine, microwave, dishwasher, fridge, washing machine)

Free cancellation
from 202 / night
4.4
prices from 202€ per night
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Apartment in Marche near Grottammare Beach
Apartment in Marche near Grottammare Beach
Apartment in Marche near Grottammare Beach
Apartment in Marche near Grottammare Beach
Apartment in Marche near Grottammare Beach
Apartment in Marche near Grottammare Beach
Apartment in Marche near Grottammare Beach
Apartment in Marche near Grottammare Beach
Apartment in Marche near Grottammare Beach
Apartment in Marche near Grottammare Beach
Apartment in Marche near Grottammare Beach
Apartment in Marche near Grottammare Beach
Apartment in Marche near Grottammare Beach
Apartment in Marche near Grottammare Beach
Apartment in Marche near Grottammare Beach
Ascoli Piceno
Apartment in Marche near Grottammare Beach
4 guests
90 m2
2 bedrooms

Ground floor: (Kitchen(stove, electric kettle, microwave, dishwasher, fridge), Living/diningroom(TV, dining table, fireplace, seating area), bedroom(bunk bed)

Free cancellation
from 224 / night
4.3
prices from 224€ per night
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Magnifique Villa with Pool
Magnifique Villa with Pool
Magnifique Villa with Pool
Magnifique Villa with Pool
Magnifique Villa with Pool
Magnifique Villa with Pool
Magnifique Villa with Pool
Magnifique Villa with Pool
Magnifique Villa with Pool
Magnifique Villa with Pool
Magnifique Villa with Pool
Magnifique Villa with Pool
Magnifique Villa with Pool
Magnifique Villa with Pool
Magnifique Villa with Pool
Amandola
Magnifique Villa with Pool
19 guests
430 m2
8 bedrooms

Ground floor: (Living room(TV, seating area), Large kitchen(TV, dining table, stove, electric kettle, coffee machine, espresso machine, oven, microwave, dishwasher, fridge-freezer)

Free cancellation
from 182 / night
4.3
prices from 182€ per night
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Apartment in Marche near Sibillini Park
Apartment in Marche near Sibillini Park
Apartment in Marche near Sibillini Park
Apartment in Marche near Sibillini Park
Apartment in Marche near Sibillini Park
Apartment in Marche near Sibillini Park
Apartment in Marche near Sibillini Park
Apartment in Marche near Sibillini Park
Apartment in Marche near Sibillini Park
Apartment in Marche near Sibillini Park
Apartment in Marche near Sibillini Park
Apartment in Marche near Sibillini Park
Apartment in Marche near Sibillini Park
Apartment in Marche near Sibillini Park
Apartment in Marche near Sibillini Park
Ascoli Piceno
Apartment in Marche near Sibillini Park
4 guests
107 m2
2 bedrooms

Ground floor: (Living room(TV, fireplace, seating area), open kitchen(dining table, stove, coffee machine, microwave, dishwasher, fridge, washing machine), bedroom(double bed)

Free cancellation
from 228 / night
4.4
prices from 228€ per night
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Hillside Comfort with Sauna
Hillside Comfort with Sauna
Hillside Comfort with Sauna
Hillside Comfort with Sauna
Hillside Comfort with Sauna
Hillside Comfort with Sauna
Hillside Comfort with Sauna
Hillside Comfort with Sauna
Hillside Comfort with Sauna
Hillside Comfort with Sauna
Hillside Comfort with Sauna
Hillside Comfort with Sauna
Hillside Comfort with Sauna
Hillside Comfort with Sauna
Hillside Comfort with Sauna
Ascoli Piceno
Hillside Comfort with Sauna
4 guests
77 m2
2 bedrooms

Mezzanine: (bedroom(double bed, air conditioning), bathroom(washbasin, toilet)) On the 1st floor: (Living room(TV, fireplace, seating area, air conditioning)

Free cancellation
from 173 / night
4.1
prices from 174€ per night
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Apartment near Assisi with pool and hot tub
Apartment near Assisi with pool and hot tub
Apartment near Assisi with pool and hot tub
Apartment near Assisi with pool and hot tub
Apartment near Assisi with pool and hot tub
Apartment near Assisi with pool and hot tub
Apartment near Assisi with pool and hot tub
Apartment near Assisi with pool and hot tub
Apartment near Assisi with pool and hot tub
Apartment near Assisi with pool and hot tub
Apartment near Assisi with pool and hot tub
Apartment near Assisi with pool and hot tub
Apartment near Assisi with pool and hot tub
Apartment near Assisi with pool and hot tub
Apartment near Assisi with pool and hot tub
Acquaviva Picena
Apartment near Assisi with pool and hot tub
5 guests
95 m2
2 bedrooms

Mezzanine: (bedroom(single bed, single bed, single bed, air conditioning)) On the 1st floor: (open kitchen(stove, electric kettle, toaster, oven, microwave, dishwasher, fridge, wa...

Free cancellation
from 207 / night
prices from 207€ per night
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Apartment in Marche near Sandy Beaches
Apartment in Marche near Sandy Beaches
Apartment in Marche near Sandy Beaches
Apartment in Marche near Sandy Beaches
Apartment in Marche near Sandy Beaches
Apartment in Marche near Sandy Beaches
Apartment in Marche near Sandy Beaches
Apartment in Marche near Sandy Beaches
Apartment in Marche near Sandy Beaches
Apartment in Marche near Sandy Beaches
Apartment in Marche near Sandy Beaches
Apartment in Marche near Sandy Beaches
Apartment in Marche near Sandy Beaches
Apartment in Marche near Sandy Beaches
Apartment in Marche near Sandy Beaches
San Benedetto del Tronto
Apartment in Marche near Sandy Beaches
5 guests
95 m2
2 bedrooms

Mezzanine: (bedroom(single bed, single bed, single bed, air conditioning)) On the 1st floor: (open kitchen(stove, electric kettle, toaster, oven, microwave, dishwasher, fridge, wa...

Free cancellation
from 206 / night
4.2
prices from 206€ per night
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Relaxing Retreat in San Savino
Relaxing Retreat in San Savino
Relaxing Retreat in San Savino
Relaxing Retreat in San Savino
Relaxing Retreat in San Savino
Relaxing Retreat in San Savino
Relaxing Retreat in San Savino
Relaxing Retreat in San Savino
Relaxing Retreat in San Savino
Relaxing Retreat in San Savino
Relaxing Retreat in San Savino
Relaxing Retreat in San Savino
Relaxing Retreat in San Savino
Relaxing Retreat in San Savino
Relaxing Retreat in San Savino
Ascoli Piceno
Relaxing Retreat in San Savino
5 guests
80 m2
2 bedrooms

Ground floor: (open kitchen(TV, dining table, stove, electric kettle, coffee machine, microwave, dishwasher, fridge, washing machine, air conditioning)

Free cancellation
from 219 / night
4.2
prices from 220€ per night
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Large Group Retreat with Pool
Large Group Retreat with Pool
Large Group Retreat with Pool
Large Group Retreat with Pool
Large Group Retreat with Pool
Large Group Retreat with Pool
Large Group Retreat with Pool
Large Group Retreat with Pool
Large Group Retreat with Pool
Large Group Retreat with Pool
Large Group Retreat with Pool
Large Group Retreat with Pool
Large Group Retreat with Pool
Large Group Retreat with Pool
Large Group Retreat with Pool
Amandola
Large Group Retreat with Pool
15 guests
330 m2
6 bedrooms

Ground floor: (Living room(TV, seating area), Large kitchen(TV, dining table, stove, electric kettle, coffee machine, espresso machine, oven, microwave, dishwasher, fridge-freezer)

Free cancellation
from 185 / night
4.3
prices from 186€ per night
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Scenic Hideaway with Pool
Scenic Hideaway with Pool
Scenic Hideaway with Pool
Scenic Hideaway with Pool
Scenic Hideaway with Pool
Scenic Hideaway with Pool
Scenic Hideaway with Pool
Scenic Hideaway with Pool
Scenic Hideaway with Pool
Scenic Hideaway with Pool
Scenic Hideaway with Pool
Scenic Hideaway with Pool
Scenic Hideaway with Pool
Scenic Hideaway with Pool
Scenic Hideaway with Pool
Amandola
Scenic Hideaway with Pool
8 guests
260 m2
3 bedrooms

Ground floor: (Living room(TV), storage, washing machine, ironing board, iron) On the 1st floor: (Living room(TV, fireplace, seating area), dining room(dining table)

Free cancellation
from 98 / night
3.9
prices from 99€ per night
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Cozy Retreat with Garden
Cozy Retreat with Garden
Cozy Retreat with Garden
Cozy Retreat with Garden
Cozy Retreat with Garden
Cozy Retreat with Garden
Cozy Retreat with Garden
Cozy Retreat with Garden
Cozy Retreat with Garden
Cozy Retreat with Garden
Cozy Retreat with Garden
Cozy Retreat with Garden
Cozy Retreat with Garden
Cozy Retreat with Garden
Cozy Retreat with Garden
Ascoli Piceno
Cozy Retreat with Garden
2 guests
43 m2
1 bedroom

On the 1st floor: (open kitchen(TV, dining table, stove, seating area, electric kettle, toaster, coffee machine, microwave, dishwasher, fridge, washing machine)

Free cancellation
from 110 / night
4.3
prices from 111€ per night
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Guest reviews of our holiday apartments in Ascoli Piceno & surrounding area

4.2

Apartment in Grottammare with Jacuzzi &...

Acquaviva Picena

View Spanish

The apartment is well-equipped and had all the amenities we needed. It is pet-friendly, which was a big plus for us since we brought our dog. The area was quiet, and we loved having easy access to local parks. A relaxing stay overall!


from 147€ night
5.0

Splendid location suitable for groups.

Villa La Fonte

Ripatransone

View Italian

Splendid location suitable for groups.

Group of friends who rent a property every year to spend New Year's together. Definitely one of the best solutions ever found. The house was perfectly heated (rare in winter for such large structures), we found a thorough cleaning with scented sheets. Super equipped kitchen with quality appliances. We also appreciated the wood-fired oven where we cooked with excellent results. The external parts are impeccably cared for and the kindness of the owners allows us to recommend this house to everyone without reservation, sure to make a good impression. For the summer, we would like to point out the beautiful swimming pool with a sea view (about 20 minutes by car to the closest beach). Everything is ok, thank you.


from 375€ night
5.0

Just amazing

Villa delle Rose

Montalto delle Marche

Just amazing

We really enjoyed the stay at Villa Delle Rose. The house is big and comfortable, nothing was missing. The pool and the view were just amazing and the hosts are always ready to help! The beach is at 15 minutes away and people are charming. We definitely have to go back!


from 330€ night

Popular regions and locations for your holiday homes with pool in Ascoli Piceno & surrounding area

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