50 Best Vacation Rentals in Cyclades - Holiday Lettings - Cabins

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Villas Mykonos
970 properties
Apartments Santorini
808 properties
Apartments Paros
509 properties
Villas Naxos
321 properties
Villas Tinos
164 properties
Villas Syros
142 properties
Andros
137 properties
Kea
113 properties
Villas Milos
77 properties
Apartments Sifnos
60 properties
Villas Serifos
40 properties
Apartments Ios
39 properties
Villas Antiparos
37 properties
Koufonissi
24 properties
Kithnos
18 properties
Apartments Folegandros
11 properties
Kimolos
9 properties
Amorgos
5 properties

Cyclades

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3,504 Vacation rentals

(9) Excellent 

32

Naxos Town Vacation villa rental

Naxos / Naxos Town

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Set on the beautiful hillside amidst landscaped gardens and exceptional views,this delightful property is a wonderful choice for your vacation in Naxos. Fully equipped throughout,tastefully furnished and a light and airy interior. A twin bedroom room downstairs,la …see more

from $103 / night

$721 - $1,282 / week

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Responds fast!
avg. 3 hours 20 minutes

from $103 / night

(20) Excellent 

20

Vacation villa with swimming pool in Pyrgos

Santorini / Pyrgos

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Fantastic restored detached villa in the village of Exogonia, with a private plunge pool, sun terraces and fantastic sunrise views to the beach resort of Kamari and the island of Anafi. The villa has 2 double bedrooms, both en suite. The property sleeps 6 (with …see more

from $285 / night

$1,653 - $2,792 / week

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from $285 / night

(7) Excellent 

21

Fira Vacation villa rental

Santorini / Fira

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Air conditioning
The Painters House is a lovingly restored traditional villa right in the heart of the old town of Fira. Just a few minutes walk from the famous Caldera and the main square, the villa offers luxurious accommodation in a quiet location whilst providing easy access to the …see more

from $269 / night

$1,883 / week

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Responds fast!
avg. 2 hours 44 minutes

from $269 / night

(12) Excellent 

51

Vacation villa with shared pool in Mikri Vigla

Naxos / Mikri Vigla

3 10 6 nights min

  • 3 bedrooms
  • sleeps 10
  • 6 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Casa Aragosta is a beautiful home in stunning surroundings and only 70 meters from the sea! Quite Perfect! The Villa is located in Mikri Vigla ,on the West coast of the island and approx 18 km from the main town,Chora. Naxos is the largest island in the …see more

from $149 / night

$1,042 / week

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avg. 3 hours 20 minutes

from $149 / night

(3) Very Good 

16

Vacation gite in Platis Gialos

Sifnos / Platis Gialos

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly
Parisians of Greek origin, we manage our lodging Artemis Studios with love and care. 5 minutes walk from the best beach of the island and the village of Platis Yialos, our house offers a view of the bay and the deep blue! All rooms can be booked separately. They enjoy p …see more

from $69 / night

$455 - $717 / week

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avg. 1 hour 25 minutes

from $69 / night

(5) Good 

9

Vacation b&b in Karavostasis

Folegandros / Karavostasis

4 20 1 night min

  • 4 bedrooms
  • sleeps 20
  • 1 night min
  • Air conditioning
  • Private garden
Welcome to Aegean Star Hotel Apartments! Folegandros … The small diamond of Cyclades! The most southern island of the Cyclades cluster between Santorini and Milos. Folegandros extent, reaches the 32 km2 and its distance from Piraeus is 102 n.m. …see more

from $109 / night

$109 / week

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from $109 / night

(6) Excellent 

31

Vacation villa with swimming pool in Stelida

Naxos / Stelida

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
A truely unique property ,Almiriki Villa. Innovative,stylish and ecologically friendly ,the Villa is one of five completely independent houses ,sensitively carved into the hillside on the North facing side of Stelida hill, encompassing the surrounding landscape and fl …see more

from $332 / night

$2,323 - $2,804 / week

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avg. 3 hours 20 minutes

from $332 / night

(26) Excellent 

23

Vacation villa in Tinos

Cyclades / Tinos

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Tinos is one of the biggest Greek islands of the Cyclades. It is located between Andros and Mykonos. "Panormos Art Villas" is built on the east edge of the village within the borders of the bay overlooking the fishing boats and luxury vessels that contribu …see more

from $172 / night

$801 - $1,831 / week

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from $172 / night

(6) Very Good 

19

Naoussa Vacation villa rental

Paros / Naoussa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Swimming pool
Villa Anatuzi is a unique luxurious villa built with much love and affection in a charming Cycladic spirit. The villa is positioned on a hill slope, 400 meters from the sea front next to the spectacular Acropolis, in the local village of Kolimbithres. The view of the e …see more

from $342 / night

$2,389 / week

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from $342 / night

(8) Very Good 

38

Vacation apartment rental

Naxos / Plaka

2 5 6 nights min

  • 2 bedrooms
  • sleeps 5
  • 6 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This exceptional apartment, in a small group of 5,is finished to a very high standard ,including all fittings,and is located in a perfect setting with stunning views of the Aegean and a wonderful pool from which you can enjoy the vista! Fully equipped throughout,wit …see more

from $172 / night

$1,202 - $1,442 / week

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avg. 3 hours 20 minutes

from $172 / night

(6) Very Good 

16

Villa rental in Aspro Horio with shared pool

Paros / Aspro Horio

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Villa Effie is located in a tranquil traditional Greek village called Aspro Horio. It has peaceful surrounding with a choice of beaches 5-7min drive. It has a shared pool for those lazy afternoons and is ideal for a family get away holiday for sharing quality t …see more

from $115 / night

$801 / week

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from $115 / night

(17) Very Good 

33

Vacation townhouse rental

Naxos / Naxos Town

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
This beautiful Classic Townhouse built on the original base of the Ancient Venetian city ,hundreds of years ago,was renovated in 2010 ,displaying a tasteful mix of Cycladic features and contemporary facilities. A single storey property,with a double bedroom and a ver …see more

from $103 / night

$721 - $961 / week

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Responds fast!
avg. 3 hours 20 minutes

from $103 / night

(1) Excellent 

18

Vacation apartment in Naoussa

Paros / Naoussa

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Our apartment is located 5 minutes walk from the sandy beach equipped, close to the shops and 10 minutes walk from the center of Naoussa (bars, restaurants and shops). The apartment is spacious and fully air conditioned. Large separate bedroom, kitchen with all amenitie …see more

from $52 / night

$319 - $455 / week

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avg. 27 minutes

from $52 / night

20

Studio rental in Sifnos

Cyclades / Sifnos

Studio 19 2 nights min

  • Studio
  • sleeps 19
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Sifnos is among the most beautiful Greek islands, perfectly suited for vacation and relaxation. Taking into consideration the needs of couples and families our group of rooms and apartments offers the perfect choice for relaxing vacation at accessible price. It consists …see more

from $52 / night

$401 - $801 / week

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from $52 / night

(9) Excellent 

24

Vacation villa with shared pool in Folegandros

Cyclades / Folegandros

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Welcome to LIthia. Villa Myrtia is one of 3 self-catering houses along with Villa Levanda and Villa Elia. It sleeps 5 people. It is a charming house with an antique brass double bed ( 140cms/4'6'') on the upper ground floor with a galley kitchen and bathroom. It has 2 b …see more

from $147 / night

$1,027 / week

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Responds fast!
avg. 3 hours 51 minutes

from $147 / night

(1) Excellent 

15

Vacation gite in Platis Gialos

Sifnos / Platis Gialos

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Parisians of Greek origin, we manage our house with love and care. 5 minutes walk from the best beach of the island and the village of Platis Yialos, our house offers a view of the bay and the deep blue! All rooms can be booked separately. They enjoy private terraces an …see more

from $40 / night

$281 / week

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Responds fast!
avg. 1 hour 25 minutes

from $40 / night

(8) Excellent 

33

Villa rental in Mikri Vigla

Naxos / Mikri Vigla

2 5 6 nights min

  • 2 bedrooms
  • sleeps 5
  • 6 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Oasis Garden Villa is a stylish 2 bedroomed,3 storey property that has an amazing sun terrace,with dedicated,comfortable seating affording panoramic views of mountains and sea. Spectacular indeed! Set in idyllic and picturesque gardens with vine and bougainvillea cove …see more

from $182 / night

$1,274 - $1,752 / week

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avg. 3 hours 20 minutes

from $182 / night

9

Mykonos Town Vacation villa rental

Mykonos Town / Mykonos Town

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The Star Light Villa (300 sq m.) is on the highest elevation of the island offering to their privileged guests a stunning panoramic view of sunsets, the Aegean Sea and the town of Mykonos. It is built in three levels; the ground level features 1 masterbedroom with d …see more

from $916 / night

$6,408 / week

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from $916 / night

(3) Excellent 

44

Apartment rental in Parikia

Paros / Parikia

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Niriides Studios are comprised of 14 traditional Cycladic vacation rentals ideally located directly on beautiful Krios beach. Each a/c studio apartment has a private entrance & includes a kitchen, single or double beds, full bath with shower, new flat screen TV + balco …see more

from $88 / night

$614 / week

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from $88 / night

(3) Very Good 

13

Perissa Vacation b&b rental

Santorini / Perissa

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Our SPICY CAYENNE APARTMENT sleeps four adults comfortably, and features an upstairs loft, private balcony, full kitchen and flat screen TV. The main room has a new queen sized bed and dining table, adjacent to the bathroom and kitchen, and a cute wooden staircase bri …see more

from $92 / night

$1,202 / week

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from $92 / night

61

Vacation villa with swimming pool in Santa Maria

Paros / Santa Maria

8 16 4 nights min

  • 8 bedrooms
  • sleeps 16
  • 4 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
The extremely stylish three-level Villa Veni is located on one of the most privileged spots, few steps away from the sandy beach of mikri Santa Maria, into a magnificent garden with swimming pool and BBQ! A dwelling that is characterized by elegance and style and provi …see more

from $449 / night

$3,140 / week

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from $449 / night

(1) Excellent 

26

Vacation villa with swimming pool in Choulakia

Mykonos / Choulakia

5 14 min stay varies

  • 5 bedrooms
  • sleeps 14
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
2016 Winner at World Luxury Hotel Awards - Blue Villas Collection - Best Serviced Luxury Villas in Europe GUESTS LOVE THIS VILLA BECAUSE Feel like a king of your castle in total recluse | Gorgeous pool area and surrounding open-air lounging spaces | Breathtaking views …see more

from $1,586 / night

$11,101 - $17,444 / week

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from $1,586 / night

(7) Excellent 

28

Vacation home in Antiparos Town

Antiparos / Antiparos Town

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Aiolos Home is one of four, newly constructed (2016), detached Cycladic stonehouses with spectacular views of the Sifneikos Gialos bay. The houses are set on a private property of 4000 sq meters, less than a minute walk (100 meters) from the sandy beach. Sifneikos Gialo …see more

from $115 / night

$572 - $2,724 / week

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Responds fast!
avg. 1 hour 46 minutes

from $115 / night

(1) Excellent 

21

Apartment rental in Plaka

Milos / Plaka

5 9 min stay varies

  • 5 bedrooms
  • sleeps 9
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Monastiraki Rosario is an old monastery/house built togther with a little Catholic church by the french consulate, Louis Brest, in 1820 who discovered the "Venus of Milo", bought and gave it to the Louvre museum in Paris. The house is located in Plaka, the historical c …see more

from $286 / night

$2,289 / week

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from $286 / night

6

Vacation studio in Ormos Agiou Ioannou

Tinos / Ormos Agiou Ioannou

Studio 3 2 nights min

  • Studio
  • sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Air conditioning
The 28 sqm studio is part of "Nostos" resort, which is located just 30 meters from 2 beautiful beachs at Agios Ioannis Porto area just 6,5 km from the port of Tinos. It has terrace with great sea view, it is fully equipped and it sleeps 3 persons. The property is in …see more

from $46 / night

$284 - $529 / week

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from $46 / night

(16) Excellent 

16

Vacation villa in Emporio

Santorini / Emporio

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
A unique experience, combining a traditional winery, working artists studio and holiday villa. Lovingly restored and converted into holiday accommodation and studio by local artist Jon Call, the 'Canava' building dates back to 1835, situated in a semi rural locat …see more

from $285 / night

$1,763 - $2,218 / week

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from $285 / night

(1) Excellent 

40

Villa rental in Agios Sostis

Tinos / Agios Sostis

2 8 4 nights min

  • 2 bedrooms
  • sleeps 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
90 Sqm, 2 Separate Bedrooms 2 Bathrooms Extra Sleeping Space For 4 More. Ideally located at Agios Sostis in the island of Tinos Greece. Custom Architected Cycladic home with character. Very quiet and private outdoor areas with stunning views. Three Large veranda …see more

from $110 / night

$750 - $1,650 / week

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from $110 / night

(5) Very Good 

9

Home rental in Mykonos Town

Mykonos / Mykonos Town

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning

from $229 / night

$1,373 / week

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Responds fast!
avg. 54 minutes

from $229 / night

(2) Excellent 

7

Kea Vacation studio rental

Cyclades / Kea

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Perched on the top of Ioulida, the Chora of Kea, KEA VILLAS is a hospitable holiday complex that provides its guests the essence of Greek hospitality, genuine warmth and friendliness. Seven Suites and Villas, with a panoramic view at Aegean Sea and the picturesque Chora …see more

from $109 / night

$761 / week

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from $109 / night

(3) Excellent 

30

Serifos Vacation villa rental

Cyclades / Serifos

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Spend the holiday of your dreams at the most picturesque island of Cyclades at Serifos,Karavi!. It is located between the two most beautiful beaches at Serifos, just 30 m from the beach. It s 15 minutes distance on foot to the central port (market, restaurants, shops, …see more

from $206 / night

$1,362 / week

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from $206 / night

(2) Good 

11

Perissa Vacation b&b rental

Santorini / Perissa

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome To GREEK GODDESS SPICY BEACH APARTMENTS. Hosts Zoi Metaxa and John Lutfey specialize in unique, relaxing, comfortable accommodations with a personal touch, and are committed to making your stay a memory that you will cherish forever. Our INDIGO STUDIO APARTME …see more

from $58 / night

$687 / week

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from $58 / night

(6) Excellent 

36

Vacation villa with swimming pool in Melanes

Naxos / Melanes

5 10 6 nights min

  • 5 bedrooms
  • sleeps 10
  • 6 nights min
  • Beach/lakeside relaxation
  • Nearest beach 9 mi
  • Swimming pool
Villas Guilena ,comprising of the Main house ,Guest house and separate Apartment accommodating up to 10 persons, are located in the beautiful mountain valley of Melanes. Peaceful with only the sound of goat bells yet only 15 minutes drive from the stunning beaches of A …see more

from $229 / night

$1,602 - $2,964 / week

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Responds fast!
avg. 3 hours 20 minutes

from $229 / night

17

Vacation apartment in Hermoupolis

Syros / Hermoupolis

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child friendly
Adorable little houses, ground floor two-bedroom apartments in a beautiful neoclassical building in Hermoupolis. With sea-view terrace, fully equipped, with parking space, very close to cafes, bakery, mini and supermarkets, taverns, as well as at the sports center and t …see more

from $29 / night

$201 / week

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from $29 / night

(2) Very Good 

41

Villa accommodation in Choulakia with swimming pool

Mykonos / Choulakia

4 9 4 nights min

  • 4 bedrooms
  • sleeps 9
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Andromeda, our family villa in Mykonos, offers the picture that a visitor has always wanted to experience: watching the endless Aegean Sea and the blue sky, while relaxing in the infinity swimming pool and enjoying a drink! Guests of this luxurious villa may enjoy their …see more

from $458 / night

$3,204 / week

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from $458 / night

(4) Excellent 

45

Vacation home in Emporio

Santorini / Emporio

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
Théa (Θέα), greek for "view" is a name righteously given to the apartment as it overlooks both the aegean sea, and the santorinian windmills. Shades of White is a newly constructed, traditionally designed complex of apartments located in the village of Emporio. The ma …see more

from $182 / night

$1,274 / week

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from $182 / night

14

Vacation gite in Platis Gialos

Sifnos / Platis Gialos

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Parisians of Greek origin, we manage our house with love and care. 5 minutes walk from the best beach of the island and the village of Platis Yialos, our house offers a view of the bay and the deep blue! All rooms can be booked separately. They enjoy private terraces an …see more

from $57 / night

$399 / week

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Responds fast!
avg. 1 hour 25 minutes

from $57 / night

5

Vacation apartment in Ftelia

Mykonos / Ftelia

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly
a very nice and cosy apartment in a quiet , very nice and famous area of ftelia beach of mykonos island. The apartment has 2 bedrooms ,one double bed and 2 single beds, total up to 4 people, kitchen and a bathroom. Very close to ftelia beach with a stunning and amazing …see more

from $115 / night

$801 / week

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from $115 / night

(1) Excellent 

8

Vacation home in Finikas

Syros / Finikas

3 7 1 night min

  • 3 bedrooms
  • sleeps 7
  • 1 night min
  • Nearest beach 0.1 mi
  • Child friendly
  • Car not necessary
Unique family home, on the bay with uninterrupted views of the Aegean sea. Steps from veranda lead directly to the sea, harbour views, non stop relaxation and fun in the sun for all family members. One minute walk to local bakery, supermarket, cycle hire, cook, and ta …see more

from $171 / night

$1,024 / week

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Responds fast!
avg. 1 hour 57 minutes

from $171 / night

22

Vacation apartment in Aliki

Paros / Aliki

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Comfortable apartment, located on the ground floor. a traditional house, with separate entrance, 2 bedrooms, kitchen, bathroom, washing machine, WiFi, A / C, mosquito nets, sheets and towels and beach provided, terrace and small garden with sunny bbq and sun loungers. P …see more

from $46 / night

$916 - $1,108 / week

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from $46 / night

21

Batsi Vacation apartment rental

Andros / Batsi

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Just steps from Batsi’s village square and 400 metres from the beach, Amorani Studios offers self-catering apartments with beautiful views of the village and free private parking. Amorani Studios’ location on the hillside of Batsi allows guests of Amorani Studios to en …see more

from $58 / night

$401 / week

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from $58 / night