50 Best Vacation Rentals in Cyclades - Holiday Lettings - Cabins

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Villas Mykonos
1,044 properties
Apartments Santorini
827 properties
Apartments Paros
485 properties
Villas Naxos
266 properties
Villas Tinos
128 properties
Villas Syros
117 properties
Andros
115 properties
Kea
105 properties
Villas Milos
84 properties
Apartments Sifnos
66 properties
Villas Antiparos
49 properties
Apartments Ios
33 properties
Villas Serifos
32 properties
Koufonissi
19 properties
Amorgos
17 properties
Apartments Folegandros
13 properties
Kithnos
6 properties

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3,443 Vacation rentals

12

Vacation villa in Plintri

Mykonos / Plintri

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly
The Villa Vrachos is a creation of one of the oldest families of Mykonos. A complex consisting of an apartment (4 persons) 50 sq.m. with private pool and two pool studios (3 & 4 people). Located in a very privileged position as it is close to the airport and with easy …see more

from $164 / night

$984 - $2165 / week

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from $164 / night

(6) Excellent 

24

Vacation apartment in Plaka

Naxos / Plaka

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Evriali is a new beachfront apartment built in 2012 on a privileged location at the end of Plaka beach, with a large garden -more than 3000 m2- of herbs, fruits, flowers and trees that end to a path that leads you straight to the beach. Just a few steps to the beac …see more

from $164 / night

$1148 - $1990 / week

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from $164 / night

(7) Excellent 

42

Vacation apartment in Folegandros

Cyclades / Folegandros

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
AMOUDAKI APARTMENT Agali is perhaps the most beautiful beach of Folegandros and the ideal place for your stay on the island. One spacious sunny two bedroom apartment has made with special care and Cycladic style just a few meters from the sea. Our apartme …see more

from $49 / night

$326 - $1247 / week

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from $49 / night

(7) Excellent 

24

Vacation villa rental

Naxos / Melanes

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Beach/lakeside relaxation
  • Nearest beach 9 mi
  • Swimming pool
Villa Guilena Main house is a light and airy 2 storey,2 bedroomed, fully equipped property, nestled in the beautiful Melanes valley. Peaceful, with only the sound of goat bells, enjoy the wonderful pool with its panoramic mountain views, bask in uninterrupted sunsh …see more

from $115 / night

$804 - $2449 / week

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from $115 / night

(3) Very Good 

26

Melanes Vacation villa rental

Naxos / Melanes

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
White walls, blue doors and windows, such are the traditional Kykladic houses such is this authentic ancient house. Inside, white, stone and honey are the colours. On the ground floor there are a full kitchen, a sitting room and a dining room. On the first floor, there …see more

from $90 / night

$624 - $733 / week

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from $90 / night

(1) Excellent 

26

Home rental in Chora

Ios / Chora

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Romantic house is a new property in a beautiful location of Ios.The house is situated 1.5km from the buzzing village of Ios.There are amazing sea views from the balcony.The area is quite and just what is needed to enjoy a relaxing holiday on the beautiful island of Ios. …see more

from $110 / night

$766 / week

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from $110 / 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 $196 / night

$1356 - $3038 / week

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from $196 / night

(3) Excellent 

21

Vacation apartment in Manganari

Ios / Manganari

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.15 mi
  • Suitable for children age 5+
Manganari is 25 km from Ios Village. Is one of the most popular destination on Ios boasting a set of beautiful beaches with golden sand and crystal emerald water. …see more

from $60 / night

$418 / week

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from $60 / night

(6) Very Good 

15

Vacation villa in Parikia

Paros / Parikia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
20% DISCOUNT.. Only 2 weeks remaining . Sleeps up to 6. 2 bedrooms , 1 other another room with sofabed plus sitting room Panoramic Sea view Large Patio with built in barbeque, private pool, 4 pool side sunbeds and cover. Free Wifii Included. Central heating, A …see more

from $168 / night

$1097 - $1935 / week

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from $168 / night

(9) Excellent 

19

Apartment rental in Mykonos Town

Mykonos Town / Mykonos Town

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Unique Living Experience Inside the energy charged spaces of Castle Panigirakis, with the most spectacular view of Mykonos, two luxurious residences of unique beauty are built, that are there to offer you a special life experience, you will never forget. The t …see more

from $174 / night

$1518 / week

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from $174 / night

21

Vacation apartment with shared pool in Faros

Sifnos / Faros

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
DESCRIPTION IN ENGLISH & FRENCH AVAILBLE | French | You are right next to the southern beaches of the island of Sifnos! It would be ideal if you could rent a house of 120 m2 in the complex of "Lighthouse" which is 700 meters from the village of Faros. This is a 60m2 apa …see more

from $99 / night

$689 / week

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from $99 / night

14

Sifnos / Platis Gialos

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

from $55 / night

$383 / week

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from $55 / night

27

Villa rental in Pitrofos with swimming pool

Andros / Pitrofos

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Villa Melissa is situated at the southwest side of Andros at an ideal location that provides a marvelous view of the sea extending from behind the cliffs and the islands of Yaros, Kea ( Tzia ) and Siros at the horizon. At a close distance from the house there are …see more

from $164 / night

$2679 / week

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from $164 / night

(1) Excellent 

46

Villa rental in Tourlos

Mykonos / Tourlos

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Villa Aeracura is situated high above the hills at a most beautiful and panoramic location, overlooking the endless blue of the horizon. The islands of Delos, Rhenia and other islets sprinkled in the horizon form a spectacular setting for a most photogenic sunset. The l …see more

from $179 / night

$1139 - $6284 / week

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from $179 / night

(1) Very Good 

18

Psarou Vacation home rental

Mykonos / Psarou

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
The Space The villa is located in the exclusive area of Agios Lazaros. It consists of three (3) bedrooms (a/c in all bedrooms), three shower rooms (1 en-suite + 2), an open plan living area with a fireplace and a fully-equipped kitchen. The architecture and interior d …see more

from $733 / night

$5126 / week

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from $733 / night

12

Vacation villa in Kionia

Tinos / Kionia

3 7 5 nights min

  • 3 bedrooms
  • Sleeps 7
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
A traditional cycladic house that combines absolute privacy with amazing panoramic sea view day and night. Our villa stands in a relatively isolated small cliff so quiet that most of the day you can only hear the wind and the passing goats. Ideal for family vacations aw …see more

from $217 / night

$1518 / week

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from $217 / night

(5) Excellent 

24

Vacation apartment rental

Naxos / Galanado

2 6 6 nights min

  • 2 bedrooms
  • Sleeps 6
  • 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 $131 / night

$912 - $1367 / week

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from $131 / night

(6) Excellent 

32

Vacation cave house in Fira

Santorini / Fira

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Air conditioning
The Raki Cave offers combination of traditional Santorinian architecture and an enviable central location within Fira. All the conveniences and attractions the capital has to offer are within easy walking distance. Guests are therefore able to take advantage of not havi …see more

from $93 / night

$651 - $1531 / week

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from $93 / night

(6) 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 $143 / night

$995 - $1914 / week

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from $143 / night

(7) Very Good 

25

Andros Town Vacation apartment rental

Andros / Andros Town

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Two one-bedroom apartments in 1920's stone-built newly renovated house. Huge sea-facing veranda, ideal to sit out, eat and drink and enjoy panoramic views of village and sea. Stenies, a very green, traffic-less village, is the most aristocratic of Andros, 15 minute walk …see more

from $55 / night

$328 - $886 / week

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from $55 / night

(11) Very Good 

21

Townhouse rental in Naxos Town

Naxos / Naxos Town

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Ask about children
The Goudi House is a beautifuly renovated turn of the 20th century property that was originally owned by a Greek Orthodox Papa and then in 1980 bought by a Greek carpenter for his family and 5 children who then added 2 extra floors . An old marble mortar (Goudi) was f …see more

from $99 / night

$689 - $1378 / week

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from $99 / night

(2) Excellent 

16

Sifnos / Platis Gialos

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

from $55 / night

$383 / week

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from $55 / night

28

Vacation villa in Tourlos

Mykonos / Tourlos

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Set on a hill overlooking the Aegean Sea, Villa Desiree has gorgeous views and a location close to Mykonos main town (Chora) and several famed beaches. The property’s traditional and modern decor offers contemporary luxury, and four bedrooms on three levels provide pr …see more

from $182 / night

$1153 - $7285 / week

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from $182 / night

(3) Excellent 

64

Villa rental in Akrotiri

Santorini / Akrotiri

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Nearest beach 0 mi
  • Child friendly
  • Air conditioning
The Vineyard villa is a fully renovated villa located at the heart of Akrotiri. The house has a wonderful outdoor area of 7 acres surrounded by vineyards,overlooking the sea and the beautiful medieval settlement of Akrotiri. A private traditional church "Saint Andreas" …see more

from $212 / night

$1410 - $4098 / week

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from $212 / night

(2) Very Good 

22

Vacation home in Mykonos Town

Mykonos / Mykonos Town

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Anna-Maria's Maisonette I was completely refurbished in summer 2010 and is a classic Myconian style two-stored stone house of 70 sq.m.t is situated on the top of the hill between Kalafatis, Kalo Livadi and Ag. Anna beaches, offering unbreakable view over the Aegean isla …see more

from $82 / night

$547 - $1383 / week

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from $82 / night

(5) Excellent 

34

Kastraki Vacation apartment rental

Naxos / Kastraki

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
The renovated apartments “LIANA MAROULI” is a fully furnished room complex built with Love and respect not only to our island's traditional architecture and the contemporary aisthetics. The wood,the white stone and the decorative details are the main structure's feature …see more

from $60 / night

$477 / week

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from $60 / night

18

Vacation apartment with shared pool in Faros

Sifnos / Faros

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
DESCRIPTION IN ENGLISH & FRENCH AVAILBLE | French | You are right next to the southern beaches of the island of Sifnos! It would be ideal if you could rent a house of 120 m2 in the complex of "Lighthouse" which is 700 meters from the village of Faros. This is a 60m2 apa …see more

from $99 / night

$689 / week

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from $99 / night

(28) Excellent 

24

Exo Gonia Vacation villa rental

Santorini / Exo Gonia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Located in the peaceful residential village of Exo Gonia, Cavern House Helios is ideally located for exploring Santorini with the beaches of Kamari and the island's capital Fira both within just 15 minutes' drive. The award-winning taverna Metaximas is just a 3 minute w …see more

from $160 / night

$890 - $1914 / week

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from $160 / night

(7) Very Good 

23

Villa rental in Mykonos Town with swimming pool

Mykonos / Mykonos Town

5 8 3 nights min

  • 5 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
A stunning Villa which has been used as a private family holiday home is now available for rental. It can be fully staffed (optional) with all amenities and the latest gadgets. It is located in the sought after area of Agio Sofia with beautiful views overlooking the the …see more

from $645 / night

$4515 - $5870 / week

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from $645 / night

(1) Excellent 

37

Vacation apartment rental

Paros / Naoussa

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.6 mi
  • Child friendly
Villa Viglakia is a small family business run by Philippe and his wife Carina who live on the premises. We welcome visitors all year round. Villa Viglakia is in the exclusive area of Santa Maria, which is in the North of Paros and arguably the most picturesque part of t …see more

from $66 / night

$438 - $711 / week

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from $66 / night

(1) Excellent 

55

Hotel apartment rental in Ornos

Mykonos / Ornos

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Filoxenia Apartments Filoxenia Apartments are situated in Ornos, 50m from the beach and 2.5km from Mykonos Town. Ornos is a picturesque village where are many fish boats that anchor. The sandy and clean beach at the inlet of the homonymous bay is very …see more

from $88 / night

$613 / week

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from $88 / night

(6) Very Good 

20

Vacation apartment rental

Naxos / Naxos Town

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Sunset Apartment is perfectly located in the Glyfada Alyko area with stunning sunsets. You are so close youi can nearly touch them! The colours are spectacular! Our delightful apartment has everything you would need for a wonderful relaxing holiday in this amazing lo …see more

from $44 / night

$307 - $536 / week

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from $44 / night

(3) Excellent 

20

Vacation apartment in Ios

Cyclades / Ios

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning
Romantic Loft is a quiet relaxing get away for couples. We offer a fully equiped kitchen,dining area,and a bedroom on a loft. The apartment is situated 1.5 km from the lively village of Ios. The apartment has amazing views of the port and the village. The ne …see more

from $50 / night

$345 / week

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from $50 / night

(7) Excellent 

19

Vacation apartment in Piso Livadi

Paros / Piso Livadi

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
The apartment is on the 2nd floor and has veranda with pergolas. The location of the apartment is quite, 50m from the nearest beach Logaras, close to the shops and restaurants but at the same time away from the noise of the village. It combines easy access to …see more

from $55 / night

$380 / week

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from $55 / night

(6) Excellent 

20

Vacation villa rental

Cyclades / Paros

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Do you want to spend your holidays in your summerhouse on Paros Island in Greece? Then, "Parian Holiday Villas" is the perfect place for you! This luxury villa is divided into 3 adjacent charming houses with accomodation possibilities, Villa Panorama up to 8 p …see more

from $179 / night

$1253 - $2240 / week

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from $179 / night

(2) Excellent 

45

Vacation home in Emporio

Santorini / Emporio

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
Shades of White is a newly constructed , traditional complex of apartments located in the Village of Emporio. Fira the capital of Santorini is 7 klm away and the famous black beaches of Perivolos & Perissa are only 2 klm. The complex of Shades of White overlooks …see more

from $121 / night

$766 - $1640 / week

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from $121 / night

16

Naxos / Galini

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden

from $47 / night

$328 / week

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from $47 / night

(19) Excellent 

28

Windmill rental in Tripiti

Milos / Tripiti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly
For your holidays think outside the box! Experience them in a charming windmill. Located on Milos, the island of Aphrodite, high on a hilltop in the traditional Tripiti community just 5 kilometers from the port, this locale allows for a unique holiday setting yet …see more

from $93 / night

$651 / week

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from $93 / night

6

Vacation apartment in Ios

Cyclades / Ios

1 3 4 nights min

  • 1 bedroom
  • Sleeps 3
  • 4 nights min
  • Nearest beach 0.15 mi
  • Child friendly
  • Pet friendly
Manganari moments is a new apartment which is 150m from the sea.The apartment has an amazing view of Manganari beach golden sand and beautiful clear blue sea. Our apartment sleeps three persons,has a equipped kitchen and a large balcony looking out to the sea. The area …see more

from $61 / night

$421 / week

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from $61 / night

(9) Very Good 

33

Apartment rental in Logaras

Paros / Logaras

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
The Meltemi 4-5 person's apartment has a well equipped kitchen, 2 bedrooms, 2 bathrooms with toilets, 2 balconies at the front site, and behind a big private terrace under a big beautiful pine tree in the quiet traditional Greek island garden with many trees, flowers an …see more

from $77 / night

$536 / week

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from $77 / night

1