50 Best Vacation Rentals in Cyclades - Holiday Lettings - Cabins

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Villas Mykonos
997 properties
Apartments Santorini
819 properties
Apartments Paros
487 properties
Villas Naxos
273 properties
Villas Syros
128 properties
Villas Tinos
126 properties
Andros
117 properties
Kea
114 properties
Villas Milos
84 properties
Apartments Sifnos
60 properties
Apartments Ios
40 properties
Villas Antiparos
37 properties
Villas Serifos
34 properties
Koufonissi
19 properties
Apartments Folegandros
12 properties
Kimolos
9 properties
Kithnos
9 properties
Amorgos
6 properties

Cyclades

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3,376 Vacation rentals

(3) Excellent 

85

Villa rental in Fira Firostefani

Santorini / Fira Firostefani

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly
Stilvi Suite is a Duplex Suite located in Firostefani village, only 500 meters away from Fira the capital of Santorini overlooking the Volcano and the Deep Blue Sea of Aegean . Brand new Suite with traditional comfort and style , surprises every guest with …see more

from $492 / night

$3,445 / week

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from $492 / night

(10) Very Good 

8

Home rental in Mykonos Town

Mykonos Town / Mykonos Town

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Car not necessary
The air-conditioned house sleeps two people and has a fully equipped kitchen / dining area. Bedding, towels and beach towels are provided. The house has a HD television with Blu-ray player. The balcony is the perfect place to take your morning cof …see more

from $149 / night

$1,041 / week

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avg. 3 hours 44 minutes

from $149 / night

(5) 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 $369 / night

$2,584 / week

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from $369 / night

(15) 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 $111 / night

$775 - $1,550 / week

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avg. 2 hours 55 minutes

from $111 / night

21

Agios Prokopios Vacation villa rental

Naxos / Agios Prokopios

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
It comprises two floors with a spectacular view. The second level has two bedrooms, a double and a single with pull-out bed, and a bathroom. Both bedrooms open onto two spacious, pergola shaded verandas, complete with seating area and a wonderful view of the sea. The g …see more

from $271 / night

$1,895 / week

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from $271 / night

(25) Excellent 

30

Vacation villa with swimming pool in Glinado

Naxos / Glinado

6 16 Min stay varies

  • 6 bedrooms
  • Sleeps 16
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Swimming pool
Cassandra Villa is a unique,large property set in 7000sq.metres of land in the valley of Iria with amazing views to the Aegean,the island of Paros opposite and the surrounding lush valley. The property is a 2 storey, 6 bedroomed house,3 of which are doubles, and 1 twin, …see more

from $173 / night

$1,046 - $3,445 / week

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avg. 2 hours 55 minutes

from $173 / night

(13) 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 $308 / night

$1,661 - $2,399 / week

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from $308 / night

(10) Excellent 

Certificate of Excellence

23

Vacation villa in Imerovigli

Santorini / Imerovigli

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
In Imerovigli, one of the most beautiful villages on Santorini, 400 m. above sea level on the northwest side of the island, you can find "Ventus Paradiso Villa". Built with respect for our Cycladic architectural tradition and regard for your absolute comfort, our villa …see more

Certificate of Excellence

from $369 / night

$2,461 - $6,643 / week

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from $369 / night

21

Koundouros Vacation home rental

Kea / Koundouros

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Property to rent in the island of Kea- At the area of Koundouros which is located in the west side of the island,, only 500m away from the sea, placed in the islands' best spot within an area of 4 acres.The house is positioned on an amphitheatric spot with no other bui …see more

from $98 / night

$861 / week

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avg. 37 minutes

from $98 / night

(1) Very Good 

15

Vacation apartment in Poseidonia

Syros / Poseidonia

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
The “Archipelagos apartment - 50 sq.m - sea view" is situated in Posidonia, in the most stately village of Syros, with its castles and modern villas. Posidonia is located at the south-west side of the island, 10km from Hermoupolis. It is one of the few green areas of th …see more

from $62 / night

$382 - $665 / week

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avg. 2 hours 42 minutes

from $62 / night

(1) Excellent 

24

Vacation home in Gavrion

Andros / Gavrion

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
5 minutes (2km) from the port of Andros (Gavrion), commerce, cafes, restaurants, several beaches. A unique holiday experience is expecting you living in a lovely bioclimatic little house! Designed to minimize the energy consumption, and provide the best comforts combini …see more

from $100 / night

$694 - $930 / week

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avg. 3 hours 51 minutes

from $100 / night

24

Vacation apartment in Parikia

Paros / Parikia

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
The apartment is on the 1st floor. It is composed of two parts including a chamber. The main room has a double bed and a single bed; the chamber is equipped with a double bed. A total of 5 beds. The apartment has a kitchenette with: - refrigerator - hotplate - microwave …see more

from $68 / night

$474 / week

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avg. 2 hours 52 minutes

from $68 / night

(1) Excellent 

11

Vacation apartment in Marathi

Mykonos / Marathi

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
Maren Apartments is a new lake-side complex situated 5 minutes away from Panormos beach and 10 minutes away from Ag.Sostis beach or the town. It has one bedroom. The bedroom has two single beds which they can easily be converted in a double bed. Occupancy is 2 people. …see more

from $123 / night

$738 / week

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avg. 2 hours 31 minutes

from $123 / night

(2) 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 $93 / night

$646 / week

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from $93 / night

23

Vacation villa with swimming pool in Mykonos Town

Mykonos / Mykonos Town

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Aegean Pearl Villa is a fun summer house part of a group of residences located in one the most panoramic sides of Mykonos (KANALIA ) with views that range from the island of Tinos to the island of Delos and the sunset within the blink of an eye. The easy access to Mykon …see more

from $585 / night

$4,090 / week

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from $585 / night

18

Vacation home in Pollonia

Milos / Pollonia

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Child friendly
Our holiday homes FELIX and BEATE are situated on the peninsula Pelekuda, facing west and the open sea. The rooms and their large kitchen are on 5 levels, each with it´s own balkony, plus the vaste roof terrace. We built and designed the houses in the traditional simple …see more

from $197 / night

$1,378 - $2,153 / week

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from $197 / night

23

Vacation hotel apartment in Milos

Cyclades / Milos

6 5 2 nights min

  • 6 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
It is 47 m2 apartments - 79 m2 consisting of 2 separate bedrooms (one with a double bed and one with two single beds), a living room, a kitchen, fully air conditioned, bathroom with hydromassage, private courtyard with table and chairs. The kitchen has fridge, stove and …see more

from $185 / night

$1,230 / week

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from $185 / night

11

Naoussa Vacation private room rental

Paros / Naoussa

5 14 2 nights min

  • 5 bedrooms
  • Sleeps 14
  • 2 nights min
  • Child friendly
Villa Klery offers studios for rent for holidays in Naoussa, island of Paros in Greece. It is located in a quiet neighborhood just a few minutes walk from the beach and downtown. Villa Klery The apartments are surrounded by a shady courtyard with flowering shrubs and cl …see more

from $62 / night

$434 / week

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from $62 / night

(2) Excellent 

8

Milopotas Vacation apartment rental

Ios / Milopotas

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
Ostria Village is built at a distance of 800m from Mylopotas, the most beautiful beach of the island. The compound consists of 10 one or two room houses, providing space for 2-5 persons. It offers every comfort and a fantastic view All houses can be reached by wh …see more

from $80 / night

$517 - $2,387 / week

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avg. 2 hours 44 minutes

from $80 / 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 $222 / night

$1,538 - $3,186 / week

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avg. 2 hours 55 minutes

from $222 / night

17

Vacation villa rental

Mykonos / Ornos

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
"Villa Maria" is located in one of the most distinct areas on the island, with unlimited view of the Aegean Sea and the Cycladic Islands of Delos, Paros and Naxos. The villa is designed according to the local architecture and combines tradition with modern amenities. Of …see more

from $677 / night

$4,736 / week

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avg. 3 hours 41 minutes

from $677 / night

(12) Excellent 

26

Vacation apartment with swimming pool in Plaka

Naxos / Plaka

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This exclusive and contemporary apartment and separate studio are situated in a spectacular location,with stunning views of the Aegean and the neighbouring island of Paros. Exceptional pool and comprehensively equipped outdoor kitchen,with BBQ and choices of comfortable …see more

from $185 / night

$1,292 - $2,670 / week

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avg. 2 hours 55 minutes

from $185 / 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 $56 / night

$434 - $868 / week

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from $56 / 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 $117 / night

$818 / week

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from $117 / night

65

Vacation villa with swimming pool in Santa Maria

Paros / Santa Maria

8 19 4 nights min

  • 8 bedrooms
  • Sleeps 19
  • 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 $483 / night

$3,376 / week

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from $483 / night

(3) Very Good 

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 priv …see more

from $208 / night

$1,323 - $7,102 / week

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avg. 27 minutes

from $208 / night

(2) Excellent 

37

Vacation villa rental

Cyclades / Kea

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
In a 2000 sq/m building ground, beautiful 240sq/m villa with an amazing view of the Aegean sea and unforgettable sunsets. The villa accommodates ten persons. It is fully furnished and house-hold equipped. TV and Air conditioning is available in every room. Two times pe …see more

from $738 / night

$3,445 - $6,569 / week

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avg. 2 hours 7 minutes

from $738 / night

(5) Excellent 

17

Villa rental in Paros with shared pool

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 $173 / night

$1,206 - $2,325 / week

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avg. 2 hours 17 minutes

from $173 / night

(3) Excellent 

Certificate of Excellence

46

Villa rental in Tourlos with shared pool

Mykonos / Tourlos

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 …see more

Certificate of Excellence

from $203 / night

$1,292 - $7,130 / week

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avg. 27 minutes

from $203 / night

(4) 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 $259 / night

$1,809 - $3,014 / week

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avg. 2 hours 55 minutes

from $259 / night

(18) Very Good 

16

Vacation hotel apartment in Batsi

Andros / Batsi

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.15 mi
  • Child friendly
The Bella Vista Villa in Andros is comprised of 4 tastefully furnished and spacious studio that is especially designed to offer comfortable and carefree accommodation. The property is an AA’ class establishment and operates from March 15 to November 30. The Bella …see more

from $37 / night

$222 - $431 / week

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from $37 / 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 $185 / night

$3,014 / week

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avg. 2 hours 27 minutes

from $185 / night

16

Vacation cottage in Galini

Naxos / Galini

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
'Jenny' is Greek and means fulfillment, happiness. That's what is found at this beautiful location with a large garden. No immediate neighbors. The absolute peace and quiet in the bamboo, the old House is framed boxes, where and the proximity to the Sea (8 minutes by …see more

from $53 / night

$369 / week

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from $53 / night

(1) Excellent 

18

Vacation villa with swimming pool in Plaka

Naxos / Plaka

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Panoramic view of the Aegean Sea and sandy coves: on this island, undoubtedly one of the most beautiful in the Cyclades, the climate is pleasant, generous nature, beautiful beaches and the remains of the surprising antiquity. Overlooking sandy beaches at 100 m below ' …see more

from $515 / night

$3,593 - $7,558 / week

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from $515 / night

(3) Excellent 

25

Vacation villa in Mykonos Town

Mykonos / Mykonos Town

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
Take advantage of a 20% discount on last minute bookings regarding August 2017! This villa is built in walking distance from Super Paradise beach, in accordance to the traditional Mykonos architecture. It offers unobstructed panoramic views of Super Paradise bay, the s …see more

from $698 / night

$4,883 / week

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avg. 1 hour 26 minutes

from $698 / night

21

Vacation apartment with shared pool in Tourlos

Mykonos / Tourlos

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Studio Mystique 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. Th …see more

from $68 / night

$431 - $4,030 / week

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avg. 27 minutes

from $68 / night

(8) 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 $93 / night

$646 / week

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from $93 / night

(5) Excellent 

38

Vacation apartment in Oia

Santorini / Oia

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Welcome home to Fava! An unforgettable experience. Our goal is to make you feel that Fava is your own home and Santorini, your island. The Fava Eco-Residences are housed in a group of splendid and unique captain houses of the mid 19th century, located at the highest poi …see more

from $117 / night

$736 - $3,582 / week

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from $117 / night

15

Vacation villa in Aliki

Paros / Aliki

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Located on the southern coast of the island of Paros, on the sandy and protected cove of Farangas, just 10km from Paroikia the capital of Paros, this villa is ideal for families with children as well as groups of friends looking for relaxation and seclusion. Bui …see more

from $369 / night

$2,756 - $4,822 / week

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from $369 / night

(1) Excellent 

17

Vacation villa in Aliki

Paros / Aliki

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
In the beautiful island of Paroswe have created the Paros Luxury Villas. This beautiful buildings is situated on a hilltop in Aliki offering panoramic view of the Aegean Sea. It is the ideal place to enjoy that view of Antiparos, Aliki and the neighboring islands. Th …see more

from $246 / night

$1,723 / week

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from $246 / night