50 Best Vacation Rentals in Cyclades - Holiday Lettings - Cabins

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3,528 Vacation rentals

(7) Excellent 

36

Vacation villa with swimming pool in Melanes

Naxos / Melanes

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • 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 $206 / night

$2,398 - $2,717 / week

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avg. 3 hours 8 minutes

from $206 / night

(7) 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 $240 / night

$1,680 - $2,800 / week

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avg. 3 hours 8 minutes

from $240 / night

(10) Very Good 

9

Home rental in Mykonos Town

Mykonos / Mykonos Town

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning

from $58 / night

$343 / week

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Responds fast!
avg. 1 hour 48 minutes

from $58 / night

(12) Excellent 

47

Vacation villa in Alyki

Paros / Alyki

6 15 min stay varies

  • 6 bedrooms
  • sleeps 15
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
In the beautiful island of Paros, and more specifically in Aliki, we have created the Paros Afrodite Luxury Villas . This beautiful building is situated on a hilltop in Aliki offering panoramic view of the Aegean Sea. It is the ideal place to enjoy that view of Antiparo …see more

from $229 / night

$1,600 / week

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from $229 / night

(5) Excellent 

20

Vacation cottage in Sifnos

Cyclades / Sifnos

2 7 7 nights min

  • 2 bedrooms
  • sleeps 7
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Restored traditional stone barn and sheepfold (themonia) at the top of Ano Petali. Two indipendent bedrooms, a common room on the 1st floor and a small kitchen and bathroom carved on the bedrock. Fully eqquipped for relaxing holidays or inspiration. Near the capital Apo …see more

from $160 / night

$960 / week

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from $160 / night

(3) Very Good 

Certificate of Excellence

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

Certificate of Excellence

from $98 / night

$680 / week

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Responds fast!
avg. 1 hour 26 minutes

from $98 / night

62

Vacation villa in Santa Maria

Paros / Santa Maria

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Air conditioning
Villa Filizi is a 115 sqm villa with 2 bedrooms , 2 bathrooms and a spacious living room / dining area/ kitchen. Outside there is a big veranda with a sitting area and a barbecue. You can relax and enjoy the garden view or the Aegean blue. The Space: Villa Filizi is a 1 …see more

from $157 / night

$1,096 / week

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from $157 / 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

(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 $115 / night

$800 - $1,999 / week

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avg. 3 hours 8 minutes

from $115 / night

(1) Excellent 

24

Vacation apartment in Vathi

Sifnos / Vathi

1 4 6 nights min

  • 1 bedroom
  • sleeps 4
  • 6 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Cosy and spacious studios, 30 meters from the beach of Vathi. Each studio can house 1-4 people in a one-space area, including one large double bed and one or two sofa beds, confortable enough to acccomodate 1 or 2 children. Each studio has a large private shaded terrace …see more

from $57 / night

$400 / week

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from $57 / night

(10) Excellent 

42

Vacation home rental

Cyclades / Serifos

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
A dreamy stone made 65sqm summerhouse with olive green woodwork, in the magnificent (and awarded) sandy bay of Ganema, in Serifos island. The house located just 350m away from the beach in a complex of 4 houses built in 2010, following 100% the local architectural line. …see more

from $143 / night

$1,000 / week

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avg. 1 hour 4 minutes

from $143 / night

(1) Excellent 

37

Exomvourgo Vacation villa rental

Tinos / Exomvourgo

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Villa Elea is a luxury traditional villa with private pool and sweeping sea view in Tinos, in the village of Ktikados, a traditional protected settlement. This spacious two-floor, 4-bedroom villa is the perfect place to enjoy the brilliant Greek sun and cool Aegean bre …see more

from $486 / night

$3,229 / week

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from $486 / night

(8) Excellent 

53

Donousa Town Vacation studio rental

Donousa / Donousa Town

Studio 10 5 nights min

  • Studio
  • sleeps 10
  • 5 nights min
  • Air conditioning
With respect to tradtitional architecture, we created Stenosa, a fine accomodation experience of the highest quality possible. Stenosa was designed to blend naturally with the environment and the local architecture, while also standing out due to its unique design char …see more

from $115 / night

$800 / week

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from $115 / 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

$360 / week

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from $52 / night

(27) Excellent 

20

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

$800 - $1,600 / week

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from $172 / night

(1) Excellent 

53

Vacation villa in Kionia

Tinos / Kionia

3 7 7 nights min

  • 3 bedrooms
  • sleeps 7
  • 7 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 $229 / night

$1,600 - $2,000 / week

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from $229 / night

(11) Very Good 

31

Apartment rental in Milos

Cyclades / Milos

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
ATTENTION! THE HOUSE IS FULLY RENOVATED DURING WINTER 2016 UP TO NOW AND THERE ARE NO NEW PHOTOS TAKEN AVAILABLE AFTER RENOVATION YET. IT HAS A NEW KITCHEN, LARGE BATHROOM AND MORE. We are situated in a small village, called Firopotamos, one of the unique villages in M …see more

from $115 / night

$800 / week

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from $115 / night

25

Vacation villa with shared pool in Agios Sostis

Tinos / Agios Sostis

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 0.9 mi
  • Swimming pool
  • Child friendly
Bar with refreshing cocktails Restaurant Cuisine Breakfast A la Carte or Room service “Comfort Villa” Two Bedroom, accommodates max 4-5 persons Description: 100 m2, features 2 bedrooms, 2 bathrooms and 1 WC, 400 m2 private garden, amazing Aegean Sea view, parking spac …see more

from $229 / night

$1,599 / week

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from $229 / night

(4) Excellent 

41

Tinos Vacation home rental

Cyclades / Tinos

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 2 mi
  • Child friendly
  • Private garden
Tinos Ecolodge is a small lodge in Nature, surrounded by the fantastic Aegean sea and the island terraced landscape. Its situated at the east coast of Tinos, near a river stream with old plane trees and oak trees, very rare ecosystem for the Aegean! Totally peaceful, wi …see more

from $92 / night

$640 / week

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from $92 / night

(4) Excellent 

25

Triandaros Vacation home rental

Tinos / Triandaros

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Tinos Habitart is located close to the traditional village of Triandaros on the beautiful Island of Tinos. The settlement of Tinos Habitart includes vacation villas for rent and a group of neighboring traditional buildings (a windmill, a dovecote, a renovated traditiona …see more

from $286 / night

$2,000 / week

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from $286 / night

(4) Excellent 

26

Agios Sostis Vacation villa rental

Tinos / Agios Sostis

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.35 mi
  • Child friendly
A traditional looking spacious Greek villa with stunning sea-views, ideally situated next to one of the most beautiful sandy beaches of Tinos Island and only a short drive from the main town. Spectacular Aegean sea-views with the Islands of Mykonos, Delos and Syros in …see more

from $98 / night

$680 - $1,240 / week

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avg. 1 hour 55 minutes

from $98 / night

(2) Excellent 

20

Vacation villa in Milopotas

Ios / Milopotas

6 12 3 nights min

  • 6 bedrooms
  • sleeps 12
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This luxurious beach front property, located just metres from the popular Mylopotas Beach, comprises three fabulous individual villas and a large, beautifully landscaped outdoor communal space. The newly built property with stunning views of the Aegean Sea is the envy o …see more

from $686 / night

$4,800 / week

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from $686 / night

(4) Very Good 

32

Vacation home in Ornos

Mykonos / Ornos

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
The villa, a two-storey cubic private property, that is bathed in light, with uninterrupted views of the sunset, the crystal sea of the blue Aegean and the Islands of Tinos & Delos, is located in Pouli, Ano Diakoftis, a very privileged area, only 3km from Mykonos town. …see more

from $458 / night

$3,200 / week

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avg. 1 hour 51 minutes

from $458 / night

30

Vacation villa with swimming pool in Ornos

Mykonos / Ornos

6 12 3 nights min

  • 6 bedrooms
  • sleeps 12
  • 3 nights min
  • Nearest beach 0.2 mi
  • Swimming pool
  • Child friendly
Cavo Nano is a 6 bedroom villa in Mykonos with elegance and style, reserving all valuable island housing features, dedicated to accommodate its guests in privacy and comfortness, according to modern living standards. It is an extra spacious 2 floor residence, situated r …see more

from $515 / night

$3,600 / week

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from $515 / 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 $137 / night

$959 / week

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avg. 1 hour 6 minutes

from $137 / 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 $115 / night

$800 - $1,760 / week

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avg. 3 hours 8 minutes

from $115 / night

(28) Excellent 

30

Vacation villa with swimming pool in Glinado

Naxos / Glinado

6 16 7 nights min

  • 6 bedrooms
  • sleeps 16
  • 7 nights min
  • 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 $458 / night

$3,200 / week

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avg. 3 hours 8 minutes

from $458 / night

24

Vacation apartment in Piso Livadi

Paros / Piso Livadi

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning
Apartments / Rooms villa Giorgio is a small family business made with love and warmth to welcome you .It is located in the picturesque piso livadi, 100 meters from the port. We have apartments rooms which guarantee visitors a pleasant stay. All our rooms can accommodate …see more

from $69 / night

$480 / week

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from $69 / night

(2) Excellent 

44

Vacation b&b in Milos

Cyclades / Milos

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Nearest beach 3 mi
  • Air conditioning
A two-storey suite located on a clifftop at the southern part of Milos within the NATURA 2000 nature protection area. Enjoy relaxation in a serene Cycladic landscape and an outstanding view. Nearby beaches are classified among the best in the Aegean. -This two-storey ho …see more

from $183 / night

$1,280 / week

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from $183 / night

(2) Excellent 

13

Platis Gialos Vacation gite rental

Sifnos / Platis Gialos

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly
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 $58 / night

$400 / week

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avg. 1 hour 26 minutes

from $58 / night

(7) Excellent 

28

Vacation villa in Pollonia

Milos / Pollonia

3 9 min stay varies

  • 3 bedrooms
  • sleeps 9
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
'Aloni' is an old farmhouse carved in the rock of a small hill in a land of 4000m2. It was recently renovated with the utmost respect to the original structure and the environment. The house has three independent entrance doors providing autonomy to each of its three …see more

from $183 / night

$1,280 / week

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avg. 3 hours 41 minutes

from $183 / night

11

Pollonia Vacation home rental

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 simpl …see more

from $331 / night

$2,284 / week

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from $331 / night

(1) Excellent 

14

Vacation gite in Platis Gialos

Sifnos / Platis Gialos

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • 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 $58 / night

$400 / week

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avg. 1 hour 26 minutes

from $58 / night

26

Vacation apartment in Koundouros

Kea / Koundouros

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 0.1 mi
  • Child friendly
  • Pet friendly
Beach House Pi, a fully supported luxury apartment at Kastellakia Bay Villas, is one unit in Villa Aperon. Completely separate, with its own living room area, kitchen and terrace and sea views, it occupies the garden level and you may request a guest studio (3 person c …see more

from $212 / night

$1,480 / week

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from $212 / night

6

Vacation studio in Apollonia

Sifnos / Apollonia

Studio 2 2 nights min

  • Studio
  • sleeps 2
  • 2 nights min
  • Child friendly
  • Air conditioning
Our grand father house became 3 small houses with terrace for every house. This listing is for the studio. A beautiful little house in the traditional pavements of Apollonia with a beautiful terrace. with a nice bathroom and fully equipped even with a washing machine, …see more

from $80 / night

$560 / week

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from $80 / night

(1) Excellent 

15

Vacation gite in Platis Gialos

Sifnos / Platis Gialos

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • 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

$280 / week

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Responds fast!
avg. 1 hour 26 minutes

from $40 / night

(43) Excellent 

Certificate of Excellence

25

Villa rental in Exo Gonia with swimming pool

Santorini / Exo Gonia

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Located in the peaceful residential village of Exo Gonia, Cavern House Anthea 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

Certificate of Excellence

from $289 / night

$1,536 - $3,167 / week

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from $289 / night

(8) Very Good 

29

Vacation villa with swimming pool in Mykonos Town

Mykonos / Mykonos Town

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Villa V is located in the settlement of CAVO DELOS, which is famous for its tranquility as well as for its ideal location, overlooking the endless blue of the Aegean Sea and the dazzling sunset against the backdrop of the sacred island of Delos. Villa V has an area of …see more

from $1,029 / night

$7,200 / week

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from $1,029 / 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

$3,200 / week

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from $458 / night

(1) Excellent 

39

Vacation villa in Naxos Town

Naxos / Naxos Town

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Villa ‘Azure’ is a beautifully private beach Villa which offers luxury accommodation combined with panoramic sea views at Aegean sea. It consists of 2 floors &. sleeps up to 6 adults. ground floor: · 3 bedrooms with double beds , a/c. · two large …see more

from $458 / night

$3,200 / week

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from $458 / night