50 Best Vacation Rentals in Cyclades - Holiday Lettings - Cabins

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Villas Mykonos
970 properties
Apartments Santorini
805 properties
Apartments Paros
466 properties
Villas Naxos
290 properties
Villas Syros
141 properties
Villas Tinos
130 properties
Andros
117 properties
Kea
106 properties
Villas Milos
89 properties
Villas Antiparos
51 properties
Apartments Sifnos
46 properties
Villas Serifos
39 properties
Apartments Ios
34 properties
Koufonissi
19 properties
Apartments Folegandros
13 properties
Kithnos
8 properties
Amorgos
6 properties

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3,316 Vacation rentals

(15) Excellent 

20

Vacation villa with swimming pool in Exo Gonia

Santorini / Exo Gonia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 $294 / night

$1525 - $2874 / week

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from $294 / night

(26) Excellent 

26

Megalochori Vacation villa rental

Santorini / Megalochori

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
Following a seven year restoration, this exceptional 17th century residence is now accepting reservations. Situated in a beautiful setting, our spacious and elegantly appointed "Winery Estate" accommodates 12 guests in complete privacy with 5 comfortably sized bedr …see more

from $478 / night

$2574 - $7095 / week

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avg. 2 hours 43 minutes

from $478 / night

(6) Very Good 

22

Vacation home in Megalochori

Santorini / Megalochori

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly
Situated in the traditional village of Megalachori (pop 350), near the ferry port of Athinios, this property is a few minutes walk from the main cobbled square of this beautiful and charming village. There you can enjoy two excellent restaurants and the local taverna.Th …see more

from $112 / night

$587 - $1173 / week

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avg. 2 hours 3 minutes

from $112 / 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 $141 / night

$986 - $1478 / week

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avg. 2 hours 43 minutes

from $141 / night

(13) 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 $106 / night

$739 - $1478 / week

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avg. 2 hours 43 minutes

from $106 / night

(13) Excellent 

16

Vacation villa in Emborio

Santorini / Emborio

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 $235 / night

$2287 / week

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from $235 / night

(1) Excellent 

25

Drios Vacation villa rental

Paros / Drios

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
A lovely family house with swimming pool, situated on the south side of Paros, between Alyki fishing village with traditional tavernas and the famous Golden beach of Paros, next to tranquil semi-private beaches. Its premium uphill position offers spectacular view of the …see more

from $270 / night

$1889 / week

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avg. 3 hours 57 minutes

from $270 / night

(2) Excellent 

18

Apartment rental in Monolithos

Santorini / Monolithos

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Rodothea on the Beach is a typical one bedroom greek island decorated apartment based at Monolithos area, which is just few steps from the well – known Monolithos Beach. The apartment has been tastefully furnished and decorated aiming at offering you the ultimate comfor …see more

from $100 / night

$698 - $1085 / week

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avg. 1 hour 16 minutes

from $100 / night

(30) 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 $220 / night

$1026 - $1994 / week

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avg. 2 hours 43 minutes

from $220 / night

(1) Very Good 

23

Vacation home in Parikia

Paros / Parikia

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.9 mi
  • Child friendly
For rent on Paros island: a typical island house located above the harbor road of Paroikia, the island's main town, in the 'Castro', the ancient and Venetian center of the town. All of the beauties of the island are within walking distance or easy reach – the old town, …see more

from $94 / night

$821 / week

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from $94 / night

(1) Excellent 

39

Vacation home in Ormos Korthiou

Andros / Ormos Korthiou

1 3 5 nights min

  • 1 bedroom
  • Sleeps 3
  • 5 nights min
  • Nearest beach 4 mi
  • Child friendly
  • Air conditioning
Our stone residence is seated in one of Andros' most beautiful and virgin areas. A breathtaking ocean view, a true aegean islands' balcony. Enjoy fishing, hiking, swimming and nature! Find peace and serenity, within the aromas of thyme and sage. The beach is nearby for …see more

from $94 / night

$645 - $763 / week

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avg. 2 hours 3 minutes

from $94 / night

(13) Excellent 

38

Vacation home in Mykonos Town

Mykonos / Mykonos Town

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
A simple and elegant holiday villa in a quiet area with panoramic sea and sunset view, most suitable for families.Spacious paved terrace, private heated swimming pool with protective fence (removable) for small children, BBQ with outdoor dining table, fenced property. O …see more

from $411 / night

$2874 / week

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avg. 2 hours 36 minutes

from $411 / night

(7) Excellent 

22

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 $153 / night

$1068 - $1314 / week

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avg. 2 hours 43 minutes

from $153 / night

(37) Excellent 

25

Villa rental in Exo Gonia with swimming pool

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 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

from $278 / night

$1220 - $2510 / week

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avg. 2 hours 43 minutes

from $278 / night

(43) Excellent 

24

Villa rental in Fira

Santorini / Fira

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
"Villa Dakoronia" was recently renovated from an old theran villa, is situated on the top of the cliff ridge along the traditional caldera path between Fira and Firostefani, facing the spectacular Caldera view. The sunlight villa is located between the cable car (90m …see more

from $470 / night

$3120 - $7060 / week

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from $470 / night

(4) 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 $188 / night

$1314 - $1806 / week

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avg. 2 hours 43 minutes

from $188 / night

(10) Excellent 

23

Apartment rental in Monolithos

Santorini / Monolithos

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Rodothea on the Beach is a typical one bedroom greek island decorated apartment based at Monolithos area, which is just few steps from the well – known Monolithos Beach. The apartment has been tastefully furnished and decorated aiming at offering you the ultimate comfo …see more

from $112 / night

$581 - $1085 / week

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avg. 1 hour 16 minutes

from $112 / night

(11) Excellent 

40

Vacation home rental

Paros / Logaras

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Villa San Dimitrio is a self-catering accommodation located in Logaras. Free WiFi access is available.Accommodation will provide you with a TV, a balcony and a patio. There is a full kitchen with a dishwasher and an oven,barbecue. Featuring a shower, private bathrooms a …see more

from $155 / night

$943 - $2631 / week

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avg. 2 hours 34 minutes

from $155 / 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
. 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, Air conditioning, TV, DVD player, Dis …see more

from $258 / night

$1097 - $1806 / week

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from $258 / night

(10) 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 $235 / night

$1642 - $2545 / week

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avg. 2 hours 43 minutes

from $235 / night

10

Vacation home rental

Cyclades / Serifos

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 3 mi
  • Child friendly
In the heart of the viage built with traditional architecture.Close to all shops,bars and restaurants,2 min walk from the public parking.Wooden loft inside to be your bedroom.Eco friendly construction.Handmade decoration.The bathroom is inside the home (many Serifos tra …see more

from $63 / night

$534 / week

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from $63 / night

(4) Excellent 

16

Platis Gialos Vacation gite rental

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 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 $59 / night

$411 / week

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avg. 1 hour 31 minutes

from $59 / night

(12) Excellent 

23

Vacation villa in Megalochori

Santorini / Megalochori

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
A beautiful villa that is ideal for an unforgettable honeymoon or a luxurious holiday. Beautifully restored, this large and very private villa has been renovated to a high standard yet retained its best Greek features. Situated in the traditional village of M …see more

from $270 / night

$1636 - $2575 / week

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avg. 2 hours 3 minutes

from $270 / night

(1) Excellent 

27

Gavrio Vacation home rental

Andros / Gavrio

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
This 2 bedroom house is situated on the north-west side of Andros Island overlooking the famous Cavo D’ Oro sea-passage and facing the neighbouring island of Evia where you can enjoy the beautiful ocean and sunset view. It is a combination of traditional and romantic ho …see more

from $153 / night

$1068 / week

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from $153 / night

(21) 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 $118 / night

$821 - $3284 / week

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avg. 2 hours 43 minutes

from $118 / night

(31) Excellent 

21

Vacation villa with swimming pool in Mykonos Town

Mykonos / Mykonos Town

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
The Villa Hurmuses experience is about memories — unforgettable memories that have been made and the beautiful memories that are possible. Tucked in a serene corner near Mykonos Town, Villa Hurmuses offers the details the discerning traveler seeks including award-winni …see more

from $1525 / night

$10672 / week

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from $1525 / night

(10) Excellent 

36

Vacation villa rental

Mykonos Town / Mykonos Town

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
OFFER FOR JUNE! Only 2450 euro per week! A new, semi-detached house on the hills overlooking Mykonos Town. A spacious villa with a private pool. The property is located on the hills north-east of Mykonos Town, near the church of Ayia Sophia, only 2 kilometres from th …see more

from $417 / night

$2915 / week

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avg. 1 hour 40 minutes

from $417 / night

13

Katapola Vacation home rental

Amorgos / Katapola

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
A beautiful house in a beautiful location.. Our house is just 5 minutes from the port of Katapola surrounded by an amazing garden and a natural water spring. Let us not forget the view to the deep blue sea. It's a place that has been in the family for 3 generations and …see more

from $176 / night

$1173 / week

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avg. 36 minutes

from $176 / night

(3) Excellent 

30

Vacation home in Parikia

Paros / Parikia

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Ideally located in the old town, this typical old house was completely renovated in June 2014. House of 110m2 with garden which is rare to find accommodation in the old town. It is close to the sea. The interior is contemporary and particularly suitable for families wit …see more

from $118 / night

$821 / week

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from $118 / night

(3) Excellent 

46

Vacation home rental

Paros / Parikia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This old house typical of the Cyclades was renovated in 2015. It is located in the historic town of Naoussa, in one of the many flowers and typical winding streets of the Cyclades. This is a very quiet, yet very close to shopping, the harbor, the ferry terminal, beaches …see more

from $129 / night

$903 / week

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from $129 / night

38

Windmill rental in Pyrgos

Santorini / Pyrgos

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
Nestled in the picturesque medieval village of Pyrgos, the three storey imposing Anemoscope Windmill gazes in admiration at the Aegean Sea, the villages and Santorini’s famous Caldera. The Windmill has 120 sq. meters interior areas and is decorated with a composition of …see more

from $329 / night

$2299 / week

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from $329 / 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 $212 / night

$1466 - $3284 / week

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avg. 2 hours 43 minutes

from $212 / night

(8) 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 $153 / night

$1068 - $2053 / week

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avg. 2 hours 43 minutes

from $153 / night

16

Vacation apartment in Mykonos Town

Mykonos / Mykonos Town

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Air conditioning
This sweet apartment is build in the Mykonian style located at Agios Vasillis above the old port walking distend 5 minutes to Mykonos town. At the entrance of the apartment you find the bath room kitchen living room on the connected terrace you find the bed room the t …see more

from $141 / night

$986 / week

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from $141 / night

(11) Excellent 

20

Vacation home with swimming pool in Naoussa

Paros / Naoussa

2 10 Min stay varies

  • 2 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
The traditional-style stone villa Naousa is, as the name suggests on the outskirts of Naousa (1 600 meters measured from the center of Naousa and the small fishing port) on a hill with spectacular views over the bay of Naoussa. The nearest supermarket is only 600 meter …see more

from $212 / night

$1760 - $4105 / week

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avg. 2 hours 28 minutes

from $212 / night

21

Studio rental in Batsi

Andros / Batsi

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • 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 $42 / night

$247 / week

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from $42 / night

(2) Excellent 

21

Golden Beach Vacation villa rental

Paros / Golden Beach

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The villa consists of the Main House and an independent Guest house. The Main house offers 3 bedrooms with double beds, 2 bathrooms, 1 toilet, kitchen, dinning room and a living room. The Main House has been built for special needs people, both indoors and outdoors. …see more

from $704 / night

$4926 / week

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avg. 1 hour 27 minutes

from $704 / night

(3) 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 $97 / night

$674 - $1279 / week

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avg. 1 hour 2 minutes

from $97 / night

(15) Very Good 

22

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 $83 / night

$575 - $986 / week

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avg. 2 hours 43 minutes

from $83 / night

(4) Excellent 

55

Vacation hotel apartment in Megas Gialos

Syros / Megas Gialos

7 4 2 nights min

  • 7 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 20 mi
  • Child friendly
Very carefully built, in a wider estate of 4000 square meters and 30 meters away from the seaside, our studios are fully equipped with: Bathroom Kitchen (private in every studio and one of common use for every three rooms). Refrigerator TV Telephone …see more

from $88 / night

$528 - $1314 / week

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from $88 / night