50 Best Vacation Rentals in Cyclades - Holiday Lettings - Cabins

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Villas Mykonos
995 properties
Apartments Santorini
806 properties
Apartments Paros
497 properties
Villas Naxos
285 properties
Villas Syros
141 properties
Villas Tinos
136 properties
Andros
118 properties
Kea
106 properties
Villas Milos
83 properties
Villas Antiparos
50 properties
Apartments Sifnos
43 properties
Villas Serifos
36 properties
Apartments Ios
34 properties
Koufonissi
19 properties
Amorgos
16 properties
Apartments Folegandros
13 properties
Kithnos
9 properties

Cyclades

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3,286 Vacation rentals

(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 $203 / night

$1404 - $3144 / week

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avg. 2 hours 25 minutes

from $203 / 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 $216 / night

$1010 - $1963 / week

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avg. 2 hours 26 minutes

from $216 / night

(10) 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 $179 / night

$1560 / week

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from $179 / night

(27) 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 $1230 / night

$8610 / week

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from $1230 / 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 $450 / night

$2987 - $6760 / week

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from $450 / night

(24) 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 $470 / night

$2534 - $6985 / week

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avg. 2 hours 26 minutes

from $470 / night

(6) Excellent 

37

Kea Vacation villa rental

Cyclades / Kea

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly
Our villa is situated in a privileged elevated position offering an unreal view to the sunset and nearby islands. Ideally located just 3.5km from the picturesque port in a quite and totally private area provides to option to either relax at home and enjoy the sea and vi …see more

from $558 / night

$3900 / week

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avg. 30 minutes

from $558 / 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 $274 / night

$1201 - $2471 / week

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avg. 2 hours 26 minutes

from $274 / 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 $360 / night

$2516 / week

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from $360 / night

(14) 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 $281 / night

$1460 - $2751 / week

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from $281 / 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 $156 / night

$1092 - $2106 / week

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avg. 1 hour 45 minutes

from $156 / night

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 $169 / night

$1011 - $2224 / week

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avg. 3 hours 42 minutes

from $169 / night

(4) Excellent 

24

Tinos Town Vacation home rental

Tinos / Tinos Town

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly
A wonderful combination of a comfortable, bright and spacious waterfront home, which has a large terrace with stunning sea-views and is conveniently located very close to the beach and every amenity. Tastefully decorated with comfortable furniture and traditional Gree …see more

from $92 / night

$640 - $1217 / week

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avg. 1 hour 3 minutes

from $92 / night

(7) Excellent 

16

Vacation home in Livadi

Serifos / Livadi

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Serifos View is located in the best place of Serifos one of the most wonderful Islands of South Eastern Complex of Cyclades in Aegean Sea. Serifos View combines the joy of the traditional Cyclades Architecture with the leisure of enjoying swimming in the crystal clear …see more

from $64 / night

$320 - $768 / week

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from $64 / night

14

Vacation apartment in Mykonos Town

Mykonos Town / Mykonos Town

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
Comfortable studios situated in the heart of the center of Mykonos island,just 100m from the main bus terminal of the island and between famous clubs,bars and restaurants ,just 20m from the supermarket.....studios provide tv,electric cooker ,fridge,a/c Spaziosi s …see more

from $34 / night

$214 - $1348 / week

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from $34 / 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 $186 / night

$1887 - $2319 / week

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avg. 1 hour 45 minutes

from $186 / 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 $259 / night

$1567 - $2465 / week

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avg. 2 hours 51 minutes

from $259 / 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 $396 / night

$2769 / week

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avg. 1 hour 41 minutes

from $396 / 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 $146 / night

$1022 - $1965 / week

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avg. 2 hours 25 minutes

from $146 / 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 $45 / night

$315 - $551 / week

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avg. 2 hours 25 minutes

from $45 / night

13

Platis Gialos Vacation gite rental

Sifnos / Platis Gialos

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • 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 $51 / night

$351 / week

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avg. 2 hours 13 minutes

from $51 / 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 $135 / night

$944 - $1415 / week

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avg. 2 hours 25 minutes

from $135 / night

(2) Very Good 

53

Hotel apartment rental in Ornos

Mykonos / Ornos

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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 $58 / night

$368 - $1357 / week

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avg. 2 hours 27 minutes

from $58 / 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 $62 / night

$495 / week

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from $62 / night

(10) Excellent 

23

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 2 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 $368 / night

$2730 / week

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avg. 2 hours 17 minutes

from $368 / night

(14) 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 $113 / night

$786 - $3144 / week

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avg. 2 hours 25 minutes

from $113 / night

(4) Excellent 

18

Condo rental in Plaka with shared pool

Naxos / Plaka

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 700 mi
  • Swimming pool
This stylish and welcoming 2 bedroomed property,in an excellent location,only 700 meters from Plaka beach ,is finished to a very high standard and is fully equipped throughout. Completed in 2015, in a small complex of 6 properties it has a private garden and a shared …see more

from $169 / night

$1179 - $1572 / week

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avg. 2 hours 25 minutes

from $169 / night

(8) 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 $118 / night

$826 - $2516 / week

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avg. 2 hours 25 minutes

from $118 / 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 $102 / night

$708 - $1415 / week

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avg. 2 hours 25 minutes

from $102 / 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 $166 / night

$1080 - $1905 / week

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avg. 3 hours 40 minutes

from $166 / 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 $225 / night

$2190 / week

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from $225 / night

(6) 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 $156 / night

$1092 / week

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from $156 / night

(10) Excellent 

23

Apartment rental in Monólithos

Santorini / Monólithos

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 $107 / night

$556 - $1039 / week

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avg. 1 hour 7 minutes

from $107 / night

(8) 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 $51 / night

$337 - $1292 / week

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avg. 2 hours 34 minutes

from $51 / night

(5) Excellent 

15

Vacation apartment in Naxos Town

Naxos / Naxos Town

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
L'Ephemere Apartment is newly renovated,light and spacious and perfectly located only a few minutes walk from the beautiful St George's beach. Well equipped throughout, the property has a good sized bedroom with double bed and small terrace ,and a large and light living …see more

from $79 / night

$551 - $786 / week

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avg. 2 hours 25 minutes

from $79 / night

25

Fira Vacation villa rental

Santorini / Fira

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
Inspired by the black volcanic nature and infused with traditional Cycladic architecture, the Day Dream Luxury Suites are the perfect combination of minimal design, true style and pure luxury. Pamper yourself in one of its infinity pools or Jacuzzis and gaze at the hori …see more

from $262 / night

$1833 / week

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from $262 / 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 $808 / night

$5654 / week

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avg. 32 minutes

from $808 / night

44

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 $223 / night

$1560 / week

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from $223 / night

(5) Very Good 

34

Vacation studio in Logaras

Paros / Logaras

Studio 3 3 nights min

  • Studio
  • Sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
The Meltemi Studio for two adults and one child, has a kitchen, a bathroom, and a private terrace in the quiet traditional Greek island garden with many trees, flowers and herbs. It is also possible to combine the studio with an extra 1/2 persons room with its own t …see more

from $51 / night

$354 / week

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avg. 1 hour 16 minutes

from $51 / night

(47) Very Good 

11

Oia Vacation studio rental

Santorini / Oia

Studio 3 3 nights min

  • Studio
  • Sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Suitable for children age 5+
Thea Studios is located just below the main promenade street in Oia with a stunning view of the Caldera. Surrounded by exclusive hotels we offer an affordable alternative with the same amazing view. The studios and apartments sleep 2-4 people and are simply furnished wi …see more

from $118 / night

$674 - $1236 / week

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avg. 3 hours 41 minutes

from $118 / night

1