50 Best Vacation Rentals in Cyclades - Holiday Lettings - Cabins

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Villas Mykonos
990 properties
Apartments Santorini
767 properties
Apartments Paros
464 properties
Villas Naxos
241 properties
Villas Tinos
125 properties
Andros
113 properties
Villas Syros
108 properties
Kea
97 properties
Villas Milos
75 properties
Apartments Sifnos
62 properties
Villas Antiparos
49 properties
Villas Serifos
34 properties
Apartments Ios
28 properties
Koufonissi
20 properties
Amorgos
18 properties
Apartments Folegandros
13 properties
Kithnos
6 properties

Cyclades

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3,204 Vacation rentals

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(5) 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 $140 / night

$834 - $1176 / week

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from $140 / night

(13) Excellent 

26

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
The Glinado 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 twi  …see more

from $106 / night

$742 - $2968 / week

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from $106 / night

(9) Excellent 

19

Apartment rental in Mykonos Town

Mykonos Town / Mykonos Town

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Unique Living ExperienceInside 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 $170 / night

$1484 / week

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from $170 / night

(2) Excellent 

64

Villa rental in Akrotiri

Santorini / Akrotiri

3 8 2 nights min

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

from $207 / night

$1378 - $4007 / week

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from $207 / 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 $265 / night

$1378 - $2597 / week

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from $265 / 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 $53 / night

$371 / week

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from $53 / night

35

Villa rental in Mykonos Town with swimming pool

Mykonos Town / Mykonos Town

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Villa Divine is located in the area of Kounoupas at only 5 minutes drive from Mykonos town and about 7- 10 minutes drive from many of the most famous beaches of the island. Villa Divine is a brand new property, one of the most luxurious on the island and its design, gre  …see more

from $1256 / night

$8792 - $18696 / week

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from $1256 / night

(9) 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 $159 / night

$1113 - $2300 / week

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from $159 / night

(3) Excellent 

21

Vacation apartment in Manganari

Ios / Manganari

1 3 Min stay varies

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

from $59 / night

$409 / week

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from $59 / 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 $96 / night

$668 - $1188 / week

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from $96 / 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  …see more

from $155 / night

$862 - $1854 / week

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from $155 / night

(2) Excellent 

43

Vacation home in Emporio

Santorini / Emporio

2 4 Min stay varies

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

from $133 / night

$928 - $1590 / week

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from $133 / night

46

Villa rental in Tourlos

Mykonos / Tourlos

3 8 Min stay varies

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

from $175 / night

$1113 - $6143 / week

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from $175 / night

(2) Very Good 

23

Villa accommodation in Choulakia with swimming pool

Mykonos / Choulakia

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Our Mykonos luxurious pool villa offers the image that a visitor has always wanted to experience! Watching the endless Aegean Sea and the blue sky, while standing in the infinite swimming pool and enjoying a drink! Guests of this luxurious villa with unbreakable view ma  …see more

from $371 / night

$2650 - $8903 / week

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from $371 / night

(1) Excellent 

21

Vacation villa with swimming pool in Kionia

Tinos / Kionia

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our recently built stone villa is a three- storey blend in the environment stone house. It is very cool in the summer and very warm in the wintertime. It has all sorts of natural air- conditioning, ventilation systems and fans if needed. A floor- mounted electrical air-  …see more

from $488 / night

$3445 / week

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from $488 / night

(5) Excellent 

13

Vathi Vacation apartment rental

Sifnos / Vathi

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
It's a newly built (in 2012), 46 m2, first floor apartment located on the beautiful and picturesque beach of Vathy in Sifnos, just 30 meters away from the sea.It is fully furnished and equipped. It can accommodate up to 4 persons.It consists of a kitchen, a  …see more

from $62 / night

$431 / week

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from $62 / night

(12) 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 r  …see more

from $212 / night

$1272 - $2067 / week

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from $212 / 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 $96 / night

$668 - $1336 / week

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from $96 / 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 $117 / night

$817 - $1484 / week

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from $117 / night

(1) Excellent 

39

Vacation home in Ormos Korthiou

Andros / Ormos Korthiou

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 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 n  …see more

from $106 / night

$668 / week

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from $106 / night

(3) Very Good 

26

Monólithos Vacation home rental

Santorini / Monólithos

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Child friendly
  • Air conditioning
Alexandro's House On The Beach. Monolithos Area Is A Very Peaceful Area And Very Close To Everywhere That You Want To Go. Sleeps 6 (2 bedrooms) The property is just on the beach! In front of the house there is a small traditional harbor which you can easily buy  …see more

from $91 / night

$631 - $1373 / week

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from $91 / night

(1) Excellent 

57

Vacation apartment in Ornos

Mykonos / Ornos

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
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 well protected from the northern  …see more

from $85 / night

$594 / week

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from $85 / 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 $128 / night

$891 - $1336 / week

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from $128 / night

(19) Excellent 

28

Windmill rental in Tripiti

Milos / Tripiti

2 4 Min stay varies

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

from $91 / night

$631 / week

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from $91 / night

(2) Excellent 

24

Mykonos Town Vacation castle rental

Mykonos Town / Mykonos Town

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Unique Living ExperienceInside 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 $287 / night

$2968 / week

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from $287 / night

23

Agios Stefanos Vacation apartment rental

Mykonos / Agios Stefanos

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
Perfect sea view apartment in agios stefanos (near the beach of agios stefanos). Its near mykonos town 3klm away, bus stop 3 min away, mini market near us & restaurants. Its near the new port of mykonos. It has one bedroom with a double bed, and a big living room  …see more

from $64 / night

$446 / week

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from $64 / night

18

Paros / Parikia

Studio 2 Min stay varies

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

 …see more

from $38 / night

$260 - $483 / week

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from $38 / night

(3) Excellent 

41

Kea Vacation villa rental

Cyclades / Kea

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 5 mi
  • Swimming pool
  • Child friendly
Villa Oliva is a luxurious architect estate with an infinity pool situated in a beautiful property of 2500 sq.m., full of olive and oak trees. It is located in the area of “Pera Meria", the greenest region of the island. The villa blends in the land with man  …see more

from $212 / night

$1484 / week

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from $212 / night

(20) Excellent 

42

Kastraki Vacation studio rental

Naxos / Kastraki

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Thalassa Naxos is quietly situated right on Kastraki Beach in Naxos. It offers self-catered accommodation with free Wi-Fi and balcony with Aegean Sea views. A kitchenette with dining area, cooking facilities and fridge is included in all the air-conditioned units at the  …see more

from $34 / night

$228 - $258 / week

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from $34 / night

12

Vacation apartment rental

Milos / Triovassalos

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning
Studio with view to village of Plaka , clean, renovated, in a quiet place that can offer you relaxation and tranquility to enjoy your holiday. Very close to beaches Iot Spot as Fyropotamos, Sarakiniko and Plathiena. We offer FREE parking for bike and quad just outside t  …see more

from $27 / night

$149 - $350 / week

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from $27 / 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  …see more

from $101 / night

$504 - $981 / week

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from $101 / night

(9) 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 home in a quiet area with panoramic sea and sunset views, 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 $371 / night

$2597 - $2756 / week

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from $371 / night

38

Villa accommodation in Sifnos

Cyclades / Sifnos

4 11 7 nights min

  • 4 bedrooms
  • Sleeps 11
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
This 230 sqm villa with a land plot of 5,500 sqm, is ideally located in one of the of the most beautiful parts of Sifnos, on the side of a steep slope overlooking the Aegean Blue, Platis Gialos Bay and its astonishing sandy beach. Surrounded by gardens and large separat  …see more

from $360 / night

$2518 - $5498 / week

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from $360 / night

(2) Very Good 

50

Vacation home in Ornos

Mykonos / Ornos

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
"BLUE DAISY" is part of Houses Complex (construction 2009), located in Ornos beach (less than 30 meters - 1' walking distance) and at a distance of less than 3 km from Mykonos town, connected frequently by local bus ot taxis. High quality external const  …see more

from $96 / night

$668 / week

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from $96 / night

(1) Very Good 

18

Oia Vacation villa rental

Santorini / Oia

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
Perched on the cliffs of Perivolas, Pegasus Villa offers cave-style accommodation with arched ceilings and a furnished terrace overlooking the caldera and the volcano. Ammoudi Beach is 1.5 km away. Pegasus villa is minimally decorated with respect to the Cycladic style  …see more

from $292 / night

$2041 / week

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from $292 / 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 $191 / night

$1325 - $2968 / week

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from $191 / night

9

Vacation apartment in Logaras

Paros / Logaras

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Ask about children
It is a spacious apartment with great sea view balcony. Renovated in 2015, gives an atmosphere of relaxation that will make your stay an unforgettable experience! The apartment is equipped with a kitchenette, plasma TV, hair dryer and free wifi. There is a bus stop, m  …see more

from $32 / night

$223 - $276 / week

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from $32 / night

(7) Excellent 

24

Vacation villa rental

Naxos / Melanes

2 4 6 nights min

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

from $112 / night

$779 - $2375 / week

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from $112 / night

(6) Excellent 

24

Vacation apartment in Plaka

Naxos / Plaka

1 4 Min stay varies

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

from $159 / night

$1113 - $1781 / week

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from $159 / night

15

Vacation villa in Naxos Town

Naxos / Naxos Town

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
2 Story 1 Bedroom 2 Bathroom Maisonette With Private Balcony & Amazing Sea View. Nestled in amongst a well tended garden are two maisonettes and one apartment with private balconies on to breathtaking views. The Villas' garden with exotic flowers, gurgling fou  …see more

from $75 / night

$483 - $1177 / week

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from $75 / night