50 Best Vacation Rentals in Cyclades - Holiday Lettings - Cabins

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Villas Mykonos
983 properties
Apartments Santorini
727 properties
Apartments Paros
478 properties
Villas Naxos
249 properties
Villas Tinos
119 properties
Andros
110 properties
Villas Syros
105 properties
Kea
92 properties
Villas Milos
68 properties
Villas Antiparos
50 properties
Apartments Sifnos
41 properties
Villas Serifos
35 properties
Apartments Ios
27 properties
Amorgos
18 properties
Koufonissi
14 properties
Apartments Folegandros
13 properties
Kithnos
7 properties

Cyclades

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3,125 Vacation rentals

Travelers going to Cyclades are booking July dates now. Secure your vacation rental today and have the perfect trip.

(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 $266 / night

$1379 - $2598 / week

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from $266 / 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 $213 / night

$1273 - $2068 / week

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from $213 / night

(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

(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

$1379 - $4009 / week

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from $207 / night

48

Aliki Vacation villa rental

Paros / Aliki

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Suitable for children age 5+
Traditional Cycladic styled villa in Aliki village. It was built in 2015 and is located 500 meters from Aliki's downtown with its restaurants and cafes and the main beach. It is in a countryside quiet area, 12 kilometers from Parikia (capital - main Port) and 2 kil  …see more

from $85 / night

$594 / week

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from $85 / night

5

Vacation villa in Fira

Santorini / Fira

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 $578 / night

$4046 / week

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from $578 / 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

(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 cabl  …see more

from $297 / night

$2683 - $6384 / week

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from $297 / 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

(3) Excellent 

17

Pollonia Vacation apartment rental

Milos / Pollonia

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Air conditioning
This 1st floor bright apartment is situated in a prime and quiet location in Pollonia of Milos. It has an amazing sea view and it is only a short walk from local restaurants and coffee shops. It can accommodate 2 + 1 guests and it consists of one separate bedroom  …see more

from $128 / night

$891 / week

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from $128 / 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

$669 - $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 $154 / night

$855 - $1839 / week

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from $154 / night

(1) Excellent 

26

Vacation hotel apartment with shared pool in Adamas

Milos / Adamas

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
High-standard services from Rooms and Apartments Orizontes Studios hotel, rooms and apartments in Milos is located in Adamas, the port of Milos, in an idylic location traditionaly built, only 15 minutes away from the center providing all the peace and quiet that our vis  …see more

from $91 / night

$631 / week

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from $91 / night

(5) Very Good 

15

Adamas Vacation hotel apartment rental

Milos / Adamas

6 14 1 night min

  • 6 bedrooms
  • Sleeps 14
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
IN A IDEAL AND CALM ENVIROMENT 5 MINUTES AWAY FROM THE PORT AND JUST 400 METRES FROM THE BEACH PAPIKINOU ,LOOKING FARAWAY AEGEAN,ROOMS 'ANTONIS' OFFERS YOU EXCELLENT SERVICE TO EACH VISITOR.THE BUILDING HAS 5 DOUBLE ROOMS AND ONE APPARTMENT FOR FOUR P  …see more

from $32 / night

$223 - $483 / week

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from $32 / night

(2) Excellent 

25

Vari Vacation home rental

Syros / Vari

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
This beautiful guest house is perfect for those who want to relax in a place that offers natural beauty and tranquility, only 2km away from the sandy beach and bars, restaurants and shops. Set in the property “Anna’s Villa” in the classy area of Chrous  …see more

from $111 / night

$712 - $996 / week

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from $111 / night

(3) Excellent 

46

Amorgos / Aegiali

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Air conditioning

 …see more

from $54 / night

$372 - $594 / week

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from $54 / 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

(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 $160 / night

$1114 - $2301 / week

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from $160 / night

(1) Excellent 

53

Hotel apartment rental in Ornos

Mykonos / Ornos

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Filoxenia ApartmentsFiloxenia 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 $85 / night

$594 / week

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from $85 / night

13

Amorgos / Aegiali

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

 …see more

from $54 / night

$372 - $706 / week

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from $54 / night

(1) Very Good 

35

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 ApartmentsFiloxenia 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 $128 / night

$902 / week

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from $128 / night

(46) 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 $112 / night

$637 - $1167 / week

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from $112 / night

(8) 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 $191 / night

$1591 - $3712 / week

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from $191 / night

(13) Excellent 

27

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 $107 / night

$743 - $2969 / week

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from $107 / night

(9) Excellent 

21

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 $350 / night

$2333 - $4136 / week

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from $350 / 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

$2042 / week

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from $292 / night

13

Vacation home in Faros

Sifnos / Faros

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
DESCRIPTION IN ENGLISH & FRENCH AVAILABLE | French | We are just off of the most picturesque beaches of Sifnos Fassolou, Faros, Chrissopigi and Glyfou. The 50m² houses are cozy and comfortable for both a family for a couple or a group of friends. Then we reco  …see more

from $128 / night

$891 / week

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from $128 / night

20

Vacation studio in Logaras

Paros / Logaras

Studio 2 1 night min

  • Studio
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
We offer apartments, studios and rooms for 2 and 3 persons Our studios are with kitchen, refrigerator, TV, Air-condition, WC and balcony. Our rooms are with refrigerator, Air-condition, TV, WC and balcony. Free Wi-Fi Internet access. Also we have private pa  …see more

from $25 / night

$170 - $409 / week

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from $25 / night

(3) Very Good 

26

Melanes Vacation villa rental

Naxos / Melanes

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
White walls, blue doors and windows, such are the traditional Kykladic houses such is this authentic ancient house. Inside, white, stone and honey are the colours. On the ground floor there are a full kitchen, a sitting room and a dining room. On the first floor, there  …see more

from $88 / night

$610 - $716 / week

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from $88 / night

(11) Very Good 

39

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 $96 / night

$669 / week

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from $96 / night

(6) Excellent 

16

Vacation villa rental

Cyclades / Milos

3 7 4 nights min

  • 3 bedrooms
  • Sleeps 7
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Suitable for children age 5+
Mata's house is a beautifully renovated traditional island property with stunning views of the Aegean Sea. This large 3 bedroom house is located in the lovely village of Plaka. Peaceful night and day, yet just a 5 minute stroll to individual and charming tavernas  …see more

from $186 / night

$1220 - $2068 / week

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from $186 / night

(4) Excellent 

19

Tinos Town Vacation windmill rental

Tinos / Tinos Town

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
The windmill is located in a peninsula with a 360° panoramic view on the Aegean Sea and its islands, on the ancient Venetian port and the church of Stavros, on the mountains and on the city of Tinos. Very close to the house there is a series of beautiful sand beache  …see more

from $138 / night

$965 - $1930 / week

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from $138 / night

(4) Excellent 

37

Vacation guest house in Ornos

Mykonos / Ornos

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Great location in a quiet neighborhood: -1min walking from Ornos beach and less than 2 min from Korfos beach -1 min from the nearest bus station and supermarket -3 min from Ornos center - 35 min walking or 5-7min driving (3km) to the famous Mykonos downtown  …see more

from $22 / night

$637 - $1230 / week

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from $22 / 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

12

Vacation studio rental

Paros / Aliki

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
All of the studios of Anixis are bright and comfortable, and well-maintained with daily cleaning. The studios are air-conditioned, and have fully-equipped kitchenette with large fridge, TV with satellite channels, wi-fi, and private bathroom with shower. There are doubl  …see more

from $43 / night

$266 - $488 / week

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from $43 / 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

35

Vacation home with swimming pool in Ornos

Mykonos / Ornos

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Nobody else than a guest can better describe our place.... Please read below his experience, as it was communicated to us.... "Though Mykonos is regarded, by some, as party central of all the Greek Isles, no home is more serene, idyllic, secluded, or visually stun  …see more

from $319 / night

$2227 / week

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from $319 / night

32

Vacation villa in Apollonia

Sifnos / Apollonia

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 7 mi
  • Child friendly
This traditional 145sqm stone house of Cycladic architecture is situated in a 2.000 M2 plot, surrounded by big amphitheatric verandas and a Mediterranean garden with olive trees and palm trees.. In the center of the garden there is a threshing floor (aloni). The house i  …see more

from $228 / night

$1591 - $2651 / week

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from $228 / night

(2) Excellent 

24

Vacation villa with shared pool in Folegandros

Cyclades / Folegandros

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Villa Elia is on the Lithia property alongside Villa Levanda and Myrtia. It is quiet, charming and comfortable with wonderful views, It is self-catering but we provide you daily with fresh bread and fruit etc. for you to make your own Greek breakfast! It has a s  …see more

from $123 / night

$861 / week

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from $123 / night

(1) Excellent 

26

Home rental in Chora

Ios / Chora

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Romantic house is a new property in a beautiful location of Ios.The house is situated 1.5km from the buzzing village of Ios.There are amazing sea views from the balcony.The area is quite and just what is needed to enjoy a relaxing holiday on the beautiful island of Ios.  …see more

from $107 / night

$743 / week

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from $107 / night