50 Best Vacation Rentals in Cyclades - Holiday Lettings - Cabins

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Villas Mykonos
1,023 properties
Apartments Santorini
815 properties
Apartments Paros
537 properties
Villas Naxos
316 properties
Villas Syros
138 properties
Villas Tinos
128 properties
Andros
127 properties
Kea
111 properties
Villas Milos
83 properties
Apartments Sifnos
59 properties
Villas Antiparos
44 properties
Apartments Ios
40 properties
Villas Serifos
39 properties
Koufonissi
21 properties
Apartments Folegandros
11 properties
Kithnos
10 properties
Kimolos
9 properties
Amorgos
5 properties

Cyclades

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3,527 Vacation rentals

(15) Very Good 

18

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 $165 / night

$1,156 - $1,486 / week

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avg. 3 hours 10 minutes

from $165 / night

22

Vacation studio in Mykonos Town

Mykonos / Mykonos Town

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Air conditioning
Memories studio is the ideal place for those who want to enjoy the famous restaurants and the nightlife of Mykonos, but on the same time wish to relax in a beautiful and friendly ambience. The studio is brand new, combine a nostalgic atmosphere with all modern comforts …see more

from $354 / night

$2,476 / week

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from $354 / night

(2) Excellent 

44

Apartment rental in Parikia

Paros / Parikia

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Niriides Studios are comprised of 14 traditional Cycladic vacation rentals ideally located directly on beautiful Krios beach. Each a/c studio apartment has a private entrance & includes a kitchen, single or double beds, full bath with shower, new flat screen TV + balco …see more

from $89 / night

$619 / week

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from $89 / night

(1) Excellent 

18

Batsi Vacation studio rental

Andros / Batsi

Studio 4 3 nights min

  • Studio
  • Sleeps 4
  • 3 nights min
  • Nearest beach 0 mi
  • Child friendly
  • Car not necessary
The property is a beautiful place to spend your relaxation time. All studios and apartments offer magnificent views to the village, the bay and the sea, Visitors appreciate the unique traditional decoration with many handycrafts prepared by Mrs Nana, your hostess. Studi …see more

from $59 / night

$378 / week

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avg. 1 hour 34 minutes

from $59 / night

12

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! Studio 2 has a large room with two beds and a pr …see more

from $59 / night

$413 / week

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avg. 2 hours 34 minutes

from $59 / night

(9) Excellent 

32

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 $106 / night

$743 - $1,321 / week

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avg. 3 hours 10 minutes

from $106 / night

(10) 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 $118 / night

$826 / week

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avg. 3 hours 10 minutes

from $118 / night

(13) Excellent 

16

Vacation villa in Emporio

Santorini / Emporio

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 $295 / night

$1,297 - $2,299 / week

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from $295 / night

(2) Excellent 

20

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 $136 / night

$1,033 - $1,317 / week

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avg. 1 hour 11 minutes

from $136 / night

(1) Excellent 

30

Vacation villa with shared pool in Alyki

Paros / Alyki

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
The villa has 2 bedrooms and two bathrooms (1 en-suit) and it can accomodate up to 6 people. It has a fully equipped fitted kitchen and bathrooms. You can enjoy the breathtaking sea view that our villa provides! Cleaning service is included in the price. There is …see more

from $136 / night

$951 / week

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from $136 / night

(17) Excellent 

20

Vacation villa with swimming pool in Pyrgos

Santorini / Pyrgos

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • 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 $296 / night

$1,299 - $2,893 / week

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from $296 / night

(2) Excellent 

8

Milopotas Vacation apartment rental

Ios / Milopotas

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
Ostria Village is built at a distance of 800m from Mylopotas, the most beautiful beach of the island. The compound consists of 10 one or two room houses, providing space for 2-5 persons. It offers every comfort and a fantastic view All houses can be reached by wh …see more

from $77 / night

$496 - $2,291 / week

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from $77 / night

(25) Excellent 

30

Vacation villa with swimming pool in Glinado

Naxos / Glinado

6 16 Min stay varies

  • 6 bedrooms
  • Sleeps 16
  • Min stay varies
  • 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 $165 / night

$1,002 - $3,301 / week

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avg. 3 hours 10 minutes

from $165 / night

(1) Excellent 

18

Vacation villa with swimming pool in Plaka

Naxos / Plaka

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Panoramic view of the Aegean Sea and sandy coves: on this island, undoubtedly one of the most beautiful in the Cyclades, the climate is pleasant, generous nature, beautiful beaches and the remains of the surprising antiquity. Overlooking sandy beaches at 100 m below ' …see more

from $490 / night

$3,424 - $7,202 / week

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from $490 / night

(43) Excellent 

24

Villa rental in Fira

Santorini / Fira

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • 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 $472 / night

$3,301 / week

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from $472 / night

18

Vacation villa with shared pool in Naoussa

Paros / Naoussa

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Swimming pool
It consists of 3 levels. On the first level (semi-basement) there are 2 bedrooms for 5 guests, 1 bathroom and outdoor space. From this level you can go to the yard and the common swimming pool and through an interior staircase to the first floor. On the second level t …see more

from $213 / night

$1,486 / week

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avg. 2 hours 48 minutes

from $213 / night

(4) Excellent 

31

Vacation villa with swimming pool in Stelida

Naxos / Stelida

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
A truely unique property ,Almiriki Villa. Innovative,stylish and ecologically friendly ,the Villa is one of five completely independent houses ,sensitively carved into the hillside on the North facing side of Stelida hill, encompassing the surrounding landscape and fl …see more

from $342 / night

$2,393 - $2,888 / week

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avg. 3 hours 10 minutes

from $342 / 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 $142 / night

$991 / week

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avg. 1 hour 9 minutes

from $142 / night

(6) Very Good 

33

Villa rental in Mikri Vigla

Naxos / Mikri Vigla

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • 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 $118 / night

$826 - $1,816 / week

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avg. 3 hours 10 minutes

from $118 / night

15

Vacation guest house rental

Santorini / Imerovigli

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Air conditioning
Wake up in the morning, open the door and get out to your private veranda just to find that you are standing on the highest spot of Imerovigli. Enjoy your breakfast at your balcony and then relax into your jetted hot tub. The interior is designed with curves and arches. …see more

from $236 / night

$2,358 - $3,537 / week

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from $236 / night

22

Apartment rental in Mikri Vigla

Naxos / Mikri Vigla

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 250 mi
  • Child friendly
on Orkos beach between Placa and Mikri Vigla we have 3 apartments 250meters from the sea .all the apartments have panoramic view.the apartments are available all the year.every apartment have big kitchen ,living room ,WC, 2 balcony.washing machine.fire place, barbecue.t …see more

from $71 / night

$495 / week

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avg. 1 hour 36 minutes

from $71 / night

9

Mykonos Town Vacation villa rental

Mykonos Town / Mykonos Town

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The Star Light Villa (300 sq m.) is on the highest elevation of the island offering to their privileged guests a stunning panoramic view of sunsets, the Aegean Sea and the town of Mykonos. It is built in three levels; the ground level features 1 masterbedroom with d …see more

from $943 / night

$6,601 / week

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from $943 / night

13

Vacation apartment rental

Naxos / Naxos Town

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
In a quiet area of ​​Naxos Town, at the foot of the Venetian castle and a few meters from the street that leads to the harbor is our family complex. A Cycladic architecture complex ideal for your accommodation. This is a suite for tow people or a appartment for four peo …see more

from $89 / night

$702 / week

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from $89 / night

20

Imerovigli Vacation villa rental

Santorini / Imerovigli

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The Deluxe Suite of the Azar Villas in Santorini is a private suite with amazing views to the sea, one bedroom, one bathroom and a veranda with an infinity pool with 2 seated hydro-massages. This suite is the perfect choice for those who seek undisturbed calmness and re …see more

from $319 / night

$2,228 / week

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avg. 3 hours 37 minutes

from $319 / night

(5) Very Good 

19

Naoussa Vacation villa rental

Paros / Naoussa

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Swimming pool
Villa Anatuzi is a unique luxurious villa built with much love and affection in a charming Cycladic spirit. The villa is positioned on a hill slope, 400 meters from the sea front next to the spectacular Acropolis, in the local village of Kolimbithres. The view of the e …see more

from $354 / night

$2,476 / week

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from $354 / night

(2) Excellent 

21

Vacation villa in Naoussa

Paros / Naoussa

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning
Luxurious traditional villa 85sq.m. in a complex of houses in Paros,with amazing view to the bay of Naousa.It consists of 70 sq.m. ground floor and 14.5 sq.m. "cozy" loft.It has 1 master bedroom ,living room,kitchen and 1 bathroom on the ground floor,2 or 3 single beds …see more

from $236 / night

$1,297 - $2,240 / week

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avg. 3 hours 9 minutes

from $236 / night

20

Studio rental in Sifnos

Cyclades / Sifnos

Studio 19 2 nights min

  • Studio
  • Sleeps 19
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Sifnos is among the most beautiful Greek islands, perfectly suited for vacation and relaxation. Taking into consideration the needs of couples and families our group of rooms and apartments offers the perfect choice for relaxing vacation at accessible price. It consists …see more

from $53 / night

$413 - $826 / week

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from $53 / night

(5) Excellent 

17

Villa rental in Parikia with shared pool

Paros / Parikia

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 $165 / night

$1,156 - $2,228 / week

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avg. 2 hours 43 minutes

from $165 / night

(2) Good 

11

Perissa Vacation b&b rental

Santorini / Perissa

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome To GREEK GODDESS SPICY BEACH APARTMENTS. Hosts Zoi Metaxa and John Lutfey specialize in unique, relaxing, comfortable accommodations with a personal touch, and are committed to making your stay a memory that you will cherish forever. Our INDIGO STUDIO APARTME …see more

from $59 / night

$709 / week

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from $59 / night

(16) Very Good 

33

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

$578 - $991 / week

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avg. 3 hours 10 minutes

from $83 / night

(6) Excellent 

28

Vacation villa in Pollonia

Milos / Pollonia

3 9 4 nights min

  • 3 bedrooms
  • Sleeps 9
  • 4 nights min
  • 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 $189 / night

$1,321 / week

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from $189 / night

(11) Excellent 

Certificate of Excellence

23

Vacation villa in Imerovigli

Santorini / Imerovigli

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
In Imerovigli, one of the most beautiful villages on Santorini, 400 m. above sea level on the northwest side of the island, you can find "Ventus Paradiso Villa". Built with respect for our Cycladic architectural tradition and regard for your absolute comfort, our villa …see more

Certificate of Excellence

from $472 / night

$2,947 - $6,484 / week

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from $472 / night

28

Vacation home in Tinos

Cyclades / Tinos

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
VILLA KARDIANI, a Tinian villa in an uncompromising version, at the heart of the traditional settlement with a fantastic view of the Aegean, promises its guests to honour the silent terms of a twofold agreement: the unique quality of residence with the true experience o …see more

from $348 / night

$2,087 / week

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avg. 2 hours 3 minutes

from $348 / night

(1) Excellent 

11

Vacation apartment in Marathi

Mykonos / Marathi

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
Maren Apartments is a new lake-side complex situated 5 minutes away from Panormos beach and 10 minutes away from Ag.Sostis beach or the town. It has one bedroom. The bedroom has two single beds which they can easily be converted in a double bed. Occupancy is 2 people. …see more

from $118 / night

$708 / week

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from $118 / night

(24) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $118 / night

$826 / week

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avg. 1 hour 32 minutes

from $118 / night

(3) Excellent 

45

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
Théa (Θέα), greek for "view" is a name righteously given to the apartment as it overlooks both the aegean sea, and the santorinian windmills. Shades of White is a newly constructed, traditionally designed complex of apartments located in the village of Emporio. The ma …see more

from $148 / night

$1,032 / week

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from $148 / 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 recommend acc …see more

from $65 / night

$454 / week

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from $65 / night

18

Studio rental in Parikia

Paros / Parikia

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
The studio is located on the 1st floor and is composed of: - 2 single beds or joined to make a double bed (on request). It has a kitchenette with: - fridge - hob - crockery and kitchen utensils, D private bathrooms, A balcony (with table and chairs for 2 people, umbrell …see more

from $42 / night

$290 / week

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avg. 2 hours 46 minutes

from $42 / night

14

Apartment rental in Andros Town

Andros / Andros Town

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Pet friendly
A brand new house at the heart of the old town of Andros, and indeed at its most historical place. The visitor has the unique opportunity to live with the natives in a unique place, since it is surrounded by special architectural aesthetics edifices. In parallel, the vi …see more

from $71 / night

$472 / week

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from $71 / night

(1) Very Good 

17

Batsi Vacation studio rental

Andros / Batsi

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
The Bella Vista Villa in Andros is comprised of 4 tastefully furnished and spacious apartments and studios that are specially designed to offer a comfortable and carefree stay at some of the lowest rates for luxury accommodation. Each studio has 2 single beds pushed tog …see more

from $42 / night

$283 / week

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from $42 / night