50 Best Vacation Rentals in Cyclades - Holiday Lettings - Cabins

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Villas Mykonos
936 properties
Apartments Santorini
744 properties
Apartments Paros
473 properties
Villas Naxos
236 properties
Andros
115 properties
Villas Tinos
113 properties
Villas Syros
104 properties
Kea
98 properties
Villas Milos
65 properties
Villas Antiparos
47 properties
Apartments Sifnos
41 properties
Villas Serifos
40 properties
Apartments Ios
25 properties
Amorgos
15 properties
Koufonissi
14 properties
Apartments Folegandros
13 properties
Kithnos
8 properties

Cyclades

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3,070 Vacation rentals

(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 $270 / night

$1400 - $2637 / week

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from $270 / 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 $114 / night

$646 - $1184 / week

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from $114 / 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 $173 / night

$1507 / week

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from $173 / night

19

Vacation home rental

Mykonos / Ornos

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
A cosy and a warm house very close to ornos beach. The house has a bedroom with a double bed,a living room with sofa bed for 2 more people and one more bed for the 5th person, tv and a kitchen fully equipped,bathroom with a built shower. Outdoors 2 verandas with dining  …see more

from $130 / night

$905 / week

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from $130 / night

(1) Excellent 

4

Vacation apartment in Marathi

Mykonos / Marathi

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 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 two bedrooms. Each bedroom has two single beds which they can easily be converted in a double bed. Occupancy is 4 people  …see more

from $130 / night

$905 / week

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from $130 / 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 $54 / night

$377 - $754 / week

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from $54 / night

(1) Very Good 

24

Villa rental in Paraga with shared pool

Mykonos / Paraga

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The property for rent is a fully furnished, newly built villa, 140 sq.m., situated at KTIMA LENO - LENO ESTATE, an area in Mykonos called Leno at the south part of the island, protected by the strong northerly winds. It offers views to the seas of Psarrou (Nammos bar re  …see more

from $453 / night

$3165 / week

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from $453 / night

25

Vacation villa in Agios Ioannis Diakoftis

Mykonos / Agios Ioannis Diakoftis

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Our Villa lie on a magnificent location especially protected from the wind, with a heavenly view to the Aegean, the historical island of Delos and the colorful sunset. The unique location of the villa offers our guests’ privacy as well as convenience since the villa i  …see more

from $2261 / night

$15822 / week

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from $2261 / night

9

Zefiria Vacation private room rental

Milos / Zefiria

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
Situated in Agia Kiriaki Beach, 10 km from Adamas Port, Thalassopetra features plenty of view of the sea and of Aghia Kyriaki beach. Free private parking is available on site. Every room at this hotel is air conditioned and comes with a TV. The rooms are fitted with a  …see more

from $49 / night

$340 / week

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from $49 / night

(1) Very Good 

18

Psarou Vacation home rental

Mykonos / Psarou

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights 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 $495 / night

$3459 / week

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from $495 / night

21

Apartment rental in Mikri Vigla

Naxos / Mikri Vigla

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • 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 $108 / night

$754 / week

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from $108 / night

(5) Very Good 

39

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 $65 / night

$453 - $754 / week

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from $65 / 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 $108 / night

$754 / week

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from $108 / night

(1) Excellent 

23

Home rental in Golden Beach with swimming pool

Paros / Golden Beach

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
The house is located on the island of Paros on the slope of a hill with a south-east direction. During the summer, the sun shines from the sunrise to the early evening directly on the house. From all rooms and from the spacious terrace you can enjoy a panorama view of t  …see more

from $151 / night

$969 - $4090 / week

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from $151 / 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 $162 / night

$1131 - $2336 / week

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from $162 / night

(1) Excellent 

21

Vacation home in Livadi

Serifos / Livadi

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Modern Cycladic, newly-built (2016), fully-equipped, spacious house located in Livadakia: just 100m from the sandy beach Livadakia, 7mins walk from the Port and 5mins walk from the heart of the island's life, Livadi. A luxurious house for a memorable stay! Welcome to o  …see more

from $87 / night

$162 - $743 / week

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from $87 / 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

$377 - $716 / week

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from $54 / night

(2) Good 

12

Vacation studio in Mykonos Town

Mykonos Town / Mykonos Town

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • Suitable for children age 5+
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,a/c,electric cooker ,fridgeSpaziosi s  …see more

from $54 / night

$829 / week

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from $54 / 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 $194 / night

$1615 - $3767 / week

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from $194 / 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 $108 / night

$646 - $1023 / week

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from $108 / night

(6) Very Good 

22

Vacation home in Megalochori

Santorini / Megalochori

2 4 Min stay varies

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

from $103 / night

$539 - $1077 / week

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from $103 / 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 $296 / night

$2072 / week

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from $296 / 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 $92 / night

$641 / week

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from $92 / 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 $35 / night

$232 - $262 / week

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from $35 / night

(12) Very Good 

22

Vacation townhouse rental

Naxos / Naxos Town

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
This beautiful Classic Townhouse built on the original base of the Ancient Venetian city ,hundreds of years ago,was renovated in 2010 ,displaying a tasteful mix of Cycladic features and contemporary facilities.A single storey property,with a double bedroom and a ver  …see more

from $54 / night

$377 - $905 / week

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from $54 / 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 $97 / night

$679 - $1357 / week

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from $97 / night

(1) Excellent 

25

Vacation villa in Agios Ioannis

Serifos / Agios Ioannis

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Ask about pets
ASPES VILLAS Breathtaking view, near Psili Ammos beach (award winning beach 2003) 3 beautiful independent villas built on the rock, perfectly in tune with the environment, with an exclusive view of the unique blue of the Aegean sea Each villa separately, modernly decora  …see more

from $140 / night

$980 / week

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from $140 / night

(1) Excellent 

8

Cyclades / Amorgos

1 2 1 night min

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

 …see more

from $108 / night

$754 - $1357 / week

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from $108 / night

(3) Very Good 

10

Vacation studio with shared pool in Elia

Mykonos / Elia

Studio 3 1 night min

  • Studio
  • Sleeps 3
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Live a romantic getaway facing the sea from your balcony and feel the relaxing breeze of the Aegean. An open plan area with two singles or one double bed with a private bathroom with shower and a fully equipped kitchenette, provide accommodation with a touch of quality  …see more

from $68 / night

$428 - $1658 / week

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from $68 / night

5

Vacation apartment in Aliki

Paros / Aliki

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Air conditioning
This studio is in a perfect location. The beach, tennis- and basketball-court, childrens playground, restaurant and kiosk, as well as the bus stop, are just 150 m away. The centre of the village is in walking distance. There you can find your favorite restaurants, cafes  …see more

from $28 / night

$167 / week

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from $28 / night

(2) Excellent 

40

Vacation home with shared pool in Platys Gialos

Mykonos / Platys Gialos

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
The house (120 s.m.) is situated at Ktima Lino (Paraga area), in a small complex, it is surrounded by a wonderful garden with palm trees and it has a very big swimming pool. The house's veranda has a fantastic sea view and is overlooking the beaches of Paraga and Agia A  …see more

from $431 / night

$3391 / week

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from $431 / 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 com  …see more

from $103 / night

$512 - $996 / week

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from $103 / night

(1) Excellent 

20

Apartment rental in Plaka

Milos / Plaka

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Monastiraki Rosario is an old monastery/house built togther with a little Catholic church by the french consulate, Louis Brest, in 1820 who discovered the "Venus of Milo", bought and gave it to the Louvre museum in Paris. The house is located in Plaka, the historical t  …see more

from $216 / night

$1776 - $2745 / week

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from $216 / 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

$381 - $1016 / week

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from $64 / 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 $216 / night

$1292 - $2099 / week

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from $216 / night

(11) 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 $248 / night

$1502 - $2363 / week

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from $248 / night

(3) Excellent 

22

Vacation villa in Pyrgos

Santorini / Pyrgos

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 7 mi
  • Child friendly
  • Car not necessary
Small Architect's House is privately owned two story Stylish house that is part of the traditional village of Pyrgos. As most residences in this picturesque village it follows the architecture and style of the cycladic area. The lower level is partially into the vo  …see more

from $97 / night

$746 / week

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from $97 / night

(7) Very Good 

23

Villa rental in Mykonos Town with swimming pool

Mykonos / Mykonos Town

5 8 3 nights min

  • 5 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
A stunning Villa which has been used as a private family holiday home is now available for rental. It can be fully staffed (optional) with all amenities and the latest gadgets. It is located in the sought after area of Agio Sofia with beautiful views overlooking the the  …see more

from $635 / night

$4445 - $5779 / week

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from $635 / night

(1) Excellent 

16

Vacation b&b rental

Santorini / Perissa

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
OUR SAPPHIRE STUDIO APARTMENT is extremely cozy, and sleeps three adults comfortably, with a double sized bed and additional single bed. There is a flat screen TV adjacent to the bathroom. Please enjoy the swimming pool or try one of our Spicy cocktails at the p  …see more

from $87 / night

$539 - $969 / week

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from $87 / night

(2) Excellent 

7

Kea Vacation studio rental

Cyclades / Kea

Studio 2 4 nights min

  • Studio
  • Sleeps 2
  • 4 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Pet friendly
Perched on the top of Ioulida, the Chora of Kea, KEA VILLAS is a hospitable holiday complex that provides its guests the essence of Greek hospitality, genuine warmth and friendliness. Seven Suites and Villas, with a panoramic view at Aegean Sea and the picturesque Chora  …see more

from $65 / night

$453 / week

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from $65 / night

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