Villas in Cyclades and houses – Holiday Lettings - Holiday Rentals Cyclades

Close

View larger map

Also consider

Europe Holidays
430742 properties
Greece Holidays
16382 properties
Coastal Cottages
222 properties
Luxury Villas
2684 properties
Villas Mykonos
966 properties
Villas Santorini
723 properties
Villas Paros
481 properties
Villas Naxos
249 properties
Villas Tinos
119 properties
Villas Andros
111 properties
Villas Syros
105 properties
Villas Kea
92 properties
Villas Milos
68 properties
Villas Antiparos
50 properties
Villas Sifnos
41 properties
Apartments Serifos
35 properties
Villas Ios
27 properties
Villas Amorgos
18 properties
Villas Koufonissi
14 properties
Apartments Folegandros
13 properties
Kithnos
7 properties

Cyclades

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

3,134 Holiday homes

Travellers going to Cyclades are booking June dates now. Secure your holiday home today and have the perfect trip.

(3) Excellent 

17

Pollonia holiday 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 £104 / night

£725 / week

Book View

from £104 / night

(5) Excellent 

40

Holiday 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 £114 / night

£678 - £957 / week

Book View

from £114 / night

(13) Excellent 

27

Holiday 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 km
  • Swimming pool
“Relaxing Naxos holiday in large family house with great swimming pool.” It was an indulgence for just my wife and I to occupy this large villa but from the moment we were met from our ferry by Lesley with our hire car until we departed we enjoyed the  …see more

from £87 / night

£604 - £2414 / week

Book View

from £87 / night

(14) Excellent 

20

Holiday 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 km
  • Swimming pool
Fantastic villa in the village of Exogonia, private pool, sun terraces, sunrise views to the beach resort of Kamari and the island of Anafi, 2 double bedrooms both en suite, sleeps 6 (sofa bed in lounge), all new furniture and features.  …see more

from £216 / night

£1121 - £2113 / week

Book View

from £216 / night

(1) Excellent 

37

Exomvourgo holiday villa rental

Tinos / Exomvourgo

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Villa Elea is a luxury traditional villa with private pool and sweeping sea view in Tinos, in the village of Ktikados, a traditional protected settlement. This spacious two-floor, 4-bedroom villa is the perfect place to enjoy the brilliant Greek sun and cool Aegean bre  …see more

from £332 / night

£2207 - £3669 / week

Book View

from £332 / night

(7) Excellent 

22

Naxos Town holiday villa rental

Naxos / Naxos Town

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
Stunning beaches and a variety of water sports nearby. Short distance from the main town ,Chora. Daily boat charters. Suitable for couples and families.Mini market and bakery with fresh bread daily close by .Horse riding along beautiful beaches  …see more

from £78 / night

£544 - £966 / week

Book View

from £78 / 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 km
  • Swimming pool
“One of the best rentals we ever stay in.” This rental was in a great location.It had breath taking views.Every morning we just would go out and sit on one of our many patios.Memo and Joanna was like family to us we hated to leave them,We would just si  …see more

from £242 / night

£2182 - £5190 / week

Book View

from £242 / 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 km
  • 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 £302 / night

£2156 - £7242 / week

Book View

from £302 / night

(6) Excellent 

36

Holiday 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 km
  • Swimming pool
The Villas Guilena sleep up to 10 people and are located in a peaceful valley yet only 15 minutes drive from some stunning beaches.Stunning pool and terraces for al fresco dining.Suitable for families and couplesWater sports Horse riding Hiking Walking Tours  …see more

from £156 / night

£1078 - £2414 / week

Book View

from £156 / night

48

Aliki holiday villa rental

Paros / Aliki

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • 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 £69 / night

£483 / week

Book View

from £69 / 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 km
  • Child friendly
“Three wonderful days in a wonderful place.” We had a great stay at the windmill. Everything was very clean and furnished with great attention to detail. The kitchen was fully equipped and cold soft drinks and beer were provided when we arrived. The ve  …see more

from £74 / night

£513 / week

Book View

from £74 / night

(8) Excellent 

20

Holiday home with swimming pool in Naoussa

Paros / Naoussa

2 10 Min stay varies

  • 2 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly
Check in after 1600 -Check until 1000 2nd house (2 bedrooms) can be rented additionally. Please ask for details!  …see more

from £156 / night

£1294 - £3018 / week

Book View

from £156 / night

(3) Very Good 

26

Melanes holiday villa rental

Naxos / Melanes

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
Kyklades, Naxos island, Agean sea, clear blue water, wonderful beaches, ramble, hike, ride, view, surf, boat  …see more

from £71 / night

£496 - £582 / week

Book View

from £71 / night

32

Holiday villa in Apollonia

Sifnos / Apollonia

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • 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 £185 / night

£1294 - £2156 / week

Book View

from £185 / night

(12) Very Good 

22

Holiday 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
“Location, location, location” We just spent 10 wonderful days here at Naxos. This little townhouse is absolutely charming, situated in the old town, with authentic, Greek atmosphere and interior. The Naxos labyrinth with its unique, ancient architect  …see more

from £44 / night

£302 - £725 / week

Book View

from £44 / night

(2) Very Good 

20

Holiday home rental

Cyclades / Kimolos

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
Family stone house of the 17th c., fully renovated, fully equiped  …see more

from £71 / night

£616 - £857 / week

Book View

from £71 / night

(28) Excellent 

24

Exo Gonia holiday villa rental

Santorini / Exo Gonia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • 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 £125 / night

£695 - £1495 / week

Enquire View

from £125 / night

(6) Very Good 

20

Holiday apartment rental

Naxos / Naxos Town

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
Stunning sunsets.Protected Cedar Forest covered dunes. Incredible beaches. Views to mountains and sea. Short walk to the beach and tavernas.<br />Beaches. Boat tours. Spring walks. Horse riding. Peaceful area  …see more

from £35 / night

£242 - £423 / week

Book View

from £35 / night

(6) Excellent 

51

Holiday 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
“Great time” We are delighted by our stay at Casa Aragosta. The house is great and very close to the beach. Naxos is also a great island to visit. We had a good time and Lesley was very helpful.  …see more

from £113 / night

£785 - £1509 / week

Book View

from £113 / night

(9) Excellent 

26

Holiday 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 £130 / night

£906 - £1871 / week

Book View

from £130 / night

38

Holiday villa with swimming pool in Exo Gialos Thias

Fira / Exo Gialos Thias

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly
Sienna Resort offers the perfect setting for a relaxing holiday to be with friends or family. The Villas are located in Exo gialos, in a private and quiet area (2km from the centre of Fira), close to the beaches and local attractions. Each villa at Sienna Resort off  …see more

from £380 / night

£3880 / week

Book View

from £380 / night

(1) Excellent 

21

Holiday 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. The views from this outdoors living area are uniquely serene and one can see up to 15 islands!  …see more

from £397 / night

£2802 / week

Book View

from £397 / night

(46) Very Good 

11

Oia holiday studio rental

Santorini / Oia

Studio 3 3 nights min

  • Studio
  • Sleeps 3
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children age 5+
“Live in the postcard view” We enjoyed sitting on the balcony for most of the time, we stayed in Oia. No need to go aound like other tourists. Simply the best view you can find in Oia. Surrounded by luxury hotels, this is a reasonable vacation rental  …see more

from £91 / night

£518 - £949 / week

Book View

from £91 / 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
Each one bedroom apartment can accommodate up to 4 people and provides full domestic facilities. Apartments are located 100 metres far from Ornos beach.<br />For any questions please do not hesitate to contact us.Free airport/port shuttle is provided upon request.  …see more

from £69 / night

£483 / week

Book View

from £69 / 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 £78 / night

£544 / week

Book View

from £78 / night

(2) Excellent 

43

Holiday home in Emporio

Santorini / Emporio

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • 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 £108 / night

£755 - £1294 / week

Book View

from £108 / night

15

Oia holiday cave house rental

Santorini / Oia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Ask owner if suitable for children
  • Air conditioning
  • Pet friendly
it is about 100 steps from the main pedestrian street of Oia where all the shops and restaurants are (website hidden) is only five minutes walking distance from the commercial centrer of the village .The appartment is only 7 minutes walking distance from the bus station  …see more

from £69 / night

£483 - £2233 / week

Book View

from £69 / night

(4) Excellent 

19

Tinos Town holiday windmill rental

Tinos / Tinos Town

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
“Unique Experience in a Quality Home” We had a wonderful stay at this beautiful home in Tinos. The owner Matthaios could not have been more helpful and despite our language barriers we managed to get by. The windmill itself has been beautifully renov  …see more

from £113 / night

£785 - £1569 / week

Book View

from £113 / night

13

Amorgos / Aegiali

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £44 / night

£302 - £574 / week

Book View

from £44 / night

(5) Very Good 

15

Adamas holiday hotel apartment rental

Milos / Adamas

6 14 1 night min

  • 6 bedrooms
  • Sleeps 14
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
QUIET,CALM,FAMILY PLACE,BIG GARDEN,FRIENDLY AND KIND OWNERS.  …see more

from £26 / night

£182 - £393 / week

Book View

from £26 / night

(1) Very Good 

7

Amorgos / Aegiali

1 2 1 night min

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

 …see more

from £31 / night

£212 - £363 / week

Book View

from £31 / 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 km
  • Ask owner if suitable for 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 £78 / night

£544 - £1087 / week

Book View

from £78 / night

(1) Excellent 

26

Plaka holiday apartment rental

Naxos / Plaka

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
New studios & apartments at Plaka beach for 2-5 people with sea view, 7 km from Naxos town, on the beach(30m), private beach, private parking, kitchen with full equipment, a/c, TV led, very comfortable beds, balcony-veranda with sea view, Free Wi-Fi, hypoallergenic  …see more

from £22 / night

£151 / week

Book View

from £22 / night

(3) Excellent 

28

Holiday home in Antiparos Town

Antiparos / Antiparos Town

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
Aiolos Home is one of four, newly constructed (2016), detached Cycladic stonehouses with spectacular views of the Sifneikos Gialos bay. The houses are set on a private property of 4000 sq meters, less than a minute walk (100 meters) from the sandy beach. Sifneikos Gialo  …see more

from £138 / night

£966 / week

Book View

from £138 / night

(1) Very Good 

18

Oia holiday 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 £238 / night

£1660 / week

Book View

from £238 / night

(6) Excellent 

30

Holiday cave house in Fira

Santorini / Fira

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Air conditioning
“Fabulous” This cave house was amazing. It is only a few minutes walk from the main square in Fira with all of its bars and restaurants. The cave is an ideal base for getting around the island - the main bus station is less than 5 minutes walk so get  …see more

from £74 / night

£513 - £1207 / week

Book View

from £74 / night

(2) Very Good 

22

Holiday home in Mykonos Town

Mykonos / Mykonos Town

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
Anna-Maria's Maisonette III provides ideal accommodation in Mykonos with unbreakable view over Aegean Sea overlooking 3 beaches. It has 2 bedrooms, 2 bathrooms and accommodates up to five people. Balcony & patio with sunbeds, veranda as an outdoor dining area,  …see more

from £65 / night

£432 - £1091 / week

Book View

from £65 / night

5

Holiday 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 £470 / night

£3289 / week

Book View

from £470 / night

15

Holiday villa in Naxos Town

Naxos / Naxos Town

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • 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 £65 / night

£421 - £533 / week

Book View

from £65 / night

32

Paraga holiday villa rental

Mykonos / Paraga

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Nearest beach 3 km
  • Swimming pool
  • Child friendly
Σε μια από της πιο προνομιακές περιοχές της Μυκόνου  …see more

from £345 / night

£2328 - £5173 / week

Book View

from £345 / night

Top Destination reviews

Beach Studios, Sifnos
Gorgeous Studio in the best Sifnos place

1. This place is perfect. Located in the small village of Vathi, we are a family of 4 people who spent 2 weeks in one of the studio. Really nicely decorated and with a huge balcony above the Crystal sea, this is a really quite and relax place. There … see more
Flora Studios and Apartment
Summer holidays

My family and I decided to spend our vacations to Flora Studios and Apartment and we are not disappoint.Great place,very clean and the onwers kind and helful!!!After all we fell very lucky for our choise !!! … see more
Flora Studios and Apartments
Once in a lifetime experience!!!

We stayed in Flora's Studios for 10 days last July and we were delighted!!! Firstly, the Studios are set in a convenient location and have a breathtaking view of the island. When you sit in the balcony and enjoy the beautiful sunset you feel peace … see more
Raki Cave
Fabulous

This cave house was amazing. It is only a few minutes walk from the main square in Fira with all of its bars and restaurants. The cave is an ideal base for getting around the island - the main bus station is less than 5 minutes walk so getting to a … see more
Rodothea on the Beach- Santorini-Monolithos
Great Apartment with Wonderful View of the Sea!

Great apartment, exactly what I was looking for in a long-term rental. Located on Monolithos Beach, with beautiful views of the sea & magnificent sunrises. Loved being here in the winter as it was quiet, though the buses only run three times a day. L … see more
Adams on the Beach, Santorini, Monolithos
Lovely apartment - recommended

We spent a week in this lovely apartment. It was beautifully clean and comfortable. We loved the view over the sea and spent many mornings and evenings relaxing there. … see more