Cyclades Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

3,690 Houses

(30) Excellent 

    42

    SantoriniParadise: PINK Cave, 3 terraces outdoor jacuzzi Caldera View

    Santorini / Oia

    Oia villa

    3 4 1 night min

    • 3 bedrooms
    • sleeps 4
    • 1 night min
    • Beach / lakeside relaxation
    • Child Friendly
    • Car not necessary
    “Incredible stay in an iconic home!” Maria was a wonderful host. She went out of her way to make us feel welcome and sat down with us and gave us a great overview of the island's activities. The house is iconic and is able to be seen on the postcards!
    …see more

    Price per night from

    $262

    Price per night from

    $262

    (13) Excellent 

      43

      NK Cave House Villa

      Santorini / Fira

      Fira villa

      1 4 min stay varies

      • 1 bedroom
      • sleeps 4
      • min stay varies
      • Child Friendly
      • Air conditioning

      Price per night from

      $300

      Price per night from

      $300

      (20) Excellent 

        32

        ANTELMI VILLA CALDERA FIROSTEFANI

        Santorini / Firostefani

        Firostefani villa

        4 10 2 nights min

        • 4 bedrooms
        • sleeps 10
        • 2 nights min
        • Nearest beach 3 mi
        • Swimming pool
        • Child Friendly

        Price per night from

        $1,101

        Responds fast!
        avg. 3 hours 45 minutes

        Price per night from

        $1,101

          10

          Auli House

          Andros / Agios Petros

          Agios Petros house

          1 3 2 nights min

          • 1 bedroom
          • sleeps 3
          • 2 nights min
          • Child Friendly
          • Air conditioning
          • Private garden

          Price per night from

          $91

          Price per night from

          $91

          (3) Excellent 

            55

            Iliana by the beach: Your own Private Beach House and Garden; Walk To Everything

            Cyclades / Naxos

            Naxos house

            3 7 3 nights min

            • 3 bedrooms
            • sleeps 7
            • 3 nights min
            • Beach / lakeside relaxation
            • Nearest beach 0.05 mi
            • Child Friendly

            Price per night from

            $125

            Price per night from

            $125

            (2) Excellent 

              44

              Seafront House Mandrakia

              Milos / Triovassalos

              Triovassalos house

              2 4 3 nights min

              • 2 bedrooms
              • sleeps 4
              • 3 nights min
              • Child Friendly
              • Air conditioning
              • Private garden

              Price per night from

              $170

              Responds fast!
              avg. 1 hour 29 minutes

              Price per night from

              $170

              (14) Excellent 

                17

                Santorini (Greece) cave house

                Santorini / Firostefani

                Firostefani house

                2 4 3 nights min

                • 2 bedrooms
                • sleeps 4
                • 3 nights min
                • Nearest beach 8 mi
                • Ask about children
                • Pet Friendly
                “Perfect!” Myself and 2 friends just spent four nights in Spiti Martin and it was a great choice! We were looking for an authentic cave house experience without too much hassle, and the the owner is responsive and helpful. I didn't know much about th
                …see more

                Price per night from

                $287

                Responds fast!
                avg. 1 hour 42 minutes

                Price per night from

                $287

                (2) Very Good 

                  40

                  Courtyard of the Stars Villa, renovated 19th c winery

                  Santorini / Emporio

                  Emporio villa

                  4 10 3 nights min

                  • 4 bedrooms
                  • sleeps 10
                  • 3 nights min
                  • Nearest beach 6 mi
                  • Swimming pool
                  • Child Friendly

                  Price per night from

                  $326

                  Responds fast!
                  avg. 35 minutes

                  Price per night from

                  $326

                  (1) Excellent 

                    12

                    Scenic seaside house with pool

                    Serifos / Livadi

                    Livadi villa

                    2 6 7 nights min

                    • 2 bedrooms
                    • sleeps 6
                    • 7 nights min
                    • Swimming pool
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $248

                    Responds fast!
                    avg. 2 hours 2 minutes

                    Price per night from

                    $248

                    (3) Very Good 

                      29

                      STUDIOS WITH SEA VIEW BY THE BEACH OF KALO LIVADI

                      Mykonos / Kalo Livadi

                      Kalo Livadi studio

                      Studio 2 1 night min

                      • Studio
                      • sleeps 2
                      • 1 night min
                      • Beach / lakeside relaxation
                      • Nearest beach 0.1 mi
                      • Child Friendly

                      Price per night from

                      $59

                      Price per night from

                      $59

                      (1) Excellent 

                        66

                        Watching The Sea

                        Andros / Ormos Korthiou

                        Ormos Korthiou house

                        2 6 3 nights min

                        • 2 bedrooms
                        • sleeps 6
                        • 3 nights min
                        • Nearest beach 0.5 mi
                        • Child Friendly
                        • Air conditioning

                        Price per night from

                        $105

                        Price per night from

                        $105

                        (4) Excellent 

                          36

                          Traditional Waterfront House

                          Milos / Triovassalos

                          Triovassalos house

                          2 4 min stay varies

                          • 2 bedrooms
                          • sleeps 4
                          • min stay varies
                          • Beach / lakeside relaxation
                          • Nearest beach 0 mi
                          • Ask about children

                          Price per night from

                          $176

                          Responds fast!
                          avg. 1 hour 29 minutes

                          Price per night from

                          $176

                            10

                            Eneos Beach Villas

                            Kithnos / Loutra

                            Loutra villa

                            4 10 5 nights min

                            • 4 bedrooms
                            • sleeps 10
                            • 5 nights min
                            • Beach / lakeside relaxation
                            • Child Friendly
                            • Air conditioning

                            Price per night from

                            $990

                            Price per night from

                            $990

                            (47) Excellent 

                              43

                              SantoriniParadise: PARADISE, outdoor Hot Tub, Caldera panorama!

                              Santorini / Oia

                              Oia villa

                              2 4 1 night min

                              • 2 bedrooms
                              • sleeps 4
                              • 1 night min
                              • Beach / lakeside relaxation
                              • Nearest beach 2 mi
                              • Child Friendly
                              “Amazing Greek Island experience” We rented both the Santorini Paradise and Helios houses for eleven people. They were absolutely wonderful. The views are spectacular. The houses were clean to start with and cleaned every day. Helios had just recently
                              …see more

                              Price per night from

                              $205

                              Price per night from

                              $205

                              (1) Excellent 

                                37

                                Sea view 3 bedroom condo

                                Andros / Paleopoli

                                Paleopoli house

                                3 5 2 nights min

                                • 3 bedrooms
                                • sleeps 5
                                • 2 nights min
                                • Swimming pool
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $202

                                Responds fast!
                                avg. 1 hour 31 minutes

                                Price per night from

                                $202

                                (1) Excellent 

                                  49

                                  Maria Beach House, Feet-in-the-Water Apartement, Tranquil, on Private Beach

                                  Kea / Koundouros

                                  Koundouros house

                                  2 5 min stay varies

                                  • 2 bedrooms
                                  • sleeps 5
                                  • min stay varies
                                  • Beach / lakeside relaxation
                                  • Nearest beach 0.02 mi
                                  • Child Friendly

                                  Price per night from

                                  $441

                                  Responds fast!
                                  avg. 2 hours 51 minutes

                                  Price per night from

                                  $441

                                  (32) Excellent 

                                    28

                                    LOCATION LOCATION LOCATION-PRIVATE POOL with views to INFINITY- House/Villa

                                    Santorini / Imerovigli

                                    Imerovigli villa

                                    3 8 min stay varies

                                    • 3 bedrooms
                                    • sleeps 8
                                    • min stay varies
                                    • Nearest beach 5 mi
                                    • Swimming pool
                                    • Child Friendly
                                    “Awesome, Beautiful - Villa Santorini” Our family stayed at Villa Santorini for a week in august 2013. Before our arrival the owners communicated with detail what to expect, things to see and even helped us with travel information for our stop-over in
                                    …see more

                                    Price per night from

                                    $625

                                    Responds fast!
                                    avg. 3 hours 49 minutes

                                    Price per night from

                                    $625

                                    (1) Excellent 

                                      24

                                      Lito: Lovely Sunsets House by the sea

                                      Tinos / Agios Romanos

                                      Agios Romanos house

                                      3 7 min stay varies

                                      • 3 bedrooms
                                      • sleeps 7
                                      • min stay varies
                                      • Beach / lakeside relaxation
                                      • Nearest beach 0 mi
                                      • Child Friendly

                                      Price per night from

                                      $79

                                      Price per night from

                                      $79

                                      (6) Excellent 

                                        15

                                        Villa Kastro-Luxury house in the Old Town of Paros

                                        Paros / Parikia

                                        Parikia apartment

                                        1 2 min stay varies

                                        • 1 bedroom
                                        • sleeps 2
                                        • min stay varies
                                        • Beach / lakeside relaxation
                                        • Car not necessary
                                        • Air conditioning

                                        Price per night from

                                        $105

                                        Responds fast!
                                        avg. 3 hours 19 minutes

                                        Price per night from

                                        $105

                                        (13) Excellent 

                                          14

                                          Lydia's House - indoor heated splash pool, Caldera view

                                          Santorini / Oia

                                          Oia villa

                                          3 6 2 nights min

                                          • 3 bedrooms
                                          • sleeps 6
                                          • 2 nights min
                                          • Child Friendly
                                          • Car not necessary
                                          • Air conditioning
                                          “A Corner of Heaven” Just checked out and felt like we were leaving home. House was some steps below the heart of the village and close to the Castle where people gather for sunset. Even so, it was private, quiet, clean, and oh so cool on days we cam
                                          …see more

                                          Price per night from

                                          $274

                                          Price per night from

                                          $274

                                            29

                                            Sea view condo

                                            Andros / Paleopoli

                                            Paleopoli house

                                            2 4 2 nights min

                                            • 2 bedrooms
                                            • sleeps 4
                                            • 2 nights min
                                            • Swimming pool
                                            • Child Friendly
                                            • Air conditioning

                                            Price per night from

                                            $175

                                            Responds fast!
                                            avg. 1 hour 31 minutes

                                            Price per night from

                                            $175

                                            (3) Excellent 

                                              39

                                              Octopus Garden Beach House

                                              Tinos / Tinos Town

                                              Tinos Town house

                                              2 4 2 nights min

                                              • 2 bedrooms
                                              • sleeps 4
                                              • 2 nights min
                                              • Nearest beach 0 mi
                                              • Child Friendly
                                              • Air conditioning

                                              Price per night from

                                              $105

                                              Responds fast!
                                              avg. 18 minutes

                                              Price per night from

                                              $105

                                              (7) Excellent 

                                                18

                                                Spacious, Modern and Comfortable Sea View

                                                Paros / Parikia

                                                Parikia villa

                                                3 7 min stay varies

                                                • 3 bedrooms
                                                • sleeps 7
                                                • min stay varies
                                                • Beach / lakeside relaxation
                                                • Nearest beach 2 mi
                                                • Swimming pool

                                                Price per night from

                                                $202

                                                Price per night from

                                                $202

                                                  45

                                                  Villa Artisti Mykonos by OWNER

                                                  Mykonos / Elia

                                                  Elia villa

                                                  6 12 3 nights min

                                                  • 6 bedrooms
                                                  • sleeps 12
                                                  • 3 nights min
                                                  • Nearest beach 1 mi
                                                  • Swimming pool
                                                  • Child Friendly

                                                  Price per night from

                                                  $2,604

                                                  Price per night from

                                                  $2,604

                                                  (21) Excellent 

                                                    71

                                                    SantoriniParadise: HELIOS or SISTERHOOD of traveling pants + hot tub

                                                    Santorini / Oia

                                                    Oia house

                                                    1 5 1 night min

                                                    • 1 bedroom
                                                    • sleeps 5
                                                    • 1 night min
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 2 mi
                                                    • Child Friendly
                                                    “Wonderful Getaway” We had an amazing stay at the Helios cave house. On arrival we were treated to a bottle of wine and some delicious nibbles on the terrace above the house, which Maria uses to welcome her guests. The view from the terrace is absolute
                                                    …see more

                                                    Price per night from

                                                    $227

                                                    Price per night from

                                                    $227

                                                    (26) Excellent 

                                                      66

                                                      SantoriniParadise: BLUE & WHITE Cave House, Santorini, Oia + hot tub!

                                                      Santorini / Oia

                                                      Oia villa

                                                      2 4 1 night min

                                                      • 2 bedrooms
                                                      • sleeps 4
                                                      • 1 night min
                                                      • Beach / lakeside relaxation
                                                      • Nearest beach 3 mi
                                                      • Child Friendly
                                                      “lovely with generous outdoor space” The Blue and White with it's stunning view is located just far enough below the main street,and a five minute walk to the sunset view, to give valued privacy.My daughter and I could enjoy breakfast,everything provid
                                                      …see more

                                                      Price per night from

                                                      $216

                                                      Price per night from

                                                      $216

                                                        12

                                                        Aelia Superior Villa with Private Pool

                                                        Paros / Nea Chryssi Akti

                                                        Nea Chryssi Akti villa

                                                        7 15 min stay varies

                                                        • 7 bedrooms
                                                        • sleeps 15
                                                        • min stay varies
                                                        • Beach / lakeside relaxation
                                                        • Nearest beach 0.2 mi
                                                        • Swimming pool

                                                        Price per night from

                                                        $951

                                                        Price per night from

                                                        $951

                                                          19

                                                          Holiday room in Zefyria

                                                          Milos / Zefiria

                                                          Zefiria room

                                                          1 2 1 night min

                                                          • 1 bedroom
                                                          • sleeps 2
                                                          • 1 night min
                                                          • Child Friendly

                                                          Price per night from

                                                          $46

                                                          Responds fast!
                                                          avg. 3 hours 28 minutes

                                                          Price per night from

                                                          $46

                                                            14

                                                            TRADITIONAL STONE RESIDENCE "KONAKI"

                                                            Andros / Paleopoli

                                                            Paleopoli house

                                                            1 4 7 nights min

                                                            • 1 bedroom
                                                            • sleeps 4
                                                            • 7 nights min
                                                            • Nearest beach 3 mi
                                                            • Child Friendly
                                                            • Air conditioning

                                                            Price per night from

                                                            $180

                                                            Price per night from

                                                            $180

                                                            (1) Excellent 

                                                              24

                                                              Enjoy the beauties of Mykonos like never before!

                                                              Mykonos / Mykonos Town

                                                              Mykonos Town apartment

                                                              2 5 5 nights min

                                                              • 2 bedrooms
                                                              • sleeps 5
                                                              • 5 nights min
                                                              • Nearest beach 5 mi
                                                              • Swimming pool
                                                              • Child Friendly

                                                              Price per night from

                                                              $378

                                                              Responds fast!
                                                              avg. 48 minutes

                                                              Price per night from

                                                              $378

                                                              (5) Excellent 

                                                                10

                                                                Secret Garden maisonette 4

                                                                Paros / Naoussa

                                                                Naoussa house

                                                                1 4 min stay varies

                                                                • 1 bedroom
                                                                • sleeps 4
                                                                • min stay varies
                                                                • Beach / lakeside relaxation
                                                                • Nearest beach 0 mi
                                                                • Child Friendly

                                                                Price per night from

                                                                $91

                                                                Price per night from

                                                                $91

                                                                (25) Excellent 

                                                                  35

                                                                  Seaside Naxos • Villa Dimitra • 3 BDR • 3.5 BATH • Sleeps 8 at Plaka Beach

                                                                  Naxos / Plaka

                                                                  Plaka villa

                                                                  3 8 3 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 8
                                                                  • 3 nights min
                                                                  • Beach / lakeside relaxation
                                                                  • Nearest beach 0.2 mi
                                                                  • Child Friendly
                                                                  “A wonderful, comfortable and quiet place” We stayed in the house in august 2013. The house is just perfect: large, comfortable, extremely quiet, and perfectly equipped. I cannot mention a single flaw. The house is at walking distance (200m) from the
                                                                  …see more

                                                                  Price per night from

                                                                  $248

                                                                  Responds fast!
                                                                  avg. 2 hours 44 minutes

                                                                  Price per night from

                                                                  $248

                                                                  (1) Excellent 

                                                                    34

                                                                    Luxury house with Parikia bay views and pool, beach in walking distance

                                                                    Paros / Parikia

                                                                    Parikia house

                                                                    2 3 7 nights min

                                                                    • 2 bedrooms
                                                                    • sleeps 3
                                                                    • 7 nights min
                                                                    • Beach / lakeside relaxation
                                                                    • Nearest beach 0.5 mi
                                                                    • Swimming pool

                                                                    Price per night from

                                                                    $170

                                                                    Price per night from

                                                                    $170

                                                                    (19) Very Good 

                                                                      23

                                                                      Mimallis traditional houses in Milos, Anoi house

                                                                      Cyclades / Milos

                                                                      Milos apartment

                                                                      1 2 3 nights min

                                                                      • 1 bedroom
                                                                      • sleeps 2
                                                                      • 3 nights min
                                                                      • Nearest beach 2 mi
                                                                      • Child Friendly
                                                                      • Air conditioning
                                                                      “Beautiful apartment in Plaka.” We spent 6 nights in this wonderful apartment and didn't want to leave. The apartment is in a great location, in the middle of the old town. It was a great place to come home to after spending the day at the beach. Rest
                                                                      …see more

                                                                      Price per night from

                                                                      $100

                                                                      Price per night from

                                                                      $100

                                                                      (4) Excellent 

                                                                        10

                                                                        Maistrali Studio SIROCCO

                                                                        Syros / Finikas

                                                                        Finikas studio

                                                                        Studio 2 2 nights min

                                                                        • Studio
                                                                        • sleeps 2
                                                                        • 2 nights min
                                                                        • Nearest beach 2 mi
                                                                        • Ask about children
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $52

                                                                        Price per night from

                                                                        $52

                                                                        (1) Excellent 

                                                                          24

                                                                          Carpe Diem Villa I with Private Infinity Pool

                                                                          Mykonos / Mykonos Town

                                                                          Mykonos Town villa

                                                                          4 10 min stay varies

                                                                          • 4 bedrooms
                                                                          • sleeps 10
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $508

                                                                          Responds fast!
                                                                          avg. 38 minutes

                                                                          Price per night from

                                                                          $508

                                                                          (1) Excellent 

                                                                            18

                                                                            Apartment with Panoramic Sea View for 1-4 persons

                                                                            Paros / Parikia

                                                                            Parikia apartment

                                                                            1 4 min stay varies

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • min stay varies
                                                                            • Child Friendly
                                                                            • Car not necessary
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $72

                                                                            Price per night from

                                                                            $72

                                                                            (7) Excellent 

                                                                              35

                                                                              VERY SPACIOUS - View - cave house for 6 people - jacuzzi - 3bdr: Spiti Barbara

                                                                              Santorini / Firostefani

                                                                              Firostefani house

                                                                              3 6 5 nights min

                                                                              • 3 bedrooms
                                                                              • sleeps 6
                                                                              • 5 nights min
                                                                              • Beach / lakeside relaxation
                                                                              • Nearest beach 7 mi
                                                                              • Swimming pool

                                                                              Price per night from

                                                                              $626

                                                                              Price per night from

                                                                              $626