Five Cays Settlement Rentals

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Filtering by: Swimming pool

307 Houses

(1) Excellent 

    18

    Breezy Villa

    Providenciales / Five Cays Settlement

    Five Cays Settlement villa

    4 8 min stay varies

    • 4 bedrooms
    • sleeps 8
    • min stay varies
    • Swimming pool
    • Child Friendly
    • Air conditioning

    Price per night from

    $1,071

    Price per night from

    $1,071

    (1) Very Good 

      14

      BEAUTIFUL WATERFRONT 4 BEDROOM VILLA, NEAR TAYLOR BAY & SAPODILLA BEACH

      Providenciales / Five Cays Settlement

      Five Cays Settlement villa

      4 8 min stay varies

      • 4 bedrooms
      • sleeps 8
      • min stay varies
      • Swimming pool
      • Child Friendly
      • Air conditioning

      Price per night from

      $685

      Responds fast!
      avg. 1 hour 18 minutes

      Price per night from

      $685

        20

        Windchaser Villa 2, Private Pool, Ocean View

        Providenciales / Five Cays Settlement

        Five Cays Settlement villa

        4 10 min stay varies

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

        Price per night from

        $839

        Responds fast!
        avg. 1 hour 50 minutes

        Price per night from

        $839

          22

          Windchaser Villa 1, Private Pool, Ocean View

          Providenciales / Five Cays Settlement

          Five Cays Settlement villa

          4 10 min stay varies

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

          Price per night from

          $839

          Responds fast!
          avg. 1 hour 50 minutes

          Price per night from

          $839

            39

            Beach Villa Shambhala Luxury 5BR on Long Bay Beach

            Providenciales / Five Cays Settlement

            Five Cays Settlement villa

            5 10 7 nights min

            • 5 bedrooms
            • sleeps 10
            • 7 nights min
            • Swimming pool
            • Child Friendly
            • Air conditioning

            Price per night from

            $1,700

            Price per night from

            $1,700

            Great rentals within 20 miles that match your search

            Distance approx 5.37 km from Five Cays Settlement Show on Map

            (1) Excellent 

              21

              Villa Stark

              Providenciales / Turtle Cove

              Turtle Cove villa

              10 20 1 night min

              • 10 bedrooms
              • sleeps 20
              • 1 night min
              • Swimming pool
              • Child Friendly
              • Air conditioning

              Price per night from

              $11,933

              Price per night from

              $11,933

              Distance approx 1.89 km from Five Cays Settlement Show on Map

                23

                Beautiful Four Bedroom Beach Property

                Providenciales / Grace Bay

                Grace Bay house

                4 8 min stay varies

                • 4 bedrooms
                • sleeps 8
                • min stay varies
                • Swimming pool
                • Child Friendly
                • Air conditioning

                Price per night from

                $3,935

                Responds fast!
                avg. 4 minutes

                Price per night from

                $3,935

                Distance approx 0.1 km from Five Cays Settlement Show on Map

                  35

                  KARANA PENTHOUSE Luxury Loft - On Beach - Ocean Views & Breeze - Pool

                  Providenciales / Long Bay Beach

                  Long Bay Beach penthouse

                  1 3 min stay varies

                  • 1 bedroom
                  • sleeps 3
                  • min stay varies
                  • Swimming pool
                  • Child Friendly
                  • Air conditioning

                  Price per night from

                  $400

                  Responds fast!
                  avg. 3 hours 41 minutes

                  Price per night from

                  $400

                  Distance approx 16.37 km from Five Cays Settlement

                  (1) Excellent 

                    47

                    Empyrean Villas - Aquamarine

                    North Caicos / Whitby

                    Whitby villa

                    2 6 3 nights min

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

                    Price per night from

                    $257

                    Price per night from

                    $257

                    Distance approx 6.71 km from Five Cays Settlement Show on Map

                      14

                      Sunset Ridge Hotel (Double Room 2)

                      Turks and Caicos Islands / Providenciales

                      Providenciales guest house

                      1 4 1 night min

                      • 1 bedroom
                      • sleeps 4
                      • 1 night min
                      • Swimming pool
                      • Child Friendly
                      • Air conditioning

                      Price per night from

                      $211

                      Price per night from

                      $211

                      Distance approx 0.1 km from Five Cays Settlement Show on Map

                        34

                        Wyakha 1 BR On Beach - Garden View - Pool - Peaceful - SUPs & Kayaks (Unit #3)

                        Providenciales / Long Bay Beach

                        Long Bay Beach apartment

                        1 3 3 nights min

                        • 1 bedroom
                        • sleeps 3
                        • 3 nights min
                        • Swimming pool
                        • Child Friendly
                        • Air conditioning

                        Price per night from

                        $205

                        Responds fast!
                        avg. 3 hours 41 minutes

                        Price per night from

                        $205

                        Distance approx 1.69 km from Five Cays Settlement Show on Map

                        (1) Excellent 

                          41

                          Pelican Nest,Cocoa Villa- 4,000 sq./ft on Grace Bay beach

                          Providenciales / Grace Bay

                          Grace Bay house

                          4 8 min stay varies

                          • 4 bedrooms
                          • sleeps 8
                          • min stay varies
                          • Swimming pool
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $1,060

                          Responds fast!
                          avg. 2 hours 5 minutes

                          Price per night from

                          $1,060

                          Distance approx 10.96 km from Five Cays Settlement

                          (8) Excellent 

                          Certificate of Excellence

                            55

                            Caicos Dream large oceanview 3 bedroom condo at beautiful Northwest Point Resort

                            Turks and Caicos Islands / Providenciales

                            Providenciales condo

                            3 8 min stay varies

                            • 3 bedrooms
                            • sleeps 8
                            • min stay varies
                            • Nearest beach 0 mi
                            • Swimming pool
                            • Child Friendly

                            Certificate of Excellence

                            Price per night from

                            $308

                            Responds fast!
                            avg. 28 minutes

                            Price per night from

                            $308

                            Distance approx 1.83 km from Five Cays Settlement Show on Map

                            (38) Excellent 

                              33

                              Romantic vacation at La Casita

                              Turks and Caicos Islands / Providenciales

                              Providenciales studio

                              Studio 2 min stay varies

                              • Studio
                              • sleeps 2
                              • min stay varies
                              • Beach / lakeside relaxation
                              • Nearest beach 0 mi
                              • Swimming pool
                              “Loved evey minute” We spent 11 wonderful days in the upper unit , and loved every minute of it . The owners were very friendly , but not imposing . The landscaping, pool area was lovely . Short walk to a deserted beach .Four minute drive to Cafe Marke

                              Price per night from

                              $257

                              Price per night from

                              $257

                              Distance approx 6.71 km from Five Cays Settlement Show on Map

                                18

                                Sunset Ridge Hotel (Double Room 1)

                                Turks and Caicos Islands / Providenciales

                                Providenciales guest house

                                1 2 1 night min

                                • 1 bedroom
                                • sleeps 2
                                • 1 night min
                                • Swimming pool
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $211

                                Price per night from

                                $211

                                Distance approx 0.1 km from Five Cays Settlement Show on Map

                                  42

                                  Wyakha 3BR Townhome - On Beach - Ocean Views - Pool - Beach Chairs (Unit 3-4)

                                  Providenciales / Long Bay Beach

                                  Long Bay Beach townhouse

                                  2 5 min stay varies

                                  • 2 bedrooms
                                  • sleeps 5
                                  • min stay varies
                                  • Swimming pool
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $472

                                  Responds fast!
                                  avg. 3 hours 41 minutes

                                  Price per night from

                                  $472

                                  Distance approx 6.7 km from Five Cays Settlement Show on Map

                                    14

                                    Sunset Ridge Hotel (Single Room 8)

                                    Turks and Caicos Islands / Providenciales

                                    Providenciales guest house

                                    1 2 1 night min

                                    • 1 bedroom
                                    • sleeps 2
                                    • 1 night min
                                    • Swimming pool
                                    • Child Friendly
                                    • Air conditioning

                                    Price per night from

                                    $177

                                    Price per night from

                                    $177

                                    Distance approx 1.89 km from Five Cays Settlement Show on Map

                                      42

                                      Beautiful Six Bedroom Property

                                      Providenciales / Grace Bay

                                      Grace Bay house

                                      6 12 5 nights min

                                      • 6 bedrooms
                                      • sleeps 12
                                      • 5 nights min
                                      • Swimming pool
                                      • Child Friendly
                                      • Air conditioning

                                      Price per night from

                                      $16,695

                                      Responds fast!
                                      avg. 4 minutes

                                      Price per night from

                                      $16,695

                                      Distance approx 8.53 km from Five Cays Settlement

                                      (34) Excellent 

                                        29

                                        Coconut Beach Villa-BEACHFRONT-Sapodilla Bay Beach-Stunning Sunsets!

                                        Turks and Caicos Islands / Providenciales

                                        Providenciales villa

                                        6 12 7 nights min

                                        • 6 bedrooms
                                        • sleeps 12
                                        • 7 nights min
                                        • Beach / lakeside relaxation
                                        • Nearest beach 0 mi
                                        • Swimming pool
                                        “Stunning Villa - Literally, paradise.” This villa was such an amazing place to stay. It fit 6 of us comfortably and had all the amenities one could possibly want - lots of linens and towels, clean/beautiful/modern kitchen, adorable straw beachside hut

                                        Price per night from

                                        $1,510

                                        Responds fast!
                                        avg. 3 hours 23 minutes

                                        Price per night from

                                        $1,510

                                        Distance approx 6.71 km from Five Cays Settlement Show on Map

                                          14

                                          Sunset Ridge Hotel (Single Room 2)

                                          Turks and Caicos Islands / Providenciales

                                          Providenciales guest house

                                          1 2 1 night min

                                          • 1 bedroom
                                          • sleeps 2
                                          • 1 night min
                                          • Swimming pool
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $177

                                          Price per night from

                                          $177

                                          Distance approx 1.76 km from Five Cays Settlement Show on Map

                                            41

                                            See Turtle House

                                            Turks and Caicos Islands / Providenciales

                                            Providenciales house

                                            3 8 min stay varies

                                            • 3 bedrooms
                                            • sleeps 8
                                            • min stay varies
                                            • Nearest beach 1 mi
                                            • Swimming pool
                                            • Child Friendly

                                            Price per night from

                                            $400

                                            Price per night from

                                            $400

                                            Distance approx 3.16 km from Five Cays Settlement Show on Map

                                              44

                                              Beautiful Five Bedroom Property

                                              Providenciales / Leeward

                                              Leeward house

                                              6 14 5 nights min

                                              • 6 bedrooms
                                              • sleeps 14
                                              • 5 nights min
                                              • Swimming pool
                                              • Child Friendly
                                              • Air conditioning

                                              Price per night from

                                              $12,544

                                              Responds fast!
                                              avg. 4 minutes

                                              Price per night from

                                              $12,544

                                              Distance approx 9.22 km from Five Cays Settlement

                                                25

                                                Villa Paradiso

                                                Turks and Caicos Islands / Providenciales

                                                Providenciales villa

                                                7 14 min stay varies

                                                • 7 bedrooms
                                                • sleeps 14
                                                • min stay varies
                                                • Swimming pool
                                                • Child Friendly
                                                • Air conditioning

                                                Price per night from

                                                $1,369

                                                Price per night from

                                                $1,369

                                                Distance approx 0.1 km from Five Cays Settlement Show on Map

                                                (1) Excellent 

                                                  38

                                                  Karana 3 BR Luxury Villa - On Beach - Ocean Views - Prvt Pool - Serene & Natural

                                                  Providenciales / Long Bay Beach

                                                  Long Bay Beach villa

                                                  3 7 min stay varies

                                                  • 3 bedrooms
                                                  • sleeps 7
                                                  • min stay varies
                                                  • Beach / lakeside relaxation
                                                  • Nearest beach 0.1 mi
                                                  • Swimming pool

                                                  Price per night from

                                                  $810

                                                  Responds fast!
                                                  avg. 3 hours 41 minutes

                                                  Price per night from

                                                  $810

                                                  Distance approx 1.31 km from Five Cays Settlement Show on Map

                                                  (17) Excellent 

                                                    23

                                                    5-STAR REGENT GRAND .... OCEAN FRONT Premium Suite on Grace Bay

                                                    Providenciales / Grace Bay

                                                    Grace Bay apartment

                                                    2 6 6 nights min

                                                    • 2 bedrooms
                                                    • sleeps 6
                                                    • 6 nights min
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 0 mi
                                                    • Swimming pool
                                                    “Great Stay at Grand Calabash” This is a beautiful condo in the Regent Grand. Everything was just as the owner described in the Vrbo listing. The owner (Andrew) was extremely responsive and made everything easy. The size of the unit is fantastic and th

                                                    Price per night from

                                                    $770

                                                    Responds fast!
                                                    avg. 2 hours 57 minutes

                                                    Price per night from

                                                    $770

                                                    Distance approx 7.67 km from Five Cays Settlement

                                                    (11) Very Good 

                                                      27

                                                      Developers own penthouse directly on the finest snorkelling reef on Grace Bay

                                                      Turks and Caicos Islands / Providenciales

                                                      Providenciales apartment

                                                      2 4 min stay varies

                                                      • 2 bedrooms
                                                      • sleeps 4
                                                      • min stay varies
                                                      • Beach / lakeside relaxation
                                                      • Swimming pool
                                                      • Ask about children
                                                      “Trip of a lifetime!” Leanne, I just wanted to thank you so much for helping make our vacation the best ever!! Coral Gardens is truly a hidden gem, much nicer for the island in my estimation than the big high rise type developments that seem to be over

                                                      Price per night from

                                                      $697

                                                      Price per night from

                                                      $697

                                                      Distance approx 3.97 km from Five Cays Settlement Show on Map

                                                      (3) Excellent 

                                                        22

                                                        Sunrise Ridge

                                                        Providenciales / Grace Bay

                                                        Grace Bay house

                                                        3 7 5 nights min

                                                        • 3 bedrooms
                                                        • sleeps 7
                                                        • 5 nights min
                                                        • Beach / lakeside relaxation
                                                        • Swimming pool
                                                        • Child Friendly

                                                        Price per night from

                                                        $740

                                                        Responds fast!
                                                        avg. 1 hour 37 minutes

                                                        Price per night from

                                                        $740

                                                        Distance approx 10.94 km from Five Cays Settlement

                                                          16

                                                          3 bdrm, oceanfront , beach, views, pool, hot tub

                                                          Providenciales / Turtle Cove

                                                          Turtle Cove apartment

                                                          3 6 1 night min

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • 1 night min
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $913

                                                          Price per night from

                                                          $913

                                                          Distance approx 2.81 km from Five Cays Settlement Show on Map

                                                            12

                                                            TURTLE TAIL ESTATE

                                                            Providenciales / Turtle Cove

                                                            Turtle Cove villa

                                                            7 14 min stay varies

                                                            • 7 bedrooms
                                                            • sleeps 14
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Child Friendly
                                                            • Car not necessary

                                                            Price per night from

                                                            $11,404

                                                            Price per night from

                                                            $11,404

                                                            Distance approx 4.13 km from Five Cays Settlement Show on Map

                                                            (13) Excellent 

                                                              40

                                                              Turtle Breeze Villa

                                                              Turks and Caicos Islands / Providenciales

                                                              Providenciales villa

                                                              6 12 7 nights min

                                                              • 6 bedrooms
                                                              • sleeps 12
                                                              • 7 nights min
                                                              • Beach / lakeside relaxation
                                                              • Swimming pool
                                                              • Child Friendly
                                                              “Paradise! Private, beautiful, peaceful, and relax to the max!” A week at the Turtle Breeze Villa is a week in paradise. The unique layout of this private home feels like you're in your own minature resort! With stylish suites in seperate buildings w

                                                              Price per night from

                                                              $1,963

                                                              Price per night from

                                                              $1,963

                                                              Distance approx 6.71 km from Five Cays Settlement Show on Map

                                                                14

                                                                Sunset Ridge Hotel (Single Room 3)

                                                                Turks and Caicos Islands / Providenciales

                                                                Providenciales guest house

                                                                1 2 1 night min

                                                                • 1 bedroom
                                                                • sleeps 2
                                                                • 1 night min
                                                                • Swimming pool
                                                                • Child Friendly
                                                                • Air conditioning

                                                                Price per night from

                                                                $177

                                                                Price per night from

                                                                $177

                                                                Distance approx 1.37 km from Five Cays Settlement Show on Map

                                                                  23

                                                                  Beautiful Six Bedroom Property

                                                                  Turks and Caicos Islands / Providenciales

                                                                  Providenciales house

                                                                  6 12 5 nights min

                                                                  • 6 bedrooms
                                                                  • sleeps 12
                                                                  • 5 nights min
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $2,672

                                                                  Responds fast!
                                                                  avg. 4 minutes

                                                                  Price per night from

                                                                  $2,672

                                                                  Distance approx 10.87 km from Five Cays Settlement

                                                                  (2) Average 

                                                                    15

                                                                    Ocean pool views 1 bdrm private beach hot tub nice

                                                                    Turks and Caicos Islands / Providenciales

                                                                    Providenciales apartment

                                                                    1 3 3 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 3
                                                                    • 3 nights min
                                                                    • Beach / lakeside relaxation
                                                                    • Swimming pool
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $400

                                                                    Price per night from

                                                                    $400

                                                                    Distance approx 7.17 km from Five Cays Settlement

                                                                    (3) Very Good 

                                                                      32

                                                                      Three Cays Villa

                                                                      Turks and Caicos Islands / Providenciales

                                                                      Providenciales villa

                                                                      4 8 7 nights min

                                                                      • 4 bedrooms
                                                                      • sleeps 8
                                                                      • 7 nights min
                                                                      • Beach / lakeside relaxation
                                                                      • Nearest beach 0.1 mi
                                                                      • Swimming pool

                                                                      Price per night from

                                                                      $1,028

                                                                      Responds fast!
                                                                      avg. 2 hours 55 minutes

                                                                      Price per night from

                                                                      $1,028

                                                                      Distance approx 3.97 km from Five Cays Settlement Show on Map

                                                                        15

                                                                        Grace Bay Beach Ocean Villas, Hibiscus Villa. Rated #1 On Trip Advisor.

                                                                        Providenciales / Turtle Cove

                                                                        Turtle Cove villa

                                                                        2 6 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 6
                                                                        • min stay varies
                                                                        • Nearest beach 0 mi
                                                                        • Swimming pool
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $297

                                                                        Price per night from

                                                                        $297

                                                                        Distance approx 1.95 km from Five Cays Settlement Show on Map

                                                                        (44) Excellent 

                                                                          28

                                                                          Villa Tropica - Near beach, Luxury Villa, Pool

                                                                          Turks and Caicos Islands / Providenciales

                                                                          Providenciales villa

                                                                          5 12 min stay varies

                                                                          • 5 bedrooms
                                                                          • sleeps 12
                                                                          • min stay varies
                                                                          • Beach / lakeside relaxation
                                                                          • Nearest beach 0.3 mi
                                                                          • Swimming pool
                                                                          “My new favorite island!!! Not to mention a terrific home...” This was our first time visiting Turks & Caicos and I have to say that it was an extremely impressive experience. We were a group of 5 adults and 4 kids ranging from 15 months to 7 years ol

                                                                          Price per night from

                                                                          $657

                                                                          Responds fast!
                                                                          avg. 2 hours 25 minutes

                                                                          Price per night from

                                                                          $657

                                                                          Distance approx 6.71 km from Five Cays Settlement Show on Map

                                                                            14

                                                                            Sunset Ridge Hotel (Full Bedroom 1)

                                                                            Turks and Caicos Islands / Providenciales

                                                                            Providenciales guest house

                                                                            1 2 1 night min

                                                                            • 1 bedroom
                                                                            • sleeps 2
                                                                            • 1 night min
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $240

                                                                            Price per night from

                                                                            $240

                                                                            Distance approx 4.74 km from Five Cays Settlement Show on Map

                                                                              14

                                                                              Extra special Bonus rate...

                                                                              Providenciales / Turtle Cove

                                                                              Turtle Cove apartment

                                                                              1 4 4 nights min

                                                                              • 1 bedroom
                                                                              • sleeps 4
                                                                              • 4 nights min
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $200

                                                                              Price per night from

                                                                              $200