Vacation Rentals with Pool in Clearwater

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Filtering by: Swimming pool

1,880 vacation rentals
    26

    3BR w/ Roof Deck on Waterway

    Florida / Clearwater

    Clearwater house

    3 6 5 nights min

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

    Price per night from

    $334

    Price per night from

    $334

    (2) Excellent 

      24

      Dog-Friendly 2BR, 2BA Clearwater House w/ Pool, 5 Miles from the Beach

      Florida / Clearwater

      Clearwater house

      2 6 min stay varies

      • 2 bedrooms
      • sleeps 6
      • min stay varies
      • Swimming pool
      • Ask about children
      • Air conditioning

      Price per night from

      $165

      Price per night from

      $165

      (15) Excellent 

        40

        Beautiful relaxing getaway close to the beach

        Florida / Clearwater

        Clearwater apartment

        1 3 min stay varies

        • 1 bedroom
        • sleeps 3
        • min stay varies
        • Beach / lakeside relaxation
        • Nearest beach 6 mi
        • Swimming pool
        “Beautiful condo, close proximity to beach, relaxing and lovely stay!!” We had such a lovely time at the condo. The owners are incredibly wonderful to communicate with and so gracious and attentive to needs. The place was spotless and beautifully decor
        …see more

        Price per night from

        $70

        Price per night from

        $70

          21

          Remodeled 2brms Condo. Fantastic location! 15 min from Clearwater beach

          Florida / Clearwater

          Clearwater apartment

          2 4 min stay varies

          • 2 bedrooms
          • sleeps 4
          • min stay varies
          • Nearest beach 11 mi
          • Swimming pool
          • Child Friendly

          Price per night from

          $92

          Responds fast!
          avg. 3 hours 54 minutes

          Price per night from

          $92

          (4) Excellent 

            43

            Relaxing Condo Near the Beach, Private End Unit, Gated Complex, Heated Pool

            Florida / Clearwater

            Clearwater condo

            1 4 7 nights min

            • 1 bedroom
            • sleeps 4
            • 7 nights min
            • Nearest beach 2 mi
            • Swimming pool
            • Child Friendly

            Price per night from

            $79

            Responds fast!
            avg. 1 hour 23 minutes

            Price per night from

            $79

            (16) Excellent 

            Certificate of Excellence

              27

              Romance On The Beach! Great View of the Beach!

              Clearwater / Clearwater Beach

              Clearwater apartment

              2 min stay varies

              • sleeps 2
              • min stay varies
              • Beach / lakeside relaxation
              • Swimming pool
              • Air conditioning
              “Great place to stay!” We went to Clearwater for an extended weekend and celebrate my husband's 55th birthday. We wanted to be close to the beach and walking distance to restaurants....well we found it! You couldn't ask to be closer and the studio apa
              …see more

              Certificate of Excellence

              Price per night from

              $201

              Responds fast!
              avg. 2 hours 59 minutes

              Price per night from

              $201

              (39) Excellent 

                41

                LUXURY 5*SUITE,3 BEDS,2 BATH, POOL,HOT TUB ,WATER VIEWS. DISCOUNTS APPLY ..

                Florida / Clearwater

                Clearwater condo

                3 10 min stay varies

                • 3 bedrooms
                • sleeps 10
                • min stay varies
                • Beach / lakeside relaxation
                • Nearest beach 0.06 mi
                • Swimming pool
                “Harbor View Grande Suite # 707 Excellent 5 Star *****” A Big Thank you to the owners and Staff of 707. The accommodations where beyond our expectations. The décor was professionally done and the Suite was spotless upon arrival. The champagne was a
                …see more

                Price per night from

                $242

                Responds fast!
                avg. 2 hours 34 minutes

                Price per night from

                $242

                (18) Very Good 

                Certificate of Excellence

                  35

                  Clearwater Beach Cambria House

                  Clearwater / Clearwater Beach

                  Clearwater house

                  3 6 min stay varies

                  • 3 bedrooms
                  • sleeps 6
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Swimming pool
                  • Child Friendly
                  “Best Vacation Ever!!!” We vacationed at Cambria House for six nights in October. The house is located on a dead end street about thirty steps to the white sandy beach.We could sit on our porch and see the beach and watch beautiful sunsets! We grilled
                  …see more

                  Certificate of Excellence

                  Price per night from

                  $384

                  Responds fast!
                  avg. 2 hours 59 minutes

                  Price per night from

                  $384

                  (3) Excellent 

                    10

                    Bay Harbor Condo in Clearwater Beach

                    Clearwater / Clearwater Beach

                    Clearwater condo

                    3 8 7 nights min

                    • 3 bedrooms
                    • sleeps 8
                    • 7 nights min
                    • Swimming pool
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $228

                    Price per night from

                    $228

                      24

                      beautiful condo with magnificent views of mandalay

                      Florida / Clearwater

                      Clearwater apartment

                      1 2 90 nights min

                      • 1 bedroom
                      • sleeps 2
                      • 90 nights min
                      • Beach / lakeside relaxation
                      • Nearest beach 0.9 mi
                      • Swimming pool

                      Price per night from

                      $91

                      Price per night from

                      $91

                      (4) Very Good 

                        34

                        Exclusive Tropical Retreat in Sunny Clearwater Bea

                        Florida / Clearwater

                        Clearwater house

                        4 12 30 nights min

                        • 4 bedrooms
                        • sleeps 12
                        • 30 nights min
                        • Beach / lakeside relaxation
                        • Swimming pool
                        • Child Friendly

                        Price per night from

                        $397

                        Price per night from

                        $397

                        (20) Excellent 

                        Certificate of Excellence

                          24

                          GulfSideSuite at 30 seconds Walk to the Beach. WOW

                          Clearwater / Clearwater Beach

                          Clearwater apartment

                          1 2 min stay varies

                          • 1 bedroom
                          • sleeps 2
                          • min stay varies
                          • Beach / lakeside relaxation
                          • Swimming pool
                          • Air conditioning
                          “Wonderful beach location.” My husband and I just returned from a weeks stay at this terrific beach studio. It is as described by the owner and you can trust the photos. The place was immaculately clean and just steps from the sand and sea. Beach ch
                          …see more

                          Certificate of Excellence

                          Price per night from

                          $201

                          Responds fast!
                          avg. 2 hours 59 minutes

                          Price per night from

                          $201

                          (1) Excellent 

                            29

                            Bay Harbor 401 4th Floor Condo with Panoramic Water View

                            Florida / Clearwater

                            Clearwater apartment

                            3 8 min stay varies

                            • 3 bedrooms
                            • sleeps 8
                            • min stay varies
                            • Swimming pool
                            • Ask about children

                            Price per night from

                            $177

                            Responds fast!
                            avg. 2 hours 7 minutes

                            Price per night from

                            $177

                              25

                              Lavish 3BR Condo w/ Outdoor Patio, Hot Tub, Pool & Intracoastal Waterway View

                              Florida / Clearwater

                              Clearwater apartment

                              3 8 min stay varies

                              • 3 bedrooms
                              • sleeps 8
                              • min stay varies
                              • Swimming pool
                              • Ask about children
                              • Air conditioning

                              Price per night from

                              $248

                              Price per night from

                              $248

                              (5) Very Good 

                                32

                                404 Dockside

                                Florida / Clearwater

                                Clearwater apartment

                                3 8 min stay varies

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

                                Price per night from

                                $168

                                Responds fast!
                                avg. 2 hours 59 minutes

                                Price per night from

                                $168

                                (29) Excellent 

                                  30

                                  Avalon at Clearwater

                                  Florida / Clearwater

                                  Clearwater apartment

                                  1 3 7 nights min

                                  • 1 bedroom
                                  • sleeps 3
                                  • 7 nights min
                                  • Nearest beach 18 mi
                                  • Swimming pool
                                  • Air conditioning
                                  “Location,Location,Location” Terrific get-a-way. Quiet, comfortable ,very clean, has everything you could want .Very close to other locations such as Tampa ,Dunedin. Beautiful beaches. Fabulous sunsets. .Great restaurants within walking distances. Co
                                  …see more

                                  Price per night from

                                  $83

                                  Price per night from

                                  $83

                                  (4) Excellent 

                                    29

                                    Surfside Condos 202 Beachfront Condo

                                    Florida / Clearwater

                                    Clearwater apartment

                                    3 8 7 nights min

                                    • 3 bedrooms
                                    • sleeps 8
                                    • 7 nights min
                                    • Swimming pool
                                    • Ask about children
                                    • Air conditioning
                                    “Wonderful !” This condo was perfect for what we needed. As only a couple, the master bedroom was wonderful with it’s king size bed and a sliding door to the deck . It has a great oceanfront view and we had awesome sunsets every night from our bal
                                    …see more

                                    Price per night from

                                    $403

                                    Responds fast!
                                    avg. 2 hours 7 minutes

                                    Price per night from

                                    $403

                                      20

                                      2401 Margolin Lane/Super Red Hot Mansion for You $155/Day Starting At

                                      Florida / Clearwater

                                      Clearwater house

                                      5 20 2 nights min

                                      • 5 bedrooms
                                      • sleeps 20
                                      • 2 nights min
                                      • Nearest beach 20 mi
                                      • Swimming pool
                                      • Child Friendly

                                      Price per night from

                                      $178

                                      Responds fast!
                                      avg. 2 hours 11 minutes

                                      Price per night from

                                      $178

                                      (12) Very Good 

                                        21

                                        Waterfront Studio on Clearwater Beach

                                        Florida / Clearwater

                                        Clearwater studio

                                        Studio 2 3 nights min

                                        • Studio
                                        • sleeps 2
                                        • 3 nights min
                                        • Beach / lakeside relaxation
                                        • Nearest beach 0 mi
                                        • Swimming pool
                                        “Room C4!” We really enjoyed our trip to Clearwater! This condo is in a fantastic spot, within walking distance to everything. It has a cute little courtyard, pool, and a fantastic dock to fish off of and watch the dolphins swimming. It was just my h
                                        …see more

                                        Price per night from

                                        $133

                                        Responds fast!
                                        avg. 2 hours 48 minutes

                                        Price per night from

                                        $133

                                        (4) Excellent 

                                          55

                                          IT'S WARM HERE! The Blue Heaven, AMAZING Beach Condo

                                          Clearwater / Clearwater Beach

                                          Clearwater condo

                                          2 6 2 nights min

                                          • 2 bedrooms
                                          • sleeps 6
                                          • 2 nights min
                                          • Beach / lakeside relaxation
                                          • Swimming pool
                                          • Child Friendly

                                          Price per night from

                                          $258

                                          Responds fast!
                                          avg. 52 minutes

                                          Price per night from

                                          $258

                                          (15) Excellent 

                                          Certificate of Excellence

                                            32

                                            Beautiful 2 bedroom condo,mins. drive to beach, pool

                                            Clearwater / Clearwater Beach

                                            Clearwater apartment

                                            2 6 min stay varies

                                            • 2 bedrooms
                                            • sleeps 6
                                            • min stay varies
                                            • Beach / lakeside relaxation
                                            • Nearest beach 7 mi
                                            • Swimming pool

                                            Certificate of Excellence

                                            Price per night from

                                            $126

                                            Responds fast!
                                            avg. 11 minutes

                                            Price per night from

                                            $126

                                              22

                                              Dockside 402 2 BR / 2 BA Waterfront Late January Specials - Clearwater Beach

                                              Florida / Clearwater

                                              Clearwater condo

                                              2 6 7 nights min

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

                                              Price per night from

                                              $145

                                              Price per night from

                                              $145

                                              (4) Excellent 

                                                16

                                                Dock of the Bay - Beautiful Upscale Waterfront 2 KING BR/2BA Condo

                                                Florida / Clearwater

                                                Clearwater condo

                                                2 7 7 nights min

                                                • 2 bedrooms
                                                • sleeps 7
                                                • 7 nights min
                                                • Swimming pool
                                                • Child Friendly
                                                • Car not necessary

                                                Price per night from

                                                $267

                                                Responds fast!
                                                avg. 35 minutes

                                                Price per night from

                                                $267

                                                  29

                                                  Clearwater Beach Cottage w/ Pool Near Sugary Sand!

                                                  Florida / Clearwater

                                                  Clearwater house

                                                  2 6 2 nights min

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

                                                  Price per night from

                                                  $201

                                                  Responds fast!
                                                  avg. 9 minutes

                                                  Price per night from

                                                  $201

                                                  (1) Excellent 

                                                    21

                                                    YOUR HOME AWAY FROM HOME from CLEARWATER BEACH!!!

                                                    Florida / Clearwater

                                                    Clearwater condo

                                                    1 4 min stay varies

                                                    • 1 bedroom
                                                    • sleeps 4
                                                    • min stay varies
                                                    • Nearest beach 5 mi
                                                    • Swimming pool
                                                    • Suitable for children age 5+

                                                    Price per night from

                                                    $99

                                                    Responds fast!
                                                    avg. 1 hour 0 minutes

                                                    Price per night from

                                                    $99

                                                    (7) Excellent 

                                                      28

                                                      Clearwater Beach 3-bedroom Waterfront Luxury Condo

                                                      Clearwater / Clearwater Beach

                                                      Clearwater condo

                                                      3 6 min stay varies

                                                      • 3 bedrooms
                                                      • sleeps 6
                                                      • min stay varies
                                                      • Beach / lakeside relaxation
                                                      • Nearest beach 0.5 mi
                                                      • Swimming pool

                                                      Price per night from

                                                      $150

                                                      Price per night from

                                                      $150

                                                      (2) Excellent 

                                                        24

                                                        Affordable Luxury Directly On The Gulf Of Mexico.

                                                        Florida / Clearwater

                                                        Clearwater apartment

                                                        1 4 min stay varies

                                                        • 1 bedroom
                                                        • sleeps 4
                                                        • min stay varies
                                                        • Beach / lakeside relaxation
                                                        • Nearest beach 0.3 mi
                                                        • Swimming pool

                                                        Price per night from

                                                        $86

                                                        Responds fast!
                                                        avg. 38 minutes

                                                        Price per night from

                                                        $86

                                                          32

                                                          304 Island Key

                                                          Florida / Clearwater

                                                          Clearwater condo

                                                          3 8 min stay varies

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

                                                          Price per night from

                                                          $169

                                                          Responds fast!
                                                          avg. 2 hours 59 minutes

                                                          Price per night from

                                                          $169

                                                          (9) Excellent 

                                                            28

                                                            Beautiful Condo at The Avalon Clearwater

                                                            Florida / Clearwater

                                                            Clearwater apartment

                                                            1 2 min stay varies

                                                            • 1 bedroom
                                                            • sleeps 2
                                                            • min stay varies
                                                            • Nearest beach 6 mi
                                                            • Swimming pool
                                                            • Car not necessary
                                                            “Most Perfect Stay Anywhere” Everything was perfect. Host was most accommodating. Highly recommend to everyone for perfect stay. Beautifully appointed condo. Everything worked perfectly. Great pool for warm afternoons. Friendly neighbors. Close to ever
                                                            …see more

                                                            Price per night from

                                                            $86

                                                            Price per night from

                                                            $86

                                                            (3) Excellent 

                                                              24

                                                              New listing: Pool View In Avalon at Clearwater, Fully renovated !

                                                              Florida / Clearwater

                                                              Clearwater apartment

                                                              1 4 7 nights min

                                                              • 1 bedroom
                                                              • sleeps 4
                                                              • 7 nights min
                                                              • Nearest beach 5 mi
                                                              • Swimming pool
                                                              • Child Friendly

                                                              Price per night from

                                                              $98

                                                              Responds fast!
                                                              avg. 3 hours 27 minutes

                                                              Price per night from

                                                              $98

                                                              (1) Excellent 

                                                                35

                                                                203 Bay Harbor

                                                                Florida / Clearwater

                                                                Clearwater apartment

                                                                3 8 7 nights min

                                                                • 3 bedrooms
                                                                • sleeps 8
                                                                • 7 nights min
                                                                • Swimming pool
                                                                • Child Friendly
                                                                • Air conditioning
                                                                “Family Vacation” We booked this vacation in Clearwater for 2 families. The condo was awesome with a huge amount of room. We had 3 bedrooms and a pullout couch for 3 small children. There was kids games and DVDs. The condo was so close to the beach - c
                                                                …see more

                                                                Price per night from

                                                                $187

                                                                Responds fast!
                                                                avg. 2 hours 59 minutes

                                                                Price per night from

                                                                $187

                                                                (5) Very Good 

                                                                  13

                                                                  (2035) Cozy Villa in Sunny Clearwater, Florida

                                                                  Florida / Clearwater

                                                                  Clearwater villa

                                                                  2 5 7 nights min

                                                                  • 2 bedrooms
                                                                  • sleeps 5
                                                                  • 7 nights min
                                                                  • Nearest beach 11 mi
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  “A nice quiet holiday stay.” The place was perfect for our needs, a nice quiet holiday house in a friendly neighbourhood. A short drive to several very nice beaches and restaurants as well as having a nice little pool in the complex and a small back y
                                                                  …see more

                                                                  Price per night from

                                                                  $110

                                                                  Price per night from

                                                                  $110

                                                                    21

                                                                    Luxury Clearwater Beach Villa w/ Waterfront Views!

                                                                    Florida / Clearwater

                                                                    Clearwater apartment

                                                                    3 6 7 nights min

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

                                                                    Price per night from

                                                                    $194

                                                                    Responds fast!
                                                                    avg. 9 minutes

                                                                    Price per night from

                                                                    $194

                                                                      28

                                                                      Bayway Luxury Townhome

                                                                      Florida / Clearwater

                                                                      Clearwater house

                                                                      3 6 7 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 6
                                                                      • 7 nights min
                                                                      • Swimming pool
                                                                      • Ask about children
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $373

                                                                      Price per night from

                                                                      $373

                                                                      (14) Very Good 

                                                                        25

                                                                        (2024) Cozy Villa in Sunny Clearwater, Florida

                                                                        Florida / Clearwater

                                                                        Clearwater villa

                                                                        2 4 7 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 4
                                                                        • 7 nights min
                                                                        • Nearest beach 12 mi
                                                                        • Swimming pool
                                                                        • Child Friendly
                                                                        “very comfortable” the villa was extremely clean and comfortable! A great place to rent with no inconvenience. Definitely a recommendation! Thank you!
                                                                        …see more

                                                                        Price per night from

                                                                        $109

                                                                        Price per night from

                                                                        $109

                                                                        (4) Excellent 

                                                                          21

                                                                          Elegant Beach Front Penthouse on Desirable Belleair Beach, FL 2B/2B

                                                                          Florida / Clearwater

                                                                          Clearwater condo

                                                                          2 4 min stay varies

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

                                                                          Price per night from

                                                                          $155

                                                                          Responds fast!
                                                                          avg. 2 hours 12 minutes

                                                                          Price per night from

                                                                          $155

                                                                          (1) Average 

                                                                            18

                                                                            Clearwater Beach Condo 3BR fits 6-10

                                                                            Florida / Clearwater

                                                                            Clearwater condo

                                                                            3 6 2 nights min

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

                                                                            Price per night from

                                                                            $229

                                                                            Responds fast!
                                                                            avg. 47 minutes

                                                                            Price per night from

                                                                            $229

                                                                            (9) Excellent 

                                                                              25

                                                                              Luxury Condo near Clearwater Beach

                                                                              Florida / Clearwater

                                                                              Clearwater apartment

                                                                              1 3 min stay varies

                                                                              • 1 bedroom
                                                                              • sleeps 3
                                                                              • min stay varies
                                                                              • Nearest beach 4 mi
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              “CLEARWATER'S BEST KEPT SECRET” The pictures sold me on this condo. It is exactly as it shows. Very clean, smells good. Great locations, all stores close on the same road as condo. Close to the beach. Owner kept in close contact throughout our pre-book
                                                                              …see more

                                                                              Price per night from

                                                                              $102

                                                                              Responds fast!
                                                                              avg. 3 hours 54 minutes

                                                                              Price per night from

                                                                              $102