Dog Friendly Vacation Rentals in Longboat Key - FlipKey

Close

Enter dates for more accurate prices

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

Filtering by: Pets allowed

382 pet friendly apartments in Longboat Key

(3) Excellent 

    18

    Charming Beach House in Longboat Key/ pool/pet/dock

    Florida / Longboat Key

    Longboat Key house

    3 6 7 nights min

    • 3 bedrooms
    • sleeps 6
    • 7 nights min
    • Beach / lakeside relaxation
    • Nearest beach 0.02 mi
    • Swimming pool

    Price per night from

    $253

    Price per night from

    $253

      24

      Longboat Key Condo w/ Pool Access- Walk to Bay!

      Florida / Longboat Key

      Longboat Key apartment

      2 8 min stay varies

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

      Price per night from

      $109

      Responds fast!
      avg. 11 minutes

      Price per night from

      $109

      (2) Very Good 

        8

        Longboat Key Retreat

        Florida / Longboat Key

        Longboat Key house

        2 4 7 nights min

        • 2 bedrooms
        • sleeps 4
        • 7 nights min
        • Beach / lakeside relaxation
        • Child Friendly
        • Air conditioning
        “Beach house” We really enjoyed our stay at the beach house The owners were friendly and available for questions. The access to the beach is a little tricky but they do provide a map with instructions to show you how to reach the access, which is act

        Price per night from

        $147

        Price per night from

        $147

          12

          55+ Community with pool and club house

          Florida / Longboat Key

          Longboat Key villa

          2 6 90 nights min

          • 2 bedrooms
          • sleeps 6
          • 90 nights min
          • Child Friendly
          • Air conditioning
          • Pet Friendly

          Price per night from

          $80

          Price per night from

          $80

            15

            Private Bungalow on Canal a block from Beach

            Florida / Longboat Key

            Longboat Key house

            2 4 min stay varies

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

            Price per night from

            $201

            Responds fast!
            avg. 3 hours 55 minutes

            Price per night from

            $201

              19

              BBB on Marbury lane-Beach, boating, BBQ!

              Florida / Longboat Key

              Longboat Key house

              3 8 6 nights min

              • 3 bedrooms
              • sleeps 8
              • 6 nights min
              • Child Friendly
              • Pet Friendly

              Price per night from

              $287

              Responds fast!
              avg. 3 hours 52 minutes

              Price per night from

              $287

                24

                Lovely Tropical Longboat Town house

                Florida / Longboat Key

                Longboat Key townhouse

                2 6 min stay varies

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

                Price per night from

                $147

                Responds fast!
                avg. 7 minutes

                Price per night from

                $147

                  24

                  Charming Longboat Key Condo w/Lanai, Walk to Beach

                  Florida / Longboat Key

                  Longboat Key condo

                  2 4 6 nights min

                  • 2 bedrooms
                  • sleeps 4
                  • 6 nights min
                  • Child Friendly
                  • Air conditioning
                  • Pet Friendly

                  Price per night from

                  $98

                  Responds fast!
                  avg. 30 minutes

                  Price per night from

                  $98

                    22

                    Beautiful Island Sanctuary Best Location in South Longboat Key!

                    Florida / Longboat Key

                    Longboat Key house

                    3 8 7 nights min

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

                    Price per night from

                    $483

                    Responds fast!
                    avg. 3 hours 1 minutes

                    Price per night from

                    $483

                      36

                      The Beach House on Longboat Key - FANTASTIC LOCATION!

                      Florida / Longboat Key

                      Longboat Key cottage

                      3 9 min stay varies

                      • 3 bedrooms
                      • sleeps 9
                      • min stay varies
                      • Swimming pool
                      • Ask about children
                      • Air conditioning

                      Price per night from

                      $142

                      Price per night from

                      $142

                      (28) Very Good 

                        25

                        Pet Friendly on Longboat Key

                        Florida / Longboat Key

                        Longboat Key apartment

                        2 6 2 nights min

                        • 2 bedrooms
                        • sleeps 6
                        • 2 nights min
                        • Beach / lakeside relaxation
                        • Child Friendly
                        • Car not necessary
                        “What a Find!!!” This is a one of the best locations on Longboat. We visit Longboat every year to see my father. We were able to find this condo out from just a simple google search. The condo was very clean. We loved the decorations and the full kitch

                        Price per night from

                        $120

                        Price per night from

                        $120

                        (57) Very Good 

                          13

                          Castle in the Sky Near Beach and Tennis

                          Florida / Longboat Key

                          Longboat Key house

                          4 10 2 nights min

                          • 4 bedrooms
                          • sleeps 10
                          • 2 nights min
                          • Beach / lakeside relaxation
                          • Nearest beach 2 mi
                          • Child Friendly
                          “Awesome stay” We had a great stay! Our Family of 9 people fit very comfortable, all the rooms were equipped with all the essentials, although is an older home it was very clean and had lots of space. We had Good communication with the owner.

                          Price per night from

                          $228

                          Responds fast!
                          avg. 2 hours 49 minutes

                          Price per night from

                          $228

                          Great rentals within 20 miles that match your search

                          Distance approx 7.31 km from Longboat Key Show on Map

                          (3) Very Good 

                            26

                            Charming 'Old Florida' one bed apartment, Sarasota

                            Southwest Gulf Coast / Sarasota

                            Sarasota apartment

                            1 2 2 nights min

                            • 1 bedroom
                            • sleeps 2
                            • 2 nights min
                            • Beach / lakeside relaxation
                            • Air conditioning
                            • Pet Friendly

                            Price per night from

                            $97

                            Responds fast!
                            avg. 21 minutes

                            Price per night from

                            $97

                            Distance approx 5.61 km from Longboat Key Show on Map

                            (1) Very Good 

                              17

                              Splendid Vacation Home

                              Southwest Gulf Coast / Sarasota

                              Sarasota house

                              3 7 29 nights min

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

                              Price per night from

                              $204

                              Responds fast!
                              avg. 2 hours 40 minutes

                              Price per night from

                              $204

                              Distance approx 5.72 km from Longboat Key Show on Map

                                11

                                Stay near the heart of Sarasota

                                Southwest Gulf Coast / Sarasota

                                Sarasota house

                                3 6 8 nights min

                                • 3 bedrooms
                                • sleeps 6
                                • 8 nights min
                                • Child Friendly
                                • Air conditioning
                                • Pet Friendly

                                Price per night from

                                $102

                                Price per night from

                                $102

                                Distance approx 7.62 km from Longboat Key

                                (19) Excellent 

                                  48

                                  Best in Siesta Village! 1.5 blocks to best beaches! - Casa Van Lopik (Canal)

                                  Florida / Siesta Key

                                  Siesta Key house

                                  3 10 3 nights min

                                  • 3 bedrooms
                                  • sleeps 10
                                  • 3 nights min
                                  • Beach / lakeside relaxation
                                  • Child Friendly
                                  • Car not necessary
                                  “Great value, beautiful town!” Just spent two night in the beautiful siesta key for a ladies weekend. We had such a blast the night life was great and wasn't a far walk to siesta key village. The beach was little further but still not to bad. Bring you

                                  Price per night from

                                  $261

                                  Responds fast!
                                  avg. 2 hours 36 minutes

                                  Price per night from

                                  $261

                                  Distance approx 9.96 km from Longboat Key

                                  (1) Excellent 

                                    26

                                    Casita Blanca- 2BR, Private Beach Access, Communal Heated Pool [Sleeps 4]

                                    Southwest Gulf Coast / Sarasota

                                    Sarasota house

                                    2 4 min stay varies

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

                                    Price per night from

                                    $273

                                    Price per night from

                                    $273

                                    Distance approx 12.22 km from Longboat Key

                                    (6) Excellent 

                                      22

                                      Cozy Cabana West - Private Pool - Close to Beach

                                      Anna Maria Island / Holmes Beach

                                      Holmes Beach villa

                                      2 6 min stay varies

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

                                      Price per night from

                                      $184

                                      Responds fast!
                                      avg. 2 hours 32 minutes

                                      Price per night from

                                      $184

                                      Distance approx 7.12 km from Longboat Key Show on Map

                                      (1) Excellent 

                                        20

                                        Vacation Sarasota in great location to all venues....

                                        Southwest Gulf Coast / Sarasota

                                        Sarasota house

                                        3 6 4 nights min

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

                                        Price per night from

                                        $142

                                        Responds fast!
                                        avg. 1 hour 56 minutes

                                        Price per night from

                                        $142

                                        Distance approx 9.14 km from Longboat Key Show on Map

                                          20

                                          Barb's BaySide Retreat

                                          Anna Maria Island / Bradenton Beach

                                          Bradenton Beach house

                                          3 6 3 nights min

                                          • 3 bedrooms
                                          • sleeps 6
                                          • 3 nights min
                                          • Nearest beach 4 mi
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $142

                                          Responds fast!
                                          avg. 3 hours 2 minutes

                                          Price per night from

                                          $142

                                          Distance approx 9.48 km from Longboat Key

                                            21

                                            AAA Accommodation in The Meadows - Sarasota

                                            Florida / Fruitville

                                            Fruitville condo

                                            2 6 14 nights min

                                            • 2 bedrooms
                                            • sleeps 6
                                            • 14 nights min
                                            • Nearest beach 14 mi
                                            • Swimming pool
                                            • Child Friendly

                                            Price per night from

                                            $98

                                            Responds fast!
                                            avg. 1 hour 4 minutes

                                            Price per night from

                                            $98

                                            Distance approx 10.72 km from Longboat Key

                                            (28) Excellent 

                                            Certificate of Excellence

                                              46

                                              Heated Pool 2 Bed 3 Bath near Siesta Key

                                              Southwest Gulf Coast / Sarasota

                                              Sarasota house

                                              2 4 3 nights min

                                              • 2 bedrooms
                                              • sleeps 4
                                              • 3 nights min
                                              • Nearest beach 3 mi
                                              • Swimming pool
                                              • Child Friendly
                                              “Florida Trip” We rented this lovely home through Flipkey. This was a great rental for two couples and had everything you could possibly want at your fingertips. Just like home. Location was great and is located in a nice quiet neighborhood. Monica, th

                                              Certificate of Excellence

                                              Price per night from

                                              $165

                                              Responds fast!
                                              avg. 44 minutes

                                              Price per night from

                                              $165

                                              Distance approx 7.55 km from Longboat Key Show on Map

                                                24

                                                Bradenton House w/Screened Lanai & Private Pool!

                                                Southwest Gulf Coast / Bradenton

                                                Bradenton house

                                                4 10 5 nights min

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

                                                Price per night from

                                                $170

                                                Responds fast!
                                                avg. 10 minutes

                                                Price per night from

                                                $170

                                                Distance approx 7.63 km from Longboat Key

                                                (17) Very Good 

                                                  49

                                                  Top in Siesta Village at Best Beaches, Food & Entertainment! - Casa Van Lopik(J)

                                                  Florida / Siesta Key

                                                  Siesta Key house

                                                  3 10 3 nights min

                                                  • 3 bedrooms
                                                  • sleeps 10
                                                  • 3 nights min
                                                  • Beach / lakeside relaxation
                                                  • Nearest beach 0.1 mi
                                                  • Child Friendly
                                                  “Location, Location, Location!” Great house. Just as pictured and described. Dan and Jon are super-easy hosts. I like the little things - that the house is set up and fully ready. Abundance of supplies and towels, even beach chairs await! This having

                                                  Price per night from

                                                  $261

                                                  Responds fast!
                                                  avg. 2 hours 36 minutes

                                                  Price per night from

                                                  $261

                                                  Distance approx 10.13 km from Longboat Key

                                                  (21) Excellent 

                                                  Certificate of Excellence

                                                    42

                                                    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (3)

                                                    Florida / Siesta Key

                                                    Siesta Key house

                                                    1 4 3 nights min

                                                    • 1 bedroom
                                                    • sleeps 4
                                                    • 3 nights min
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 0.1 mi
                                                    • Child Friendly
                                                    “Old man and the sea unit c” The owner of the unit was extremely helpful from start to finish. Prior to arrival receiving a large information e mail containing everything you would ever need to know about the unit and area was a great benefit. The unit

                                                    Certificate of Excellence

                                                    Price per night from

                                                    $126

                                                    Responds fast!
                                                    avg. 2 hours 36 minutes

                                                    Price per night from

                                                    $126

                                                    Distance approx 10.04 km from Longboat Key

                                                    (1) Excellent 

                                                      16

                                                      Newly Updated 3 Bedroom Pool Home - Close to Beach

                                                      Southwest Gulf Coast / Sarasota

                                                      Sarasota house

                                                      3 7 min stay varies

                                                      • 3 bedrooms
                                                      • sleeps 7
                                                      • min stay varies
                                                      • Beach / lakeside relaxation
                                                      • Nearest beach 13 mi
                                                      • Swimming pool

                                                      Price per night from

                                                      $142

                                                      Responds fast!
                                                      avg. 36 minutes

                                                      Price per night from

                                                      $142

                                                      Distance approx 6.97 km from Longboat Key Show on Map

                                                      (1) Excellent 

                                                        23

                                                        New 6 Bedroom, Luxury Home in Gated Community

                                                        Florida / Siesta Key

                                                        Siesta Key house

                                                        6 14 7 nights min

                                                        • 6 bedrooms
                                                        • sleeps 14
                                                        • 7 nights min
                                                        • Beach / lakeside relaxation
                                                        • Swimming pool
                                                        • Child Friendly

                                                        Price per night from

                                                        $992

                                                        Price per night from

                                                        $992

                                                        Distance approx 10.86 km from Longboat Key

                                                          25

                                                          Designer Home Near the Best Beach in the US: Don't Miss SUMMER & FALL $$$$ DEALS

                                                          Southwest Gulf Coast / Sarasota

                                                          Sarasota house

                                                          3 6 7 nights min

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

                                                          Price per night from

                                                          $195

                                                          Price per night from

                                                          $195

                                                          Distance approx 19.64 km from Longboat Key

                                                            22

                                                            Nice in Nokomis

                                                            Florida / Nokomis

                                                            Nokomis house

                                                            2 4 27 nights min

                                                            • 2 bedrooms
                                                            • sleeps 4
                                                            • 27 nights min
                                                            • Child Friendly
                                                            • Air conditioning
                                                            • Pet Friendly

                                                            Price per night from

                                                            $136

                                                            Responds fast!
                                                            avg. 32 minutes

                                                            Price per night from

                                                            $136

                                                            Distance approx 12.79 km from Longboat Key

                                                            (35) Very Good 

                                                            Certificate of Excellence

                                                              46

                                                              Gorgeous views,spectacular home!

                                                              Anna Maria Island / Anna Maria

                                                              Anna Maria house

                                                              5 12 min stay varies

                                                              • 5 bedrooms
                                                              • sleeps 12
                                                              • min stay varies
                                                              • Beach / lakeside relaxation
                                                              • Swimming pool
                                                              • Child Friendly
                                                              “Nice needed some better cleaning” House was in a great location. Plenty of room. Needed better cleaning and some minor repairs. We would stay again though.

                                                              Certificate of Excellence

                                                              Price per night from

                                                              $487

                                                              Responds fast!
                                                              avg. 37 minutes

                                                              Price per night from

                                                              $487

                                                              Distance approx 16.47 km from Longboat Key

                                                              (4) Excellent 

                                                                12

                                                                Private, quiet, and very safe on 1 acre wooded lot just north of Lakewood Ranch

                                                                Southwest Gulf Coast / Bradenton

                                                                Bradenton house

                                                                3 5 min stay varies

                                                                • 3 bedrooms
                                                                • sleeps 5
                                                                • min stay varies
                                                                • Nearest beach 30 mi
                                                                • Swimming pool
                                                                • Child Friendly

                                                                Price per night from

                                                                $137

                                                                Price per night from

                                                                $137

                                                                Distance approx 7.64 km from Longboat Key

                                                                (2) Very Good 

                                                                  10

                                                                  2 bedroom/1 bath Contemporary Beach Cottage

                                                                  Florida / Siesta Key

                                                                  Siesta Key house

                                                                  2 6 4 nights min

                                                                  • 2 bedrooms
                                                                  • sleeps 6
                                                                  • 4 nights min
                                                                  • Child Friendly
                                                                  • Air conditioning
                                                                  • Pet Friendly

                                                                  Price per night from

                                                                  $194

                                                                  Price per night from

                                                                  $194

                                                                  Distance approx 10.27 km from Longboat Key

                                                                  (4) Very Good 

                                                                    18

                                                                    vacation rentals

                                                                    Southwest Gulf Coast / Sarasota

                                                                    Sarasota condo

                                                                    2 6 1 night min

                                                                    • 2 bedrooms
                                                                    • sleeps 6
                                                                    • 1 night min
                                                                    • Beach / lakeside relaxation
                                                                    • Nearest beach 1 mi
                                                                    • Swimming pool

                                                                    Price per night from

                                                                    $97

                                                                    Responds fast!
                                                                    avg. 3 hours 13 minutes

                                                                    Price per night from

                                                                    $97

                                                                    Distance approx 4.61 km from Longboat Key Show on Map

                                                                      25

                                                                      NEW! Sarasota Home w/Large Backyard & Water Access

                                                                      Florida / Tallevast

                                                                      Tallevast house

                                                                      2 5 min stay varies

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

                                                                      Price per night from

                                                                      $108

                                                                      Responds fast!
                                                                      avg. 10 minutes

                                                                      Price per night from

                                                                      $108

                                                                      Distance approx 11.15 km from Longboat Key

                                                                        22

                                                                        Chic~ Pet Friendly~ Brand New Heated Pool/Spa

                                                                        Anna Maria Island / Holmes Beach

                                                                        Holmes Beach house

                                                                        2 4 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 4
                                                                        • min stay varies
                                                                        • Beach / lakeside relaxation
                                                                        • Swimming pool
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $245

                                                                        Price per night from

                                                                        $245

                                                                        Distance approx 10.91 km from Longboat Key

                                                                        (10) Very Good 

                                                                          41

                                                                          Tropical Pool Home Near Siesta Key, Pet Friendly! Private POOL

                                                                          Southwest Gulf Coast / Sarasota

                                                                          Sarasota house

                                                                          2 4 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 4
                                                                          • min stay varies
                                                                          • Nearest beach 3 mi
                                                                          • Swimming pool
                                                                          • Ask about children

                                                                          Price per night from

                                                                          $75

                                                                          Price per night from

                                                                          $75

                                                                          Distance approx 19.27 km from Longboat Key

                                                                            12

                                                                            Casey Key 1-Bed Villa #2

                                                                            Florida / Nokomis

                                                                            Nokomis villa

                                                                            1 3 3 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 3
                                                                            • 3 nights min
                                                                            • Child Friendly
                                                                            • Air conditioning
                                                                            • Pet Friendly

                                                                            Price per night from

                                                                            $131

                                                                            Responds fast!
                                                                            avg. 3 hours 40 minutes

                                                                            Price per night from

                                                                            $131

                                                                            Distance approx 10.69 km from Longboat Key Show on Map

                                                                            (7) Very Good 

                                                                              16

                                                                              Beach House on Anna Maria Island-Rental Openings

                                                                              Anna Maria Island / Holmes Beach

                                                                              Holmes Beach villa

                                                                              3 6 7 nights min

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

                                                                              Price per night from

                                                                              $228

                                                                              Price per night from

                                                                              $228