Vacation Rentals with Hot Tub in Longboat Key

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Filtering by: Jacuzzi or hot tub

362 vacation rentals
    5

    Two Story Condo on the Gulf of Mexico

    Florida / Longboat Key

    Longboat Key condo

    4 10 7 nights min

    • 4 bedrooms
    • sleeps 10
    • 7 nights min
    • Beach / lakeside relaxation
    • Swimming pool
    • Child Friendly

    Price per night from

    $537

    Price per night from

    $537

      22

      Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

      Florida / Longboat Key

      Longboat Key condo

      2 6 7 nights min

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

      Price per night from

      $331

      Price per night from

      $331

        28

        GORGEOUS gated Multi-level LONGBOAT KEY HOME with DOCK ~ Near beach & private!

        Florida / Longboat Key

        Longboat Key house

        4 8 30 nights min

        • 4 bedrooms
        • sleeps 8
        • 30 nights min
        • Beach / lakeside relaxation
        • Nearest beach 0.4 mi
        • Swimming pool

        Price per night from

        $152

        Responds fast!
        avg. 1 hour 42 minutes

        Price per night from

        $152

        (3) Excellent 

          24

          Longboat Key Bayfront condo in Bay Isles

          Florida / Longboat Key

          Longboat Key condo

          2 4 90 nights min

          • 2 bedrooms
          • sleeps 4
          • 90 nights min
          • Child Friendly

          Price per night from

          $209

          Price per night from

          $209

            20

            Short Term Rental Condo

            Florida / Longboat Key

            Longboat Key apartment

            2 4 30 nights min

            • 2 bedrooms
            • sleeps 4
            • 30 nights min
            • Child Friendly
            • Air conditioning

            Price per night from

            $148

            Price per night from

            $148

              51

              Beach Paradise on the Gulf of Mexico, toes in the sand,sunsets, tennis, gym, it

              Florida / Longboat Key

              Longboat Key condo

              3 6 21 nights min

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

              Price per night from

              $186

              Responds fast!
              avg. 21 minutes

              Price per night from

              $186

              (1) Average 

                28

                Beach Castle Resort 6

                Florida / Longboat Key

                Longboat Key apartment

                2 6 3 nights min

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

                Price per night from

                $308

                Price per night from

                $308

                (2) Very Good 

                  22

                  Beach & Tennis Enthusists Vacation Condo

                  Florida / Longboat Key

                  Longboat Key condo

                  3 6 min stay varies

                  • 3 bedrooms
                  • sleeps 6
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Nearest beach 0 mi
                  • Child Friendly

                  Price per night from

                  $212

                  Price per night from

                  $212

                  (57) Very Good 

                    13

                    Castle in the Sky Near Beach and Tennis

                    Florida / Longboat Key

                    Longboat Key house

                    4 10 min stay varies

                    • 4 bedrooms
                    • sleeps 10
                    • min stay varies
                    • 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.
                    …see more

                    Price per night from

                    $222

                    Price per night from

                    $222

                    Great rentals within 20 miles that match your search

                    Distance approx 4.64 km from Longboat Key Show on Map

                    (8) Very Good 

                      9

                      St.Armands Circle condo ( Kingston Arms )

                      Southwest Gulf Coast / Sarasota

                      Sarasota apartment

                      2 6 7 nights min

                      • 2 bedrooms
                      • sleeps 6
                      • 7 nights min
                      • Swimming pool
                      • Child Friendly
                      • Car not necessary

                      Price per night from

                      $155

                      Price per night from

                      $155

                      Distance approx 5.12 km from Longboat Key Show on Map

                        47

                        Tastefully decorated Townhouse Condo - IMG Academy

                        Southwest Gulf Coast / Bradenton

                        Bradenton townhouse

                        2 4 min stay varies

                        • 2 bedrooms
                        • sleeps 4
                        • min stay varies
                        • Beach / lakeside relaxation
                        • Nearest beach 10 mi
                        • Swimming pool

                        Price per night from

                        $76

                        Responds fast!
                        avg. 3 hours 44 minutes

                        Price per night from

                        $76

                        Distance approx 12.75 km from Longboat Key

                        (2) Excellent 

                          27

                          Beautiful gated community near Siesta Key beach and downtown Sarasota

                          Southwest Gulf Coast / Sarasota

                          Sarasota house

                          2 4 5 nights min

                          • 2 bedrooms
                          • sleeps 4
                          • 5 nights min
                          • Swimming pool
                          • Air conditioning
                          • Private garden
                          “Great location and community” We loved our stay here. The location suited us. The community is clean and quiet. The people are friendly. Everything worked out for us, our first time renting. We would stay here again. Thank you.
                          …see more

                          Price per night from

                          $113

                          Responds fast!
                          avg. 3 hours 23 minutes

                          Price per night from

                          $113

                          Distance approx 10.18 km from Longboat Key

                          (14) Excellent 

                            34

                            Late SALE Sep/Oct only -Lakeside villa Uni. Park,golf,cycles,pool, beach

                            Southwest Gulf Coast / Sarasota

                            Sarasota villa

                            3 4 30 nights min

                            • 3 bedrooms
                            • sleeps 4
                            • 30 nights min
                            • Beach / lakeside relaxation
                            • Nearest beach 20 mi
                            • Swimming pool
                            “A perfect setting and location” Everything about this vacation is perfect from start to finish. Joyce guides you through the pre vacation procedure seamlessly. All relevant information is sent concerning local amenities and events occurring duri
                            …see more

                            Price per night from

                            $209

                            Responds fast!
                            avg. 50 minutes

                            Price per night from

                            $209

                            Distance approx 4.9 km from Longboat Key Show on Map

                            (19) Excellent 

                              11

                              bring A Boat, 12 Minutes To Sarasota Bay

                              Southwest Gulf Coast / Sarasota

                              Sarasota house

                              2 4 2 nights min

                              • 2 bedrooms
                              • sleeps 4
                              • 2 nights min
                              • Nearest beach 4 mi
                              • Swimming pool
                              • Air conditioning
                              “Great Spot: Helpful Host, Attractive Accommodations, Relaxing Hot Tub” Nestled within the first golfing/housing development in Florida (c. 1924),Whitfield Estates, Jim's renovated1960s house is an especially easy place to stay. It has a very large liv
                              …see more

                              Price per night from

                              $140

                              Responds fast!
                              avg. 1 hour 47 minutes

                              Price per night from

                              $140

                              Distance approx 6.38 km from Longboat Key Show on Map

                                24

                                SHOREWALK VACATION VILLA

                                Southwest Gulf Coast / Bradenton

                                Bradenton apartment

                                2 4 5 nights min

                                • 2 bedrooms
                                • sleeps 4
                                • 5 nights min
                                • Beach / lakeside relaxation
                                • Nearest beach 15 mi
                                • Swimming pool

                                Price per night from

                                $146

                                Price per night from

                                $146

                                Distance approx 6.9 km from Longboat Key Show on Map

                                  24

                                  Sarasota, Beaches, Lido, Down Town, Siesta

                                  Southwest Gulf Coast / Sarasota

                                  Sarasota house

                                  4 10 7 nights min

                                  • 4 bedrooms
                                  • sleeps 10
                                  • 7 nights min
                                  • Nearest beach 8 mi
                                  • Swimming pool
                                  • Child Friendly

                                  Price per night from

                                  $260

                                  Price per night from

                                  $260

                                  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

                                    $993

                                    Price per night from

                                    $993

                                    Distance approx 12.02 km from Longboat Key

                                      22

                                      Timberwoods Vacation Villas Best Value in Sarasota - Villa 2

                                      Southwest Gulf Coast / Sarasota

                                      Sarasota villa

                                      2 6 7 nights min

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

                                      Price per night from

                                      $272

                                      Responds fast!
                                      avg. 2 hours 37 minutes

                                      Price per night from

                                      $272

                                      Distance approx 11.97 km from Longboat Key

                                        29

                                        LUX VILLAs close to sparkling Siesta Key Beach.

                                        Florida / Osprey

                                        Osprey villa

                                        2 6 1 night min

                                        • 2 bedrooms
                                        • sleeps 6
                                        • 1 night min
                                        • Nearest beach 7 mi
                                        • Swimming pool
                                        • Child Friendly

                                        Price per night from

                                        $139

                                        Price per night from

                                        $139

                                        Distance approx 12.61 km from Longboat Key

                                        (1) Excellent 

                                          27

                                          LUX CONDOs near beautiful, sparkling Siesta Key Beach.

                                          Florida / Gulf Gate Branch

                                          Gulf Gate Branch condo

                                          1 4 1 night min

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

                                          Price per night from

                                          $104

                                          Price per night from

                                          $104

                                          Distance approx 7.44 km from Longboat Key

                                          (40) Excellent 

                                            27

                                            A Siesta Tropical Retreat - Island Pool Oasis

                                            Florida / Siesta Key

                                            Siesta Key house

                                            3 9 min stay varies

                                            • 3 bedrooms
                                            • sleeps 9
                                            • min stay varies
                                            • Beach / lakeside relaxation
                                            • Nearest beach 0.64 mi
                                            • Swimming pool
                                            “Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)a
                                            …see more

                                            Price per night from

                                            $212

                                            Price per night from

                                            $212

                                            Distance approx 11.7 km from Longboat Key

                                            (102) Excellent 

                                            Certificate of Excellence

                                              37

                                              Anna Maria Island Private Tropical Garden Home

                                              Anna Maria Island / Holmes Beach

                                              Holmes Beach house

                                              3 6 7 nights min

                                              • 3 bedrooms
                                              • sleeps 6
                                              • 7 nights min
                                              • Beach / lakeside relaxation
                                              • Nearest beach 0.64 mi
                                              • Swimming pool
                                              “Best rental, best hosts -- hands down!” I booked this rental with the intention of relaxing on the beach, soaking up the sun and hanging out with family for just over a week. Hurricane Irma had other plans, and we had to cut our vacation short. But
                                              …see more

                                              Certificate of Excellence

                                              Price per night from

                                              $292

                                              Responds fast!
                                              avg. 2 hours 46 minutes

                                              Price per night from

                                              $292

                                              Distance approx 19.48 km from Longboat Key

                                                34

                                                Cutest little bungalow west of the trail.

                                                Florida / Nokomis

                                                Nokomis house

                                                2 5 7 nights min

                                                • 2 bedrooms
                                                • sleeps 5
                                                • 7 nights min
                                                • Nearest beach 1 mi
                                                • Child Friendly
                                                • Air conditioning

                                                Price per night from

                                                $99

                                                Price per night from

                                                $99

                                                Distance approx 9.89 km from Longboat Key

                                                (5) Excellent 

                                                  32

                                                  SARASOTA : Paradise for golfers and beach lovers

                                                  Southwest Gulf Coast / Sarasota

                                                  Sarasota house

                                                  4 8 30 nights min

                                                  • 4 bedrooms
                                                  • sleeps 8
                                                  • 30 nights min
                                                  • Beach / lakeside relaxation
                                                  • Nearest beach 13 mi
                                                  • Swimming pool

                                                  Price per night from

                                                  $265

                                                  Price per night from

                                                  $265

                                                  Distance approx 9.42 km from Longboat Key Show on Map

                                                    13

                                                    3 Bedroom Oasis w/Pool,hot tub, pool table, wetbar, boat parking and more!

                                                    Florida / Palma Sola

                                                    Palma Sola house

                                                    3 8 4 nights min

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

                                                    Price per night from

                                                    $285

                                                    Price per night from

                                                    $285

                                                    Distance approx 5.05 km from Longboat Key Show on Map

                                                      24

                                                      NEW! Sarasota Cottage - 4-min Walk to Lido Beach!

                                                      Southwest Gulf Coast / Sarasota

                                                      Sarasota cottage

                                                      1 4 min stay varies

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

                                                      Price per night from

                                                      $126

                                                      Responds fast!
                                                      avg. 36 minutes

                                                      Price per night from

                                                      $126

                                                      Distance approx 8.66 km from Longboat Key Show on Map

                                                        26

                                                        Bradenton Beach Club 242

                                                        Florida / Cortez

                                                        Cortez condo

                                                        2 6 7 nights min

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • 7 nights min
                                                        • Swimming pool
                                                        • Child Friendly
                                                        • Car not necessary

                                                        Price per night from

                                                        $244

                                                        Price per night from

                                                        $244

                                                        Distance approx 11.99 km from Longboat Key

                                                          7

                                                          Villa in Resort Style Community

                                                          Florida / Gulf Gate Branch

                                                          Gulf Gate Branch villa

                                                          2 4 7 nights min

                                                          • 2 bedrooms
                                                          • sleeps 4
                                                          • 7 nights min
                                                          • Child Friendly

                                                          Price per night from

                                                          $111

                                                          Price per night from

                                                          $111

                                                          Distance approx 9.5 km from Longboat Key

                                                            40

                                                            Large 1300sqft 2BR2BA 4th Floor Siesta Key Crescent Beach WiFi No Road to Cross

                                                            Florida / Siesta Key

                                                            Siesta Key apartment

                                                            2 5 min stay varies

                                                            • 2 bedrooms
                                                            • sleeps 5
                                                            • min stay varies
                                                            • Nearest beach 0.1 mi
                                                            • Swimming pool
                                                            • Child Friendly

                                                            Price per night from

                                                            $164

                                                            Price per night from

                                                            $164

                                                            Distance approx 12.02 km from Longboat Key

                                                              22

                                                              Timberwoods Vacation Villas Best Value in Sarasota - Villa 4

                                                              Southwest Gulf Coast / Sarasota

                                                              Sarasota villa

                                                              2 5 7 nights min

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

                                                              Price per night from

                                                              $279

                                                              Responds fast!
                                                              avg. 2 hours 37 minutes

                                                              Price per night from

                                                              $279

                                                              Distance approx 14.4 km from Longboat Key

                                                              (4) Excellent 

                                                                19

                                                                Luxurious Lakeside Villa -Pool,Spa & Games Room

                                                                Southwest Gulf Coast / Bradenton

                                                                Bradenton villa

                                                                3 6 7 nights min

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

                                                                Price per night from

                                                                $184

                                                                Price per night from

                                                                $184

                                                                Distance approx 6.36 km from Longboat Key Show on Map

                                                                  28

                                                                  Haagen's Turtle Nest

                                                                  Southwest Gulf Coast / Bradenton

                                                                  Bradenton apartment

                                                                  2 5 7 nights min

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

                                                                  Price per night from

                                                                  $125

                                                                  Price per night from

                                                                  $125

                                                                  Distance approx 13.53 km from Longboat Key

                                                                  (6) Excellent 

                                                                    24

                                                                    A Paradise for Golfers and Tennis players

                                                                    Southwest Gulf Coast / Bradenton

                                                                    Bradenton apartment

                                                                    3 6 14 nights min

                                                                    • 3 bedrooms
                                                                    • sleeps 6
                                                                    • 14 nights min
                                                                    • Swimming pool
                                                                    • Child Friendly
                                                                    • Air conditioning
                                                                    “River strand condo” Been here 1 week and everything has been great. Owners are very helpful. River Strand has great golf, tennis, pools.
                                                                    …see more

                                                                    Price per night from

                                                                    $141

                                                                    Responds fast!
                                                                    avg. 2 hours 37 minutes

                                                                    Price per night from

                                                                    $141

                                                                    Distance approx 12.03 km from Longboat Key

                                                                    (2) Excellent 

                                                                      18

                                                                      Timberwoods Vacation Villa Best Value in Sarasota

                                                                      Southwest Gulf Coast / Sarasota

                                                                      Sarasota villa

                                                                      2 4 7 nights min

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

                                                                      Price per night from

                                                                      $99

                                                                      Responds fast!
                                                                      avg. 3 hours 48 minutes

                                                                      Price per night from

                                                                      $99

                                                                      Distance approx 9.22 km from Longboat Key

                                                                      (6) Excellent 

                                                                        21

                                                                        Gorgeous Condo directly on #1 Beach in USA - #111

                                                                        Florida / Siesta Key

                                                                        Siesta Key condo

                                                                        1 3 14 nights min

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

                                                                        Price per night from

                                                                        $269

                                                                        Price per night from

                                                                        $269

                                                                        Distance approx 10.64 km from Longboat Key

                                                                        (27) Excellent 

                                                                          11

                                                                          Tara Golf and Country Club

                                                                          Southwest Gulf Coast / Bradenton

                                                                          Bradenton house

                                                                          4 10 7 nights min

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

                                                                          Price per night from

                                                                          $214

                                                                          Price per night from

                                                                          $214

                                                                          Distance approx 6.43 km from Longboat Key Show on Map

                                                                            31

                                                                            Luxury lakefront Sunshine Shorewalk 2B condo, 1 km. IMG Academy, 10 min to beach

                                                                            Southwest Gulf Coast / Bradenton

                                                                            Bradenton villa

                                                                            2 4 7 nights min

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

                                                                            Price per night from

                                                                            $85

                                                                            Price per night from

                                                                            $85

                                                                            Distance approx 9.6 km from Longboat Key Show on Map

                                                                              12

                                                                              2/2 Bradenton Condo available for 30+ day rentals $2000 monthly

                                                                              Southwest Gulf Coast / Bradenton

                                                                              Bradenton condo

                                                                              2 6 30 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 6
                                                                              • 30 nights min
                                                                              • Child Friendly

                                                                              Price per night from

                                                                              $78

                                                                              Price per night from

                                                                              $78