Vacation Rentals & House Rentals in Little Gasparilla Island

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925 house rentals

(5) Excellent 

    28

    Relaxing Private Island House (LGI)

    Southwest Gulf Coast / Little Gasparilla Island

    Little Gasparilla Island house

    2 4 7 nights min

    • 2 bedrooms
    • sleeps 4
    • 7 nights min
    • Beach / lakeside relaxation
    • Nearest beach 0 mi
    • Child Friendly

    Price per night from

    $196

    Price per night from

    $196

    (2) Very Good 

      24

      BEACHFRONT | Beautiful | Relaxing Views of the Gulf | Little Gasparilla Island

      Southwest Gulf Coast / Little Gasparilla Island

      Little Gasparilla Island condo

      2 4 min stay varies

      • 2 bedrooms
      • sleeps 4
      • min stay varies
      • Nearest beach 0.1 mi
      • Swimming pool
      • Child Friendly

      Price per night from

      $172

      Responds fast!
      avg. 1 hour 50 minutes

      Price per night from

      $172

      (19) Excellent 

      Certificate of Excellence

        38

        Gulf Front Beach Condo (Little Gasparilla Island)

        Southwest Gulf Coast / Little Gasparilla Island

        Little Gasparilla Island condo

        2 5 3 nights min

        • 2 bedrooms
        • sleeps 5
        • 3 nights min
        • Beach / lakeside relaxation
        • Swimming pool
        • Suitable for children age 5+
        “LGI Spring Break 2018” LGI is an amazing place and my family enjoyed every minute of our time there. Pam was a very gracious and attentive host who was great to work with. We have already begun thinking about a return trip to the island and would not
        …see more

        Certificate of Excellence

        Price per night from

        $229

        Price per night from

        $229

          16

          Sea Star Beach House: Sunsets Galore!

          Southwest Gulf Coast / Little Gasparilla Island

          Little Gasparilla Island house

          3 7 min stay varies

          • 3 bedrooms
          • sleeps 7
          • min stay varies
          • Beach / lakeside relaxation
          • Child Friendly
          • Air conditioning

          Price per night from

          $360

          Responds fast!
          avg. 2 hours 35 minutes

          Price per night from

          $360

          (2) Very Good 

            24

            Island Home Retreat PRIVATE DOCK Free Kayaks Free Wi-Fi

            Southwest Gulf Coast / Little Gasparilla Island

            Little Gasparilla Island house

            3 8 min stay varies

            • 3 bedrooms
            • sleeps 8
            • min stay varies
            • Child Friendly
            • Car not necessary
            • Air conditioning

            Price per night from

            $224

            Price per night from

            $224

            (2) Very Good 

              38

              "The Round House" - An Island Original!

              Southwest Gulf Coast / Little Gasparilla Island

              Little Gasparilla Island cottage

              2 6 min stay varies

              • 2 bedrooms
              • sleeps 6
              • min stay varies
              • Beach / lakeside relaxation
              • Child Friendly
              • Car not necessary

              Price per night from

              $367

              Responds fast!
              avg. 2 hours 35 minutes

              Price per night from

              $367

              (13) Excellent 

                33

                Hibiscus House - Beachfront Bliss on the Gulf!

                Southwest Gulf Coast / Little Gasparilla Island

                Little Gasparilla Island cottage

                3 5 5 nights min

                • 3 bedrooms
                • sleeps 5
                • 5 nights min
                • Beach / lakeside relaxation
                • Nearest beach 0 mi
                • Child Friendly
                “Tom Sawyer for one month” This was the first time we have ever done this kind of vacation--one month on an island. It was terrific!! Ran on the beach with our dog; great ocean (I know its the Gulf); very friendly folks; great fishing and a tremendous
                …see more

                Price per night from

                $458

                Responds fast!
                avg. 2 hours 35 minutes

                Price per night from

                $458

                (10) Very Good 

                  46

                  Coconut Hideaway: Gulf-Front Dream House!

                  Southwest Gulf Coast / Little Gasparilla Island

                  Little Gasparilla Island villa

                  3 6 5 nights min

                  • 3 bedrooms
                  • sleeps 6
                  • 5 nights min
                  • Beach / lakeside relaxation
                  • Child Friendly
                  • Air conditioning
                  “The island get away that so many resorts promise you...but this” I've been here a few different times, and I'm always sad to leave. It is the island get away that so many resorts promise you...but this is the real thing! The beach is very secluded, an
                  …see more

                  Price per night from

                  $430

                  Responds fast!
                  avg. 2 hours 35 minutes

                  Price per night from

                  $430

                    14

                    LaTeDa Beach House

                    Southwest Gulf Coast / Little Gasparilla Island

                    Little Gasparilla Island house

                    3 6 7 nights min

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

                    Price per night from

                    $360

                    Price per night from

                    $360

                    (2) Excellent 

                      42

                      Lucky Me ! A Waterfont Retreat

                      Southwest Gulf Coast / Little Gasparilla Island

                      Little Gasparilla Island house

                      3 8 3 nights min

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

                      Price per night from

                      $264

                      Price per night from

                      $264

                      (2) Average 

                        22

                        Serenity Cottage on Little Gasparilla Island

                        Southwest Gulf Coast / Little Gasparilla Island

                        Little Gasparilla Island cottage

                        2 4 min stay varies

                        • 2 bedrooms
                        • sleeps 4
                        • min stay varies
                        • Beach / lakeside relaxation
                        • Child Friendly
                        • Air conditioning

                        Price per night from

                        $229

                        Responds fast!
                        avg. 2 hours 35 minutes

                        Price per night from

                        $229

                        (1) Excellent 

                          25

                          Coconut Palm Cottage - Tropical Beach Getaway

                          Southwest Gulf Coast / Little Gasparilla Island

                          Little Gasparilla Island cottage

                          2 4 min stay varies

                          • 2 bedrooms
                          • sleeps 4
                          • min stay varies
                          • Beach / lakeside relaxation
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $229

                          Responds fast!
                          avg. 2 hours 54 minutes

                          Price per night from

                          $229

                          (1) Excellent 

                            22

                            RoseMary's Beach House: Beachfront Elegance

                            Southwest Gulf Coast / Little Gasparilla Island

                            Little Gasparilla Island house

                            2 4 7 nights min

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

                            Price per night from

                            $320

                            Responds fast!
                            avg. 2 hours 35 minutes

                            Price per night from

                            $320

                              20

                              Island Dream House

                              Southwest Gulf Coast / Little Gasparilla Island

                              Little Gasparilla Island house

                              3 10 min stay varies

                              • 3 bedrooms
                              • sleeps 10
                              • min stay varies
                              • Child Friendly
                              • Air conditioning
                              • Pet Friendly

                              Price per night from

                              $344

                              Responds fast!
                              avg. 2 hours 35 minutes

                              Price per night from

                              $344

                                21

                                Angler's Paradise - A Fisherman's Dream!

                                Southwest Gulf Coast / Little Gasparilla Island

                                Little Gasparilla Island cottage

                                2 4 min stay varies

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

                                Price per night from

                                $229

                                Responds fast!
                                avg. 2 hours 35 minutes

                                Price per night from

                                $229

                                  9

                                  BELLISSIMA BY THE BEACH

                                  Southwest Gulf Coast / Little Gasparilla Island

                                  Little Gasparilla Island cottage

                                  2 4 2 nights min

                                  • 2 bedrooms
                                  • sleeps 4
                                  • 2 nights min
                                  • Air conditioning
                                  • Private garden

                                  Price per night from

                                  $487

                                  Price per night from

                                  $487

                                    20

                                    Island paradise Little Gasparilla island

                                    Southwest Gulf Coast / Little Gasparilla Island

                                    Little Gasparilla Island condo

                                    2 6 2 nights min

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

                                    Price per night from

                                    $166

                                    Price per night from

                                    $166

                                      13

                                      Beautiful Waterfront Condo at Boca Grande North - A Serene, Happy Space!

                                      Southwest Gulf Coast / Little Gasparilla Island

                                      Little Gasparilla Island condo

                                      2 6 5 nights min

                                      • 2 bedrooms
                                      • sleeps 6
                                      • 5 nights min
                                      • Nearest beach 3 mi
                                      • Swimming pool
                                      • Child Friendly

                                      Price per night from

                                      $344

                                      Price per night from

                                      $344

                                        26

                                        ★ Secluded Holiday Retreat/ Island Paradise & Waterfront Condo ★

                                        Southwest Gulf Coast / Little Gasparilla Island

                                        Little Gasparilla Island condo

                                        2 4 min stay varies

                                        • 2 bedrooms
                                        • sleeps 4
                                        • min stay varies
                                        • Beach / lakeside relaxation
                                        • Nearest beach 0.1 mi
                                        • Swimming pool

                                        Price per night from

                                        $205

                                        Responds fast!
                                        avg. 3 hours 10 minutes

                                        Price per night from

                                        $205

                                        Great rentals within 20 miles that match your search

                                        Distance approx 18.33 km from Little Gasparilla Island

                                        (5) Excellent 

                                          34

                                          Luxury Venice Home with (heated) Private Pool and Lake View

                                          Southwest Gulf Coast / Venice

                                          Venice house

                                          4 8 14 nights min

                                          • 4 bedrooms
                                          • sleeps 8
                                          • 14 nights min
                                          • Beach / lakeside relaxation
                                          • Nearest beach 3 mi
                                          • Swimming pool
                                          “I wish I was there right now :) !!!” My family and I had a wonderful time while at this beautiful, brand new, and completely furnished home. This was our first vacation since our daughter was born, and this place was the perfect retreat for the entir
                                          …see more

                                          Price per night from

                                          $224

                                          Price per night from

                                          $224

                                          Distance approx 15.09 km from Little Gasparilla Island

                                          (1) Excellent 

                                            29

                                            Paradise is Awaiting You in a Boaters Community

                                            Southwest Gulf Coast / Punta Gorda

                                            Punta Gorda house

                                            3 8 min stay varies

                                            • 3 bedrooms
                                            • sleeps 8
                                            • min stay varies
                                            • Beach / lakeside relaxation
                                            • Swimming pool
                                            • Child Friendly

                                            Price per night from

                                            $162

                                            Price per night from

                                            $162

                                            Distance approx 1.35 km from Little Gasparilla Island Show on Map

                                              25

                                              Coral Creek Landings Town Home-3 Bedroom-3 Bath

                                              Southwest Gulf Coast / Placida

                                              Placida townhouse

                                              3 6 30 nights min

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

                                              Price per night from

                                              $144

                                              Price per night from

                                              $144

                                              Distance approx 15.1 km from Little Gasparilla Island

                                                11

                                                Waterfront with dock and heated pool

                                                Southwest Gulf Coast / Punta Gorda

                                                Punta Gorda house

                                                3 6 30 nights min

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

                                                Price per night from

                                                $172

                                                Price per night from

                                                $172

                                                Distance approx 16.16 km from Little Gasparilla Island

                                                (1) Excellent 

                                                  20

                                                  Ground Level 2 Bedroom Beach Themed Condo

                                                  Southwest Gulf Coast / Venice

                                                  Venice condo

                                                  2 6 7 nights min

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

                                                  Price per night from

                                                  $82

                                                  Responds fast!
                                                  avg. 1 hour 11 minutes

                                                  Price per night from

                                                  $82

                                                  Distance approx 15.99 km from Little Gasparilla Island

                                                    11

                                                    Third Floor Condo with Beautiful View of Golf Course and Pool

                                                    Southwest Gulf Coast / Punta Gorda

                                                    Punta Gorda apartment

                                                    2 4 30 nights min

                                                    • 2 bedrooms
                                                    • sleeps 4
                                                    • 30 nights min
                                                    • Swimming pool
                                                    • Air conditioning

                                                    Price per night from

                                                    $89

                                                    Price per night from

                                                    $89

                                                    Distance approx 13.32 km from Little Gasparilla Island

                                                    (2) Very Good 

                                                      17

                                                      Tropical Water front

                                                      Southwest Gulf Coast / Englewood

                                                      Englewood house

                                                      3 6 7 nights min

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

                                                      Price per night from

                                                      $213

                                                      Price per night from

                                                      $213

                                                      Distance approx 10.12 km from Little Gasparilla Island

                                                        15

                                                        Peaceful, Private, Paradise in Englewood. House with heated pool

                                                        Southwest Gulf Coast / Englewood

                                                        Englewood house

                                                        3 6 7 nights min

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

                                                        Price per night from

                                                        $258

                                                        Price per night from

                                                        $258

                                                        Distance approx 12.87 km from Little Gasparilla Island

                                                        (4) Very Good 

                                                          20

                                                          Chaves - 6 sleeps with heated pool

                                                          Southwest Gulf Coast / Port Charlotte

                                                          Port Charlotte house

                                                          3 6 4 nights min

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • 4 nights min
                                                          • Nearest beach 8 mi
                                                          • Swimming pool
                                                          • Ask about children
                                                          “Clean and comfortable environment” We truly enjoyed our stay at the Chaves house. It was meticulously clean and comfortable. The downside is that the cable was not working and netflix was offered on the ammenities page, but that too was not availabl
                                                          …see more

                                                          Price per night from

                                                          $115

                                                          Price per night from

                                                          $115

                                                          Distance approx 19.16 km from Little Gasparilla Island

                                                            10

                                                            Relaxing location, 3BD townhome, North Port, FL

                                                            Florida / North Port

                                                            North Port house

                                                            3 8 60 nights min

                                                            • 3 bedrooms
                                                            • sleeps 8
                                                            • 60 nights min
                                                            • Beach / lakeside relaxation
                                                            • Nearest beach 24 mi
                                                            • Swimming pool

                                                            Price per night from

                                                            $111

                                                            Responds fast!
                                                            avg. 47 minutes

                                                            Price per night from

                                                            $111

                                                            Distance approx 7.87 km from Little Gasparilla Island

                                                              27

                                                              Blue Marlin

                                                              Southwest Gulf Coast / El Jobean

                                                              El Jobean house

                                                              3 6 min stay varies

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

                                                              Price per night from

                                                              $178

                                                              Responds fast!
                                                              avg. 1 hour 32 minutes

                                                              Price per night from

                                                              $178

                                                              Distance approx 7.54 km from Little Gasparilla Island

                                                                20

                                                                BRIGHT, UPDATED, CONVENIENT, AMENITIES

                                                                Southwest Gulf Coast / Englewood

                                                                Englewood house

                                                                2 4 min stay varies

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

                                                                Price per night from

                                                                $81

                                                                Price per night from

                                                                $81

                                                                Distance approx 18.73 km from Little Gasparilla Island

                                                                  23

                                                                  Casa Indulgence in Matlacha

                                                                  Florida / Matlacha

                                                                  Matlacha house

                                                                  3 6 7 nights min

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

                                                                  Price per night from

                                                                  $802

                                                                  Price per night from

                                                                  $802

                                                                  Distance approx 16.61 km from Little Gasparilla Island

                                                                    10

                                                                    Clean, cozy home within walking distance to the S Venice ferry and boat ramp.

                                                                    Florida / South Venice

                                                                    South Venice house

                                                                    2 6 1 night min

                                                                    • 2 bedrooms
                                                                    • sleeps 6
                                                                    • 1 night min
                                                                    • Child Friendly
                                                                    • Pet Friendly

                                                                    Price per night from

                                                                    $144

                                                                    Price per night from

                                                                    $144

                                                                    Distance approx 19.83 km from Little Gasparilla Island

                                                                      17

                                                                      BEAUTIFUL PUNTA GORDA, FL CONDO PROVIDES RESORT-STYLE LIVING

                                                                      Southwest Gulf Coast / Punta Gorda

                                                                      Punta Gorda condo

                                                                      2 4 14 nights min

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

                                                                      Price per night from

                                                                      $115

                                                                      Price per night from

                                                                      $115

                                                                      Distance approx 16.61 km from Little Gasparilla Island

                                                                        8

                                                                        Sunny South Venice Beach Home with Private Beach, Bikes and Kayaks

                                                                        Florida / South Venice

                                                                        South Venice house

                                                                        2 5 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 5
                                                                        • min stay varies
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $155

                                                                        Price per night from

                                                                        $155

                                                                        Distance approx 6.32 km from Little Gasparilla Island

                                                                        (12) Excellent 

                                                                          21

                                                                          Villa Nevaeh

                                                                          Rotonda West / Rotonda Lakes

                                                                          Rotonda West villa

                                                                          3 6 4 nights min

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

                                                                          Price per night from

                                                                          $119

                                                                          Price per night from

                                                                          $119

                                                                          Distance approx 8.38 km from Little Gasparilla Island

                                                                          (1) Very Good 

                                                                            24

                                                                            Gulf To Bay Complex! 2 BR, 2 Baths, Pool, Hot tub, Dock.

                                                                            Southwest Gulf Coast / Manasota Key

                                                                            Manasota Key condo

                                                                            2 6 31 nights min

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

                                                                            Price per night from

                                                                            $171

                                                                            Responds fast!
                                                                            avg. 1 hour 3 minutes

                                                                            Price per night from

                                                                            $171

                                                                            Distance approx 18.16 km from Little Gasparilla Island

                                                                              6

                                                                              Siesta Vacation Home - Venice, FL

                                                                              Southwest Gulf Coast / Venice

                                                                              Venice house

                                                                              2 6 min stay varies

                                                                              • 2 bedrooms
                                                                              • sleeps 6
                                                                              • min stay varies
                                                                              • Ask about children
                                                                              • Air conditioning
                                                                              • Private garden

                                                                              Price per night from

                                                                              $124

                                                                              Price per night from

                                                                              $124

                                                                              About Little Gasparilla Island

                                                                              The southernmost of three islands which includes Don Pedro and Palm Islands, Little Gasparilla Island is truly a tranquil paradise, and the perfect place to live out your desert island dream.

                                                                              Why not find your perfect beachfront vacation rental by browsing FlipKey’s collection of Little Gasparilla Island properties?

                                                                              About Little Gasparilla Island

                                                                              The islands of Don Pedro, Palm Island and Little Gasparilla were once separate islands, until a hurricane in the 1960s closed the passes and destroyed the bridge from Little Gasparilla to Palm Island. Today, they are one island, and the bridge has never been rebuilt. There are no roads or cars on Little Gasparilla, giving it a lost-in-time atmosphere, accessible only by water taxi. 

                                                                              It’s said that the island was initially settled by the notorious pirate Jose Gaspar, after whom it takes its name, and he was said to have built a palace at Boca Grande. Whether he existed or not, the island today has become a popular attraction for vacationers from the surrounding area.

                                                                              Shop at the fish market in Placida on the mainland and bring your supplies across by water taxi.

                                                                              What to do

                                                                              With no stores or restaurants on the island, all that’s left to do is enjoy a thoroughly relaxing vacation. With 7 miles of pristine sand beaches, you can laze in the sun, go swimming or spot sea turtles, dolphins and manatees. Enjoy a charter fishing trip, rent a boat, or go shelling on the beach – you can even find plenty of prehistoric shark’s teeth here, and spot starfish, conchs and sand dollars. It’s not uncommon to find the beach completely empty, particularly outside of peak season, and bird watching for blue herons, osprey and white pelicans is a popular pastime.

                                                                              Take a trip to Little Gasparilla Island State Park, or enjoy the 7.5 mile walk from the south tip of the island to the north tip of Palm Island, for a lovely way to spend a sunny afternoon.

                                                                              Top Little Gasparilla Island travel tips

                                                                              The nearest airports are Sarasota Airport, just over an hour to the north, and Fort Myers, an hour to the south.

                                                                              There’s a restaurant at Palm Island Resort (with an extensive menu), but otherwise you’ll need to head to the mainland by water taxi for dinner (or cook at your vacation rental).

                                                                              You can call for a water taxi to pick you up at the local marina on the mainland – just tell them your dock number and they’ll drop you directly at your vacation rental.

                                                                              Step back in time with a vacation on Little Gasparilla Island – it’s the best way to escape it all, whether you’re enjoying a family vacation or a romantic retreat.

                                                                              With over 300 villas and condos to choose from, you’re sure to find your perfect tropical island getaway with FlipKey!