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148 cottages

    9

    Terra Palma Cottages, Historic Home in the heart of Naples

    Southwest Gulf Coast / Naples

    Naples cottage

    1 2 7 nights min

    • 1 bedroom
    • sleeps 2
    • 7 nights min
    • Swimming pool
    • Car not necessary
    • Air conditioning
    Match: Rental types Water sports All filters match

    Price per night from

    $205

    Price per night from

    $205

    (1) Excellent 

      14

      One Block to the Beach

      Southwest Gulf Coast / Naples

      Naples cottage

      3 6 6 nights min

      • 3 bedrooms
      • sleeps 6
      • 6 nights min
      • Beach / lakeside relaxation
      • Swimming pool
      • Child Friendly
      Match: Rental types Water sports All filters match

      Price per night from

      $287

      Price per night from

      $287

        12

        One Bedroom Cottage in Marco Naples Resort

        Southwest Gulf Coast / Naples

        Naples cottage

        1 4 min stay varies

        • 1 bedroom
        • sleeps 4
        • min stay varies
        • Ask about children
        • Air conditioning
        Match: Rental types Water sports All filters match

        Price per night from

        $100

        Price per night from

        $100

        These homes match some but not all of your filters. Clear all filters

        (3) Excellent 

          24

          TROPICAL PARADISE CLOSE NAPLES BEACH AND FIFTH AVE

          Southwest Gulf Coast / Naples

          Naples condo

          3 6 min stay varies

          • 3 bedrooms
          • sleeps 6
          • min stay varies
          • Swimming pool
          • Child Friendly
          • Air conditioning
          1 of 2 match: Rental types, Water sports 1 of 2 filters match

          Price per night from

          $69

          Price per night from

          $69

            24

            Updated Naples Condo w/Shared Pool - Walk to Pier!

            Southwest Gulf Coast / Naples

            Naples apartment

            2 4 min stay varies

            • 2 bedrooms
            • sleeps 4
            • min stay varies
            • Air conditioning
            1 of 2 match: Rental types, Water sports 1 of 2 filters match

            Price per night from

            $201

            Responds fast!
            avg. 17 minutes

            Price per night from

            $201

              21

              On 5th Ave - 1 1/2 Blocks from the Beach! Newly Renovated Luxury Coastal Condo

              Southwest Gulf Coast / Naples

              Naples condo

              2 6 4 nights min

              • 2 bedrooms
              • sleeps 6
              • 4 nights min
              • Child Friendly
              1 of 2 match: Rental types, Water sports 1 of 2 filters match

              Price per night from

              $287

              Price per night from

              $287

                8

                Beachfront Luxury Condo

                Naples / Vanderbilt Beach Area

                Naples condo

                2 2 30 nights min

                • 2 bedrooms
                • sleeps 2
                • 30 nights min
                • Beach / lakeside relaxation
                • Swimming pool
                • Air conditioning
                1 of 2 match: Rental types, Water sports 1 of 2 filters match

                Price per night from

                $345

                Price per night from

                $345

                (1) Excellent 

                  22

                  Enclave at Naples Gated Community- Sleeps 6

                  Southwest Gulf Coast / Naples

                  Naples condo

                  2 6 14 nights min

                  • 2 bedrooms
                  • sleeps 6
                  • 14 nights min
                  • Nearest beach 4 mi
                  • Swimming pool
                  • Child Friendly
                  1 of 2 match: Rental types, Water sports 1 of 2 filters match

                  Price per night from

                  $123

                  Responds fast!
                  avg. 17 minutes

                  Price per night from

                  $123

                    26

                    Casa Napoletana a brand new SFH 4/3 with private pool, hot tub & lake view

                    Southwest Gulf Coast / Naples

                    Naples house

                    4 7 30 nights min

                    • 4 bedrooms
                    • sleeps 7
                    • 30 nights min
                    • Nearest beach 15 mi
                    • Swimming pool
                    • Child Friendly
                    1 of 2 match: Rental types, Water sports 1 of 2 filters match

                    Price per night from

                    $258

                    Price per night from

                    $258

                      16

                      Pine Cottage - New Listing!

                      Southwest Gulf Coast / Naples

                      Naples house

                      2 4 7 nights min

                      • 2 bedrooms
                      • sleeps 4
                      • 7 nights min
                      • Nearest beach 3 mi
                      • Ask about children
                      • Air conditioning
                      1 of 2 match: Rental types, Water sports 1 of 2 filters match

                      Price per night from

                      $172

                      Price per night from

                      $172

                      (4) Excellent 

                        29

                        ALL NEW LUXURY CONDO IN FALLING WATERS RESORT. HUGE HEATED SALT WATER POOL.

                        Southwest Gulf Coast / Naples

                        Naples apartment

                        2 5 min stay varies

                        • 2 bedrooms
                        • sleeps 5
                        • min stay varies
                        • Swimming pool
                        • Air conditioning
                        1 of 2 match: Rental types, Water sports 1 of 2 filters match

                        Price per night from

                        $97

                        Responds fast!
                        avg. 54 minutes

                        Price per night from

                        $97

                          20

                          Year round or seasonal tranquil cozy cottage!

                          Southwest Gulf Coast / Naples

                          Naples guest house

                          1 3 4 nights min

                          • 1 bedroom
                          • sleeps 3
                          • 4 nights min
                          • Nearest beach 12 mi
                          • Child Friendly
                          • Air conditioning
                          1 of 2 match: Rental types, Water sports 1 of 2 filters match

                          Price per night from

                          $52

                          Responds fast!
                          avg. 2 hours 59 minutes

                          Price per night from

                          $52

                            24

                            Falling Waters

                            Southwest Gulf Coast / Naples

                            Naples condo

                            2 4 14 nights min

                            • 2 bedrooms
                            • sleeps 4
                            • 14 nights min
                            • Nearest beach 9 mi
                            • Swimming pool
                            • Child Friendly
                            1 of 2 match: Rental types, Water sports 1 of 2 filters match

                            Price per night from

                            $91

                            Price per night from

                            $91

                            (1) Excellent 

                              24

                              Naples Bungalow w/Lanai Pool - 1 Mile from Beach!

                              Southwest Gulf Coast / Naples

                              Naples house

                              2 4 min stay varies

                              • 2 bedrooms
                              • sleeps 4
                              • min stay varies
                              • Swimming pool
                              • Air conditioning
                              • Pet Friendly
                              1 of 2 match: Rental types, Water sports 1 of 2 filters match

                              Price per night from

                              $132

                              Responds fast!
                              avg. 10 minutes

                              Price per night from

                              $132

                                24

                                Luxury Dream Villa (Happiness)

                                Southwest Gulf Coast / Naples

                                Naples villa

                                3 6 14 nights min

                                • 3 bedrooms
                                • sleeps 6
                                • 14 nights min
                                • Nearest beach 12 mi
                                • Swimming pool
                                • Child Friendly
                                1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                Price per night from

                                $196

                                Price per night from

                                $196

                                (1) Excellent 

                                  44

                                  Villa "Oasis of Serenity" in Countryside Golf Club Naples

                                  Southwest Gulf Coast / Naples

                                  Naples house

                                  3 6 30 nights min

                                  • 3 bedrooms
                                  • sleeps 6
                                  • 30 nights min
                                  • Swimming pool
                                  • Child Friendly
                                  • Air conditioning
                                  1 of 2 match: Rental types, Water sports 1 of 2 filters match
                                  “Mr” The most wonderful fully furnished in every meaning of the word. Pure peaceful vacation home. We truly miss that home and wonderful pool. Pure heaven is all I can say!!

                                  Price per night from

                                  $115

                                  Price per night from

                                  $115

                                    19

                                    Stunning Cottages at Naples Bay Resort

                                    Southwest Gulf Coast / Naples

                                    Naples apartment

                                    2 6 min stay varies

                                    • 2 bedrooms
                                    • sleeps 6
                                    • min stay varies
                                    • Nearest beach 2 mi
                                    • Swimming pool
                                    • Child Friendly
                                    1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                    Price per night from

                                    $178

                                    Price per night from

                                    $178

                                    (1) Excellent 

                                      14

                                      2 BR/2 BA/Den/Garage Coach Home

                                      Southwest Gulf Coast / Naples

                                      Naples condo

                                      2 6 30 nights min

                                      • 2 bedrooms
                                      • sleeps 6
                                      • 30 nights min
                                      • Swimming pool
                                      • Child Friendly
                                      • Air conditioning
                                      1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                      Price per night from

                                      $115

                                      Price per night from

                                      $115

                                      (1) Excellent 

                                        29

                                        Naples Tropical Oasis Water Front Condo minutes to gorgeous white sand beaches!

                                        Southwest Gulf Coast / Naples

                                        Naples condo

                                        2 6 min stay varies

                                        • 2 bedrooms
                                        • sleeps 6
                                        • min stay varies
                                        • Nearest beach 9 mi
                                        • Swimming pool
                                        • Child Friendly
                                        1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                        Price per night from

                                        $86

                                        Price per night from

                                        $86

                                          13

                                          Beautiful Resort Style Living in Naples

                                          Southwest Gulf Coast / Naples

                                          Naples condo

                                          2 6 30 nights min

                                          • 2 bedrooms
                                          • sleeps 6
                                          • 30 nights min
                                          • Child Friendly
                                          • Air conditioning
                                          1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                          Price per night from

                                          $95

                                          Price per night from

                                          $95

                                          (1) Excellent 

                                            19

                                            Luxury condo Naples Bay Resort

                                            Southwest Gulf Coast / Naples

                                            Naples apartment

                                            2 5 min stay varies

                                            • 2 bedrooms
                                            • sleeps 5
                                            • min stay varies
                                            • Child Friendly
                                            1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                            Price per night from

                                            $184

                                            Price per night from

                                            $184

                                              19

                                              Pelican Bay High Rise with stunning Gulf Views

                                              Southwest Gulf Coast / Naples

                                              Naples condo

                                              2 6 30 nights min

                                              • 2 bedrooms
                                              • sleeps 6
                                              • 30 nights min
                                              • Beach / lakeside relaxation
                                              • Ask about children
                                              1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                              Price per night from

                                              $306

                                              Price per night from

                                              $306

                                              (1) Very Good 

                                                14

                                                World Tennis Club -Condo rental

                                                Southwest Gulf Coast / Naples

                                                Naples apartment

                                                2 5 21 nights min

                                                • 2 bedrooms
                                                • sleeps 5
                                                • 21 nights min
                                                • Child Friendly
                                                1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                                Price per night from

                                                $344

                                                Price per night from

                                                $344

                                                (1) Excellent 

                                                  46

                                                  Golfer's Paradise/Naples Esplanade Golf & Country Club! 3/3 Pool/Spa 16th Green

                                                  Southwest Gulf Coast / Naples

                                                  Naples house

                                                  3 6 30 nights min

                                                  • 3 bedrooms
                                                  • sleeps 6
                                                  • 30 nights min
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Air conditioning
                                                  1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                                  Price per night from

                                                  $167

                                                  Responds fast!
                                                  avg. 44 minutes

                                                  Price per night from

                                                  $167

                                                  (3) Excellent 

                                                    19

                                                    New family friendly luxury home with private pool

                                                    Southwest Gulf Coast / Naples

                                                    Naples house

                                                    3 6 min stay varies

                                                    • 3 bedrooms
                                                    • sleeps 6
                                                    • min stay varies
                                                    • Beach / lakeside relaxation
                                                    • Swimming pool
                                                    • Child Friendly
                                                    1 of 2 match: Rental types, Water sports 1 of 2 filters match
                                                    “A wondeful place to stay” We were two families with kids (12 years) who stayed for 2 weeks in April. The house is new, beautifully furnished and decorated and very clean, there is lots of space for 6 people. The kitchen is well equipped, there are pl

                                                    Price per night from

                                                    $164

                                                    Responds fast!
                                                    avg. 1 hour 9 minutes

                                                    Price per night from

                                                    $164

                                                    (3) Very Good 

                                                    Certificate of Excellence

                                                      14

                                                      Three Bedroom Pool Home with Peaceful Preserve View

                                                      Southwest Gulf Coast / Naples

                                                      Naples house

                                                      3 6 5 nights min

                                                      • 3 bedrooms
                                                      • sleeps 6
                                                      • 5 nights min
                                                      • Child Friendly
                                                      • Pet Friendly
                                                      1 of 2 match: Rental types, Water sports 1 of 2 filters match
                                                      “Wonderful” We thoroughly enjoyed our stay here. The home was just as pictured and described. We loved the home, its location in the community and the community itself. It is very private and quite, even though It is family friendly. Our two dogs loved

                                                      Certificate of Excellence

                                                      Price per night from

                                                      $172

                                                      Responds fast!
                                                      avg. 2 hours 24 minutes

                                                      Price per night from

                                                      $172

                                                      (7) Very Good 

                                                        16

                                                        Sweet Bungalow, an independent unit with private entrance, bath, parking.

                                                        Southwest Gulf Coast / Naples

                                                        Naples bungalow

                                                        1 2 2 nights min

                                                        • 1 bedroom
                                                        • sleeps 2
                                                        • 2 nights min
                                                        • Beach / lakeside relaxation
                                                        • Air conditioning
                                                        • Ask about pets
                                                        1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                                        Price per night from

                                                        $79

                                                        Responds fast!
                                                        avg. 1 hour 26 minutes

                                                        Price per night from

                                                        $79

                                                          9

                                                          SPOTLESS! Private room & private bath in SHARED condo with nice, clean owner.

                                                          Southwest Gulf Coast / Naples

                                                          Naples private room

                                                          1 2 30 nights min

                                                          • 1 bedroom
                                                          • sleeps 2
                                                          • 30 nights min
                                                          • Nearest beach 3 mi
                                                          • Swimming pool
                                                          • Air conditioning
                                                          1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                                          Price per night from

                                                          $107

                                                          Price per night from

                                                          $107

                                                            25

                                                            Naples Condo w/Golf View & Resort-Style Amenities!

                                                            Southwest Gulf Coast / Naples

                                                            Naples apartment

                                                            2 5 min stay varies

                                                            • 2 bedrooms
                                                            • sleeps 5
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Child Friendly
                                                            • Air conditioning
                                                            1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                                            Price per night from

                                                            $144

                                                            Responds fast!
                                                            avg. 10 minutes

                                                            Price per night from

                                                            $144

                                                              27

                                                              Naples Villa w/ Lanai & Pond View - 5 Mi to Beach!

                                                              Southwest Gulf Coast / Naples

                                                              Naples villa

                                                              2 5 30 nights min

                                                              • 2 bedrooms
                                                              • sleeps 5
                                                              • 30 nights min
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Air conditioning
                                                              1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                                              Price per night from

                                                              $83

                                                              Responds fast!
                                                              avg. 10 minutes

                                                              Price per night from

                                                              $83

                                                                24

                                                                Naples Condo w/Balcony, Golf Course & Water Views!

                                                                Southwest Gulf Coast / Naples

                                                                Naples apartment

                                                                3 6 min stay varies

                                                                • 3 bedrooms
                                                                • sleeps 6
                                                                • min stay varies
                                                                • Swimming pool
                                                                • Child Friendly
                                                                • Air conditioning
                                                                1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                                                Price per night from

                                                                $144

                                                                Responds fast!
                                                                avg. 10 minutes

                                                                Price per night from

                                                                $144

                                                                (1) Excellent 

                                                                  22

                                                                  Greenlinks 3 bedroom, 1st floor condo with golf course views

                                                                  Southwest Gulf Coast / Naples

                                                                  Naples apartment

                                                                  3 6 min stay varies

                                                                  • 3 bedrooms
                                                                  • sleeps 6
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Air conditioning
                                                                  1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                                                  Price per night from

                                                                  $172

                                                                  Price per night from

                                                                  $172

                                                                  (2) Excellent 

                                                                    236

                                                                    Oceanfront Naples Private Island, Paradise Found.

                                                                    Southwest Gulf Coast / Naples

                                                                    Naples house

                                                                    3 9 min stay varies

                                                                    • 3 bedrooms
                                                                    • sleeps 9
                                                                    • min stay varies
                                                                    • Beach / lakeside relaxation
                                                                    • Child Friendly
                                                                    • Car not necessary
                                                                    1 of 2 match: Rental types, Water sports 1 of 2 filters match
                                                                    “Great home in a great place” Mike met us at the dock at 3pm, as requested, and took us on a nice 45 minute boat ride to the house on Keewaydin. Very peaceful spot. We met Espen, the owner, at the house and he gave us the grand tour. The house had ev

                                                                    Price per night from

                                                                    $573

                                                                    Price per night from

                                                                    $573

                                                                      25

                                                                      Spacious home w/ private pool close to shopping, beaches, and more!

                                                                      Southwest Gulf Coast / Naples

                                                                      Naples house

                                                                      3 6 7 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 6
                                                                      • 7 nights min
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Car not necessary
                                                                      1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                                                      Price per night from

                                                                      $113

                                                                      Responds fast!
                                                                      avg. 3 hours 8 minutes

                                                                      Price per night from

                                                                      $113

                                                                      (3) Very Good 

                                                                        33

                                                                        Gulf Breeze at Vanderbilt Beach

                                                                        Southwest Gulf Coast / Naples

                                                                        Naples house

                                                                        2 8 2 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 8
                                                                        • 2 nights min
                                                                        • Nearest beach 1 mi
                                                                        • Child Friendly
                                                                        • Air conditioning
                                                                        1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                                                        Price per night from

                                                                        $281

                                                                        Responds fast!
                                                                        avg. 24 minutes

                                                                        Price per night from

                                                                        $281

                                                                        (3) Very Good 

                                                                          18

                                                                          Beachwalk at Vanderbilt Beach

                                                                          Southwest Gulf Coast / Naples

                                                                          Naples house

                                                                          2 6 2 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 6
                                                                          • 2 nights min
                                                                          • Nearest beach 1 mi
                                                                          • Child Friendly
                                                                          • Air conditioning
                                                                          1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                                                          Price per night from

                                                                          $121

                                                                          Responds fast!
                                                                          avg. 24 minutes

                                                                          Price per night from

                                                                          $121

                                                                            17

                                                                            Perfect View: 2-bedroom Unit at Prestigious Vasari

                                                                            Southwest Gulf Coast / Naples

                                                                            Naples condo

                                                                            2 5 30 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 5
                                                                            • 30 nights min
                                                                            • Nearest beach 9 mi
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                                                            Price per night from

                                                                            $161

                                                                            Price per night from

                                                                            $161

                                                                            (4) Very Good 

                                                                              21

                                                                              The Treehouse at Vanderbilt Beach

                                                                              Southwest Gulf Coast / Naples

                                                                              Naples house

                                                                              1 6 1 night min

                                                                              • 1 bedroom
                                                                              • sleeps 6
                                                                              • 1 night min
                                                                              • Nearest beach 1 mi
                                                                              • Child Friendly
                                                                              • Air conditioning
                                                                              1 of 2 match: Rental types, Water sports 1 of 2 filters match

                                                                              Price per night from

                                                                              $166

                                                                              Responds fast!
                                                                              avg. 24 minutes

                                                                              Price per night from

                                                                              $166