Holiday Rentals

Close

Enter dates for more accurate prices

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

891 Houses

    24

    Waterfront Holiday House w/ Private Pool & Dock!

    Florida / Holiday

    Holiday house

    2 6 min stay varies

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

    Price per night from

    $234

    Responds fast!
    avg. 36 minutes

    Price per night from

    $234

    (4) Excellent 

      26

      Florida Waterfront Home w/ Boat Lift & Kayaks!

      Florida / Holiday

      Holiday house

      4 10 min stay varies

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

      Price per night from

      $194

      Responds fast!
      avg. 36 minutes

      Price per night from

      $194

      (2) Excellent 

        37

        Location, Location, Water Veiw, Pool Home on Dead End Street! Beauitful Sunsets

        Florida / Holiday

        Holiday house

        2 6 1 night min

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

        Price per night from

        $154

        Price per night from

        $154

        (1) Excellent 

          25

          2 Bedroom waterfront vacation retreat

          Florida / Holiday

          Holiday house

          2 7 2 nights min

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

          Price per night from

          $172

          Responds fast!
          avg. 2 hours 15 minutes

          Price per night from

          $172

          (4) Very Good 

            21

            Riverview (Gulf Access)

            Florida / Holiday

            Holiday house

            3 6 1 night min

            • 3 bedrooms
            • sleeps 6
            • 1 night min
            • Beach / lakeside relaxation
            • Nearest beach 8 mi
            • Ask about children

            Price per night from

            $109

            Price per night from

            $109

              11

              Holiday Bliss. Private home with privacy fenced back yard with jacuzzi and pool

              Florida / Holiday

              Holiday house

              2 6 90 nights min

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

              Price per night from

              $99

              Price per night from

              $99

              (16) Excellent 

                10

                Geodesic Dome

                Florida / Holiday

                Holiday apartment

                1 5 4 nights min

                • 1 bedroom
                • sleeps 5
                • 4 nights min
                • Beach / lakeside relaxation
                • Nearest beach 3 mi
                • Swimming pool
                “Ms” Me and my children stayed for 11 days and had the most wonderful vacation!! Thank you Sharon and Ralph...y'all are the best!! We will definitely be returning!!
                …see more

                Price per night from

                $137

                Responds fast!
                avg. 3 hours 39 minutes

                Price per night from

                $137

                  29

                  NEW! Charming Holiday Home - 6 Mi. to Sunset Beach

                  Florida / Holiday

                  Holiday house

                  2 6 min stay varies

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

                  Price per night from

                  $121

                  Responds fast!
                  avg. 36 minutes

                  Price per night from

                  $121

                    24

                    3BR Holiday House w/ Direct River Access & Pool!

                    Florida / Holiday

                    Holiday house

                    3 7 min stay varies

                    • 3 bedrooms
                    • sleeps 7
                    • min stay varies
                    • Child Friendly
                    • Air conditioning
                    • Pet Friendly

                    Price per night from

                    $247

                    Responds fast!
                    avg. 36 minutes

                    Price per night from

                    $247

                      16

                      Majestic 2BR 2BA Holiday Waterfront Property W/ High Speed Internet,Private Dock

                      Florida / Holiday

                      Holiday house

                      2 6 min stay varies

                      • 2 bedrooms
                      • sleeps 6
                      • min stay varies
                      • Beach / lakeside relaxation
                      • Nearest beach 11 mi
                      • Child Friendly

                      Price per night from

                      $136

                      Responds fast!
                      avg. 57 minutes

                      Price per night from

                      $136

                      (7) Very Good 

                        40

                        Dolphin Cove Villa

                        Florida / Holiday

                        Holiday house

                        4 12 min stay varies

                        • 4 bedrooms
                        • sleeps 12
                        • min stay varies
                        • Swimming pool
                        • Ask about children

                        Price per night from

                        $615

                        Price per night from

                        $615

                        (1) Excellent 

                          30

                          Waterfront pool home on Anclote River, access to Tarpon Springs & Gulf of Mexico

                          Florida / Holiday

                          Holiday house

                          2 4 min stay varies

                          • 2 bedrooms
                          • sleeps 4
                          • min stay varies
                          • Swimming pool
                          • Air conditioning
                          • Private garden

                          Price per night from

                          $172

                          Price per night from

                          $172

                            13

                            Seasonal Duplex (2) Apartments - Interview with Owner Required Before Booking

                            Florida / Holiday

                            Holiday apartment

                            1 2 30 nights min

                            • 1 bedroom
                            • sleeps 2
                            • 30 nights min
                            • Air conditioning
                            • Private garden

                            Price per night from

                            $39

                            Price per night from

                            $39

                            (37) Excellent 

                              32

                              Gulf Coast Heaven with Private Charter Boat - 80ft Lap Pool

                              Florida / Holiday

                              Holiday house

                              3 7 3 nights min

                              • 3 bedrooms
                              • sleeps 7
                              • 3 nights min
                              • Beach / lakeside relaxation
                              • Swimming pool
                              • Child Friendly
                              “Absolutely perfect!!” We had a wonderful vacation here and we cannot say enough about how much we enjoyed ourselves. It was even better than we had expected! The house has plenty of room(we were a party of 4) and was very clean and is in top notch sha
                              …see more

                              Price per night from

                              $411

                              Price per night from

                              $411

                                24

                                NEW! Holiday Home w/Outdoor Oasis-1 Block to Shore

                                Florida / Holiday

                                Holiday house

                                2 8 min stay varies

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

                                Price per night from

                                $86

                                Responds fast!
                                avg. 36 minutes

                                Price per night from

                                $86

                                  19

                                  Snowbirds' Dream, Minutes from the Beach, Shopping, Nature and Biking Trails

                                  Florida / Holiday

                                  Holiday house

                                  2 6 3 nights min

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

                                  Price per night from

                                  $193

                                  Price per night from

                                  $193

                                    25

                                    Peace and Tranquility

                                    Florida / Holiday

                                    Holiday condo

                                    2 6 2 nights min

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

                                    Price per night from

                                    $113

                                    Responds fast!
                                    avg. 3 hours 33 minutes

                                    Price per night from

                                    $113

                                    Great rentals within 20 miles that match your search

                                    Distance approx 5.47 km from Holiday

                                    (3) Very Good 

                                      35

                                      Waterfront 3/3 Home/Dock, direct to Gulf of Mexico

                                      Florida / New Port Richey

                                      New Port Richey house

                                      3 10 7 nights min

                                      • 3 bedrooms
                                      • sleeps 10
                                      • 7 nights min
                                      • Beach / lakeside relaxation
                                      • Nearest beach 3 mi
                                      • Ask about children

                                      Price per night from

                                      $167

                                      Price per night from

                                      $167

                                      Distance approx 9.23 km from Holiday

                                      (2) Very Good 

                                        11

                                        Luxury ground floor Condo for rent

                                        Florida / Oldsmar

                                        Oldsmar condo

                                        2 4 5 nights min

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

                                        Price per night from

                                        $79

                                        Responds fast!
                                        avg. 2 hours 46 minutes

                                        Price per night from

                                        $79

                                        Distance approx 17.93 km from Holiday

                                          39

                                          NEW! Luxurious Lake View Lutz Home w/Patio & Deck

                                          Florida / Bearss Plaza

                                          Bearss Plaza house

                                          4 12 min stay varies

                                          • 4 bedrooms
                                          • sleeps 12
                                          • min stay varies
                                          • Child Friendly
                                          • Air conditioning
                                          • Pet Friendly

                                          Price per night from

                                          $440

                                          Responds fast!
                                          avg. 29 minutes

                                          Price per night from

                                          $440

                                          Distance approx 18.6 km from Holiday

                                            25

                                            Casa Del Mar - Tampa/ Rocky Point

                                            Florida / Tampa

                                            Tampa condo

                                            1 4 min stay varies

                                            • 1 bedroom
                                            • sleeps 4
                                            • min stay varies
                                            • Beach / lakeside relaxation
                                            • Swimming pool
                                            • Child Friendly

                                            Price per night from

                                            $175

                                            Price per night from

                                            $175

                                            Distance approx 14.69 km from Holiday

                                              43

                                              Single Family Home with Private Heated Pool near Safety Harbor

                                              Florida / Safety Harbor

                                              Safety Harbor house

                                              2 7 8 nights min

                                              • 2 bedrooms
                                              • sleeps 7
                                              • 8 nights min
                                              • Nearest beach 13 mi
                                              • Swimming pool
                                              • Child Friendly

                                              Price per night from

                                              $293

                                              Responds fast!
                                              avg. 3 hours 43 minutes

                                              Price per night from

                                              $293

                                              Distance approx 16.5 km from Holiday

                                              (29) Excellent 

                                                30

                                                Avalon at Clearwater

                                                Florida / Clearwater

                                                Clearwater apartment

                                                1 3 7 nights min

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

                                                Price per night from

                                                $84

                                                Price per night from

                                                $84

                                                Distance approx 14.53 km from Holiday

                                                (1) Average 

                                                  24

                                                  2 Bed 1 Bath Villa/Duplex in Tampa

                                                  Florida / Tampa

                                                  Tampa villa

                                                  2 6 3 nights min

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

                                                  Price per night from

                                                  $116

                                                  Price per night from

                                                  $116

                                                  Distance approx 16.39 km from Holiday

                                                  (6) Very Good 

                                                    13

                                                    *PARADISE LAKES CLOTHING OPTIONAL CONDO FOR RENT*

                                                    Florida / Lutz

                                                    Lutz apartment

                                                    1 3 2 nights min

                                                    • 1 bedroom
                                                    • sleeps 3
                                                    • 2 nights min
                                                    • Swimming pool
                                                    • Air conditioning
                                                    “Very clean condo. Everything I needed was provided.” Cleanliness, amenities, location. Very relaxing area. I was very pleased with my stay. Condo was well stocked with everything I needed to cook, relax and sleep.
                                                    …see more

                                                    Price per night from

                                                    $88

                                                    Responds fast!
                                                    avg. 1 hour 40 minutes

                                                    Price per night from

                                                    $88

                                                    Distance approx 12.77 km from Holiday

                                                    (1) Excellent 

                                                      6

                                                      Cozy Vacation Home 15 mins from Beaches

                                                      Florida / Dunedin

                                                      Dunedin house

                                                      4 8 3 nights min

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

                                                      Price per night from

                                                      $141

                                                      Price per night from

                                                      $141

                                                      Distance approx 15.04 km from Holiday

                                                      (1) Excellent 

                                                        15

                                                        Amazing Sunset over Clearwater Beach

                                                        Florida / Clearwater

                                                        Clearwater condo

                                                        2 4 90 nights min

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • 90 nights min
                                                        • Nearest beach 2 mi
                                                        • Child Friendly
                                                        • Car not necessary

                                                        Price per night from

                                                        $93

                                                        Price per night from

                                                        $93

                                                        Distance approx 18.18 km from Holiday

                                                          12

                                                          Little Paradise in Sunshine State

                                                          Florida / Clearwater

                                                          Clearwater apartment

                                                          1 4 1 night min

                                                          • 1 bedroom
                                                          • sleeps 4
                                                          • 1 night min
                                                          • Child Friendly
                                                          • Air conditioning
                                                          • Private garden

                                                          Price per night from

                                                          $100

                                                          Responds fast!
                                                          avg. 1 hour 38 minutes

                                                          Price per night from

                                                          $100

                                                          Distance approx 12.45 km from Holiday

                                                            24

                                                            NEW! 3BR Dunedin Home - 2.5 Blocks from Downtown!

                                                            Florida / Dunedin

                                                            Dunedin house

                                                            3 6 5 nights min

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

                                                            Price per night from

                                                            $210

                                                            Responds fast!
                                                            avg. 47 minutes

                                                            Price per night from

                                                            $210

                                                            Distance approx 15.94 km from Holiday

                                                              20

                                                              Gorgeous 3 B/R Townhome mins from Clearwater Beach

                                                              Florida / Clearwater

                                                              Clearwater townhouse

                                                              3 6 60 nights min

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

                                                              Price per night from

                                                              $147

                                                              Price per night from

                                                              $147

                                                              Distance approx 16.51 km from Holiday

                                                                30

                                                                Clearwater Avalon Palm 2 Bed. Vacation Condo

                                                                Florida / Clearwater

                                                                Clearwater condo

                                                                2 6 6 nights min

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

                                                                Price per night from

                                                                $111

                                                                Responds fast!
                                                                avg. 1 hour 1 minutes

                                                                Price per night from

                                                                $111

                                                                Distance approx 17.64 km from Holiday

                                                                (1)  

                                                                  16

                                                                  Cove Cay Condo

                                                                  Florida / Clearwater

                                                                  Clearwater apartment

                                                                  2 4 90 nights min

                                                                  • 2 bedrooms
                                                                  • sleeps 4
                                                                  • 90 nights min
                                                                  • Beach / lakeside relaxation
                                                                  • Nearest beach 11 mi
                                                                  • Swimming pool

                                                                  Price per night from

                                                                  $55

                                                                  Price per night from

                                                                  $55

                                                                  Distance approx 7.38 km from Holiday

                                                                    11

                                                                    Shebob Resorts, Inc.

                                                                    Florida / Port Richey

                                                                    Port Richey house

                                                                    2 4 3 nights min

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

                                                                    Price per night from

                                                                    $126

                                                                    Price per night from

                                                                    $126

                                                                    Distance approx 12.35 km from Holiday

                                                                    (11) Excellent 

                                                                      27

                                                                      *NEW* Spa Retreat Pool Home w/Hot Tub, Comforts & Convenient Location

                                                                      Florida / Tampa

                                                                      Tampa house

                                                                      4 8 min stay varies

                                                                      • 4 bedrooms
                                                                      • sleeps 8
                                                                      • min stay varies
                                                                      • Nearest beach 26 mi
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      “Amazing Stay! Abolutely Loved This House!” My friends and I travel every year following our favorite football team and often look for homes to rent that provide many of the amenities you might find in high end hotels. In this home we found a gem. P
                                                                      …see more

                                                                      Price per night from

                                                                      $293

                                                                      Responds fast!
                                                                      avg. 1 hour 24 minutes

                                                                      Price per night from

                                                                      $293

                                                                      Distance approx 14.95 km from Holiday

                                                                      (3) Excellent 

                                                                        16

                                                                        Cozy Cottage in Three Lakes RV Resort

                                                                        Florida / Hudson

                                                                        Hudson cottage

                                                                        1 4 min stay varies

                                                                        • 1 bedroom
                                                                        • sleeps 4
                                                                        • min stay varies
                                                                        • Ask about children
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $69

                                                                        Price per night from

                                                                        $69

                                                                        Distance approx 2.17 km from Holiday Show on Map

                                                                          6

                                                                          Vacation Mobile Home Tarpon Springs Florida

                                                                          Florida / Tarpon Springs

                                                                          Tarpon Springs house

                                                                          2 6 7 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 6
                                                                          • 7 nights min
                                                                          • Air conditioning
                                                                          • Pet Friendly

                                                                          Price per night from

                                                                          $105

                                                                          Price per night from

                                                                          $105

                                                                          Distance approx 16.46 km from Holiday

                                                                          (20) Excellent 

                                                                            79

                                                                            CLEARWATER LUXURY RESORT STYLE CONDO

                                                                            Florida / Clearwater

                                                                            Clearwater condo

                                                                            1 4 2 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • 2 nights min
                                                                            • Swimming pool
                                                                            • Ask about children
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $147

                                                                            Price per night from

                                                                            $147

                                                                            Distance approx 19.33 km from Holiday

                                                                              4

                                                                              Lovely Tropical Sunlit bedroom

                                                                              Florida / Clearwater

                                                                              Clearwater house

                                                                              1 3 1 night min

                                                                              • 1 bedroom
                                                                              • sleeps 3
                                                                              • 1 night min
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $234

                                                                              Price per night from

                                                                              $234