check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!
  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    $43
    avg/night
    • 2 BR
    • 2 BA
    • Sleeps 4
    House #555350vb
    Viewed 9 times in the last 48 hours
      $53
      avg/night
      • 2 BR
      • 2 BA
      • Sleeps 5
      Condo #339888
      Viewed 12 times in the last 48 hours
        Excellent! 4.7/5
        (15 reviews)
        $99
        avg/night
        • 2 BR
        • 2 BA
        • Sleeps 5
        Condo #101580vb
        15
        Viewed 19 times in the last 48 hours
          Excellent! 4.7/5
          (15 reviews)
          avg/night
          • 1 BR
          • 1 BA
          • Sleeps 3
          Studio #7050438
          15
          Viewed 42 times in the last 48 hours
            Wonderful! 4.8/5
            (31 reviews)
            avg/night
            • 2 BR
            • 2 BA
            • Sleeps 6
            Condo #493237vb
            31
            Viewed 19 times in the last 48 hours
              Wonderful! 4.9/5
              (36 reviews)
              avg/night
              • 6 BR
              • 4 BA
              • Sleeps 14
              House #617992vb
              36
              Viewed 53 times in the last 48 hours
                • 2 BR
                • 2 BA
                • Sleeps 10
                House #780771vb
                3
                Viewed 13 times in the last 48 hours
                  Excellent! 4.5/5
                  (10 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 6
                  House #793324vb
                  10
                  Viewed 98 times in the last 48 hours
                    • 1 BR
                    • 1 BA
                    • Sleeps 4
                    Condo #4314681
                    Viewed 8 times in the last 48 hours
                      avg/night
                      • 1 BR
                      • 1 BA
                      • Sleeps 3
                      Apartment #705685vb
                      1 Review
                      Viewed 56 times in the last 48 hours
                        • 1 BR
                        • 1 BA
                        • Sleeps 4
                        Condo #4314703
                        Viewed 7 times in the last 48 hours
                          Wonderful! 4.8/5
                          (31 reviews)
                          avg/night
                          • 5 BR
                          • 3 BA
                          • Sleeps 12
                          House #122552
                          31
                          Viewed 14 times in the last 48 hours
                            Wonderful! 4.8/5
                            (46 reviews)
                            $75
                            avg/night
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
                            Condo #350715vb
                            46
                            Viewed 38 times in the last 48 hours
                              Excellent! 4.6/5
                              (10 reviews)
                              avg/night
                              • 1 BR
                              • 1 BA
                              • Sleeps 3
                              Condo #352020vb
                              10
                              Viewed 17 times in the last 48 hours
                                Excellent! 4.7/5
                                (9 reviews)
                                $89
                                avg/night
                                • 2 BR
                                • 2 BA
                                • Sleeps 4
                                House #3717905
                                9
                                Viewed 25 times in the last 48 hours
                                  $64
                                  avg/night
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 2
                                  Cottage #871058vb
                                  Viewed 82 times in the last 48 hours
                                    $91
                                    avg/night
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 5
                                    Condo #4314688
                                    Viewed 16 times in the last 48 hours
                                      Excellent! 4.4/5
                                      (7 reviews)
                                      avg/night
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 8
                                      House #503344vb
                                      7
                                      Viewed 18 times in the last 48 hours
                                        Excellent! 4.7/5
                                        (47 reviews)
                                        $87
                                        avg/night
                                        • 1 BR
                                        • 2 BA
                                        • Sleeps 4
                                        Cottage #569142vb
                                        47
                                        Viewed 93 times in the last 48 hours
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 10
                                          Condo #908787vb
                                          1 Review
                                          Viewed 23 times in the last 48 hours
                                            avg/night
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 5
                                            House #4304897
                                            Viewed 38 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (44 reviews)
                                              $74
                                              avg/night
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 2
                                              Cottage #286132
                                              44
                                              Viewed 33 times in the last 48 hours
                                                Excellent! 4.5/5
                                                (28 reviews)
                                                $68
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 4
                                                Condo #7071017
                                                28
                                                Viewed 48 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (12 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  Condo #388110vb
                                                  12
                                                  Viewed 7 times in the last 48 hours
                                                    Exceptional! 5.0/5
                                                    (39 reviews)
                                                    $85
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    Condo #469120vb
                                                    39
                                                    Viewed 10 times in the last 48 hours
                                                      Excellent! 4.7/5
                                                      (16 reviews)
                                                      avg/night
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      Apartment #3699397
                                                      16
                                                      Viewed 16 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (62 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 8
                                                        Condo #688272vb
                                                        62
                                                        Viewed 29 times in the last 48 hours
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          House #964595vb
                                                          Viewed 20 times in the last 48 hours
                                                            $68
                                                            avg/night
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 2
                                                            Condo #964932vb
                                                            Viewed 16 times in the last 48 hours
                                                              Excellent! 4.7/5
                                                              (12 reviews)
                                                              $88
                                                              avg/night
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              Condo #7110062
                                                              12
                                                              Viewed 15 times in the last 48 hours
                                                                Very Good! 4.0/5
                                                                (10 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 9
                                                                Apartment #679825vb
                                                                10
                                                                Viewed 126 times in the last 48 hours
                                                                  Wonderful! 4.8/5
                                                                  (13 reviews)
                                                                  $60
                                                                  avg/night
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 3
                                                                  Condo #762933vb
                                                                  13
                                                                  Viewed 28 times in the last 48 hours
                                                                    Very Good! 4.1/5
                                                                    (11 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 30
                                                                    House #761511vb
                                                                    11
                                                                    Viewed 80 times in the last 48 hours
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Condo #908799vb
                                                                      Viewed 8 times in the last 48 hours
                                                                        $58
                                                                        avg/night
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        Condo #919562vb
                                                                        Viewed 29 times in the last 48 hours
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          Apartment #507876vb
                                                                          1 Review
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 2 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 10
                                                                            Townhome #4246595
                                                                            Viewed 87 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (37 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                              Condo #249876vb
                                                                              37
                                                                              Viewed 18 times in the last 48 hours
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                Condo #496263vb
                                                                                3
                                                                                Viewed 8 times in the last 48 hours
                                                                                  $73
                                                                                  avg/night
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 2
                                                                                  Studio #3546315
                                                                                  3
                                                                                  Viewed 33 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (39 reviews)
                                                                                    avg/night
                                                                                    • Studio
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    Condo #584567vb
                                                                                    39
                                                                                    Viewed 35 times in the last 48 hours
                                                                                      Exceptional! 5.0/5
                                                                                      (17 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 3
                                                                                      Cottage #608943vb
                                                                                      17
                                                                                      Viewed 35 times in the last 48 hours
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 2
                                                                                        Condo #4315457
                                                                                        Viewed 33 times in the last 48 hours
                                                                                          Excellent! 4.5/5
                                                                                          (39 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 6
                                                                                          Condo #154649
                                                                                          39
                                                                                          Viewed 65 times in the last 48 hours
                                                                                            Excellent! 4.7/5
                                                                                            (9 reviews)
                                                                                            avg/night
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 4
                                                                                            Condo #3552162
                                                                                            9
                                                                                            Viewed 44 times in the last 48 hours
                                                                                              $89
                                                                                              avg/night
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 3
                                                                                              Cottage #752765vb
                                                                                              2 Reviews
                                                                                              Viewed 54 times in the last 48 hours
                                                                                                Excellent! 4.6/5
                                                                                                (5 reviews)
                                                                                                $84
                                                                                                avg/night
                                                                                                • Studio
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                Condo #4257531
                                                                                                5
                                                                                                Viewed 14 times in the last 48 hours
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  Condo #4330816
                                                                                                  Viewed 52 times in the last 48 hours
                                                                                                    • 3 BR
                                                                                                    • 1 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 5
                                                                                                    House #664461vb
                                                                                                    3
                                                                                                    Viewed 6 times in the last 48 hours
                                                                                                      Exceptional! 5.0/5
                                                                                                      (7 reviews)
                                                                                                      $80
                                                                                                      avg/night
                                                                                                      • 1 BR
                                                                                                      • Sleeps 2
                                                                                                      Condo #4113380
                                                                                                      7
                                                                                                      Viewed 29 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Oldsmar Reviews

                                                                                                      Innisbrook Holiday

                                                                                                      4 of 5
                                                                                                      We stayed for a month at the appartment which was very well presented and clean. The gated community proved to be a safe environment with the expansive grounds of Innisbrook providing excellent opportunities for cycling and walking. This was a great base for our vacation and located close to the beaches, Dunedin and surrounding areas. Many thanks Mark for making our stay very comfortable and enjoyable.
                                                                                                      • Submitted: Nov 26, 2016
                                                                                                      • Stayed: Oct 2016

                                                                                                      Peaceful Urban Retreat

                                                                                                      5 of 5
                                                                                                      It's hard to know where to begin with the superlatives regarding Henry's perfect gem of a cottage in Tampa. The place is very much as pictured: thoughtfully decorated, well-equipped, in a charming neighborhood of '20s bungalows. What the photos online don't fully convey is all the small extras that make staying here like a trip to visit a good friend. Henry not only provides far more than the average kitchen supplies (fresh milk and oj, spices, teas, coffee, etc. etc.) but has gone the extra mile in thinking about other supplies you might have forgotten - like bug spray or nail polish remover! The bed is comfortable, bathroom is small but perfectly thought out and the shower has better water pressure than mine at home. And the selection of movies was so eclectic and wonderful my friend and I interrupted our marathon talk-fest to watch one we couldn't resist. Our only regret was not being in Tampa long enough to take full advantage of the wealth of local info our thoughtful host provided - in the form of hiking, boating, biking guides, maps to local and not-so-local attractions, and a patient willingness to be grilled for more advice any time. Henry is a perfect host and we couldn't have enjoyed our stay more.
                                                                                                      • Submitted: Nov 7, 2016
                                                                                                      • Stayed: Oct 2016

                                                                                                      Awesome!!!!

                                                                                                      5 of 5
                                                                                                      What a great condo. Very comfortable, great floor plan and very clean. This house was the cleanest rental property that we ever stayed in. The location is perfect close to restaurants, shopping, and other attractions. Definitely would recommend which is why is our 2ND time staying here. Thank You Eleni
                                                                                                      • Submitted: Nov 6, 2016
                                                                                                      • Stayed: Oct 2016