Beach rentals in Siesta Key and Villas - Holiday Lettings - Holiday Rentals Siesta Key

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2,214 Holiday homes

(30) Excellent 

    28

    Siesta Key holiday condo rental

    Florida / Siesta Key

    2 5 7 nights min

    • 2 bedrooms
    • sleeps 5
    • 7 nights min
    • Beach / lakeside relaxation
    • Nearest beach 0.01 km
    • Swimming pool
    “Oceanfront views right on the beach in the low key area of Turtle Beach” My family consists of my wife, 14 and 11 year olds, and me. This condo has a King master bedroom with a Gulf water view, and a bedroom with bunk beds. Both bedrooms have their own shower and bathroom. The condo is on the low-key more residential side of Siesta Key called Turtle Beach. It is still very near supplies, restaurants, pubs, markets, post office, grocery and lunch spots. It's just that Turtle Beach is more secluded and less "Animal House" than downtown Siesta Beach. If you want to relax, fish, lay on the beach, read a book on the patio at sunrise or sunset, and watch the sun set over the Gulf every night in your windows, then this is your place. There is a nice sized living room with couch, chairs, and flat screen TV. It has a full operational kitchen with full refrigerator and all kitchen gadgets and supplies. We made two very nice meals there, lots of breakfasts', and had friends over several times for cocktails and beach time. The condo has it's own numbered parking spot, and a marina slip for each unit with a boat ramp very nearby. You can fish for snook in the marina, or the beach is great too for fishing. The condo is near the stairs, elevator and laundry but that did not make it loud, just convenient. There is a freshwater shower and a walkway over the dune right by the condo. The common pool is small but clean and close if you want to go beach-pool-nap mode. We chartered Siesta Key Fishing Charters and caught almost 100 fish offshore, 10 huge keeper Red Grouper that we ate in the condo, froze and took home, gave away and traded for other cool stuff. We also really enjoyed eating at Big Water Seafood Market, they will clean and cook your fish, or sell you some, or feed you at their restaurant. Both of those companies can also be found highly rated on TripAdvisor. That's how I found all three....and I couldn't be happier. It was a great vacation at a chill place decorated "beachy style", on a relaxed beach near nice convenient stops, all the while having Siesta Village and Siesta Key Beach just down the road. Siesta Village is awesome and less crowded on weekdays. We had no problem parking even with the July 4th weekend and the offshore powerboat racing both that week. That being said this is a rental condo, and they are not perfect, because they are used and loved. I miss it. We will go back. And, the owners are super good at communicating, troubleshooting, returning security deposits, and all the other things we would hope work well after a great relaxing week. Be careful shopping, there are a lot of condos that say waterfront that aren't oceanfront. and lots of condos aren't really on the ocean although you are made to believe they are, but this one really is. Big Gulf of Mexico views in your face for a week. Big sunsets. Big sunburns. Big bellies full of super fresh fish. Big smiles from your family and friends. I say, book it and dare to be called Vacation Hero....

    from £315 / night

    £2,204 / week

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    avg. 30 minutes

    from £315 / night

    (2) Excellent 

      26

      Holiday villa in Siesta Key

      Florida / Siesta Key

      4 8 min stay varies

      • 4 bedrooms
      • sleeps 8
      • min stay varies
      • Beach / lakeside relaxation
      • Swimming pool
      • Child friendly

      from £178 / night

      £891 - £2,076 / week

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      Responds fast!
      avg. 56 minutes

      from £178 / night

      (1) Excellent 

        24

        Home rental in Siesta Key with swimming pool

        Florida / Siesta Key

        3 6 min stay varies

        • 3 bedrooms
        • sleeps 6
        • min stay varies
        • Beach / lakeside relaxation
        • Nearest beach 0.8 km
        • Swimming pool

        from £199 / night

        £1,389 / week

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        Responds fast!
        avg. 1 hour 44 minutes

        from £199 / night

          30

          Holiday condo in Siesta Key

          Florida / Siesta Key

          2 5 14 nights min

          • 2 bedrooms
          • sleeps 5
          • 14 nights min
          • Beach / lakeside relaxation
          • Nearest beach 1 km
          • Swimming pool

          from £101 / night

          £705 / week

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          from £101 / night

          (1) Excellent 

            38

            Holiday townhouse in Siesta Key

            Florida / Siesta Key

            2 6 min stay varies

            • 2 bedrooms
            • sleeps 6
            • min stay varies
            • Beach / lakeside relaxation
            • Nearest beach 0.1 km
            • Swimming pool

            from £208 / night

            £1,322 - £2,204 / week

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            from £208 / night

              42

              Home accommodation in Siesta Key

              Florida / Siesta Key

              3 6 min stay varies

              • 3 bedrooms
              • sleeps 6
              • min stay varies
              • Child friendly

              from £265 / night

              £1,852 - £2,204 / week

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              from £265 / night

                50

                Home rental in Siesta Key

                Florida / Siesta Key

                3 6 min stay varies

                • 3 bedrooms
                • sleeps 6
                • min stay varies
                • Child friendly

                from £202 / night

                £1,411 - £1,763 / week

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                from £202 / night

                (24) Excellent 

                  16

                  Siesta Key holiday apartment rental

                  Florida / Siesta Key

                  2 5 min stay varies

                  • 2 bedrooms
                  • sleeps 5
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Nearest beach 1 km
                  • Child friendly
                  “Awesome experience” This was our first experience renting a condo,and it exceeded our expectations. The location is excellent,close to everything but also feels very private and relaxing. The owners were quick to respond to our inquiries and they provide everything you need for a beach trip. We loved the patio area and spent most our time in the property out there grilling, and hanging out by the hammock. It was also convenient to be able to take our dog for a quick potty break right outside in the backyard. Will definitely be coming back,hopefully soon!

                  from £137 / night

                  £882 - £1,494 / week

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                  from £137 / night

                    46

                    Holiday home with swimming pool in Siesta Key

                    Florida / Siesta Key

                    4 8 min stay varies

                    • 4 bedrooms
                    • sleeps 8
                    • min stay varies
                    • Swimming pool
                    • Child friendly
                    • Air conditioning

                    from £221 / night

                    £1,543 / week

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                    Responds fast!
                    avg. 3 minutes

                    from £221 / night

                      36

                      Siesta Key holiday apartment rental

                      Florida / Siesta Key

                      2 4 min stay varies

                      • 2 bedrooms
                      • sleeps 4
                      • min stay varies
                      • Swimming pool
                      • Child friendly
                      • Air conditioning

                      from £155 / night

                      £802 - £1,168 / week

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                      Responds fast!
                      avg. 3 minutes

                      from £155 / night

                      (3) Excellent 

                        10

                        Holiday condo in Siesta Key

                        Florida / Siesta Key

                        2 6 7 nights min

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

                        from £107 / night

                        £794 / week

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                        from £107 / night

                        (3) Excellent 

                          45

                          Siesta Key holiday condo rental

                          Florida / Siesta Key

                          2 6 min stay varies

                          • 2 bedrooms
                          • sleeps 6
                          • min stay varies
                          • Swimming pool
                          • Child friendly
                          • Car not necessary

                          from £82 / night

                          £573 - £1,146 / week

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                          Responds fast!
                          avg. 2 hours 43 minutes

                          from £82 / night

                          (5) Excellent 

                            15

                            Siesta Key holiday home rental

                            Florida / Siesta Key

                            1 4 min stay varies

                            • 1 bedroom
                            • sleeps 4
                            • min stay varies
                            • Nearest beach 0.32 km
                            • Child friendly
                            • Air conditioning

                            from £105 / night

                            £735 / week

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                            from £105 / night

                            (21) Very Good 

                              24

                              Holiday townhouse in Siesta Key

                              Florida / Siesta Key

                              1 4 min stay varies

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

                              from £166 / night

                              £1,160 / week

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                              from £166 / night

                              (4) Excellent 

                                12

                                Holiday apartment in Siesta Key

                                Florida / Siesta Key

                                2 6 1 night min

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

                                from £222 / night

                                £1,549 / week

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                                Responds fast!
                                avg. 1 hour 56 minutes

                                from £222 / night

                                (15) Very Good 

                                  32

                                  Siesta Key holiday cottage rental

                                  Florida / Siesta Key

                                  1 2 3 nights min

                                  • 1 bedroom
                                  • sleeps 2
                                  • 3 nights min
                                  • Beach / lakeside relaxation
                                  • Nearest beach 0.1 km
                                  • Child friendly
                                  “wanted to stay forever!” Absolutely the perfect place for 2. Secluded but close to everything, short walk to beach and shops. Everything a person needs for a wonderful beach vacation. Daniel was exceptional to deal with, very concerned about our comfort and enjoyment despite going thro a hurricane himself. Can't wait to go back!

                                  from £79 / night

                                  £549 / week

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                                  Responds fast!
                                  avg. 2 hours 4 minutes

                                  from £79 / night

                                  (16) Excellent 

                                    21

                                    Siesta Key holiday apartment rental

                                    Florida / Siesta Key

                                    3 7 min stay varies

                                    • 3 bedrooms
                                    • sleeps 7
                                    • min stay varies
                                    • Beach / lakeside relaxation
                                    • Nearest beach 1 km
                                    • Child friendly

                                    from £176 / night

                                    £1,168 - £1,851 / week

                                    Book View

                                    from £176 / night

                                    (1) Excellent 

                                      58

                                      Condo rental in Siesta Key

                                      Florida / Siesta Key

                                      2 6 7 nights min

                                      • 2 bedrooms
                                      • sleeps 6
                                      • 7 nights min
                                      • Child friendly

                                      from £193 / night

                                      £1,345 / week

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                                      from £193 / night

                                        25

                                        Holiday townhouse in Siesta Key

                                        Florida / Siesta Key

                                        2 4 7 nights min

                                        • 2 bedrooms
                                        • sleeps 4
                                        • 7 nights min
                                        • Child friendly
                                        • Air conditioning

                                        from £202 / night

                                        £1,413 / week

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                                        from £202 / night

                                        (23) Very Good 

                                          40

                                          Home rental in Siesta Key

                                          Florida / Siesta Key

                                          2 6 3 nights min

                                          • 2 bedrooms
                                          • sleeps 6
                                          • 3 nights min
                                          • Beach / lakeside relaxation
                                          • Nearest beach 0 km
                                          • Swimming pool
                                          “Fantastic!!!” Loved it!!! This place was very clean, close enough to beach, very spacious, tastefully decorated with upgrades, decent pool, a manager on site, and more beach gear than you could ask for. ...Chairs, games, rafts, umbrellas, bikes, towels, coolers, etc. we absolutely loved it!!! We had a family of 6....Parents and 4 teenagers. We also liked that across the street was convenience stores, grocery, and restaurants. The Toasted Mango and The Fish Market have great, great food. Also, our flight was canceled to fly in, and they were out of rental cars at newly appointed airport. How relieving it was to finally show up to such a nice place and relax The owner was also so very kind to accommodate us if needed.

                                          from £265 / night

                                          £1,587 - £2,116 / week

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                                          Responds fast!
                                          avg. 1 hour 25 minutes

                                          from £265 / night

                                            45

                                            Holiday condo with shared pool in Siesta Key

                                            Florida / Siesta Key

                                            2 6 7 nights min

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

                                            from £95 / night

                                            £531 - £1,333 / week

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                                            Responds fast!
                                            avg. 3 minutes

                                            from £95 / night

                                              14

                                              Holiday cottage in Siesta Key

                                              Florida / Siesta Key

                                              1 4 min stay varies

                                              • 1 bedroom
                                              • sleeps 4
                                              • min stay varies
                                              • Child friendly
                                              • Pet friendly

                                              from £152 / night

                                              £1,062 / week

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                                              from £152 / night

                                                19

                                                Holiday apartment in Siesta Key

                                                Florida / Siesta Key

                                                3 8 7 nights min

                                                • 3 bedrooms
                                                • sleeps 8
                                                • 7 nights min
                                                • Swimming pool
                                                • Child friendly
                                                • Car not necessary

                                                from £148 / night

                                                £1,037 / week

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                                                from £148 / night

                                                (5) Excellent 

                                                  47

                                                  Holiday villa rental

                                                  Florida / Siesta Key

                                                  2 6 min stay varies

                                                  • 2 bedrooms
                                                  • sleeps 6
                                                  • min stay varies
                                                  • Beach / lakeside relaxation
                                                  • Nearest beach 0.1 km
                                                  • Swimming pool

                                                  from £135 / night

                                                  £944 / week

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                                                  Responds fast!
                                                  avg. 2 hours 10 minutes

                                                  from £135 / night

                                                  (2) Average 

                                                    42

                                                    Siesta Key holiday condo let

                                                    Florida / Siesta Key

                                                    2 5 7 nights min

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

                                                    from £195 / night

                                                    £834 - £2,018 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 3 minutes

                                                    from £195 / night

                                                      36

                                                      Holiday apartment in Siesta Key

                                                      Florida / Siesta Key

                                                      2 6 7 nights min

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

                                                      from £95 / night

                                                      £568 - £1,345 / week

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                                                      Responds fast!
                                                      avg. 3 minutes

                                                      from £95 / night

                                                      (5) Very Good 

                                                        36

                                                        Siesta Key holiday apartment rental

                                                        Florida / Siesta Key

                                                        2 6 min stay varies

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • min stay varies
                                                        • Beach / lakeside relaxation
                                                        • Nearest beach 0.2 km
                                                        • Swimming pool

                                                        from £89 / night

                                                        £617 - £1,146 / week

                                                        Book View

                                                        from £89 / night

                                                        (1)  

                                                          32

                                                          Siesta Key holiday apartment rental

                                                          Florida / Siesta Key

                                                          2 6 min stay varies

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

                                                          from £89 / night

                                                          £705 / week

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                                                          Responds fast!
                                                          avg. 3 minutes

                                                          from £89 / night

                                                          (1) Very Good 

                                                            32

                                                            Siesta Key holiday apartment rental

                                                            Florida / Siesta Key

                                                            2 8 7 nights min

                                                            • 2 bedrooms
                                                            • sleeps 8
                                                            • 7 nights min
                                                            • Child friendly
                                                            • Pet friendly

                                                            from £193 / night

                                                            £1,346 / week

                                                            Book View

                                                            from £193 / night

                                                            (10) Excellent 

                                                              24

                                                              Siesta Key holiday condo rental

                                                              Florida / Siesta Key

                                                              2 6 min stay varies

                                                              • 2 bedrooms
                                                              • sleeps 6
                                                              • min stay varies
                                                              • Beach / lakeside relaxation
                                                              • Swimming pool
                                                              • Child friendly

                                                              from £176 / night

                                                              £1,318 - £2,033 / week

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                                                              Responds fast!
                                                              avg. 2 hours 55 minutes

                                                              from £176 / night

                                                              (14) Excellent 

                                                                59

                                                                Siesta Key holiday apartment rental

                                                                Florida / Siesta Key

                                                                2 6 7 nights min

                                                                • 2 bedrooms
                                                                • sleeps 6
                                                                • 7 nights min
                                                                • Beach / lakeside relaxation
                                                                • Swimming pool
                                                                • Child friendly

                                                                from £140 / night

                                                                £974 - £2,023 / week

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                                                                Responds fast!
                                                                avg. 3 hours 45 minutes

                                                                from £140 / night

                                                                (1) Excellent 

                                                                  42

                                                                  Siesta Key holiday home rental

                                                                  Florida / Siesta Key

                                                                  3 8 min stay varies

                                                                  • 3 bedrooms
                                                                  • sleeps 8
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child friendly
                                                                  • Air conditioning

                                                                  from £125 / night

                                                                  £1,587 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 3 minutes

                                                                  from £125 / night

                                                                    35

                                                                    Holiday condo in Siesta Key

                                                                    Florida / Siesta Key

                                                                    3 6 min stay varies

                                                                    • 3 bedrooms
                                                                    • sleeps 6
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Ask owner if suitable for children
                                                                    • Air conditioning

                                                                    from £156 / night

                                                                    £1,086 / week

                                                                    Book View

                                                                    from £156 / night

                                                                    (5) Very Good 

                                                                      42

                                                                      Holiday condo with swimming pool in Siesta Key

                                                                      Florida / Siesta Key

                                                                      2 5 6 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 5
                                                                      • 6 nights min
                                                                      • Swimming pool
                                                                      • Child friendly
                                                                      • Air conditioning

                                                                      from £92 / night

                                                                      £642 / week

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                                                                      Responds fast!
                                                                      avg. 1 hour 49 minutes

                                                                      from £92 / night

                                                                        36

                                                                        Apartment rental in Siesta Key with shared pool

                                                                        Florida / Siesta Key

                                                                        2 4 14 nights min

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

                                                                        from £114 / night

                                                                        £648 - £1,179 / week

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                                                                        Responds fast!
                                                                        avg. 3 minutes

                                                                        from £114 / night

                                                                        (7) Very Good 

                                                                          26

                                                                          Siesta Key holiday villa rental

                                                                          Florida / Siesta Key

                                                                          2 6 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 6
                                                                          • min stay varies
                                                                          • Beach / lakeside relaxation
                                                                          • Nearest beach 0.2 km
                                                                          • Swimming pool

                                                                          from £159 / night

                                                                          £1,173 - £1,666 / week

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                                                                          Responds fast!
                                                                          avg. 3 hours 9 minutes

                                                                          from £159 / night

                                                                          (1) Excellent 

                                                                            36

                                                                            Apartment rental in Siesta Key with shared pool

                                                                            Florida / Siesta Key

                                                                            3 6 min stay varies

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

                                                                            from £194 / night

                                                                            £722 - £1,567 / week

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                                                                            Responds fast!
                                                                            avg. 3 minutes

                                                                            from £194 / night

                                                                              40

                                                                              Siesta Key holiday villa rental

                                                                              Florida / Siesta Key

                                                                              2 6 7 nights min

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

                                                                              from £161 / night

                                                                              £1,123 / week

                                                                              Book View

                                                                              from £161 / night

                                                                              (1) Excellent 

                                                                                29

                                                                                Siesta Key holiday condo accommodation

                                                                                Florida / Siesta Key

                                                                                2 5 min stay varies

                                                                                • 2 bedrooms
                                                                                • sleeps 5
                                                                                • min stay varies
                                                                                • Swimming pool
                                                                                • Ask owner if suitable for children
                                                                                • Air conditioning

                                                                                from £87 / night

                                                                                £605 / week

                                                                                Book View

                                                                                from £87 / night

                                                                                (4) Excellent 

                                                                                Certificate of Excellence

                                                                                  36

                                                                                  Apartment rental in Siesta Key with shared pool

                                                                                  Florida / Siesta Key

                                                                                  2 6 7 nights min

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

                                                                                  Certificate of Excellence

                                                                                  from £125 / night

                                                                                  £685 - £1,808 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 3 minutes

                                                                                  from £125 / night

                                                                                  Top Destination reviews

                                                                                  2/2 Ground Floor Condo with Patio on Intracoastal
                                                                                  Siesta Key Condo

                                                                                  Condo is beautifully situated on instracoastal shoreline on Siesta Key looking out to Sarasota on mainland. It takes approximately 10 min to walk on to the stunning beach looking out to Mexican Gulf. The condo itself was spotless and had all the amenities required to make our stay so enjoyable. The patio with table, chairs and hammock were a welcome bonus and allowed to appreciate the beautiful surroundings without having to leave the condo !!! Since the original booking, the owner has been easily contactable and responsive with any questions we had prior to our arrival. Great value for money and would not hesitate to rebook for future visits.see more
                                                                                  Lakefront Oasis 3 Bdrm House with Heated Pool minutes from village and beach
                                                                                  Mr

                                                                                  My wife and I enjoyed the most wonderful holiday in this excellent villa. It was very comfortable, had everything we needed and more, and is perfectly situated for the beaches and Siesta Key village is a short walk or bike ride away. The pool was a great bonus. All together, this was a great holiday.see more
                                                                                  Remodeled 2br 2ba with private patio, beautiful water views, walk to #1 beach
                                                                                  Paradise

                                                                                  The apt is very well appointed and spacious. Ruth is very amenable and easy to get in touch with. Having a land line so that family could contact us was a great bonus. Saved us using our u.k. mobile which can be very expensive.. local calls are free. We visit siesta every year for a month and this is one of the best places we have stayed.. close to the wonderful beach. The pool area Iis very picturesque . This with the unique siesta village nightlife. Makes it a perfect place for all ages Thanks Ruthsee more
                                                                                  Siesta Key - 2bdrm on the beach - amazing views!!
                                                                                  Awesome place! Comforts of home, but with an amazing view!!!

                                                                                  Loved our stay. Very comfortable beach getaway. Everything we needed was here. Great sunsets, beach, and pool. Saw two manatee, lots of pelican, and one turtle. The lanai overlooking the beach and water was a real hit! Would definitely stay again! … see more

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