Vacation Rentals & Beach Rentals in Siesta Key

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2,709 beach rentals

(3) Excellent 

    16

    Island House Beach Resort V39

    Florida / Siesta Key

    Siesta Key villa

    2 6 min stay varies

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

    Price per night from

    $174

    Price per night from

    $174

    (32) Excellent 

      23

      We like Blue,Siesta Blue! Cert.of Excellence 2014

      Florida / Siesta Key

      Siesta Key apartment

      2 4 7 nights min

      • 2 bedrooms
      • sleeps 4
      • 7 nights min
      • Beach / lakeside relaxation
      • Swimming pool
      • Child Friendly
      “Absolutely Wonderful” We stayed the second week of September at Bay Oaks Condos, and it was absolutely WONDERFUL! We basically had the run of the condo to ourselves, including the swimming pool, which was the only place my toddler wanted to hang out.
      …see more

      Price per night from

      $121

      Price per night from

      $121

        25

        2 Bedroom Beachfront Home on Siesta Beach!! Directly on the beach!! 47 Beach Rd

        Florida / Siesta Key

        Siesta Key townhouse

        2 4 7 nights min

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

        Price per night from

        $263

        Price per night from

        $263

        (3) Excellent 

          20

          Island House Beach Resort 14N

          Florida / Siesta Key

          Siesta Key apartment

          2 6 min stay varies

          • 2 bedrooms
          • sleeps 6
          • min stay varies
          • Swimming pool
          • Child Friendly
          • Air conditioning
          “Great getaway!” Our family enjoyed a long weekend around Labor Day weekend at Island House. We have stayed at Island House before and always have a good time. Fabulous beach, helpful staff, relaxing place to be. This was our first time staying in 14
          …see more

          Price per night from

          $226

          Price per night from

          $226

          (2) Excellent 

            16

            Island House Beach Resort V9

            Florida / Siesta Key

            Siesta Key villa

            2 6 min stay varies

            • 2 bedrooms
            • sleeps 6
            • min stay varies
            • Swimming pool
            • Child Friendly
            • Air conditioning
            “Our vacation at Siesta Key was as always relaxing and enjoyable.” Villa 9 was newly redecorated; therefore, it was a pleasure to spend 10 days in a clean, updated, and comfortable villa. The comfort of Villa 9 was worth a little bit of a walk to the
            …see more

            Price per night from

            $174

            Price per night from

            $174

            (2) Excellent 

              17

              Island House Beach Resort V25

              Florida / Siesta Key

              Siesta Key villa

              2 6 min stay varies

              • 2 bedrooms
              • sleeps 6
              • min stay varies
              • Swimming pool
              • Child Friendly
              “Spring break” Loved the location. Place was very nice for a family of 6.. The pool was warm , staff was very helpful and nice , beach was super close..
              …see more

              Price per night from

              $174

              Price per night from

              $174

              (24) Excellent 

                16

                Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment

                Florida / Siesta Key

                Siesta Key apartment

                2 5 min stay varies

                • 2 bedrooms
                • sleeps 5
                • min stay varies
                • Beach / lakeside relaxation
                • Nearest beach 1 mi
                • Child Friendly
                “Amazing!” I stayed here with my husband and we had a great time! We were in Orlando visiting family and we decided to arrange some us time. The condo was excellent and very clean! Kathy and her husband were very informative, respond quickly,and avail
                …see more

                Price per night from

                $178

                Responds fast!
                avg. 2 hours 57 minutes

                Price per night from

                $178

                (4) Excellent 

                  20

                  Island House Beach Resort 4S

                  Florida / Siesta Key

                  Siesta Key apartment

                  2 6 min stay varies

                  • 2 bedrooms
                  • sleeps 6
                  • min stay varies
                  • Swimming pool
                  • Child Friendly
                  • Air conditioning
                  “A wonderful family vacation!” We loved our stay at the Island House! The staff and property were excellent! The rental unit was perfect! the view was amazing and the pool/club house made for an ideal family trip. My children and I would love to go
                  …see more

                  Price per night from

                  $226

                  Price per night from

                  $226

                  (4) Excellent 

                    12

                    Jamaica Royale #92 on the #1 Beach in the USA!

                    Florida / Siesta Key

                    Siesta Key apartment

                    2 6 1 night min

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

                    Price per night from

                    $288

                    Responds fast!
                    avg. 1 hour 50 minutes

                    Price per night from

                    $288

                    (16) Excellent 

                      21

                      Siesta Key- Beach Chic Retreat, Siesta Key 3 Bedroom 2 Bath Apartment

                      Florida / Siesta Key

                      Siesta Key apartment

                      3 7 min stay varies

                      • 3 bedrooms
                      • sleeps 7
                      • min stay varies
                      • Beach / lakeside relaxation
                      • Nearest beach 1 mi
                      • Child Friendly
                      “This was the definition of home away from home” great value for your money...very cozy, with lots of new upgrades. Easy access to the beach and restaurants.
                      …see more

                      Price per night from

                      $228

                      Responds fast!
                      avg. 2 hours 57 minutes

                      Price per night from

                      $228

                      (5) Excellent 

                        15

                        Rates reduced on the adorable condo. Beach Access to the most beautiful Beaches

                        Florida / Siesta Key

                        Siesta Key house

                        1 4 3 nights min

                        • 1 bedroom
                        • sleeps 4
                        • 3 nights min
                        • Nearest beach 0.32 mi
                        • Child Friendly
                        • Air conditioning
                        “Book with Island Time!” We really lucked out with our first Flipkey booking. My husband and I traveled to Siesta Key last year for our honeymoon, and we returned this year to celebrate our anniversary. The property had everything we could possibly hav
                        …see more

                        Price per night from

                        $148

                        Price per night from

                        $148

                        (3) Excellent 

                          10

                          Top Floor End Unit Directly Across the Street from Siesta Key public beach

                          Florida / Siesta Key

                          Siesta Key condo

                          2 6 7 nights min

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

                          Price per night from

                          $139

                          Price per night from

                          $139

                          (20) Excellent 

                            58

                            Only 150 yards to Crescent Beach and heated pool!

                            Florida / Siesta Key

                            Siesta Key villa

                            2 4 min stay varies

                            • 2 bedrooms
                            • sleeps 4
                            • min stay varies
                            • Beach / lakeside relaxation
                            • Nearest beach 0.14 mi
                            • Swimming pool
                            “Amazing Rental” This rental was roomier than expected! Everything was perfect! The pool and beach is so close, also there is some local restaurants and shops so close by! Couldn't have asked for better!
                            …see more

                            Price per night from

                            $130

                            Responds fast!
                            avg. 2 hours 59 minutes

                            Price per night from

                            $130

                              14

                              "Cottage by the Sea" 1 Bedroom/ 1 Bath Across From Beach!!- · 3031, 3032

                              Florida / Siesta Key

                              Siesta Key cottage

                              1 4 min stay varies

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

                              Price per night from

                              $197

                              Price per night from

                              $197

                              (1) Excellent 

                                16

                                Island House Beach Resort 3N

                                Florida / Siesta Key

                                Siesta Key apartment

                                2 6 min stay varies

                                • 2 bedrooms
                                • sleeps 6
                                • min stay varies
                                • Swimming pool
                                • Child Friendly
                                • Air conditioning
                                “Relax and chill out” We have stayed at this apartment twice once in 2005 and 2008 after Island house was recommended to us by friends, the first time we stayed we all fell in love with Siesta keys and island house, and when we visited again we asked t
                                …see more

                                Price per night from

                                $226

                                Price per night from

                                $226

                                (5) Excellent 

                                  47

                                  Gulf Side Siesta Key Villa~Peaceful 1st Floor Villa, 3 pools-Jamaica Royale #100

                                  Florida / Siesta Key

                                  Siesta Key villa

                                  2 6 min stay varies

                                  • 2 bedrooms
                                  • sleeps 6
                                  • min stay varies
                                  • Beach / lakeside relaxation
                                  • Nearest beach 0.1 mi
                                  • Swimming pool
                                  “Spring break” This unit was beautifully done; recently renovated, impeccably clean and very close to the beach! The owner was e trendy helpful and accommodating. She made it easy and if you are headed to Siesta Key, you must stay here!
                                  …see more

                                  Price per night from

                                  $176

                                  Responds fast!
                                  avg. 2 hours 10 minutes

                                  Price per night from

                                  $176

                                  (17) Very Good 

                                    50

                                    Only 150 yrds to Siesta Key Beach and heated pool!

                                    Florida / Siesta Key

                                    Siesta Key villa

                                    2 4 min stay varies

                                    • 2 bedrooms
                                    • sleeps 4
                                    • min stay varies
                                    • Beach / lakeside relaxation
                                    • Nearest beach 0.14 mi
                                    • Swimming pool
                                    “I have found my happy place!” Enjoyed our recent stay here. Very comfortable and clean accomodations. I have a Tempurpedic mattress at home so that was one of the reasons I booked here. Couch in living room was also comfortable. Did not get to try
                                    …see more

                                    Price per night from

                                    $130

                                    Responds fast!
                                    avg. 2 hours 59 minutes

                                    Price per night from

                                    $130

                                      58

                                      2Bedroom/ 2Bath Condo Across From Siesta Key Beach With The Best View!!-OHAB 601

                                      Florida / Siesta Key

                                      Siesta Key condo

                                      2 6 7 nights min

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

                                      Price per night from

                                      $250

                                      Price per night from

                                      $250

                                      (23) Very Good 

                                        40

                                        Sandy Toes Siesta Key Florida (6796)

                                        Florida / Siesta Key

                                        Siesta Key house

                                        2 6 3 nights min

                                        • 2 bedrooms
                                        • sleeps 6
                                        • 3 nights min
                                        • Beach / lakeside relaxation
                                        • Nearest beach 0 mi
                                        • 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, towe
                                        …see more

                                        Price per night from

                                        $344

                                        Responds fast!
                                        avg. 55 minutes

                                        Price per night from

                                        $344

                                        (3) Excellent 

                                          45

                                          Remodeled 2br 2ba with private patio, beautiful water views, walk to #1 beach

                                          Florida / Siesta Key

                                          Siesta Key condo

                                          2 6 min stay varies

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

                                          Price per night from

                                          $107

                                          Responds fast!
                                          avg. 2 hours 29 minutes

                                          Price per night from

                                          $107

                                          (5) Very Good 

                                            42

                                            Quiet and Comfortable Condo Near Turtle Beach

                                            Florida / Siesta Key

                                            Siesta Key condo

                                            2 5 6 nights min

                                            • 2 bedrooms
                                            • sleeps 5
                                            • 6 nights min
                                            • Swimming pool
                                            • Child Friendly
                                            • Air conditioning
                                            “Siesta sweet spot” Great value for location. Nice pool, visits with the manitees. Close to everything. This time of year ocean water was amazing
                                            …see more

                                            Price per night from

                                            $119

                                            Responds fast!
                                            avg. 2 hours 45 minutes

                                            Price per night from

                                            $119

                                            (4) Excellent 

                                              16

                                              Island House Beach Resort V5

                                              Florida / Siesta Key

                                              Siesta Key villa

                                              2 6 min stay varies

                                              • 2 bedrooms
                                              • sleeps 6
                                              • min stay varies
                                              • Swimming pool
                                              • Child Friendly
                                              • Air conditioning
                                              “Great location and lovely accommodations!” This was our second year to vacation here and we plan to return next year! It is so close to the beautiful beach. Our experiences have been very relaxing and worth repeating.
                                              …see more

                                              Price per night from

                                              $174

                                              Price per night from

                                              $174

                                                19

                                                3 Bedroom/ 2 Bath unit across from Siesta Key Beach Access.- Islamorada

                                                Florida / Siesta Key

                                                Siesta Key apartment

                                                3 8 7 nights min

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

                                                Price per night from

                                                $193

                                                Price per night from

                                                $193

                                                (16) Excellent 

                                                  28

                                                  What a View!! 2/2 Cert. of Excellence Winner 2014

                                                  Florida / Siesta Key

                                                  Siesta Key apartment

                                                  2 4 7 nights min

                                                  • 2 bedrooms
                                                  • sleeps 4
                                                  • 7 nights min
                                                  • Beach / lakeside relaxation
                                                  • Swimming pool
                                                  • Child Friendly
                                                  “Beautiful and memorable vacation with our son,wife and grandchil” My husband and I rented unit B41,it was beautifull, tastefully decorated stainless steel appliances and new furniture. The owners thought of everything.Very pleased to have a washer an
                                                  …see more

                                                  Price per night from

                                                  $143

                                                  Price per night from

                                                  $143

                                                  (15) Very Good 

                                                    32

                                                    The Top Siesta Key Location, The Village Studio - Eat Shop Beach!

                                                    Florida / Siesta Key

                                                    Siesta Key cottage

                                                    1 2 3 nights min

                                                    • 1 bedroom
                                                    • sleeps 2
                                                    • 3 nights min
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 0.1 mi
                                                    • Child Friendly
                                                    “Best of the village and the beach!” Great location! Steps from Siesta Key Village with great resteraunts, shops and clubs. Beach Access 4 is just across the street and we were from the front door to the water in under 10 minutes! Beautiful beach and s
                                                    …see more

                                                    Price per night from

                                                    $121

                                                    Responds fast!
                                                    avg. 2 hours 15 minutes

                                                    Price per night from

                                                    $121

                                                    (13) Excellent 

                                                      59

                                                      Gorgeous Direct gulf Front 2 Bedroom Condo on Siesta Keys... JUST REMODELLED

                                                      Florida / Siesta Key

                                                      Siesta Key apartment

                                                      2 6 7 nights min

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

                                                      Price per night from

                                                      $181

                                                      Responds fast!
                                                      avg. 3 hours 45 minutes

                                                      Price per night from

                                                      $181

                                                      (1)  

                                                        32

                                                        Siesta Key Beach w/ Partial Gulf Views Across the Street, Renovated, Overlooks H

                                                        Florida / Siesta Key

                                                        Siesta Key apartment

                                                        2 6 min stay varies

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

                                                        Price per night from

                                                        $116

                                                        Responds fast!
                                                        avg. 4 minutes

                                                        Price per night from

                                                        $116

                                                          38

                                                          NEW Private Siesta Key Vacation Rental Home W/ Heated Pool on Quiet Street

                                                          Florida / Siesta Key

                                                          Siesta Key condo

                                                          3 6 min stay varies

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

                                                          Price per night from

                                                          $269

                                                          Price per night from

                                                          $269

                                                          (3) Very Good 

                                                            17

                                                            Island House Beach Resort 15N

                                                            Florida / Siesta Key

                                                            Siesta Key apartment

                                                            2 4 min stay varies

                                                            • 2 bedrooms
                                                            • sleeps 4
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Child Friendly
                                                            • Air conditioning
                                                            “Great Siesta Key stay!” Just returned from 4 short days on Siesta Key at Island House - 15N...and am missing everything about it! While this development was NOT built yesterday, we found it to be in great shape - nicely kept landscaping, beautiful wa
                                                            …see more

                                                            Price per night from

                                                            $226

                                                            Price per night from

                                                            $226

                                                            (5) Very Good 

                                                              36

                                                              Gulf Beach, Pool And Walk To Siesta Key Village

                                                              Florida / Siesta Key

                                                              Siesta Key apartment

                                                              2 6 min stay varies

                                                              • 2 bedrooms
                                                              • sleeps 6
                                                              • min stay varies
                                                              • Beach / lakeside relaxation
                                                              • Nearest beach 0.2 mi
                                                              • Swimming pool
                                                              “Gulf Beach, Pool And Walk To Siesta Key Village” We had the best time ever. Nice being able to wLk to village. Sunsets are beautiful. Dolphin hanging out at the pier Beaches are near. The pool is next door. Condo is very clean and great Best
                                                              …see more

                                                              Price per night from

                                                              $114

                                                              Price per night from

                                                              $114

                                                              (1) Excellent 

                                                                29

                                                                Beach Access, Heated Pool, Boat Docks, and MORE for the perfect beach getaway

                                                                Florida / Siesta Key

                                                                Siesta Key condo

                                                                2 5 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 5
                                                                • min stay varies
                                                                • Swimming pool
                                                                • Child Friendly
                                                                • Air conditioning

                                                                Price per night from

                                                                $109

                                                                Price per night from

                                                                $109

                                                                  36

                                                                  LuLu Kemp Ridley - Walk to Beach, Heated Pool, WiFi, Siesta Village just Steps A

                                                                  Florida / Siesta Key

                                                                  Siesta Key condo

                                                                  1 4 min stay varies

                                                                  • 1 bedroom
                                                                  • sleeps 4
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $174

                                                                  Responds fast!
                                                                  avg. 4 minutes

                                                                  Price per night from

                                                                  $174

                                                                  (7) Very Good 

                                                                    26

                                                                    Luxury Villa, Sleeps 6 Comfortably Located on Siesta Key Beach, Sarasota Florida

                                                                    Florida / Siesta Key

                                                                    Siesta Key villa

                                                                    2 6 min stay varies

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

                                                                    Price per night from

                                                                    $207

                                                                    Responds fast!
                                                                    avg. 3 hours 7 minutes

                                                                    Price per night from

                                                                    $207

                                                                    (5) Excellent 

                                                                      17

                                                                      Island House Beach Resort 5S

                                                                      Florida / Siesta Key

                                                                      Siesta Key apartment

                                                                      2 4 min stay varies

                                                                      • 2 bedrooms
                                                                      • sleeps 4
                                                                      • min stay varies
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Air conditioning
                                                                      “Ocean dream come true!” Love the view!!! Can't get over how nice it is to stay so close to the beach!! Lovin every minute of it.... great place to stay... would stay here again!!!
                                                                      …see more

                                                                      Price per night from

                                                                      $226

                                                                      Price per night from

                                                                      $226

                                                                      (1) Excellent 

                                                                        42

                                                                        Fido Friendly, Saltwater Pool, Only 1 mile to SK Beach, Close to the Village, Sh

                                                                        Florida / Siesta Key

                                                                        Siesta Key house

                                                                        3 8 min stay varies

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

                                                                        Price per night from

                                                                        $162

                                                                        Responds fast!
                                                                        avg. 4 minutes

                                                                        Price per night from

                                                                        $162

                                                                          32

                                                                          LJ's "Rustic Cottage"-- 2 Bedroom/ 2 Bath Steps From The Sand With Pool Access!!

                                                                          Florida / Siesta Key

                                                                          Siesta Key apartment

                                                                          2 8 7 nights min

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

                                                                          Price per night from

                                                                          $250

                                                                          Price per night from

                                                                          $250

                                                                          (10) Excellent 

                                                                            24

                                                                            Sea Shell Condo-Right On Crescent Beach-Siesta Key

                                                                            Florida / Siesta Key

                                                                            Siesta Key condo

                                                                            2 6 min stay varies

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

                                                                            Price per night from

                                                                            $261

                                                                            Responds fast!
                                                                            avg. 2 hours 55 minutes

                                                                            Price per night from

                                                                            $261

                                                                              41

                                                                              goldeneye luxury private family plantation house

                                                                              Florida / Siesta Key

                                                                              Siesta Key house

                                                                              3 6 7 nights min

                                                                              • 3 bedrooms
                                                                              • sleeps 6
                                                                              • 7 nights min
                                                                              • Nearest beach 0.5 mi
                                                                              • Swimming pool
                                                                              • Suitable for children age 5+

                                                                              Price per night from

                                                                              $320

                                                                              Price per night from

                                                                              $320

                                                                              About Siesta Key

                                                                              What was once a secret gem known to only a few, has rapidly become America's darling beach town.

                                                                              Siesta Key, located in Sarasota County and about an hour south of the Tampa Bay Area, is an eight-mile island accessible by two bridges from the mainland. Sandals and swimming suits are accepted - even expected in virtually all of the restaurants and boutiques that populated the island - especially so of those located in Siesta Key Village. The atmosphere is as cool as the white quartz sands in the daytime, and while libations and celebrations can warm up the evening, you are never to far from a tiki-esque style bar and the quiet sounds of ocean waves gliding up and down the beach.

                                                                              In 2011, Dr. Beach named Siesta Beach No. 1 in the nation for its sugary white sand. Siesta Key beach is, in fact, almost entirely composed of crushed quarts crystal. This unique composition not only makes this sand sparkle under the Florida sun, but also keeps the sand cool on even the hottest of Florida summer days. The sand is perfect for sculpting, and every year Siesta Key is home to world-class sand sculpting competitions.

                                                                              Despite its popularity, there are still quiet corners of Siesta to sneak off to and explore.

                                                                              Turtle Beach located at the southern end of Siesta Key has sand that's a bit coarser. This beach is a great fishing and snorkeling hot spot. The beach has a steeper incline and carries more shells. After a storm beachcombers might even find a petrified shark's tooth. Nearby are restaurants, shopping and a few local nightspots.

                                                                              Crescent Beach is another quieter spot, just south of Siesta Key Beach. Enjoy the same blue waters in a secluded atmosphere. This area contains coral formations and bright marine life - perfect for diving.

                                                                              Siesta Key is perfectly fit for families, singles, and couples alike. Lodging accommodations can be found throughout the key, including hundreds of vacation rentals. Though active year round, Siesta Key's peak season runs January through April. Plan to book your stay as soon as possible if your vacation is planned within that duration.

                                                                              Information provided by:Visit Sarasota County