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Holiday Rentals in Siesta Key, FL

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    Travellers to Siesta Key are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 18
    4 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 16
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 17
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 16
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Island House Beach Resort- Siesta Key Florida, Crescent Beach - This large villa is approx. 1000 sq. ft. It has 2 bedrooms, 2 baths, large living area, dining area, fully equipped kitchen, all appliances, screened lanai, central ac/heat, covered parking, free wi-fi in unit. Unlimited Long Distance.... View all property information
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    Siesta Key, Florida 34242
    1 / 15
    4.5 of 5 stars (7) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    Island House Beach Resort - Siesta Key Florida - Southwest building, 3rd floor, One bed, 2 bath, King, 2 twins in den area. This unit is 1300 sq. ft. and has fully equipped kitchen, dining area, living area, 2 porches, laundry room. Enjoy spectacular sunsets from this unit. Free Wi - Fi in unit.... View all property information
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    Siesta Key, Florida 34242
    1 / 16
    4 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Island House Beach Resort - Siesta Key Florida, Crescent Beach - The large 2 bedrooms, 2 bath villa is approx. 1000 sq. ft., non-carpeted and has a large living area, dining area, fully equipped kitchen, central ac/heat, and covered parking. The unit has a king size bed, 2 twins. It is only steps... View all property information
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    Siesta Key, Florida 34242
    1 / 16
    4.5 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Island House Beach Resort, Crescent Beach, Siesta Key Florida! Newly renovated 2 bedroom, 2 bath unit. The unit is approx. 1000 sq. ft. has a large living area, dining area, fully equipped kitchen, all appliances, central ac/heat, covered parking, screened lanai, 3 flat screen tv's, dvd, in unit... View all property information
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    Siesta Key, Florida 34242
    1 / 15
    4 of 5 stars (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Island House Beach Resort - Siesta Key Florida, Crescent Beach - This lovely 2 bedroom, 1 bath villa is located on the widest part of Crescent beach. It is approx 1000 sq. ft and has a large living area, dining room, fully equipped kitchen, screened lanai, covered parking, central ac/heat, free... View all property information
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    Siesta Key, Florida 34242
    1 / 16
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Island House Beach Resort! Siesta Key Florida - Crescent Beach. Completly remodeled January 2011!! This 1000 sq. ft villa is 2 bedrooms, 2 baths and has a large living area, full kitchen, granite counter tops, all new appliances, 2 flat screen tvs, new windows, central heat/ac, free wi-fi. The unit... View all property information
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    Siesta Key, Florida 34242
    1 / 12
    4.5 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Island House Beach Resort- Siesta Key Florida, Crescent Beach - The lovely villa is located on the widest part of Crescent Beach. It is approx. 1000 sq. ft. and is 2 bedrooms, 2 baths. The villa has a large living area, dining area, fully equipped kitchen, all appliances, central ac/heat, screened... View all property information
    Location Information
    Siesta Key, Florida 34242
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    1 / 14
    4.5 of 5 stars (6) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Island House Beach Resort- Siesta Key Florida, Crescent Beach- This large 2 bedrooms, 2 bath villa is appox. 1000 sq. ft. It has a large living area, dining area, fully equipped kitchen, all appliances, 60" high def tv in living room, 50" high def in master, dvd, free wi-fi in unit, central... View all property information
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    Siesta Key, Florida 34242
    1 / 17
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Island House Beach Resort, Siesta key, Crescent Beach!New improvements in 2014! 60" tv and entertainment center ( netflix reaady), new ac unit, new dishwasher and ceiling fans in bedrooms. Professionally decorated in October 2011. This large 2 bedrooms, 2 bath unit is approx 1000 sq. ft. It has a... View all property information
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    Siesta Key, Florida 34242
    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Island House Beach Resort! Siesta Key Florida - Crescent Beach. The 2 bedroom, 1 bath villa is 1000 sq. ft. It has a large living area, dining area, fully equipped kitchen, screened lanai, all appliances, 3 tvs, dvd, free wi-fi. It has a king size bed, 2 twins. The unit is across from our large... View all property information
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    Siesta Key, Florida 34242
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Island House Beach Resort! Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on the widest part of one of the best beaches in Florida. This condo offers a view of palm trees, white sand and the turquoise waters of the Gulf of Mexico. The view is picturesque and the... View all property information
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    Siesta Key, Florida 34242
    1 / 18
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
    • Smoking allowed
    • x
    About this property
    Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large villa is approx. 1000 sq. ft., non-carpeted, has a large living area, dining area, fully equipped kitchen, all appliances, screened lanai, central ac/heat, and covered parking, 3 tvs, dvd, free wi-fi in unit!. It has a king... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 15
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Island House Beach Resort - Siesta Key Florida, Crescent Beach. This bright spacious villa is approx. 1000 sq. ft., non-carpeted and has all the comforts and luxuries of home. Enjoy the significant renovations done including a newly renovated, fully-equipped kitchen with granite counter top, brand... View all property information
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    Siesta Key, Florida 34242
    1 / 23
    3 of 5 stars (1) Average
    6 Bedrooms, 3 Bathrooms, Sleeps 16 | Quick View
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    • Private Garden
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    • ?
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    • x
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    NEWLY BUILT GATED WATERFRONT HOME ON THE WATER!!!!!! Vanilla Sky International Properties is proud to present this wonderful Siesta Key Waterfront Home. This expansive and fully gated residence is just steps from world famous Siesta Key Beach . Perfect location between the village and crystal... View all property information
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    Siesta Key, Florida 34242
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Newly renovated, decorated and furnished, this delightful two bedroom/two bathroom second floor walk-up has plenty of living and storage space. Washer/dryer in unit. Complimentary Wi-Fi access. King bed in Master, 2 Twins in Guest. Sleeps maximum of 4 ONLY! The unit has a beautiful new... View all property information
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    Siesta Key, Florida
    1 / 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    2 BR -- 2 BA -- 4 person Max -- Small Garden -- Pond View 1138 is a small garden unit, located on the Gulfside of Midnight Pass 2 bedroom, 2 bath unit . Approx. 1100 Sq. Ft. (1200 including the lanai). Bedding: Master bedroom: King Guest Bedroom: 2 Twins Electronics: Living room: 44... View all property information
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    Siesta Key, Florida 34242
    1 / 22
    4 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Waterfront
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    • Pet-friendly
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    • x
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    • x
    About this property
    Lush landscaping and 14 acres of park-like surroundings are the setting for this quiet and peaceful 2-bedroom, 2-bath condo on beautiful Siesta Key. Located on the ground floor in Midnight Cove II with a great view of the inter-coastal waterway between Siesta Key and the mainland, this... View all property information
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    Siesta Key, Florida 34242
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    1 / 7
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2 BR. - 2 BA -- 6 Person Max. -- Large Garden -- Gulf View 6014 WPW is a Large Garden unit, located approximately 50 yards away from Crescent Beach 2 Bedroom / 2 Bath unit. Approx. 1250 Sq. Ft. (1375 including the lanai) Bedding: Master Bedroom: King Guest Bedroom: 2 Twins Electronics:... View all property information
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    Siesta Key, Florida 34242
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    Welcome to Seaside Cottage! This lovely and rare 4 bedroom 3 bathroom heated pool home has just gone under extensive renovation, leaving a spectacular beach vacation home that rivals most on Siesta Key! Completed in November 2015, our guests will now enjoy the luxury of a brand new kitchen and... View all property information
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    Siesta Key, Florida 34242
    1 / 18
    4.5 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Porch
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    • x
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    • x
    About this property
    Location! Location! Location! Walk out the door, across the street and onto the # 1 ranked beaches in America! This beautiful condo is on the ground floor, no steps, with a tropical enclosed lanai. It features 3 televisions, Tommy Bahama furnishings, a barbecue grill and high speed internet for... View all property information
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    Siesta Key, Florida 34242
    1 / 7
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2 BR. - 2 BA -- 6 Person Max. -- High Rise -- Beach View 1055-602 is a Gulfside Highrise unit, located approximately 75 yards away from Crescent Beach 2 Bedroom / 2 Bath unit. Approx. 1250 Sq. Ft. (1375 including the lanai) Bedding: Master Bedroom: King Guest Bedroom: 2 Twins... View all property information
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    Siesta Key, Florida 34242
    1 / 25
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Owner takes pride in this beautifully decorated 2nd floor unit. 2 bedroom 1 1/2 baths. Newly remodeled! Very cozy and comfortable with amazing tranquility and peacefulness courtesy of the laid back, canal-front setting. The unit features ceramic tile floors and a den-like sitting room off of the... View all property information
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    Siesta Key, Florida
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Owner takes pride in this beautifully decorated ground floor unit featuring ceramic tile floors and extended living room. Slider doors open to screens across the back of the unit and your own private back door. Step out to the serene canal waters, boat docks and swimming pool. Living room offers... View all property information
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    Siesta Key, Florida
    1 / 19
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    2 BR -- 1.5 BA -- 4 person Max -- Small Garden -- Greenbelt View 1154 is a small garden unit, located on the Gulfside of Midnight Pass 2 bedroom, 1.5 bath unit . Approx. 1100 Sq. Ft. (1200 including the lanai). Bedding: Master bedroom: King Guest Bedroom: 2 Twins Electronics: Living... View all property information
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    Siesta Key, Florida 34242
    1 / 9
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2 BR. - 2 BA -- 6 Person Max. -- High Rise -- Greenbelt View 1255 - 302 is a Bayside Midrise unit, located approximately 75 yards away from the Bay. 2 Bedroom / 2 Bath unit. Approx. 1250 Sq. Ft. (1375 including the lanai) Bedding: Master Bedroom: King Guest Bedroom: 2 Twins Electronics:... View all property information
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    Siesta Key, Florida 34242
    1 / 18
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    White Sands Village is located on Siesta Key, just few steps from Siesta Beach and directly on the canal across from Philippee Creek. Highlights of White Sands Unit 303: Free high-speed WiFi Ground floor unit More than 200 channel cable TV DVR to watch your favorite show when you want to 50 inch... View all property information
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    Siesta Key, Florida 34242
    1 / 15
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    FABULOUS DIRECT BEACHFRONT THIRD FLOOR WALK UP! 180 DEGREE PANORAMIC VIEW! Completely remodeled in Nov. 2010! Granite countertops, custom cabinetry, new furniture and porcelain tile throughout. Two bedroom 1.5 bath with washer/dryer, open balcony, Tommy Bahama decor, and so much more! The view is... View all property information
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    Siesta Key, Florida
    1 / 29
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • x
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    *** NEW *** Come and enjoy this two bedroom two bathroom condo style vacation rental located just a short walk to Siesta Key beach. The main living area has an open concept with living room and dining area in the first great room when you enter the unit. There is a full kitchen with breakfast bar... View all property information
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    Siesta Key, Florida 34242
    1 / 27
    5 of 5 stars (5) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    FREE High Speed Wireless Internet ! - just bring your Laptop. Watch the boats float by! Just steps from the Pool, Club House, and picnic area with gas Weber grills. Across the street from Crescent Beach!! Our three bedroom two story townhouse in Gulf & Bay Club Bayside is in a complex of Key... View all property information
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    Siesta Key, Florida 34242
    1 / 17
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Located directly across from world-renowned Siesta Key Public Beach, this fabulous condo is the perfect vacation retreat with an emphasis on comfort. It is within walking distance to charming Siesta Key Village with its numerous restaurants, shops, and entertainment. FREE in-unit WIFI. Our large... View all property information
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    Siesta Key, Florida 34242
    1 / 28
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • x
    About this property
    Description:Walk out the back door to the clean white sand of Siesta Key Beach. This home has private Siesta Key beach frontage on the prime section of beach, there are no homes between you and the beach. Nearly every room has a full view of the beach. The entire back of this house opens with... View all property information
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    Siesta Key, Florida 34242
    1 / 32
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Siesta Key 611 is the perfect vacation home for your getaway to sun, sand and pure relaxation! Siesta Key rents Saturday to Saturday, for a minimum of one week. To see available dates, please scroll down to the calendar. Siesta Key 611 is a newly renovated, garden level condo located in... View all property information
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    Siesta Key, Florida 34242
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2 BR. - 2 BA -- 6 Person Max. -- High Rise -- Pond/Cityscape View 1080 - 601 is a Gulfside Highrise unit, located approximately 125 yards away from Crescent Beach 2 Bedroom / 2 Bath unit. Approx. 1250 Sq. Ft. (1375 including the lanai) Bedding: Master Bedroom: King Guest Bedroom: King... View all property information
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    Siesta Key, Florida 34242
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Gorgeous intra coastal waterway views from this fifth floor 2 bed/2 bath condominium unit. Enjoy the tropical breeze from the screened lanai. Living room is furnished with sofa bed, Flat screen HDTV and DVD/CD combo. Master bedroom has king bed, Flat Screen TV and DVD player. Master bath is newly... View all property information
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    Siesta Key, Florida
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Newly renovated and professionally decorated (fall 2012) top floor 3-bedroom condo with open floor plan and cathedral ceilings! Spectacular panoramic gulf views! Enjoy sunsets from your own private outdoor sundeck. Additional amenities include: bathtub in guest bathroom, king in master bedroom, 2... View all property information
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    Siesta Key, Florida
    1 / 21
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Waterfront
    • Hot Tub
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    • Sauna
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    • x
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    About this property
    Fabulous 2nd floor gulf front condo overlooking the beautiful Gulf of Mexico! Located on the quiet end of the Island near Turtle Beach this spacious condo features extraordinary views of the beach and sunsets from the front room, the lanai, and the master bedroom. Beautifully furnished with... View all property information
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    Siesta Key, Florida 34242
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    2 BR. - 2 BA -- 6 Person Max. -- High Rise -- Beach View 1055-503 is a Gulfside Highrise unit, located approximately 75 yards away from Crescent Beach 2 Bedroom / 2 Bath unit. Approx. 1250 Sq. Ft. (1375 including the lanai) Bedding: Master Bedroom: King Guest Bedroom: King Electronics:... View all property information
    Location Information
    Siesta Key, Florida 34242
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Welcome to Jamaica Royale! We invite you to enjoy a visit to this lovely updated 2 bedroom/2 bath unit located in the beautifully landscaped garden area and only minutes away from the pristine # 1 Siesta Key beach with private access from Jamaica Royale. Enjoy a swim in any of the 3 heated pools on... View all property information
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    Siesta Key, Florida 34242
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Spectacular Gulf of Mexico views from this seventh floor, 3 bed 2 full bath spacious unit with over 1800 s.f. Extra large 25' glassed-in lanai stretches across unit to watch the famous Siesta sunsets! Ceramic tile in living areas and lanai. Many upgrades and beautifully decorated! Living room has a... View all property information
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    Siesta Key, Florida
    1 / 50
    4.5 of 5 stars (6) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Newly upgraded ( September 2015 ) with new kitchen, new vanities, newly painted and with the tiles steam cleaned this Siesta Key villa is a gem. It comes with a with a lovely heated community salt water pool and private access to the beautiful white sanded Crescent Beach! Crescent Beach on Siesta... View all property information
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    Siesta Key, Florida 34242
    1 / 19
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Enjoy the Florida lifestyle in this 4th Floor, 1400 sq. ft., 2 BDR/ 2 Bath condo overlooking the tranquil waters of the intra coastal waterway. Cross the road and you are just a few hundred feet away from your own piece of the soft white sugary sands of Crescent Beach. Master bedroom is furnished... View all property information
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    Siesta Key, Florida
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Beach front and fabulous! Everything is new and remodeled in this unit! Sun yourself on the open balcony and enjoy this 2 bedroom/2 bath in style. The living room is furnished with a LCD TV/VCR, leather sofa and decorated with brilliant colors! The master bedroom offers a king bed and a flat panel... View all property information
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    Siesta Key, Florida
    1 / 6
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 1 | Quick View
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    Gulf View Queen Bed in Master Bedroom Shower in Master Bathroom 2 Full Beds in Guest Bedroom Bathtub in Guest Bathroom Sofa Sleeper in Living Area Carpet & Tile Flooring 3 Flat Screen TV's 3 DVD Players CD Player Washer/Dryer Wifi Internet Access Garage Additional amenities include: bathtub in... View all property information
    Location Information
    Siesta Key, Florida
    1 / 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    2 BR. - 2 BA -- 6 Person Max. -- Large Garden -- Pool View 6018 is a Gulfside Highrise unit, located approximately 50 yards away from Crescent Beach 2 Bedroom / 2 Bath unit. Approx. 1250 Sq. Ft. (1375 including the lanai) Bedding: Master Bedroom: King Guest Bedroom: 2 Twins, 1 twin sized... View all property information
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    Siesta Key, Florida 34242
    1 / 9
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • x
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    • x
    About this property
    2 BR -- 1.5 BA -- 4 person Max -- Small Garden -- Pond View 1041 is a small garden unit, located on the Gulfside of Midnight Pass 2 bedroom, 1.5 bath unit . Approx. 1100 Sq. Ft. (1200 including the lanai). Bedding: Master bedroom: King Guest Bedroom: 2 Twins Electronics: Living room:... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 1
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    Newly remodeled -Queen Murphy Bed -Convenience Kitchen -Laundry Facilities on site -Patio / Grill -VCR/DVD -WiFi -Microwave NOTE: PLEASE CONTACT US FOR AVAILABILITY. We do NOT always keep this calendar current. Thanks. Visit our site to see more photos and descriptions:... View all property information
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    Siesta Key, Florida 34242
    1 / 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • Smoking allowed
    • x
    About this property
    2 BR. - 2 BA -- 6 Person Max. -- High Rise -- Greenbelt/Cityscape View 1080 - 301 is a Gulfside Highrise unit, located approximately 125 yards away from Crescent Beach 2 Bedroom / 2 Bath unit. Approx. 1250 Sq. Ft. (1375 including the lanai) Bedding: Master Bedroom: Queen Guest Bedroom: 2... View all property information
    Location Information
    Siesta Key, Florida 34242