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Holiday Rentals in Siesta Key, FL

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    Travellers to Siesta Key are booking March dates now. Secure your holiday rental today, and have the perfect trip.
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    5 of 5 bubbles (11) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Studio, 4 Bathrooms, Sleeps 14 | Quick View
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    REDUCED PRICES and SPECIALS ON TOP OF THAT! See our website (https://www.siestakeyluxuryrentalproperties.com/specials/) or give us a call at 941.349.1125 for more details. Beachfront Townhome in Siesta Key Village Area. Located on Sunset Point, directly on the beach, this Vacation Home has it... View all property information
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    Siesta Key, Florida 34242
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    4.5 of 5 bubbles (17) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1BR (sleeps 4)- Perfect for travelers in search of uncomplicated seclusion. Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests and is a four unit Key West style home located just one marlin’s length (5 steps) from... View all property information
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    Siesta Key, Florida 34242
    1 / 32
    5 of 5 bubbles (7) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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 / 22
    4.5 of 5 bubbles (31) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    Old Man and the Sea Inn - 1 marlin to the sand! 2BR (sleeps 8) - Perfect for travelers in search of uncomplicated seclusion. Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests and is a four unit Key West style home... View all property information
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    Siesta Key, Florida 34242
    1 / 19
    5 of 5 bubbles (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    GULF FRONT - GROUND FLOOR UNIT!! This spectacular 2 bedrooms, 2 baths unit is 1300 sq. ft. as is located on Crescent Beach. This condo offers a view of palm trees, white sand and turquoise waters of the Gulf of Mexico.Fully equipped kitchen, all appliances. The unit has a king size bed and 2 twins.... View all property information
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    Siesta Key, Florida 34242
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    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Island House Beach Resort! Newly remodeled!! Crescent Beach, Siesta Key Florida! This attractive complex is located on the widest part of one of the best beaches in central florida. This condo is 1300 sq. ft, non-carpeted and is located on the 4th floor. It is 2 bedrooms, 2 baths, King, 2 twins,... View all property information
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    Siesta Key, Florida 34242
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    1 / 24
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    - Expansive, panoramic gulf view from every room of this 6th floor condo. -Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. -Right on the beach with lounge chairs provided. As close as you can get to the Gulf without... View all property information
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    Siesta Key, Florida 34242
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This beautifully furnished 2 bedroom, 2 bathroom unit provides you with a stunning view of the Sarasota Bay adorned with draping trees that hide multiple varieties of birds. The recently renovated lanai is in a Key West theme with 2 chaise lounges looking out at the water and a bistro set for... View all property information
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    Siesta Key, Florida 34242
    1 / 18
    5 of 5 bubbles (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 / 41
    5 of 5 bubbles (58) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    3 Bedroom, 2.5 Bath Beach Villa (Sleeps 8-10) What makes us different than other homes you may be considering: · The Beach - The home is located on the ocean side of Beach Rd., so you just walk out your door and through our private access path. It’s literally 230 feet to Siesta Key Beach.... View all property information
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    Siesta Key, Florida 34242
    1 / 38
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Beautiful and newly remodeled three bedroom/two bath unit with ceramic tile in living areas and wood laminate in master bedroom and 2nd bedroom. Spacious with over 1800 sq. ft., fourth floor overlooking the intracoastal waterway. Large glassed in lanai makes additional space as a family room with a... View all property information
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    Siesta Key, Florida
    1 / 19
    4.5 of 5 bubbles (24) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    The Royal Palm Suite (sleeps 6) is a 3 bedroom luxury townhouse of 1,850 sq/feet over 3 floors, 2 kings and 1 queen size bed, 3 balconies (each has a Gulf View), almost all rooms have a Gulf view, a kitchen with granite counter tops, master bathroom offers a bathtub with Gulf view and a bidet.... View all property information
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    Siesta Key, Florida 34242
    1 / 19
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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 condos offers a view of the palm trees, white sand and 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 / 19
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Island House Beach Resort! Siesta Key Florida, Crescent Beach. Ground floor unit. This 2 bedroom, 2 bath condo is 1300 sq. ft. It has a large living area, dining area, fully equipped kitchen, all appliances, lanai. It has a king, 2 twins. Central heat/ac. Free Wi-Fi in unit. This beautifully... View all property information
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    Siesta Key, Florida 34242
    1 / 25
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    NEW SPECIALS - Visit our website (https://www.tropicalbreezeinn.com/specials/) or Call our Sales team for more information 941.349.1125. REMODELED RESORT ROOM - Do you want the perfect location and a quaint beach bungalow style luxury resort room, if so we have the perfect thing. This 1 Bedroom... View all property information
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    Siesta Key, Florida 34242
    1 / 7
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    The condo is in a condo hotel, a very comfortable and beautifully furnished 2nd. floor condo with a fully functional kitchen. Close to the beach, considered the number 1 beach in the US. Water (intercoastal) views from the condo. Very safe and secure location, with a management team in the... View all property information
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    Siesta Key, Florida 34242
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    1 / 40
    4.5 of 5 bubbles (7) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    -Accommodations: Condo, 2 Bedrooms + Convertible Bed, 2 Baths (Sleeps 4-6) -Expansive, panoramic gulf view from every room of this 7th (top) floor condo. -Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. -Right on the... View all property information
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    Siesta Key, Florida 34242
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Siesta key condo in sarasota Florida West coast of Florida beautiful sunsets and powdered sugar sandy beaches Condo completely tiled thru-out, Elevator, walk to number 1 rated beach, watch boats go by while enjoying your morning coffee Ringing museum, Florida studio theater St armounds Circle Fine... View all property information
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    Siesta Key, Florida 34242
    1 / 17
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This Unit is located at Island House Beach Resort on the beautiful Crescent Beach in Siesta Key Florida. It is approximately 1000 square ft. The unit is 2 bedrooms, 2 baths and is a very short distance to the beach. The unit features a xtra large living room, fully equipped kitchen, dining area,... View all property information
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    Siesta Key, Florida 34242
    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    VACATION RENTAL COMPLEX DIRECTLY ON CRESCENT BEACH, SIESTA KEY ,FL. MINIMUM RENTAL 5 DAYS- NON-SMOKING CAMPUS, 54, 1 & 2 BEDROOM UNITS. PARKING DIRECTLY ADJACENT TO VILLA, PRIVATE BEACH SHELTERS AND SHOWER. HEATED, SPA TYPE SALT POOL, SHUFFLEBOARD, BAR BQ 1/2 mi. to SIESTA KEY PUBLIC BEACH FOR... View all property information
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    Siesta Key, Florida 34242
    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    Old Man and the Sea Inn - 1 marlin to the sand! 2BR (sleeps 8) - Perfect for travelers in search of uncomplicated seclusion. Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests and is a four unit Key West style home... View all property information
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    Siesta Key, Florida 34242
    1 / 30
    4 of 5 bubbles (19) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    This Siesta Key Studio was renovated and refurbished in November 2013 it has all new furnishings throughout and is accompanied by a secluded outside area with table and chairs, BBQ and reclining sun loungers surrounded by tropical plants and foliage. Easy access - no stairs.<BR><BR>Fully equipped... View all property information
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    Siesta Key, Florida 34242
    1 / 15
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Island House Beach Resort! Crescent Beach, Siesta Key Florida. This attractive 2 bedroom, 2 bath villa is 1000 sq. ft. It has a large living room, dining area, fully equipped kitchen, all appliances, screened lanai. It is 1000 sq. ft. The unit has a king, 2 twins, sleeper sofa. It has 3 tv's, dvd,... View all property information
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    Siesta Key, Florida 34242
    1 / 32
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Harbor Towers Yacht and Racquet Club Unit 503 provides one of the best views in the building (fifth floor facing south/east). The glass enclosed Lanai with floor-to-ceiling sliding glass doors provides bright sunlight during the morning and afternoon with excellent views of the intercostal water... View all property information
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    Siesta Key, Florida 34242
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Upper floor. Walk to Siesta Key beach, only 0.2 mi from beach access 13. Clean, updated, with all the amenities you have at home. Fully equipped kitchen. Quiet and peaceful getaway yet close to shopping, dining, grocery. Park your car and use free ride anywhere on the Key. Beach chairs, umbrella,... View all property information
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    Siesta Key, Florida 34242
    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    NEWLY PAINTED AND CARPETED IN MAY '07. Step right out your back door to the soft, white sugary sand of world famous Crescent Beach! You are so close to the Gulf of Mexico in this 2/1.5 unit. Tastefully decorated and you can watch the sunset right from your screened lanai! The living room offers a... View all property information
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    Siesta Key, Florida
    1 / 28
    5 of 5 bubbles (13) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Siesta Key, Sarasota upscale vacation rental unit with a direct view of the inter-coastal water. Lush, tropical landscaping in well maintained Bay Oaks. Breathtaking view of the inter-coastal with fully appointed fishing dock. Across the street from the beach and there are no beach charges on... View all property information
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    Siesta Key, Florida 34242
    1 / 22
    8 Bedrooms, 7 Bathrooms, Sleeps 26 | Quick View
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    AVAILABLE 3/2/2017 - UNDER CONSTRUCTION - BECOMING AN 8 BED 7 BATH HOME with the Same Resort Pool in the photos with a slide, gratto, swim up bar and jacuzzi! You even have your own Private TIKI HUT next to the pool! This place has it all, its your own water park, resort, and beach paradise wrapped... View all property information
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    Siesta Key, Florida 34242
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Direct Beach front! Step out your back door to Crescent Beach and the Gulf of Mexico. Updated two bedroom/two bath 1100 s.f. unit w/ceramic tile floors, upgrades in kitchen - granite counter tops, custom cabinetry. Master bedroom has BRAND NEW King bed and guest bedroom has two twin beds.... View all property information
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    Siesta Key, Florida 34242
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    NEWLY REFURBISHED 2 BR, 1.5 BA !! New floors, paint, furniture, decor & appliances in 2012. This light and bright ground floor condo is the closest Bay unit to the pool, office, laundry and beach. The newly furnished screened lanai offers views of the beautiful tropical grounds. Living room has... View all property information
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    Siesta Key, Florida
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    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Island House Beach Resort, Siesta Key Florida, Crescent Beach - This lovely unit is approx. 1000 sq. ft. It has 2 bedrooms, 2 baths, large living area, dining area, fully equipped kitchen, all appliances, central ac/heat, 3 tvs, dvd, dedicated, non-shared wi-fi in unit, covered parking, screened... View all property information
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    Siesta Key, Florida 34242
    1 / 14
    5 of 5 bubbles (10) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Our favorite location on Siesta Key, The Siesta Key Village Studio, an accommodating ground floor one-room efficiency apartment perfectly nestled on a quiet tropical street between the best beaches, shopping and dining on the island. Wander one block to your beach, appropriately named “Sunset... View all property information
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    Siesta Key, Florida 34242
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    NEW SPECIALS - Visit our website (https://www.tropicalbreezeinn.com/specials/) or Call our Sales team for more information 941.349.1125. REMODELED- Corner Unit. There is something for everyone here on Siesta Key, and this unit puts you close to it all. Walk out of the front door of this... View all property information
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    Siesta Key, Florida 34242
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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    • x
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    Directly across from Siesta Key public beach. Ground level one bedroom one bath with full kitchen including dishwasher. Laundry facilities are adjacent. Fully stocked with everything you need for the beach. Beds: 1 King Bed, 1 Sofa Bed, 1 Crib View all property information
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    Siesta Key, Florida 34242
    1 / 22
    5 of 5 bubbles (18) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    The condo benefits from its own private pool. The living room, master bedroom, and lanai (balcony) all have stunning ocean views. The lanai, with over $10,000 of new doors and windows, is furnished with a table and chairs to enable you to dine al fresco. There is also a comfortable couch to... View all property information
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    Siesta Key, Florida 34242
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    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 2 bath villa is approx. 1000 sq. ft., non-carpeted and has a large living area, dining area, full kitchen, all appliances, screened lanai, and covered parking, central ac/heat, 3 tvs, dvd, free wi-fi in unit!.... View all property information
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    Siesta Key, Florida 34242
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    NEW SPECIALS - Visit our website (https://www.*********************/specials/) or Call our Sales team for more information *******.1125. REMODELED - Located right next to one of our two pools, and just down the street from the beach, this unit gives you the option to choose fresh or salt water... View all property information
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    Siesta Key, Florida 34242
    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Beautifully remodeled and redecorated unit with granite countertops and stainless steel appliances in the kitchen; ceramic tile throughout and updated baths! Gorgeous decor! This 2 bed/2 bath second floor 1400+ s.f. unit overlooks the tropical gardens and Gulf of Mexico! Enjoy the lazy days in... View all property information
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    Siesta Key, Florida
    1 / 33
    5 of 5 bubbles (22) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    Find Sarasota Vacation Rentals on FlipKey Take the elevator up to the 3rd floor. As soon as you step thru the front door of our condo, you will immediately see full sweeping panoramic unobstructed beach views from a 3rd floor vantage point that will take your breath away. Once inside, after... View all property information
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    Siesta Key, Florida 34242
    1 / 24
    4.5 of 5 bubbles (5) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    This luxury apartment is part of Island House Beach Resort, which is located on 280 ft. of the award-winning Crescent Beach in Siesta Key Florida. Island House offers a large heated swimming pool with sun deck, shuffleboard courts, and a recreation room with ping pong, pool & air hockey. This 1300... View all property information
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    Siesta Key, Florida 34242
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    *** NEWLY RENOVATED!*** Gorgeous 2 bedroom/1.5 bathroom Bay Side unit. Tile throughout. Extended living room area. King bed in the master bedroom and two twins in the guest bedroom. Walk out your back door to the heated pool and the boat docks. Only about a 5 minute walk to your private beach on... View all property information
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    Siesta Key, Florida 34242
    1 / 35
    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    Casa Del Soleil Welcome to Casa Del Soleil! Please Note: Sleeps 10: K, 2T, 2F, QSS There is a 7 night minimum stay If this unit is not available, please contact us for the availability of another comparable one! This is a luxury Townhouse featuring a swim spa, fabulous open floor-plan, with 3... View all property information
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    Siesta Key, Florida
    1 / 38
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    WHAT A VIEW! Very updated, tastefully modern, Bay Front Condo with AMAZING views of the water! ALL NEW, absolutely BEAUTIFUL Hardwood floors! Newer, Stainless Steel appliances in the fully equipped kitchen with dishwasher, full-size refrigerator, microwave, oven and stove. GORGEOUS bathrooms,... View all property information
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    Siesta Key, Florida 34242
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    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    • x
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    Enjoy this 2 bedroom 1 bath property located just 1 block from the beach. This unit offers an adequate kitchen with stainless steel appliances and ample living space for 4. The master bedroom is furnished with a queen-size bed and guest bedroom is furnished with two twin-size beds. The unit is... View all property information
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    Siesta Key, Florida 34242
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    THIS 2 BEDROOM/2 BATH 2ND FLOOR WALK UP UNIT HAS BEEN REMODELED!! Light ceramic tile throughout; updated kitchen with granite counter tops and stainless steel appliances! Beautifully decorated with leather sofa and reclining chair. Flat screen TV in living area; flat screen TV with DVD players in... 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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    • x
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    About this property
    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
    Location Information
    Siesta Key, Florida