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Vacation Rentals and Bungalows in Siesta Key, FL

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    Travelers to Siesta Key are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 25
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 stars (2) Excellent
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    4.5 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Harbour Towers is perfect for people that like the feeling of a grand hotel. You can play tennis on our Har-Tru tennis courts, swim in the sky blue water of Siesta Beach or relax inside at the heated swimming pools. You can jet ski or snorkel at Point of Rock.<BR><BR>You can fish off the docks at... View all property information
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    Siesta Key, Florida 34242
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This Siesta Key 3 Bedroom 2 Bath Home has been completely remodeled. This home is 1 block from the Famous Siesta Key Beach. Granite counter tops, to accent the new white cabinetry. Beautifully tiled bathrooms with all new hardware. All walls beautifully textured. Screened Lanai. Nice back yard. 1... View all property information
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    Siesta Key, Florida 34242
    1 / 26
    4.5 of 5 stars (9) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    PLEASE NOTE: The Price displayed here is NOT ACCURATE! (It does not take the "Seasonal Rate" into consideration) - Sorry - this is Flipkey's policy, not ours. This luxury third floor condo #308 is bright and airy with its extra long Lanai! The Lanai (screened porch) overlooks the Gulf,... View all property information
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    Siesta Key, Florida 34242
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    You will feel like you have arrived in Paradise when you enter the lobby. The facility is more like a resort than a condominium. Unit has 2 bedroom, 2 baths, split plan. Both bedrooms and living room open to screened lanai facing the Gulf of Mexico. Perfect setting for 4 adults or for a family with... View all property information
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    Siesta Key, Florida 34242
    1 / 29
    5 of 5 stars (24) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    We have a new 360 degree picture layout of all rooms, similar to Real Estate version. Email us for a link. ... Last Minute Discount available for Aug 23 - Sep 20... Email us for a Discounted Quote... . Winter 2017 availability: Dec 31 - Jan 21; Feb 25 - Mar 4; Apr 8 - onwards... .. Location:... View all property information
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    Siesta Key, Florida 34242
    1 / 38
    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
    1 / 28
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our House at the Beach on picture perfect Siesta Key provides you with island living in sunny Sarasota, Florida, on the Gulf of Mexico.Siesta Beach takes the #1 beach in the annual Top 10 Beaches ranking and Trip Advisor. This luxurious resort style townhouse (1400 square feet) has a full eat-in... View all property information
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    Siesta Key, Florida 34242
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    1 / 9
    5 of 5 stars (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Fabulous 2 bedroom/2 bath located in one of Siesta Key's finest Gulf to Bay complexes. This beautifully appointed unit epitomizes Island elegance with its hand-scraped dark hickory wood floors, plantation shutters and French doors enclosing the brick-paved lanai. The newly renovated kitchen... View all property information
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    Siesta Key, Florida 34242
    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Find yourself in the relaxing comforts of Siesta Villa Laughing Gull. A single-story stand-alone villa, located in the beautiful private community of Polynesian Gardens, on the tropical barrier island of Siesta Key, Fl. The peaceful tranquility of Villa Laughing Gull is the perfect place to call... View all property information
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    Siesta Key, Florida 34242
    1 / 46
    5 of 5 stars (9) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Enjoy Gulf sunsets and the sound of the surf from your 2nd floor beachfront condo. Fisherman's Cove is right on quiet Turtle Beach where you can swim, fish and walk for miles collecting shells. You can even dock your boat for FREE. Unit 205A offers the perfect place to enjoy the sea and sky from... View all property information
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    Siesta Key, Florida 34242
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Luxury hi-rise condo right on the beach. Enjoy amazing sunsets on the full lanai, with access from each bedroom. Take long walks on the beach. Location is close to shops and restaurants. Crystal Sands on Midnight Pass Rd is one of the most popular condos in Siesta Key. And our Crescent Beach is... View all property information
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    Siesta Key, Florida 34242
    1 / 12
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Delightful beach bungalow at Ebb Tide , only 2 minute walk to pool and powder white sand of Crescent beach, right across the street from restaurants,shops, bike and boat rentals, marina, 7 Eleven, and more. This darling tropical villa had everything you need for a great vacation. No one above you... View all property information
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    Siesta Key, Florida 34242
    1 / 17
    4.5 of 5 stars (2) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Villa Brisa Marina or “Sea Breeze” at 1119-1121 Crescent Street is an exciting new 4BR/4BA/2Kit home just added to our boutique collection of fine vacation homes and it’s sure to be a standout. This home features a brand new heated pool and a three minute walk to the Nation’s finest beach [no... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 13
    3 of 5 stars (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Do you need a paradise vacation? We've got the perfect vacation rental for you..You will enjoy a two bedroom first floor condo located in the plush, rolling 14 acres of greenery of Midnight Cove ii that provides a tranquil serene atmosphere. You will be able to eat breakfast on our lanai as you... View all property information
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    Siesta Key, Florida 34242
    1 / 10
    5 of 5 stars (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Siesta Village in the heart of it all! Brand new construction; second story fully furnished adorable "flat" type apartment, all stainless steel appliances,washer dryer, beachy cool amenities and a great deck over-looking all of the action in the iconic village! Enjoy coffee in the morning from... View all property information
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    Siesta Key, Florida 34242
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our high-rise Condo located in Crystal Sands Resort unit #1102, 11th floor, gives our guests a panoramic view of the beautiful Crescent Beach on Siesta Key. Watch the Sun rise in the morning and set in the evening from our unique Southwest balcony view. Our thirty-five foot balcony is accessed from... View all property information
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    Siesta Key, Florida 34242
    1 / 24
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    About this property
    If you are looking for the perfect spot for a family vacation, to escape the cold and snow, or a quiet romantic getaway this is the place for you. Recently updated throughout, this 2 bedroom 2 bath condo sleeps 6 comfortably all in real beds. Just outside your door is Crescent Beach, consistently... View all property information
    Location Information
    Siesta Key, Florida 34243
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    1 / 10
    5 of 5 stars (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    This vacation rental offers a full view of Siesta Key Beach/ The Gulf upon entry; relax and enjoy from your lanai or master bedroom. The property has been newly transformed to accommodate our guests best welcome to Siesta. From the comfort of the home décor to your fully stocked kitchen: cookware,... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 24
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Fabulous home on Siesta Key (Sarasota)( two weeks minimum stay ). Just 2 minutes drive to the beach & village. This home features 3 bedrooms and 2 baths with a large kitchen that opens to the family room. Great pool with southern exposure,and enclosed in a screen lanai for mosquito protection... View all property information
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    Siesta Key, Florida 34242
    1 / 31
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Great first impressions are evident from the moment you enter this lovely condo and enjoy the breathtaking ocean views from our private oversized lanai. We know you'll adore our comfortably decorated oceanfront condo and have the relaxing vacation you've been dreaming of. This unit unfolds as you... View all property information
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    Siesta Key, Florida 34242
    1 / 24
    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Quality rental, tastefully furnished and nice open entertaining plan. New private swimming pool. This home is located in a excellent location, very near Siesta Key Public Beach. It is convenient to Siesta Key Village, about 4 blocks and it is only a half of a block to the white quartz sands of... View all property information
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    Siesta Key, Florida 34242
    1 / 13
    4.5 of 5 stars (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    This one bedroom is a large 700 sq. ft. condominium unit in a three unit building. There are two one bedroom units available and a two bedroom unit. You can add to your group by adding another unit. The two bedroom/two bath sleep 6 and is 1400 sq. ft. plus a deck with Gulf views and excellent... View all property information
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    Siesta Key, Florida 34242
    1 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Deluxe three bedroom/two and a half bathroom duplex that sleeps 7 per unit in beds. We will allow up to eight in a unit with an additional $25 per day charge for the extra person. Rent one or both units if you have friends or family wanting to vacation together. Gulf of Mexico views from the... View all property information
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    Siesta Key, Florida 34242
    1 / 38
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    NEWLY LISTED WATERFRONT ESCAPE!!!! Brand New , Gated Residence steps from Siesta Key Beach . Perfect location between the village and crystal sands of Siesta Beach!! Bar's, Restaurants, Shopping, Sport Rentals……..EVERYTHING is within walking distance…..NO CAR NEEDED!!! This brand new 2700 sq ft... View all property information
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    Siesta Key, Florida 34242
    1 / 35
    4 of 5 stars (17) 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
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    2 BR. - 2 BA -- 4 Person Max. -- Small Garden -- Bay Front 6051 EPW is a Small Garden unit, located approximately 35 yards away from the Bay. 2 Bedroom / 2 Bath unit. Approx. 1100 Sq. Ft. (1200 including the lanai) Bedding: Master Bedroom: King Guest Bedroom: King Electronics:... View all property information
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    Siesta Key, Florida 34242
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Ocean Views
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    This beautiful high-tech home on 1 level UNIQUE created by a famous architect, is another advantage of being in a 5OOm beaches ranked among the five best in the world and located 200 m from the village (bars, restaurants, shops). From the living room and the kitchen you can enjoy direct pool and... View all property information
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    Siesta Key, Florida 34242
    1 / 23
    4 of 5 stars (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Location! Location! Location! Walk out the door, across the street and onto the #1 ranked beaches in America! This beautiful condo sleeps up to 6 people and has been newly remodeled from top to bottom including brand new appliances,granite counters,bedrooms,flooring, as well as a new bathroom. The... View all property information
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    Siesta Key, Florida 34242
    1 / 31
    5 of 5 stars (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Newer complex with a total of 38 units (two buildings) built in 2003 -Marina Del Sol- offering spacious 2,500 sq ft.- 3 bedroom, 2.5 bathroom luxury condo on the 2nd floor, elevator opening to your private foyer. Large kitchen w/ granite counters, marble master bath, master closet the size of a... View all property information
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    Siesta Key, Florida 34242
    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This second floor unit is in a deluxe triplex building that was just fully remodeled to near new condition throughout. It will accommodate 6 people in beds and two on a sleeper sofa, but you can add one or two of the large one bedroom units in the building if you have additional guests or family... View all property information
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    Siesta Key, Florida 34242
    1 / 25
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    View of Roberts Bay / Near Beaches / Great Shopping & Dining Get lost in the intoxicating relaxation of Siesta Key, in this luxurious private home. This tropical retreat is a single-family residence located at the end of a secluded dead end street in the opulent neighborhoods of northern Siesta... View all property information
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    Siesta Key, Florida 34242
    1 / 44
    5 of 5 stars (6) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    These Siesta Key deluxe townhouse rentals are located in the heart of Siesta Village - just a few steps to all the shops and restaurants and only 1 1/2 blocks (it takes us three minutes to walk) to the world famous Siesta Key Crescent Beach! Relax by your private pool. These Siesta Key townhouses... View all property information
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    Siesta Key, Florida 34242
    1 / 19
    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Lovely, fully updated 3 bedroom, 3 bath canal home 1 block from Siesta Village! Tropical private pool setting just off the main living area and the grand Master Bedroom. Second Master suite with private bath including soaking tub. All bathrooms completely redone in 2015. Quiet street literally... View all property information
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    Siesta Key, Florida 34242
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    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Oh what a great feeling you get when you are looking out over the pool to the relaxing waters of the Grand Canal. This home is special with 180 ft. of canal wrapping the back of the home so you get to enjoy the views from three bedrooms, the kitchen, living and two dinning areas. Open all the... 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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    • Pet-friendly
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    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
    1 / 39
    4.5 of 5 stars (7) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Ocean Views
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    • Pet-friendly
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    • x
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    • x
    About this property
    -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 / 24
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Balcony
    • Air Conditioning
    • Children's Pool
    • Terrace
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    • Pet-friendly
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    • x
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    • x
    About this property
    Enjoy the comfort and convenience of this spacious, first floor two-bedroom condo with a glass or screen-enclosed lanai and all the comforts of home. It's immaculate, beautifully decorated and offers a great value for your vacation stay. Sleeps 4 +. We are at 1344 Siesta Bayside Drive on beautiful... View all property information
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    Siesta Key, Florida 34242
    1 / 40
    5 of 5 stars (19) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    Our condo is on the second floor and is only 3 doors from the lovely pool, jacuzzi and fishing pier.In the summer months from May 1 - Nov 1 I offer a low rate of $850 .00 per week. In the mid winter rate goes up to $1200.00 per week and for the months of March and april the rate is $1600.00 per... View all property information
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    Siesta Key, Florida 34242
    1 / 41
    5 of 5 stars (49) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
    About this property
    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 / 30
    5 of 5 stars (9) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Across the street is our Private Access to one of the BEST beaches - Crescent Beach on Siesta Key.Gulf & Bay Club Bayside is a Resort complex of Key West style Town Homes all with one car attached garages. Gulf & Bay Club Bayside offers:* two heated pools* clubhouse with exercise/workout center and... View all property information
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    Siesta Key, Florida 34242
    1 / 25
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • x
    About this property
    Villa Margarita is a vibrant, festive newly decorated four bedroom/four bathroom/two kitchen home now available for vacation rentals with The Cottages. It’s the latest standout in our boutique collection of fine vacation homes now available for larger groups or families traveling together. Each... View all property information
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    Siesta Key, Florida 34242
    1 / 22
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Village West # 101 is the perfect place for your Siesta Key Vacation. With rentals by the day, by the week, or longer this location is sure to please. Our newly Remodeled Siesta Key Ground Floor Apartment is in the heart of the Village of Siesta Key. This apartment is well appointed and... View all property information
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    Siesta Key, Florida 34242
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
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    Central property, 1st & 2nd floor garden style unit with 2 Bedrooms and 2 Bathrooms. All rental properties are turn-key furnished and include washer & dryer. Internet access, beach access, tennis courts and exercise facilities available, access to two swimming pools. No pets are permitted on the... View all property information
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    Siesta Key, Florida 34242
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
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    2 BR. - 2 BA -- 6 Person Max. -- High Rise -- Gulf (in the distance) and Pool View 1255 - 503 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:... View all property information
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    Siesta Key, Florida 34242
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
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    2 BR -- 2 BA -- 4 person Max -- Small Garden -- Greenbelt View 1164 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... View all property information
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    Siesta Key, Florida 34242
    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
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    • x
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    • x
    About this property
    2 BR -- 2 BA -- 4 person Max -- Small Garden -- Greenbelt View 1158 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... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 21
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    1 Week Minimum Stay Required. Newly Upgraded 1BR/1 BA condo with full sleeper sofa and twin sleeper chair in LR. New Top of the Line King Size Bed will give you a great night sleep after a wonderful day at the beach and a great night in the village(2 miles from condo with free taxis,run on... View all property information
    Location Information
    Siesta Key, Florida 34242