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Vacation Rentals near Key Life Charters

8865 Midnight Pass Rd, Bayfront Marina, Siesta Key, Florida 34242-3838
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    Travelers to Siesta Key are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 100 Rentals in Siesta Key
    Siesta Key -  2bdrm on the beach - amazing views!!1 / 27
    (29)Excellent
    0.2 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Newly Renovated Waterfront Condo w/Beach Access1 / 21
    (3)Excellent
    0.3 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Gorgeous Direct gulf Front 2 Bedroom Condo on Siesta Keys... JUST REMODELLED1 / 31
    (11)Excellent
    0.5 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Quiet and Comfortable Condo Near Turtle Beach1 / 42
    (5)Very good
    0.2 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 15, 2018
    We really enjoyed our stay at Dana Z's condo. It was close to all the amenities on Siesta Key. The condo was quiet and peaceful. The water front gave us many enjoyable evenings...
    Reviewed February 21, 2018
    Great place, but needs some attention to the bed in master bedroom also a updated tv in the living room. I would recommend this place for older adults.
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    About this property
    Cozy Cove is a small condominium complex of six total units, located on the south end of Siesta Key in Sarasota, Florida. The complex sits on the Gulf side of the Key along Blind Pass. The complex itself is on the inlet with a dock at the back of the property where you will often see fish jump and...
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    Siesta Key, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Amazing Beachfront Condo, Siesta Key, 100ft+ Beach1 / 33
    (4)Very good
    0.2 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • Patio
    • Wi-Fi
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 19, 2018
    Siesta Key is our favorite domestic vacation spot. However, it has become a very popular, crowded, and loud spring break spot, especially at the public beach and the Village...
    Reviewed July 1, 2017
    We had the best vacation ever at this condo. Everything was clean and comfortable. The beach was beautiful an almost private. We enjoyed all The surrounding activities. Kayaking...
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    About this property
    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...
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    Siesta Key, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Getaway to Siesta Key. Low prices and walking distance to the beach. Free bikes.1 / 20
    (4)Very good
    2.0 miles from Key Life Charters
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
    Reviewed July 16, 2018
    This unit is amazing! There’s enough room for a family to stay comfortably and without worries if they forgot something. The unit has everything you need while on vacation! The...
    Reviewed July 13, 2018
    Totally loved this condo. Everything you need at your fingertips! Angel thinks of all the tiny things you may forget!! Location is perfect, short walk to the gorgeous beach and...
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    About this property
    Adorable, quiet, and clean home away from home on the South end of Siesta Key. Only a short five minute walk to beach at access 13, a more secluded area and away from the more crowded beaches. The king sized bed is extra comfortable with a flat screened tv, dressers, nightstands, fan, and walk in...
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    Siesta Key, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Beachfront Ground Level Suite - Remodeled - 2 king bedrooms1 / 40
    (5)Very good
    0.4 miles from Key Life Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Washer
    • Wi-Fi
    • Balcony
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 5, 2016
    If you are an avid beach goer, you're average rental experience probably includes lifting and lugging a million beach accessories and toys (if you have kids) for what seems like...
    Reviewed August 16, 2016
    This unit is literally 200 steps to the water. Fantastic ocean front appeal and it had literally the best master suite mattress that we've had in years for a vacation property...
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    About this property
    Leave your worries behind... If you're looking for a relaxing beachfront condo that's been totally remodeled you've come to the right place. Our ground-level oceanfront condo is the perfect place to unwind unplug and recharge the batteries. Fisherman's Cove is a quiet and relaxed complex on the...
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    Siesta Key, Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.2 miles from Key Life Charters
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located south Siesta Key with no busy streets to cross, it’s a leisurely stroll to the Gulf of Mexico and to Point of Rocks, the best snorkeling beach on the Key. There are many restaurants, lots of shopping, bike rentals, ice cream shops, beach equipment, etc., in a very beachy atmosphere. It’s...
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    Siesta Key, Florida
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Honey Mango Cabana – 2/1, Shared Heated Pool, Near Beach Access1 / 24
    (1)Excellent
    2.1 miles from Key Life Charters
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Honey Mango Cabana! This beautiful and vibrant 2 bedroom, 1 bathroom vacation home accommodates up to 6 people. This property is very unique as it is one half of 'Mango Manor,' which is comprised of the two separate cabanas, Honey and Juicy Mango. This provides a fantastic and unique...
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    Siesta Key, Florida
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.2 miles from Key Life Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Wi-Fi
    • Porch
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Turtle beach was just re-nourished in March 2016!! Come enjoy the great new beach at Fisherman's Cove! Leave your worries behind... If you're looking for a relaxing beachfront condo that's been totally remodeled you've come to the right place. (all new photos -just uploaded!) Our ground-level...
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    Siesta Key, Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.8 miles from Key Life Charters
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Private Yard
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to your own secluded tropical oasis. Lush island landscaping surrounding the property makes this home a unique and private setting. Private dock on protected cove 2 minutes from Sarasota Bay/ICW. Rent a boat at neighboring marina if you choose. Breathtaking large private pool, with numerous...
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    Siesta Key, Florida
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    0.9 miles from Key Life Charters
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    • Waterfront
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Ringling bungalow has a private deck area off the front of the bungalow overlooking pristine Heron Lagoon that includes two chaise lounges. This bungalow includes a full kitchen including a microwave, coffee pot, toaster, oven, and fridge. The bungalow has a queen bed in the...
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    Siesta Key, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2.1 miles from Key Life Charters
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Private Yard
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Buccaneer's Hideaway! Tucked away in this pirate's hidden cove, you will find a tranquil retreat that will soothe your soul and revitalize your life's passion for finding your next treasure! Sometimes life's high seas can take their toll on you, and escaping to your private cove for rest...
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    Siesta Key, Florida
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Flip Flop Cottages Siesta Key Florida1 / 42
    (2)Average
    0.5 miles from Key Life Charters
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Patio
    • Porch
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 22, 2015
    Nice overall for what we needed-good location for beach hoppers like ourselves. Could get to Lido beach and turn around and go to Venice beach with still many beaches between...
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    About this property
    YOUR PRIVATE GETAWAY ON THE KEY ASK ABOUT OUR SUMMER SPECIALS!!!!!!!!! Does not include Weekends or Holidays!!! Looking to relax, Flip Flop Cottages is the place to be for a quaint and private vacation in Siesta Key, Florida. Come and stay at our serene environment and enjoy and visit all the...
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    Siesta Key, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2.1 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Juicy Mango Cabana! This beautiful and vibrant 2 bedroom, 2 bathroom vacation home accommodates up to 6 people. This property is very unique as it is one half of 'Mango Manor,' which is comprised of the two separate cabanas, Juicy and Honey Mango. This provides a fantastic and unique...
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    Siesta Key, Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.0 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
    • Waterfront
    • Washer
    • Ocean Views
    • Patio
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely private Gulf of Mexico Frontage vintage home... this is a lovingly maintained private home, the home features an all wood tongue and groove interior reminding us of a New England camp. The home has extensive rear oceanfront sun decks leading to a large private gazebo, on a bluff, overlooking...
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    Siesta Key, Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.0 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to La Estrella Casita! This gorgeous freshly remodeled beach casita is the perfect getaway for you and your closest friends and family! Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and...
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    Location Information
    Siesta Key, Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.1 miles from Key Life Charters
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casita Morning Star! Our newly renovated luxury cottage (completion date of June 2017) has all the amenities your family [up to 10] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout gorgeous and decadent bathrooms, new appliances, new washers/dryers,...
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    Siesta Key, Florida
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    2.1 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    The Coral Reef and Star Fish Casitas are two separate units which can be uniquely configured to create Villa Dom Bisa, features its own brand new, private heated pool with “sun shelf” and a three minute walk to the Nation’s finest beach [no major streets to cross]. Please Note: These units [Coral...
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    Location Information
    Siesta Key, Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.1 miles from Key Life Charters
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to the Sandy Cabana! Please Note: Sleeps 8- K, K, Q, QAB These units [Sandy Cabana & Seahorse Cabana] can be rented separately. Combined, these units are called: Sandy Seahorse Cottage (Sleeps 16) If one unit is not available, please contact us for the availability of the other! The...
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    Siesta Key, Florida
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2.1 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Central Heating
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    1000 square feet This gorgeously remodeled beach casita is the perfect getaway! Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest needs. The décor is beautifully done and inspired by the soft...
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    Location Information
    Siesta Key, Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2.1 miles from Key Life Charters
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to the Seahorse Cabana! Please Note: Sleeps 8: K, K, 2T, QAB (queen air bed) These units [Sandy Cabana & Seahorse Cabana] can be rented separately. Combined, these units are called: Sandy Seahorse Cottage (Sleeps 16) If one unit is not available, please contact us for the availability of...
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    Siesta Key, Florida
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2.1 miles from Key Life Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gorgeously remodeled beach casita is the perfect getaway! Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest needs. The décor is beautifully done and inspired by the soft tones of the...
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    Location Information
    Siesta Key, Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.3 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This prime END UNIT is bright and airy with its extra windows! Its corner lanai (screened porch) overlooks both the Gulf (West), and Turtle Beach (North)! It’s right NEXT TO THE BEACH, park, and picnic area, on a scenic lagoon, and comes with a boat dock for your water toys. Three popular...
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    Location Information
    Siesta Key, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.2 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Grill
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    • Waterfront
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Siesta Key, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.1 miles from Key Life Charters
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Retreat to this amazing “Sea”-cluded gem tucked into the lovely Bianco Sands complex- just a short stroll to the warm sands of Crescent Beach and the lively Crescent Village. Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week...
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    Location Information
    Siesta Key, Florida
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sea Shell Casita- Amazing 2BR Heated Pool Casita, Near Beach Access [Sleeps 6]1 / 20
    (6)Excellent
    2.1 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed February 27, 2017
    We really enjoyed our time at the Sea Shell Casita. It was welcoming and we had help whenever we needed it - like when my mom had a shell fall down the garbage disposal! The...
    Reviewed May 16, 2016
    The owners of the Sea Shell could not have been anymore accommodating. The pool and the smell of the Honeysuckle growing was very special and the grounds were really beautiful...
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    About this property
    The Sea Shell and Sea Wave are two separate units which can be uniquely configured to create Villa Brisa Marina, an absolutely beautiful and stunning private pool home. Please Note: These units [Sea Shell & Sea Wave] can be rented separately. Combined, these units are called: Villa Brisa...
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    Location Information
    Siesta Key, Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Enchanting Toes In The Sand Gulfront Condo1 / 24
    (17)Excellent
    0.1 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Waterfront
    • Internet Access
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 23, 2018
    Our stay was perfect! Beautiful location, directly on beach, everything you need!! Sarasota is a good location as well. Nice affordable restaurants near by. Hope to return!! The...
    Reviewed July 13, 2017
    Great location. Very clean appartment. Two very spacious bedrooms each with on suite. There were five of us and my 6 year old daughter slept on the pull out sofa in the lounge...
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    About this property
    Your gulf-front vacation home in a magical, paradise cove awaits you. Located directly on beautiful Turtle Beach in Siesta Key and just steps away outside your door. There is no other resort complex like this that is so close to the beach! You’ll awaken to the energizing sight of the sun and the...
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    Location Information
    Siesta Key, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Mango Manor - Vibrant 4/3, W/Heated Pool, Right By Beach Access #13 [Sleeps 12]1 / 26
    (1)Excellent
    2.0 miles from Key Life Charters
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
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    • Air Conditioning
    • Cable/satellite TV
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 3, 2018
    Very practical. 2 separate units that realistically can sleep 10. Nice kitchens. You have your own gated pool [like a house pool]. The units have bikes and beach wagons. You are...
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    About this property
    Welcome to the Mango Manor! This beautiful and vibrant 4 bedroom, 3 bathroom vacation home accommodates up to 12 people, with a fantastic and unique configuration that allows for large families traveling together to enjoy some well deserved togetherness as well as a little self-indulgence when the...
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    Location Information
    Siesta Key, Florida
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    2.1 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Sea Wave and Sea Shell are two separate units which can be uniquely configured to create Villa Brisa Marina, an absolutely beautiful and stunning private pool home. Please Note: These units [Sea Wave & Sea Shell] can be rented separately. Combined, these units are called: Villa Brisa Marina...
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    Location Information
    Siesta Key, Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.8 miles from Key Life Charters
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
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    • Private Outdoor Pool (Heated)
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    An inviting and charming private home, Florita's Key is tastefully designed with three (3) bedrooms, two (2) baths, open floor living and dining room, full gourmet kitchen, plenty of storage room and upscale furnishings for your comfort all throughout! Florita's Key is configured for maximum...
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    Location Information
    Siesta Key, Florida
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Ground Floor1 / 44
    (5)Excellent
    0.2 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 16, 2018
    This was our first trip to Siesta Key and we loved it! The condo was nicely set up and as close to the ocean as you could get without being in it. You walked out the back door...
    Reviewed July 16, 2016
    Great condo right on beach with everything you need for you vacation. We really enjoyed our stay and will be back. Thank you!
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    About this property
    Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL   Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views.  The building is one of the closest condos to the...
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    Location Information
    Siesta Key, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.2 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Cable/satellite TV
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    • Balcony
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island Reef is a magnificent condo facility located towards the southern end of Siesta Key. This top floor unit offers captivating views of the Gulf of Mexico, nearly 1450 sq ft of living space, two bedrooms and two bathrooms. The master bedroom has a king size bed, access to the balcony, and...
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    Location Information
    Siesta Key, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.1 miles from Key Life Charters
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Air Conditioning
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    • Private Outdoor Pool (Heated)
    • Grill
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Cascada is a uniquely configured private home featuring a heated pool/waterfall, 4 bedrooms, 4 bathrooms that sleeps 12, with 2 living areas and 2 kitchens and an almost unbelievable pool courtyard surrounded by lush gardens and a tall privacy wall enclosing the entire property. Each of the...
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    Location Information
    Siesta Key, Florida
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    0.9 miles from Key Life Charters
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Hibiscus bungalow has a sitting area off the front of the bungalow that includes two wicker chairs overlooking our courtyard area. A second door from the bungalow enters to the back parking area. This bungalow includes a full kitchen including a microwave, coffee pot, toaster, oven...
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    Location Information
    Siesta Key, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Clean beach condo discounted now. All new. 2/2 walk to the beach, free bikes1 / 26
    (1)Excellent
    2.0 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 13, 2018
    I’ve stayed in siesta key over 50 times in different rooms and the last 10 or so have been at island time rentals clean modern everything you can imagine is there at you...
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    About this property
    This meticulously spotless, brand new renovated condo is finally ready for booking. It is located upstairs. It has 2 bedrooms and 2 bathrooms, king and queen both with huge walk in closets and private bathrooms. Very bright and light and decorated in a tropical & modern decor. Huge kitchen with...
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    Location Information
    Siesta Key, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Beachfront - 1-Bedroom Condo at Fisherman's Cove - Free Boat Docks -Ground level1 / 42
    (31)Excellent
    0.2 miles from Key Life Charters
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Grill
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 19, 2018
    This unit is directly on the beach...literally step outside the door on the lanai and your feet are on the beach. There is a view of the ocean from every room in this condo. The...
    Reviewed June 8, 2018
    We can’t say enough great things about this condo! It’s like your little piece of heaven right outside your door. It was supplied with so much and especially the beach items...
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    About this property
    Beachfront - One Bedroom Condo at Fisherman's Cove - Free Boat Docks     Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL   Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views.  The building is one of the closest...
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    Location Information
    Siesta Key, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Ground Floor1 / 31
    (7)Very good
    0.1 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Grill
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 3, 2017
    It was a great place, nicely equipped to enjoy the beach! Had sand toys, chairs and even beach towels!! Totally would recommend!
    Reviewed August 21, 2017
    Room was very clean and had a little bit of everything you need. It was actually nicer than what we had expected from the pics online when booking. Boat docks in great shape...
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    About this property
    Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL   Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views.  The building is one of the closest condos to the...
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    Location Information
    Siesta Key, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED1 / 44
    (26)Very good
    0.2 miles from Key Life Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 12, 2017
    Each year we have a “ladies week” at the beach with my mother, sisters, and cousin. This is the second year that we have stayed at Fisherman’s Cove. The complex is quiet and...
    Reviewed March 23, 2016
    The Sarasota area is so convenient. The condo was perfect for the 5 of us. All the necessities plus a few extras like beach chairs and coolers. The condo was clean. The...
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    Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks – Upscale – Siesta Key Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL   Top beachfront unit at Fisherman's Cove!!  Fisherman's Cove is a very rare Siesta Key condo where every unit has direct,...
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    Location Information
    Siesta Key, Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key1 / 35
    (10)Excellent
    0.1 miles from Key Life Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 6, 2018
    The property was in a great location and we had a beautiful view! Loved the ocean view from the enclosed front room and the harbor view from the door! Walked the beach and...
    Reviewed June 8, 2018
    Awesome location on the beach-but not far from Siesta Beach! The FREE trolley that runs from Turtle Beach to Siesta Beach, The Village and anywhere in between was a major bonus...
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    About this property
    Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks – Upscale – Siesta Key Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL   Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views.  The building is one...
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    Location Information
    Siesta Key, Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2.0 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to La Perlita Casita! This gorgeous freshly remodeled beach casita is the perfect getaway for you and your closest friends and family! Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest...
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    Location Information
    Siesta Key, Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.9 miles from Key Life Charters
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Housekeeping Included
    • Waterfront
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Pineapple bungalow has a sitting area off the front of the bungalow that includes two wicker chairs overlooking the courtyard area. A second door from the bungalow enters to the back parking area. This bungalow includes a full kitchen including a microwave, coffee pot, toaster,...
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    Location Information
    Siesta Key, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.0 miles from Key Life Charters
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Sauna
    • Waterfront
    • Air Conditioning
    • Housekeeping Included
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully decorated Bayfront Condo with awesome views. Look out over the little Sarasota Bay and catch the sunrise and all the activity or sit in the kitchen and look out over the ocean only a few hundreds yards away and watch the sunset. It's the best of both worlds! Turtle beach is...
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    Location Information
    Siesta Key, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Upscale1 / 29
    (12)Very good
    0.2 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 8, 2018
    10 years with sunnyside properties at fisherman's cove. two building 3-story condo complex with gated entry and private pool. very private, very quiet and very convenient to...
    Reviewed February 24, 2018
    This unit was perfect for us. It was very private location at the end of the cove. It has two new gas grills at the end of each building. The interior of unit was updated and...
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    About this property
    Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL   Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views.  The building is one of the closest condos...
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    Location Information
    Siesta Key, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.9 miles from Key Life Charters
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Housekeeping Included
    • Waterfront
    • Patio
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Dolphin bungalow has a sitting area off the front & back of the bungalow that includes two white wicker chairs. This bungalow includes a full kitchen including a microwave, coffee pot, toaster, oven and fridge. The bungalow also has a sleeper sofa in the living room, and a queen...
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    Location Information
    Siesta Key, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Turtle Beach1 / 39
    (21)Very good
    0.2 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Internet Access
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 10, 2018
    Bring a bathing suit, hat and suntan lotion. Stop at Publix (just over the bridge) before arriving or when out eating or beach hopping, and pick up food supplies. That is all...
    Reviewed August 23, 2017
    We loved our stay at Fisherman’s Cove and would not hesitate to return. At first we were looking for a condo on Siesta Beach and we’re glad we changed our mind. Siesta beach...
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    About this property
    Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL   Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views.  The building is one of the closest condos to the Gulf...
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    Location Information
    Siesta Key, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.9 miles from Key Life Charters
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Waterfront
    • Housekeeping Included
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Coquina bungalow has a sitting area off the side of the bungalow that includes two white wicker chairs. This bungalow includes a full kitchen including a microwave, coffee pot, toaster, oven, and fridge. The bungalow also has a sleeper sofa in the living room, and a queen size...
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    Location Information
    Siesta Key, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2.1 miles from Key Life Charters
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Hibiscus and Orchid Villas are two separate units which can be uniquely configured to create Villa Cascada, an absolutely beautiful and stunning private pool home. Please Note: These units [Hibiscus & Orchid] may be rented separately. Combined, these units are called: Villa Cascada (Sleeps 12)...
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    Location Information
    Siesta Key, Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.0 miles from Key Life Charters
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Grill
    • Parking
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casita Sun Star! Our newly renovated luxury cottage (completion date of June 2017) has all the amenities your family [up to 8] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout gorgeous and decadent bathrooms, new appliances, new washers/dryers, quartz...
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    Location Information
    Siesta Key, Florida
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key1 / 29
    (19)Very good
    0.2 miles from Key Life Charters
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 26, 2017
    We stayed on the 3rd floor with three bedrooms. It was a nice place and clean.We had a great time and enjoyed the ocean sounds coming through the screen when we opened them...
    Reviewed July 28, 2015
    We loved our stay at Fisherman's Cove! We don't like a lot of crowds when we take our beach vacation, so this was perfect for us. There was very little 'beach' left due to...
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    About this property
    Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks – Upscale – Siesta Key Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL   Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views.  The building is one...
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    Location Information
    Siesta Key, Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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