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Siesta Key Luxury Holiday Homes

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    Travellers to Siesta Key are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    136 Matching Rentals in Siesta KeyView all 912 rentals
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    8 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    6 Bedroom 4 Bathroom house   New pool  Siesta Key Florida  Walk to the Beach1 / 32
    (1)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Reviewed 13 July 2017
    Excellent all-around. Owner was very responsive and friendly. House was clean and in great condition upon arrival, and even bigger than expected! To top it all off, it was...
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    About this property
    Siesta Sun Villa Our home is one large house that has a 3 bed 2 bath unit. A 2 bed 1 bath unit and a 1 bed 1 bath unit. All with connecting doors so you can rent the whole house to sleep 12 guests all in beds. It is perfect for large familys, Weddings and reunions. Private back yard, Overlooking a...
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    Siesta Key, Florida 34242
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Grill
    • Internet Access
    • Hot Tub
    • Terrace
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>No better deal around! Top of the line on Siesta Key! It really doesn't get any better than this. This 2 bedroom / 3 bathroom unit has all the top of the line finishes that you would expect, such as Wolf gas stove, Sub Zero refrigerator, flat screen TVs in all rooms,...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    New 6 Bedroom, Luxury Home in Gated Community1 / 22
    (1)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
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    • Waterfront
    • Air Conditioning
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2017
    View from master bedroom was fantastic. Plenty of room for the 14 of us. Will defiantly book again. Kitchen had all appliances needed. Grill was old and had to light with a...
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    About this property
    Perfectly located, New, 6 bedrooms 4 1/2 bathrooms private home,in a gated community, combines luxury with convenience of location. We offer you a large 6000sf+ home within a short distance to the pristine beaches of Siesta Key and walking to the Village, Restaurants, shops and nightlife. Privacy...
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    Siesta Key, Florida 34242
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    The Banyan - A Tropical Retreat in Paradise1 / 25
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    Reviewed 27 April 2018
    The Banyon is a remarkably beautiful and comfortable home. There are many private seating areas inside and out. The kitchen is fully equipped; the beds are very comfortable and...
    Reviewed 12 August 2017
    We loved this place! It was so private you felt like you were in your own world with the surrounding trees and tropical landscaping, yet close to most everything. The home was...
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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...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    636ontheKey - The 'Belle of the Beach'1 / 15
    (7)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Patio
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    • Ocean Views
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4,000 SQ FT BEACHFRONT HOME 1/2 mile from Village! 4 Bedroom + Media Room - 5 Bathroom - Sleeps up to 14 and is ON THE BEACH!!! NOTE: Our home is NOT listed on Craig's List. If it is represented there it is fraudulent. Located directly on the beautiful white sands of Siesta Beach! 636...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 14
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    8 Bedrooms, 6 Bathrooms, Sleeps 24 Quick View
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    • Grill
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to The Abalone! Our newly constructed luxury cottage has all the amenities your large group [up to 24!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing from the ground floor, gorgeous...
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    Siesta Key, Florida 34242
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 24
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    8 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to The Conch! Our newest luxury cottage has all the amenities your large group [up to 24!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing from the ground floor, gorgeous and decadent...
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    Siesta Key, Florida 34242
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 12
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    8 Bedrooms, 6 Bathrooms, Sleeps 24 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to The Big Kahuna! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 24!!!] can fathom. It also boasts the very BEST location, in the heart of Siesta Key Village, just behind Gilligan's and Lelu's Coffee Shop! Inside you’ll...
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    Siesta Key, Florida 34242
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 24
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    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Balcony
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to The Nautilus! Our newly constructed luxury home is now accepting reservations. Our array of amenities and easy access to Point of Rocks Beach creates an ideal setting for large families or groups with up to 24 people. Inside you’ll enjoy contemporary porcelain wood style flooring...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Private Outdoor Pool (Heated)
    • Waterfront
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 Bedroom Beachfront Pool Home. Closest house to the beach on Siesta Key! 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. Siesta Key Paradise is nestled within walking distance of...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    DIRECTLY ON NUMBER ONE RATED BEACH IN THE USA SIESTA BEACH!!! 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. Beachfront home on Siesta Key Sunset Point. Siesta Key Beach is the...
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    Siesta Key, Florida 34242
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Balcony
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    Pet friendly
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    Smoking allowed
    About this property
    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 private residence is simply...
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    Siesta Key, Florida 34242
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Garden
    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 6 BED , 3 BATH Home is a Gorgeous Gated Residence ! Just steps from World Famous Siesta Key Beach . Perfect location between the Village and a main entrance to Siesta Key Beach!! Bar's, Restaurants, Shopping, Sport Rentals……..EVERYTHING is within walking distance…..NO CAR NEEDED!!! This new...
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    Siesta Key, Florida 34242
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    Luxury Siesta Key Four Bedroom,Five Bathroom Pool Home,180 Yards to Siesta Beach1 / 23
    (2)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
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    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 October 2018
    We had 4 adults, 5 children and a small dog. What a magnificent home. We were very impressed with the cleanliness, the beauty, and all the amenities the home offered. A...
    Reviewed 7 August 2018
    Our family looked at several homes in Siesta Key and settled on this one due to its convenient location to the public beach entrance along with direct access to the canal. We...
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    About this property
    This Luxury Four Bedroom, Four and a Half Bathroom Home will leave you breathless as you enter. There are not many large rental homes, this close to Siesta Beach, that live like this home. Most Rentals by the beach have their living area 16 feet above the ground level and the pool below, which is...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Central Heating
    • Balcony
    • Terrace
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEWLY CONSTRUCTED MODERN/CONTEMPORARY - SIESTA KEY BEACH RESIDENCE; a must-see, rare new construction on Siesta Key, much sought after modern and contemporary design, 4 Bedrooms/6 Bathrooms-Sleeps 12. Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Sunset Point Siesta Key FL  AWESOME RENTAL !!1 / 27
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    • Sauna
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 August 2017
    Could not have a better location. Steps from the sand with the village in walking distance. The beach house is a great place to stay. Everything you need. We very much enjoyed...
    Reviewed 8 July 2017
    This location is absolutely perfect! It is on the most beautiful beach and steps to an adorable village with several restaurants, shops and all the amenities you could need. It...
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    About this property
    Beach and water front on Gulf Of Mexico. A block from Siesta Key Village for lite and fine dinning, fun, shopping and nightlife. Two Master Suite King Bedrooms with Master Bath for each. Sauna, four Mexican tiled decks with panoramic views of the Gulf and beaches. Fishing Pier. Leather, stone...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Gorgeous Views of the Gulf Sea Turtle Unit Sunset Beach Resort1 / 24
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
    Reviewed 19 July 2018
    This is an amazing location. If you want to step out of your room on to Siesta Key sand this is the spot! We enjoyed our weekend getaway and will definitely be back!
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    About this property
    Directly overlooking the gulf, this designer decorated unit is literally steps to Siesta Beach. This unit has 3 bedrooms each with a queen bed, and couch set up can accommodate 2 and 2 full baths. Open plan living and dining area with spectacular views of the beach. Full size kitchen with...
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Small family owned resort that spares nothing to make your vacation one you will remember and want to repeat year after year! We pride ourselves in the details and personalized attention! Views of the gulf can't be beat from this second floor 2 bedroom, 2 bath plus den, beach front unit. Designer...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    Beautiful Duplex located 1 house away from beach! Amazing Location! These beautifully decorated duplexes feature all the conveniences of home with a fully equipped kitchen and linens provided. The duplexes sleep 16 and are equipped with a king in the master bedroom, a queen and 2 twins in the guest...
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    Siesta Key, Florida 34242
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Internet Access
    • Hot Tub
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    • Balcony
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 2 bedroom 2 bath condo right on Beach Rd! Just a short walk across the street to the beach, and only a block away from the Village. This gated community offers private balconies off the living room and the master bedroom. Enjoy your mornings overlooking the pool area, or the evenings...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    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 Admirals Watch! This beautiful, luxurious and modern 3 bedroom, 3 bathroom, heated pool, townhome boasts the best views of the world famous No. 1 Siesta Key Beach Access! With absolutely unobstructed views, this home is part of only a handful of private residences that can claim such...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa1 / 38
    (7)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2018
    My family with extended family(total of 8) shared this large home with 5 bedrooms and we had plenty of room and at same time all had our privacy when we wanted it. The kitchen...
    Reviewed 2 April 2018
    Perfect location. Very close to the beach and downtown. The sliding kitchen windows opening to the counter bar in the screened in pool and hot tub area made eating in so fun...
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    About this property
    Excellent location at only 120 Yards To The Cool White Quartz Sand Of Siesta Beach! ?This Home Has Water Frontage, Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway. This Home Entertains Excellent Because The Pool Area Is...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Condo C611 at the Gulf & Bay Club. Our first trip to Sarasota was during Thanksgiving in 2013. While visiting friends in Sarasota my wife and I fell in love with this area of SW Florida, so much so that we purchased this 3 bedroom corner unit before leaving the area and returning home....
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
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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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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy the relaxed vibe of Siesta Key! The beautiful white sand beaches that make Siesta Key the #1 beach in the US are not even a five-minute stroll away. Siesta Key Village and the famous 3 miles of the softest 99.9% quartz sand beaches draws thousands to enjoy the island life. This two...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa de Mariposa! This gorgeous property is comprised of two units, Monarch and Peacock Villa which are both mirror images of one another. Each unite features a 3 bedroom, 3 bathroom configuration with their very own common space to include a kitchen, dining area, private balconies, and...
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    Siesta Key, Florida 34242
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Location, Location!!! Come relax, our beautiful home is only 2.5 miles from the #1 beach in the US, Siesta Key!! It has northern charm with wood burning fireplace, wood floors and a florida cottage feel! Beautifully landscaped backyard, fenced in and private. Brand new kitchen, with overized eat...
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    Location Information
    Siesta Key, Florida 34231
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    PRISTINE SIESTA KEY VILLAGE HOME1 / 28
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Air Conditioning
    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    It was a perfect week for us in a perfect House.Great style and interior and we could use the bikes and kayak. Walk distance to the nice restaurants and the beach. We will...
    Reviewed 29 August 2017
    Beautiful accommodation, superbly located and very well equipped. The new swimming pool is the jewel in the crown, and Cydney was a pleasure to deal with. We would hope to go back.
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    About this property
    Hidden behind a contemporary privacy wall, enter into our front yard oasis. The perfect setting for tanning, dining and entertaining alongside the waterfall feature. Extensive renos offering a stunning gourmet kitchen, updated bathrooms, flat screen tv's in bedrooms and the most appealing Lanai...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Siesta Key’s only luxury hotel. Sitting directly on Siesta’s Quartz Beach that offers the whitest and softest sand in the World that’s always cool to the touch. Relax and make your memories is all that’s required but just minutes to down town’s rich art and cultural community. In the village of...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Washer
    • Patio
    • Ocean Views
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE BEST BEACH HOUSE SIESTA HAS EVER OFFERED, GUARANTEED!! DIRECT GULF FRONT! Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and 7-day week office(s) for your convenience and guest needs. When you dream of a Beach House that sits on the whitest & most soft sand in the...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Hot Tub
    • Ocean Views
    • Washer
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just across the street from the #1 Beach in the USA!! 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. Stunning Three Bedroom Two Bath with Private Pool and jacuzzi on Siesta...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Siesta Key Beachfront 3 Bedroom Home, Sarasota1 / 33
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Cable/satellite TV
    • Internet Access
    • Grill
    • DVD Player
    • Air Conditioning
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 September 2018
    We had a wonderful stay at Siesta Keys Florida. David ‘s home is beautiful and well maintained. It does have several bests of steps if you have any kind of handicap. My husband...
    Reviewed 30 January 2018
    This is a very nice three story three bedroom house. The first floor includes two separate garages with the house entrance in between. The second floor includes a spacious...
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    About this property
    Description:Walk out the back door to the clean white sand of Siesta Key Beach. This home has private Siesta Key beach frontage on the prime section of beach, there are no homes between you and the beach. Nearly every room has a full view of the beach. The entire back of this house opens with...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Parking
    • Terrace
    • Internet Access
    • Balcony
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gorgeous contemporary home offers all the luxuries that a beach house can possibly offer! Tastefully decorated with cathedral ceilings; offering lots of open space. A tranquil garden patio with a fountain is the perfect place to enjoy your morning coffee and right on the other side of their...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bd Waterfront Home w/Pool, Close to Siesta Beach1 / 37
    (9)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Cable/satellite TV
    • Parking
    • Patio
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 April 2018
    This newly renovated, spacious home was ideal for my guests. Best neighborhood on Siesta Key. Loved pool and expansive canal location.
    Reviewed 22 February 2018
    The home we rented on Siesta Key was amazing. It was a perfect fit for my family of 7! It was a quick walk to the beach and or you could spend the day relaxing by the pool...
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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 188 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...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedroom with Gulf View Siesta Key FL Beach Fun1 / 14
    (20)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Sauna
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2018
    We were fortunate to get this awesome rental and Richard was a pleasure to deal with. The location was perfect and the free trolley out front made it easy to get around. Will...
    Reviewed 16 August 2017
    Would highly recommend this large condo for larger family gatherings. We had 10 family members with us and the layout of the condo made it very easy to stay for the week...
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    About this property
    Enjoy our 4 bedroom, 3-1/2 bath condo with a Full Gulf view that is 75 steps from the world famous white sand of Siesta Beach. We have remodeled and updated both the kitchen and bathrooms with granite and new cabinetry and vanities. Add our 50-foot pool, sauna, and work out room all on site with...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    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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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Children's Pool
    • Balcony
    • Washer
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quiet and serene, but close to local attractions, you will love this large 4 bedroom, family friendly home with 2 kitchens, new appliances, modern furnishings, and beach buggy with all the gear! Separate living areas can accommodate one large family or two smaller ones. Each living area has its...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Antilles! Our newly constructed luxury cottage has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing from the ground floor,...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    • Air Conditioning
    • Parking
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Washer
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Eulimia! Our newly constructed luxury cottage has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing from the ground floor,...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Ohana! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 12!!!] can fathom. The location is THE premier location in the heart of Siesta Key Village, just behind Gilligan's and Lelu's Coffee Shop! Inside you’ll enjoy...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Balcony
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    • Washer
    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Stolida! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Coquina! Our newest luxury cottage has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing from the ground floor, gorgeous and...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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    Casa Junonia - 4BR/3BA Private Home, Heated Pool, Private Cabana, Walk to Beach1 / 39
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Balcony
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2018
    This home was absolutely stunning and beautifully furnished throughout. Only a couple of minutes walk to the beach. The private pool was a real bonus. The free trolley service...
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    About this property
    Welcome to Casa Junonia! Our newly constructed luxury cottage has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing from the ground floor,...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Washer
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Mahalo! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 12!!!] can fathom. The location is THE premier location in the heart of Siesta Key Village, just behind Gilligan's and Lelu's Coffee Shop! Inside you’ll enjoy...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Villa Vista Mare - Luxurious 3BD/3BA Beachfront, Heated Pool1 / 31
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Washer
    • Cable/satellite TV
    • Hot Tub
    • Patio
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 April 2017
    Great spot right across from the beach - which is about the best beach you'll ever see. Pool offers a nice change of pace. Panaramic view from the entire living area and the...
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    About this property
    Welcome to Villa Vista Mare! This beautiful and luxurious 3 bedroom, 3 bathroom, heated pool, townhome boasts the best views of the world famous No. 1 Siesta Key Beach Access! With absolutely unobstructed views, this home is part of only a handful of private residences that can claim such gorgeous...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Washer
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Tegula! Our newly constructed luxury cottage has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing from the ground floor, gorgeous...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    The Grand Canal Cottage - 5/4 Waterfront, Heated Pool, Spa, Dock, Near Beach1 / 51
    (3)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Not sure where to begin. But this was an amazing seven day experience in Siesta Key. My mom and step dad rented the house for their 20th wedding anniversary. It just so happens...
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    About this property
    The Grand Canal Cottage, perhaps one of Siesta Key’s favorite luxury vacation homes, is a highly landscaped canal-front private luxury home featuring a heated pool with sun shelf and a separate 8-person spa. It is situated on Siesta Key on the beach side of the canal system within two easy walking...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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