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Siesta Key Beach Rentals for Weddings

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    Travelers to Siesta Key are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    18 Matching Rentals in Siesta KeyView all 759 rentals
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    NEW POOL! 3 Bed 2 Bath on Siesta Key  JULY 4TH  AVAILABLE  Walk to beach POOL1 / 18
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    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
    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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    Siesta Key, Florida 34242
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 14 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 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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    Siesta Key, Florida 34242
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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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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    • Parking
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 12, 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
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 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 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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    Siesta Key, Florida 34242
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    • 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
    Rental Home - 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)
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    • 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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Grill
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    • Air Conditioning
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    • Private Outdoor Pool (Heated)
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    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 34242
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    8 Bedrooms, 6 Bathrooms, Sleeps 24 Quick View
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    • Grill
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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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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 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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    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Washer
    • Parking
    Suitability
    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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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 8 Bedrooms, 6 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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Luxury Romantic Oceanfront Siesta Beach Condo #3041 / 33
    (26)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Grill
    • Washer
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 9, 2018
    We had a wonderful stay in this unit. As soon as we arrived and saw the incredible view of the beach, we were mesmerized. You can see the beach from every room (even when the...
    Reviewed June 21, 2018
    Loved my Siesta Key stay at this condo ! The view and proximity of the beach were wonderful. The white sand was not hot on our feet and the water was clear and beautiful ! It...
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    About this property
    Find Sarasota Vacation Rentals on FlipKey Here’s 20 Main Reasons Why Our Unit is the Perfect Place for a Siesta Key Vacation 1. Take the elevator to the 3rd floor. Open the door to our unit 304. Experience an unforgettable 3rd floor vantage point...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    8 Bedrooms, 6 Bathrooms, Sleeps 24 Quick View
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    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Washer
    Suitability
    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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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 8 Bedrooms, 6 Bathrooms, Sleeps 24
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Balcony
    • Patio
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Grill
    Suitability
    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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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • 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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Siesta Key Flight and Weather Info
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    85° 70°
    August
    84° 69°
    September
    79° 63°
    October

    Additional Siesta Key Info

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    • Local time: 06:45 PM (EDT)
    • Peak travel: March - April
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