Siesta Key: Vacation Rental By Owner

Showing 20 Of 567 Vacation Rentals
  • Property-1 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (5) Exceptional
    Siesta Key, FL

    FULL BAY VIEWS FROM THIS 1ST FLOOR UNIT. YOU CAN’T GET ANY CLOSER TO THE BAY THAN THIS. Sit on your screened in Lanai while you watch the boats and wildlife.... ...more

  • Property-2 Image 1
    Condo $416 / Nightly
    • 2 Bed
    • 2 Baths
    • (25)
    Siesta Key, FL

    OPEN FOR RENTALS! You can't get much closer to the water than this! STEPS to the sand with stunning Siesta Beach views from every room! The Gulf seems to surround... ...more

  • Property-3 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 2 Baths
    Siesta Key, FL

    Miles and miles of white sand from the gentle waves of the Gulf of Mexico Our 1200 sq ft 2 bedroom 2 bathroom unit has an updated kitchen with plenty of space to... ...more

  • Property-4 Image 1
    Condo Select Dates for Price
    • 1 Bed
    • 1 Baths
    Siesta Key, FL

    Spacious 1 bedroom/1 bathroom 2nd floor condo with additional loft spaces right at the end of a quiet cul de sac on Siesta Key. View of the Gulf of Mexico from... ...more

  • Property-5 Image 1
    Condo $255 / Nightly
    • 2 Bed
    • 2 Baths
    • (4) Excellent
    Siesta Key, FL

    Beautiful 2 bedroom, 2 bath SPLIT PLAN ; both bedrooms have full Gulf views! Tile floors, updated vanity & granite counters in Master bath, walk-closets in both... ...more

  • Property-6 Image 1
    House Select Dates for Price
    • 4 Bed
    • 4 Baths
    Siesta Key, FL

    Villa Dom Brisa is a beautiful newly renovated 4 bd, 4 ba, 2 kitchen home located ONLY a 4 minute walk to the #1 beach! The properties are connected by a common... ...more

  • Property-7 Image 1
    Apartment Select Dates for Price
    • 3 Bed
    • 2 Baths
    Siesta Key, FL

    Family Tides newly renovated split level town homes in Siesta Key. Stunning remodel with all new furnishings, One King bed in first bedroom, One Queen bed in... ...more

  • Property-8 Image 1
    House $680 / Nightly
    • 6 Bed
    • 4 Baths
    • (3) Exceptional
    Siesta Key, FL

    This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments... ...more

  • Property-9 Image 1
    House $943 / Nightly
    • 6 Bed
    • 5 Baths
    • (9) Exceptional
    Siesta Key, FL

    This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments... ...more

  • Property-10 Image 1
    House Select Dates for Price
    • 4 Bed
    • 2 Baths
    • (2) Excellent
    Siesta Key, FL

    This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments... ...more

  • Property-11 Image 1
    Apartment Select Dates for Price
    • 2 Bed
    • 1 Baths
    • (1)
    Siesta Key, FL

    This 2 bedroom cottage is just steps from the powder white sands of Siesta Key Beach. Quiet, safe and a block and a half to the Village for dining, nightlife.... ...more

  • Property-12 Image 1
    House Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (11)
    Siesta Key, FL

    Welcome to Big Pass Hideaway! A three bedroom two bath private home with large lap pool located just a short walk to Shell Beach is ready to accommodate you and... ...more

  • Property-13 Image 1
    House Select Dates for Price
    • 4 Bed
    • 2 Baths
    • (2) Very Good
    Siesta Key, FL

    Paradise on the Beach!!! Spectacular 4 bedroom home directly on the Beach. Gulf-Front Sleeps 8 with beautiful private courtyard pool. When we say steps, we mean... ...more

  • Property-14 Image 1
    Bungalow Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (4) Very Good
    Siesta Key, FL

    Seashell Chateau- This gem is located in the heart of Siesta Village Beachside, with the cool white sand of Siesta Beach at one end of the block and the... ...more

  • Property-15 Image 1
    House Select Dates for Price
    • 2 Bed
    • 2 Baths
    Siesta Key, FL

    Siesta Key tropical paradise! Lovely furnished 2 bedroom 2 bath with sun-room centrally located in the heart of the Siesta Key Village on a quiet cul-de-sac with... ...more

  • Property-16 Image 1
    Cottage Select Dates for Price
    • 1 Bed
    • 1 Baths
    • (5) Excellent
    Siesta Key, FL

    Back-Unit of cottage duplex - One of the closest properties to all that Siesta Key has to offer. No car needed after you arrive. This bungalow is newly... ...more

  • Property-17 Image 1
    Condo $234 / Nightly
    • 2 Bed
    • 2 Baths
    • (7) Exceptional
    Siesta Key, FL

    Come and enjoy the island lifestyle on Siesta Key in this lovely furnished 3rd floor condo. Enjoy your morning coffee or evening cocktail on the balcony with... ...more

  • Property-18 Image 1
    Condo $254 / Nightly
    • 3 Bed
    • 3 Baths
    • (14)
    Siesta Key, FL

    Totally renovated 3 bedroom, three bathroom, 2 lanais, 2000 Sq ft Penthouse located across the street from the number one beach in the US! Each bedroom is... ...more

  • Property-19 Image 1
    House $1,014 / Nightly
    • 4 Bed
    • 4 Baths
    The Sun Dial - Only $99 Down Siesta Key, FL

    This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments... ...more

  • Property-20 Image 1
    Townhome Select Dates for Price
    • 2 Bed
    • 3 Baths
    Siesta Key, FL

    This newly refurnished town home is located less then a minutes walk to the Siesta Key Beach. It is located on a private street that is very quiet. The beach... ...more

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Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Siesta Key. Many accommodations in Siesta Key provide "Non Smoking Only", there are 19, or there are 14 of Vacation Rentals in Siesta Key with a "Pets Not Allowed", there are also 14 with "Children Welcome", which is another great reason to visit Siesta Key.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Siesta Key. The most expensive month of the next 12 months is in July, where prices hit an average of $122 a night. In June, prices will hit an average low of $144 per night.