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Siesta Key, FL Vacation Rentals

2-Bedroom - Beachfront Condo - Luxury - Directly on Crescent Beach

  • Type: Condo
    Bedrooms: 2
    Sleeps: 6
    Bathrooms: 2/0
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates:
    Weekly: $1325-1725

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Beachwalk -- Luxury Townhouse

  • Type: Townhome
    Bedrooms: 3
    Sleeps: 8
    Bathrooms: 2/1
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates:
    Weekly: $1495-2045

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Upscale - Beachfront One Bedroom Condo at Fisherman's Cove

  • Type: Condo
    Bedrooms: 1
    Sleeps: 4
    Bathrooms: 1/0
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates:
    Weekly: $790-1290

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Siesta Sunsets at Fisherman's Cove

  • Type: Condo
    Bedrooms: 2
    Sleeps: 6
    Bathrooms: 2/0
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates:
    Weekly: $1045-1645

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Beachfront Condo - Three Bedroom - Luxury

  • Type: Condo
    Bedrooms: 3
    Sleeps: 8
    Bathrooms: 2/0
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates:
    Weekly: $1545-2095

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Deluxe Town home - Garden Apartment, Private Pool

  • Type: Condo
    Bedrooms: 1
    Sleeps: 4
    Bathrooms: 1/0
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates:
    Weekly: $625-900

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Siesta Key - Sundance Rental - Affordable - Key West Style - Private Pool

  • Type: Apartment
    Bedrooms: 3
    Sleeps: 10
    Bathrooms: 3/0
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates:
    Weekly: $1350-1845

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6150 Midnight Pass Rd V37

  • Type: Villa
    Bedrooms: 2
    Sleeps: 6
    Bathrooms: 2/0
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates: Nightly: $150-234
    Weekly: $1050-1638

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6142 Midnight Pass Rd 15N

  • Type: Condo
    Bedrooms: 2
    Sleeps: 4
    Bathrooms: 2/0
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates: Nightly: $194-307
    Weekly: $1358-2149

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6150 Midnight Pass Rd V22

  • Type: Villa
    Bedrooms: 2
    Sleeps: 6
    Bathrooms: 1/1
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates: Nightly: $143-225
    Weekly: $1001-1575

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6148 Midnight Pass Rd 5S

  • Type: Condo
    Bedrooms: 2
    Sleeps: 6
    Bathrooms: 2/0
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates: Nightly: $194-307
    Weekly: $1358-2149

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6142 Midnight Pass Rd 13N

  • Type: Condo
    Bedrooms: 2
    Sleeps: 6
    Bathrooms: 2/0
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates: Nightly: $194-307
    Weekly: $1358-2149

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6146 Midnight Pass Rd 12S

  • Type: Condo
    Bedrooms: 2
    Sleeps: 6
    Bathrooms: 2/0
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates: Nightly: $194-307
    Weekly: $1358-2149

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6150 Midnight Pass Rd V19

  • Type: Villa
    Bedrooms: 2
    Sleeps: 4
    Bathrooms: 2/0
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates: Nightly: $150-234
    Weekly: $1050-1638

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6150 Midnight Pass Rd V7

  • Type: Villa
    Bedrooms: 2
    Sleeps: 6
    Bathrooms: 2/0
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates: Nightly: $150-234
    Weekly: $1050-1638

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6150 Midnight Pass Rd V35

  • Type: Villa
    Bedrooms: 2
    Sleeps: 6
    Bathrooms: 2/0
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates: Nightly: $150-234
    Weekly: $1050-1638

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Siesta Dunes Beach 38A, Gulf Side 2 bedrooms, Large Heated Pool, Wifi

  • Type: Condo
    Bedrooms: 2
    Sleeps: 6
    Bathrooms: 2/0
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates: Nightly: $120-350
    Weekly: $520-1595
    Monthly: $2414-5253

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.Updated Condo only steps from # 1 rated beach in the U.S.

  • Type: Condo
    Bedrooms: 2
    Sleeps: 5
    Bathrooms: 2/0
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates:
    Weekly: $1100
    Monthly: $3800

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House of Sun - Gulf View Condo - 3rd Level - 2 BR/2 BA - Siesta Key Beach

  • Type: Condo
    Bedrooms: 2
    Sleeps: 6
    Bathrooms: 2/0
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates: Nightly: $150-400
    Weekly: $795-1995
    Monthly: $2995-5995

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Gulfside Siesta Key Condo - Fun in the Sun!

  • Type: Condo
    Bedrooms: 2
    Sleeps: 6
    Bathrooms: 2/0
    Town: Siesta Key
    Zip Code: 34242

  • Rental Rates: Nightly: $150-350
    Weekly: $650-1595
    Monthly: $2495-4995

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Looking for the perfect place to stay on your vacation in Siesta Key, Florida? Browse our database of vacation rentals - including rental homes, condos, cottages, beach houses, and more!

Siesta Key Vacation & Rental Tips

Finding Your Vacation Home in Siesta Key, FL

When you think of Florida vacation spots, Siesta Key is probably not one of those destinations that comes to mind. This well-kept secret is one of the most amazing locations when it comes to vacation getaways. Located off the shore of Sarasota, this barrier island is 8 miles long and offers visitors a relaxing and unforgettable experience.

With its pristine white sand beaches, this is a tropical getaway that is close to everything you need. When it comes to your vacation rental, you have a few options. You can stay just a few miles away on the shores of Sarasota or you can take advantage of one of the many cottages, bungalows and rental homes on Siesta Key. If you stay near the heart of Siesta Key Village, you'll find many rentals available to you.

Love a little adventure? Then try some fishing, snorkeling or even some parasailing. The best part of staying in Siesta Key is that there isn't a bad part of this entire 8 mile island. There are numerous restaurants where you can take advantage of a seafood lover's dream. From American to International cuisine, you'll find something to satisfy your appetite. Come on over to Siesta Key, where you'll feel miles away from reality. Book our next vacation rental here and relax underneath the Florida sun.

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