Siesta Key, FL Vacation Rentals

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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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