Siesta Key Vacation Rentals

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Gulf-to-Bay Living on Longboat Key
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Waterfront condo paradise. Island living. Ground floor. 2 Bd, 2 Ba. Private harbour community, 4 heated pools, Gulf-front pavilion.

2 Bedrooms
2 Bathrooms
3 Guides
$180 / night (excl. fees & taxes)
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Golf Course Condo
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Breath taking view of the Golf Course and water with nature sounds...

2 Bedrooms
2 Bathrooms
3 Guides
$116 / night (excl. fees & taxes)
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Tropical Beach Condo!
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Peaceful and Serene

1 Bedroom
1 Bathroom
3 Guides
5IconIconIconIconIcon
11 reviews
$300 / night (excl. fees & taxes)
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Craig House with Heated Pool
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Craig House with Heated Pool

2 Bedrooms
2 Bathrooms
3 Guides
4.8IconIconIconIconIcon
107 reviews
$148 - $179 / night (excl. fees & taxes)
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Golf Course and Private Pool Views
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For the Ultimate Vacation Come Stay at Rosedale Golf & Country Club!!

2 Bedrooms
2 Bathrooms
3 Guides
$225 / night (excl. fees & taxes)
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Condo 6 miles from breathtaking Anna Maria Island
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2 bedroom, 2 bath, sleeps 6. Under 6 miles from the breathtaking Anna Maria Island beaches

2 Bedrooms
2 Bathrooms
3 Guides
$67 / night (excl. fees & taxes)
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Welcome to Paradise
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6 miles from Anna Maria Island Beaches

3 Bedrooms
2 Bathrooms
3 Guides
$170 / night (excl. fees & taxes)
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Bradenton Boho Bungalow
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NO CLEANING FEE-Heated Pool-Completely Remodeled-King Beds-Close to IMG, restaurants & beaches-2GB Fiber Internet-10% off 7+ nights

3 Bedrooms
2 Bathrooms
3 Guides
$300 - $375 / night (excl. fees & taxes)
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Mins to Anna Maria Beaches! Saltwater Pool/Hot Tub
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Mins to Anna Maria Beaches! Saltwater Pool/Hot Tub

3 Bedrooms
2 Bathrooms
3 Guides
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50 reviews
$500 / night (excl. fees & taxes)
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The Surof House
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Anna Maria Island Direct Beach/ Gulf Views

2 Bedrooms
1 Bathroom
3 Guides
$500 - $1035 / night (excl. fees & taxes)
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New! Salt Pool + Hot Tub + Anna Maria Beaches!
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New! Salt Pool + Hot Tub + Anna Maria Beaches!

3 Bedrooms
2 Bathrooms
3 Guides
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3 reviews
$300 - $525 / night (excl. fees & taxes)
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Palm Paradise
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Palm Paradise

3 Bedrooms
2 Bathrooms
3 Guides
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3 reviews
$220 / night (excl. fees & taxes)
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Sunny Retreat Near AMI, IMG, Beaches-Pet Friendly
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Sunny Retreat Near AMI Beaches & Manatee River - Pet Friendly

3 Bedrooms
2 Bathrooms
3 Guides
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15 reviews
$225 / night (excl. fees & taxes)
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Making Waves
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Heated Pool/Walk to Anna Maria Beaches/Restaurants

3 Bedrooms
3 Bathrooms
3 Guides
$900 - $1100 / night (excl. fees & taxes)
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Poolside paradise
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Poolside paradise Your family oasis

5 Bedrooms
4 Bathrooms
3 Guides
4.81IconIconIconIconIcon
21 reviews
$599 / night (excl. fees & taxes)
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Cozy Outdoor Living+Private Yard+AMI in Mins!
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Prime location+Private HTD Saltwater Pool+Spacious Master Suite w/private pool access. New Furniture, Appliances, Quartz Countertops, Travertine Patio

4 Bedrooms
2 Bathrooms
3 Guides
4.98IconIconIconIconIcon
54 reviews
$234 - $804 / night (excl. fees & taxes)
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The River House
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Relaxing Riverhouse - free parking pass in Pass A Grille beach- 30 min. drive

4 Bedrooms
3 Bathrooms
3 Guides
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3 reviews
$500 / night (excl. fees & taxes)
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Gulf Coast Paradise Hideaway
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Gulf Coast Paradise Hideaway

1 Bedroom
1 Bathroom
3 Guides
$95 / night (excl. fees & taxes)
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Florida Pool Villa Happy Gator
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10 Minutes to the Beach! Heated Pool with ♥SUNSHELF♥SW exposure♥

3 Bedrooms
2 Bathrooms
3 Guides
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102 reviews
$200 - $270 / night (excl. fees & taxes)
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First Responder•Displaced Home Owners•Pool/Hot Tub
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Heated Pool Paradise: Near Beaches & Hot Tub! EV!

4 Bedrooms
2 Bathrooms
3 Guides
4.8IconIconIconIconIcon
15 reviews
$143 - $1160 / night (excl. fees & taxes)
    21 – 40 Rentals