Vacation Rentals & Beach Rentals in Siesta Key

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458 beach rentals

Anna Maria Island Beach Palms 5B

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$235

Anna Maria Island Beach Sands

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Paradise” We loved this place, felt right at home the minute we walked in the door. Had a view minor problems and the service to deal with them was awesome. Thanks Terry for a great experience, being our first time here on anna Maria Island. If we didn't need the extra bedroom, we would have booked for next yr. Location~~!! wow, close to great restaurants Love the view...can't say enough of the sunsets and of course the dolphins, got chills every time I seen them, almost daily...first class...thanks...

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$332

Anna Maria Island Beach Palms 7A

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$189

Anna Maria Island Beach Sands 201

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$286

Anna Maria Island Beach View 207

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$187

Anna Maria Island Absolute Anna Maria-Private Beach Access-Heated Pool-Wi-Fi

Anna Maria Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“A little gem” Lovely condo, great views and ideally situated for restaurants and shopping (all within walking distance). Would definitely come back again.

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$262

Anna Maria Island Bridge Port Beach Resort

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$171

Unit #113 Sand Cay Beach Resort Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Private pool

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Price per night from

$278

Unit #211 Sand Cay Beach Resort Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Private pool

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Price per night from

$278

Anna Maria Island Beach View 208

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$241

Anna Maria Island Runaway Tropical Escape

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$191

Anna Maria Island Bay Watch Bungalow

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$235

Unit #103 Sand Cay Beach Resort Gulf Front

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Boat available Private pool

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Price per night from

$342

Unit #110 Sand Cay Beach Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Private pool

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Price per night from

$278

Unit #102 Sand Cay Beach Resort Gulf Front

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Private pool

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Price per night from

$342

Anna Maria Island Beach Sands 101

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$263

Anna Maria Island Beach Palms 2B

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$248

Anna Maria Island Beach Palms 6B

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$189

Anna Maria Island Beach Sands 203

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$215

Anna Maria Island Beach Bay Breeze

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$192

Anna Maria Island Beach Palace

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$593

Anna Maria Island Beach Palms 2A

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$187

Anna Maria Island Retreat

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$219

Brand new villa with heated pool for swimmers

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Private pool

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Price per night from

$189

35 Steps to the Sea at Runaway Bay 112

Bradenton Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Boat available Private pool

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Price per night from

$132

Anna Maria Island Beach Palms 8B

Cortez condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$192

Bradenton Beach Club Bliss-3 Bedroom-2 Bathroom Condo-2 Pools-HotTub-Private Bea

Bradenton Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

All filters match

Price per night from

$245

Anna Maria Island Beach Waves

Cortez condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$216

Island Time-Private Beach Access-Heated Pool-Water Views

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$211

Gulf Breeze Ami-2BD-2BA-Condo-Private Beach Access-Heater Pool-Water Views From

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

All filters match

Price per night from

$182

Paradise Palms-Private Beach Access-Heated Pool-Water Views From Every Room

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$227

Anna Maria Island Sun's Up B

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

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Price per night from

$479

Anna Maria Island Sun's Up A

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

All filters match

Price per night from

$494

Absolute Paradise AMI-Private Beach Access-Water Views From Every Window-Heated

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 20 minutes

Match: Boat available Private pool

All filters match

Price per night from

$257

These homes match some but not all of your filters. Clear all filters

Siesta Key Beach | Private Pool

Fruitville house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Private pool

1 of 2 filters match

Price per night from

$399

Beach house for rent in siesta key beach.

Siesta Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Responds fast! avg. 2 hours 0 minutes

1 of 2 match: Boat available, Private pool

1 of 2 filters match

Price per night from

$1,001

Condo wOcean view on Siesta

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 33 minutes

1 of 2 match: Boat available, Private pool

1 of 2 filters match

Price per night from

$401

University Park Country Club Property

Lakewood Ranch house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Boat available, Private pool

1 of 2 filters match

Price per night from

$481

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rentals in Siesta Key

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