Vacation Rentals & Beach Rentals in Anna Maria Island

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457 beach rentals

Luxury Water Front Condo - Intercoastal Waterway

Treasure Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Shared outdoor pool (heated) Private outdoor pool (unheated)

All filters match

Price per night from

$206

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2 bedroom Condo Bay Oaks Siesta Key

Sarasota condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$574

Kima 204 Direct Gulf Front in Madeira Beach

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$287

Beautiful Beach Front Condo with direct view of the Gulf of Mexico

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$287

Kima 205 Spacious 2bd/2bath Madeira Beach Gulf Front Condo Endless Views

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$287

Kima 403 2bedroom Gulf Front Condo PRICELESS SUNSETS!

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$222

Kima 102 2bed/2bath Gulf Front Condo in Madeira Beach READY TO ENJOY!!

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$287

Gulf Front Beauty, 30 Day Minimum

Indian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 5 minutes

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$192

escape to paradise

Madeira Beach apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$207

“Great stay in Sarasota” My husband and our two daughters spent a wonderful four days in Sarasota. The townhome we stayed in was beautiful and had all the amenities we needed. We spent every day at the beach and relaxed at the townhome in the evenings. We would definitely stay here again and have recommended this place to our family and friends. Thanks Louie!

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$435

1 bedroom single story condo near pool

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$295

2 bedroom poolside condo steps from ocean beach and dock on bay

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$426

1 bedroom single story ocean view

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$361

2 bedroom Florida condo unit 13 at family friendly resort

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$426

4 minute flip flop walk to the beach! Starfish 2/2

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$339

Madeira Bay Enjoy Sunrise Views from Balcony Overlooking Intracoastal Waterway

Madeira Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$230

231A Madeira Beach Yacht Club

Madeira Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$148

Luxury Waterfront Views/Pool/1400sf/2 min to Beach

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$340

Siesta Key vaca rental

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$230

Welcome to Paradise-6 miles from Anna Maria Island Beaches

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$206

Luxury Apartment, 90 Steps from the Ocean

St. Pete Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$187

A Taste of Paradise - tnzwaterside

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$316

Beachplace Building 7 Great View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$181

Walk to Beach, private condo with pool

Holmes Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$259

Frangi Pani at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$490

AMI Beach Front Condo - heated pool and less than 50 steps to the Beach!

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$345

Nice St Pete Beach Condo steps from beach and near restaurants

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$137

Oceanfront? You bet! A Must See!

Indian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$245

Direct Beachfront 2 BR Condo on Florida’S Beautiful Gulf Coast!

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$431

Siesta Key Gulf View Condo

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 33 minutes

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$447

Best of both worlds! Fish in bay or go to beach!

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Modern place in an awesome location” My family really enjoyed our time at this place. It was very clean, a convenient end unit, and close to the beautiful beach. Having the Intracoastal and pool was great, too. Being fully stocked and 2 TVs was a welcome surprise. Thanks for a great stay!

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$228

Luxury Lakerfront Condo! 2x Pools~WiFi~Lanai. By IMG~Beaches~Restaurants~AMI~SRQ

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 11 minutes

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$138

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$178

Come join us for your Winter Migration!!!!!!!!!!

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$103

Superb Lakerfront Condo! 2x Pools~WiFi~Lanai. By IMG~Beaches~Restaurants~AMI~SRQ

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 11 minutes

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$138

Beach Vacation rental

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$247

Ten35 Seaside - Direct Gulf View: Residence 601

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$927

Gorgeous Beach View Condo

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$189

Viewing 38 of 457
rentals in Anna Maria Island

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