Vacation Rentals & Beach Rentals in Anna Maria Island

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879 beach rentals

Sunsets, Cocktails and Memories!

Indian Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Spacious and beautiful” My girlfriends and I just finished our stay for the third year in a row. This is an outstanding condo. With four or five of us, there is plenty of room. The private spiral staircase to the beach is great! No waiting for the elevator with everyone else. We love sitting on the porch early in the morning and again at sunset. Spectacular views! Also you can visit the Suncoast Seabird Sanctuary which is about 1/2 block to the south. Would highly recommend this condo. We hope to be back again next year.

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

All filters match

Price per night from

$383

Stunning 2,550 Sq.ft House, FL

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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

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Price per night from

$286

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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 (heated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$574

Gorgeous Water View, Condo!Completely Renovated 2015,Wifi

Tierra Verde condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$201

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 (heated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$431

Kima 204 Direct Gulf Front in Madeira Beach

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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

1 of 2 filters match

Price per night from

$287

“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 (heated), 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 (heated), 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 (heated), 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 (heated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$361

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 (heated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$137

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 (heated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$426

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 (heated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$287

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 (heated), 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 (heated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$222

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 (heated), 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 (heated), 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 (heated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$207

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 (heated), 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 (heated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$148

Siesta Key Gulf View Condo

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 39 minutes

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

1 of 2 filters match

Price per night from

$448

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 (heated), 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 (heated), 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 (heated), 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 (heated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$187

Beachplace Building 7 Great View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$490

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 (heated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$229

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 (heated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$138

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 (heated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$138

Oceanfront? You bet! A Must See!

Indian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$245

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 (heated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$339

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 (heated), Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$345

A Taste of Paradise - tnzwaterside

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$316

Gorgeous Beach View Condo

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$190

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

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$104

Ten35 Seaside - Direct Gulf View: Residence 601

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$929

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rentals in Anna Maria Island

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