Vacation Rentals & Beach Rentals in Anna Maria Island

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380 beach rentals

Luxury Penthouse Condo Overlooking Beach/Gulf

Treasure Island apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Review” The place was amazing! Perfect weather and a great week! Thank you so much for the opportunity! We had the best week!

Match: Jacuzzi or hot tub Wheelchair adapted

All filters match

Price per night from

$286

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A Gulf Front Paradise ! Newly updated , wide open wall to wall view, spacious cl

Bradenton Beach condo

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 16 minutes

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$458

The Salty Dog on North Shore

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$389

Madeira Towers 302 Beachfront 3 bedroom 2 bath at Madeira Towers

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$388

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$490

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$490

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$489

Beachfront view, toes in the sand and gulf. Simply paradise, book now your beach

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 16 minutes

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$275

Responds fast! avg. 16 minutes

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$127

Responds fast! avg. 16 minutes

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$168

Luxury waterfront home with a heated pool and spa!

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$537

Prime location, comfort, and sunset views – your perfect getaway awaits!

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 minutes

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$212

Resort Style Community. Quick Walk to Beach. Heated Pool. Near Great Restaurants

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 minutes

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$115

Fishermans Cove FC Unit 205B *

Gulf Gate Estates condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$266

GBR204 Gulf View 1BR 2BA

St. Pete Beach condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$234

GBR602 Gulf Front 1BR 1.5BA

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$282

GBR603 Gulf View 1BR 2BA

St. Pete Beach condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$252

GBR402 Gulf Front 1BR 1.5BA

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$279

GBR503 Gulf View 1BR 2BA

St. Pete Beach condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$249

GBR404 Gulf View 1BR 2BA

St. Pete Beach condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$244

GBR202 Gulf Front 1BR 1.5BA

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$264

GBR304 Gulf View 1BR 2BA

St. Pete Beach condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$241

GBR301 Gulf Front 1BR 1.5BA

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$275

GBR302 Gulf Front 1BR 1.5BA

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$275

GBR504 Gulf View 1BR 2BA

St. Pete Beach condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$249

GBR303 Gulf View 1BR 2BA

St. Pete Beach condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$241

GBR403 Gulf View 1BR 2BA

St. Pete Beach condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$244

GBR401 Gulf Front 1BR 1.5BA

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$279

GBR502 Gulf Front 1BR 1.5BA

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$281

GBR201 Gulf Front 1BR 1.5BA

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$264

GBR604 Gulf View 1BR 2BA

St. Pete Beach condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$252

GBR601 Gulf Front 1BR 1.5BA

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$282

GBR501 Gulf Front 1BR 1.5BA

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$281

Madeira Towers 802 Renovated Madeira Towers Beachfront 2 Bedroom 2 Bathroom Cond

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 50 minutes

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$119

Backyard Tiny House Oasis!

St. Petersburg guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$101

Beach Front Ocean Sands

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$448

Peace and Quiet in Gated Community on Boca Ciega Bay

Gulfport apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$77

WATERFRONT WITH DOCK

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$156

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