Vacation Rentals & Beach Rentals in Anna Maria Island

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501 beach rentals

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ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared indoor pool Shared outdoor pool (unheated)

All filters match

Price per night from

$161

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared indoor pool Shared outdoor pool (unheated)

All filters match

Price per night from

$172

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared indoor pool Shared outdoor pool (unheated)

All filters match

Price per night from

$172

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

LaPlaya 205D-Spectacular sunsets from your private Gulf-front lanai or sundeck.

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$414

LaPlaya 102B-Directly on the beach with the warm Gulf waters waiting!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$339

LaPlaya 107A-Soak up the sun or float in the warm Gulf waters.

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$311

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

1 of 2 filters match

Price per night from

$414

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

1 of 2 filters match

Price per night from

$376

LaPlaya 106A-Beach front! Steps to the white sand and turquoise Gulf of Mexico.

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$376

LaPlaya 204D-Beach-lovers paradise! 200 feet of private beach

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$414

LaPlaya 206C-Gorgeous vistas of the Gulf

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$414

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

1 of 2 filters match

Price per night from

$220

LaPlaya 104A- Gulf front! Walk right from your lanai onto the private beach.

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$311

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

1 of 2 filters match

Price per night from

$414

LaPlaya 101E-Relax on your private lanai under the palms!

Longboat Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$275

Monthly Rental, 2 bed, 2 bath, Ocean view.

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$115

Tortuga Shoals

Tierra Verde townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$413

Full Kitchen - Shared pool - By LoveRentals

Holmes Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 39 minutes

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

1 of 2 filters match

Price per night from

$210

Steps from beach! Air-conditioned - shared pool

Holmes Beach villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 39 minutes

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

1 of 2 filters match

Price per night from

$109

Bay Mariner - Gorgeous water front condo!

Tallevast studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 39 minutes

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

1 of 2 filters match

Price per night from

$99

Steps from Beach! Grill - Wifi - By LoveRentals

Holmes Beach villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 39 minutes

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

1 of 2 filters match

Price per night from

$158

2 bed Condo in peaceful Shorewalk. Close to IMG, Beaches, shops and restaurant

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$115

Guest House, 750 sq ft, private, with all amenities, parking and pool

St. Petersburg cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$98

Blue Heron Studio / Condo 2 miles from Airport!

Tallevast studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 39 minutes

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

1 of 2 filters match

Price per night from

$119

Sunset Beach 101 Beach Front Unit

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 39 minutes

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

1 of 2 filters match

Price per night from

$366

Casa Sea Esta Executive Studio / Condo at Sara Cay

Tallevast studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 39 minutes

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

1 of 2 filters match

Price per night from

$92

Hibiscus Hideaway B - Top Floor Unit

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 39 minutes

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

1 of 2 filters match

Price per night from

$283

Shorewalk waterfront Condo Bradenton

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Nice and affordable condo convenient to shopping and restaurants.” This unit has been updated and is a very comfortable place to stay. The owner responded promptly when we contacted him.

Responds fast! avg. 2 hours 1 minutes

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

1 of 2 filters match

Price per night from

$95

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: Shared indoor pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$265

The Jitterbug Apt: Central 1 bedroom w pullout bed, 10 mins to DTSP pet friendly

Pinellas Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$172

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: Shared indoor pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$537

Responds fast! avg. 16 minutes

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

1 of 2 filters match

Price per night from

$232

Responds fast! avg. 16 minutes

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

1 of 2 filters match

Price per night from

$168

Updated w/bay view , across from the beach , pool, elevator , close restaurants

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 16 minutes

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

1 of 2 filters match

Price per night from

$174

Responds fast! avg. 16 minutes

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

1 of 2 filters match

Price per night from

$127

Walk to the beach, from this remodeled condo! Pool, WIFI, restaurants, shopping

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 16 minutes

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

1 of 2 filters match

Price per night from

$139

Great Value in a Beachfront Condo. Walk Over to Johns Pass and Step Out the Doo

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 minutes

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

1 of 2 filters match

Price per night from

$178

Beachfront Private Walkout Balcony. Heated Pool. Perfect Quick & Easy Getaway.

Treasure Island studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 minutes

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

1 of 2 filters match

Price per night from

$166

Viewing 38 of 501
rentals in Anna Maria Island

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