Vacation Rentals & Beach Rentals in Anna Maria Island

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70 beach rentals

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared indoor pool Pool or snooker table

All filters match

Price per night from

$172

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ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pool or snooker table, Shared indoor pool

1 of 2 filters match

Price per night from

$161

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pool or snooker table, Shared indoor pool

1 of 2 filters match

Price per night from

$172

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: Pool or snooker table, Shared indoor pool

1 of 2 filters match

Price per night from

$339

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

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared indoor pool

1 of 2 filters match

Price per night from

$414

1 of 2 match: Pool or snooker table, Shared indoor pool

1 of 2 filters match

Price per night from

$414

1 of 2 match: Pool or snooker table, Shared indoor pool

1 of 2 filters match

Price per night from

$414

1 of 2 match: Pool or snooker table, Shared indoor pool

1 of 2 filters match

Price per night from

$376

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: Pool or snooker table, 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: Pool or snooker table, Shared indoor pool

1 of 2 filters match

Price per night from

$414

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: Pool or snooker table, Shared indoor pool

1 of 2 filters match

Price per night from

$311

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: Pool or snooker table, Shared indoor pool

1 of 2 filters match

Price per night from

$311

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

Longboat Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pool or snooker table, Shared indoor pool

1 of 2 filters match

Price per night from

$275

1 of 2 match: Pool or snooker table, Shared indoor pool

1 of 2 filters match

Price per night from

$220

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: Pool or snooker table, Shared indoor pool

1 of 2 filters match

Price per night from

$376

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$489

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$489

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$489

Redington Towers 1 Beachfront 2 Bedroom Condo

Redington Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$218

NEW! Luxurious Coastal Condo 5 minutes to Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$401

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$229

WATERFRONT WITH DOCK

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$156

Split Leaf at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$489

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$489

Coconut at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$489

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

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pool or snooker table, Shared indoor pool

1 of 2 filters match

Price per night from

$115

Shorewalk Condo ED near the Beaches Anna Maria Island, Longboat Key, IMG, Shops

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$401

Beach front condo on Redington Shores

Redington Shores condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$134

Ideal Retreat next to USA's #1 Beach—Siesta Key

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$161

REDUCED FOR APRIL!

Madeira Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“get away” My experience was kinda shaky at first , I was given the wrong gate code to get in complex, plus there were a couple of wristbands for pool entry missing and a blind that was messed up,but was able to be fixed in about 15 minutes. Our reservations were never given to property managers at office as well, but as soon as Jennifer responded she was able to take care of that. I have been to 2 other units there and this unit is the most modern by far and is very clean,and a great spot in the complex.

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$171

Condo on the Key

St. Petersburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

“Immaculate” I had a wonderful stay at the condo in the key. Robin was easy to work with and always responsive. The condo was very clean and well stocked. If you are looking for a place where you can lay back and relax this is a nice condo. I loved that it's in a gated area.

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$207

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 25 minutes

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$258

LUXURY WATERFRONT CONDO ON ISLA DEL SOL/St.Pete's

St. Petersburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$430

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$435

Spacious clean quiet home facing the Boca Ciega Bay in Isla del Sol

St. Pete Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$166

Gulf and Bay Club 3bdrm “E” Luxury END CORNER Unit - RIGHT ON BEACH

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$903

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$344

1 of 2 match: Shared indoor pool, Pool or snooker table

1 of 2 filters match

Price per night from

$310

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rentals in Anna Maria Island

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