Vacation Rentals & Beach Rentals in Anna Maria Island

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132 beach rentals

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ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared indoor pool Cycling trips

All filters match

Price per night from

$173

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Trendy 4bd3bath Home in St Pete Arts District

St. Petersburg house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$207

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Cycling trips, 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: Cycling trips, Shared indoor pool

1 of 2 filters match

Price per night from

$173

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: Cycling trips, Shared indoor pool

1 of 2 filters match

Price per night from

$311

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: Cycling trips, Shared indoor pool

1 of 2 filters match

Price per night from

$340

1 of 2 match: Cycling trips, Shared indoor pool

1 of 2 filters match

Price per night from

$377

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: Cycling trips, Shared indoor pool

1 of 2 filters match

Price per night from

$311

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

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Cycling trips, Shared indoor pool

1 of 2 filters match

Price per night from

$415

LaPlaya 206C-Gorgeous vistas of the Gulf

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Cycling trips, Shared indoor pool

1 of 2 filters match

Price per night from

$415

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: Cycling trips, Shared indoor pool

1 of 2 filters match

Price per night from

$377

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: Cycling trips, Shared indoor pool

1 of 2 filters match

Price per night from

$415

1 of 2 match: Cycling trips, Shared indoor pool

1 of 2 filters match

Price per night from

$221

1 of 2 match: Cycling trips, Shared indoor pool

1 of 2 filters match

Price per night from

$415

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

Longboat Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Cycling trips, Shared indoor pool

1 of 2 filters match

Price per night from

$276

1 of 2 match: Cycling trips, Shared indoor pool

1 of 2 filters match

Price per night from

$415

Piece of Paradise on Beautiful Anna Maria Island VRC 20-000087

Holmes Beach villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$148

Lido Beach Villa, 1.2k sf, 1 block to the beach

Lido Key villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$184

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$183

BEACH FRONT CONDO *** MADEIRA BEACH

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$368

2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!

Bradenton Beach cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Best home away from home at the beach.” I spent a lot of time searching for a bungalow at the beach and my expectations were surpassed when I opened the door! The owners were thoughtful in design, layout and furnishings to provide a laid back experience at the beach. I wished I could have stayed forever - it was that nice. I especially enjoyed the fully stocked kitchen which included colorful dishes to match the colorful walls and great blue floor! Best of all - location - you can walk everywhere as you are right in the historic Bridge Street neighborhood.

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$246

Steps to beach and bay on beautiful Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$101

NW Bradenton Exectitive Home

Bradenton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$493

Coastal Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$173

Anna Maria Island Bay Watch Bungalow

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$239

Elegant condo on beach!

Indian Shores condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$150

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

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Cycling trips, Shared indoor pool

1 of 2 filters match

Price per night from

$115

Beautiful Sunkst Cottage Bradenton Beach - AMI-Tropical Setting - Heated Pool

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$517

Beautiful Island on Boca Ciega Bay & The Beach

St. Petersburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$115

3 Bed/2 Bath Handicap Madeira Beach Gulf side Condo w/ Heated pool and Spa

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$345

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$1,001

Luxurious 2 BR Condo-Short Walk to Siesta Beach/1 Small Dog (25 lbs Max) Allowed

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“a fine 2 weeks in Siesta” charming property, that was comfortable for four. The unit was very clean and fresh upon arrival. The neighbours were friendly and the overall property well kept. Siesta Key is a quiet community with usual shopping amenities over the causeway. This property was a brief 10 minute walk to the beach. Would we stay again, yes.

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$166

Anna Maria Island Beach Paradise 10

Holmes Beach studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$228

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$144

Executive Waterfront Home

St. Petersburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$259

Boca Ciega Condo, #203, St Petersburg, Florida

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$206

SAPPHIRE - HARBOR ISLE

Bradenton Beach townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$287

Boca Ciega Condo, #109, St Petersburg, Florida

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Cycling trips

1 of 2 filters match

Price per night from

$206

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rentals in Anna Maria Island

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