Vacation Rentals & Beach Rentals in Anna Maria Island

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15 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: Children's pool Skiing – property near ski resort

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Price per night from

$172

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1 of 2 match: Skiing – property near ski resort, Children's pool

1 of 2 filters match

Price per night from

$574

CFP! St.PeteBeach Rental for 4! 01/09-11/2017. College Football Nat'l Champs

St. Pete Beach studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 of 2 match: Skiing – property near ski resort, Children's pool

1 of 2 filters match

Price per night from

$574

Remodeled Sunset Vistas 303N - Booking for Summer 2021, with No Cleaning Fees!

Treasure Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Skiing – property near ski resort, Children's pool

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Price per night from

$259

"Lovers Den" Your Hidden Private Gem

Gulfport condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Skiing – property near ski resort, Children's pool

1 of 2 filters match

Price per night from

$149

Your Hidden Private Gem "La Playa Azul"

Gulfport condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Skiing – property near ski resort, Children's pool

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Price per night from

$212

Anna Maria Islands best location Heated pool Best prices!

Anna Maria Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Skiing – property near ski resort, Children's pool

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Price per night from

$861

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Skiing – property near ski resort, Children's pool

1 of 2 filters match

Price per night from

$224

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Skiing – property near ski resort, Children's 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: Skiing – property near ski resort, Children's pool

1 of 2 filters match

Price per night from

$172

Another Day in Paradise

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 1 minutes

1 of 2 match: Children's pool, Skiing – property near ski resort

1 of 2 filters match

Price per night from

$545

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Skiing – property near ski resort, Children's pool

1 of 2 filters match

Price per night from

$206

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Skiing – property near ski resort, Children's pool

1 of 2 filters match

Price per night from

$192

*** SUPER SPECIAL RATES at Harbor Towers ***

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

1 of 2 match: Skiing – property near ski resort, Children's pool

1 of 2 filters match

Price per night from

$114

A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect Luxury” Our 5-week stay at this vacation rental was absolutely perfect. The house was everything you could ask for and more. We have stayed in many vacation rentals in the last 20 or so years that we have been coming to anna Maria Island and I have to say this one was right at the top of the list. The kitchen was outfitted with everything you could want. The beds were very comfortable. The neighborhood was nice and quiet. Short walk to the beach. The owners were very nice to deal with and always responded quickly and were very warm and helpful. Definitely can recommend this vacation rental.

1 of 2 match: Skiing – property near ski resort, Children's pool

1 of 2 filters match

Price per night from

$475

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