Vacation Rentals & Beach Rentals in Anna Maria Island

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159 beach rentals

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children's pool Safe

All filters match

Price per night from

$173

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1 of 2 match: Safe, Children's pool

1 of 2 filters match

Price per night from

$577

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: Safe, Children's pool

1 of 2 filters match

Price per night from

$577

"Lovers Den" Your Hidden Private Gem

Gulfport condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Safe, Children's pool

1 of 2 filters match

Price per night from

$150

Your Hidden Private Gem "La Playa Azul"

Gulfport condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Safe, Children's pool

1 of 2 filters match

Price per night from

$213

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: Safe, Children's pool

1 of 2 filters match

Price per night from

$259

Anna Maria Islands best location Heated pool Best prices!

Anna Maria Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Safe, Children's pool

1 of 2 filters match

Price per night from

$866

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Safe, Children's pool

1 of 2 filters match

Price per night from

$162

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Safe, Children's pool

1 of 2 filters match

Price per night from

$173

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Safe, Children's pool

1 of 2 filters match

Price per night from

$224

Sunset Beach Paradise

Treasure Island studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$60

SUNSET VISTA ON LONGBOAT KEY

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$289

Gulfview front house

St. Pete Beach house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$185

Tiny Home Camping Experience

St. Petersburg yurt

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$289

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: Safe, Children's pool

1 of 2 filters match

Price per night from

$479

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Safe, Children's pool

1 of 2 filters match

Price per night from

$207

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Safe, Children's pool

1 of 2 filters match

Price per night from

$193

*** 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: Safe, Children's pool

1 of 2 filters match

Price per night from

$115

Pass-A-Grille Beach House

St. Pete Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$220

TROPICCAL, 4 min from the beaches! Meticulously cleaned and sanitized!

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

“Lovely home in an awesome location!” Literally a minute's drive from the beach, this very clean and welcoming home is also convenient to great restaurants and shopping opportunities. It really is in a perfect location, especially considering the affordable price. Walking to restaurants and a rental shop is easy thanks to the sidewalk on Cortes. We even enjoyed a morning run to the beach - biking to the beach would also be a great option (3.5 mi one way.) The home might appear small at first, but we fit 6 comfortably, including 4 teenagers! The best part is the lovely décor that greets you after a long day at the beach or running around. Two thumbs up!

Responds fast! avg. 2 hours 33 minutes

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$145

🏝Paradise on the Sarasota Bay, Close to Gulf Beaches🏝 (Sarasota)

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$195

Sunset Beach One Bedroom Gulf View

Treasure Island apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$230

Siesta Key beach & sunsets - 2018 Spring & Summer openings!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$131

Cute Efficiency Apartment - nice neighborhood

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Great place to stay in sarasota” Very nice one bedroom apartment with everything you need. Close to everything. Quiet neighborhood. Just a great piece of mind renting from Terry had no worries at all.

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$104

Renovated 1BR Haven - 2 Mins from Sunset Beach!

Treasure Island house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 3 minutes

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$206

Beautiful Treasure Island, St. Pete Beach 2br/2bth Sunset Beach Condo waterfront

Treasure Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$305

#7 Loft Apartment in Historic District Downtown Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$306

Family Tides - High Tides: By Beachside Management

Siesta Key apartment

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$551

SBC303 1BR 1BA

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$189

SBC408 2BR 2BA

Treasure Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$212

SBC504 1BR 1BA

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$189

SBC405 1BR 1BA

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$181

SBC407 1BR 1BA

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$189

SBC402 1BR 1BA

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$189

SBC307 1BR 1BA

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$189

SBC403 1BR 1BA

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$189

SBC304 1BR 1BA

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$189

SBC604 1BR 1BA

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Safe

1 of 2 filters match

Price per night from

$229

Viewing 38 of 159
rentals in Anna Maria Island

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