Vacation Rentals & Beach Rentals in Anna Maria Island

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297 beach rentals

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Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children's pool Pets allowed

All filters match

Price per night from

$224

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1 of 2 match: Pets allowed, Children's pool

1 of 2 filters match

Price per night from

$573

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: Pets allowed, Children's pool

1 of 2 filters match

Price per night from

$573

Your Hidden Private Gem "La Playa Azul"

Gulfport condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Children's pool

1 of 2 filters match

Price per night from

$212

"Lovers Den" Your Hidden Private Gem

Gulfport condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Pets allowed, Children's pool

1 of 2 filters match

Price per night from

$149

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: Pets allowed, Children's pool

1 of 2 filters match

Price per night from

$258

Anna Maria Islands best location Heated pool Best prices!

Anna Maria Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Children's pool

1 of 2 filters match

Price per night from

$859

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, 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: Pets allowed, Children's pool

1 of 2 filters match

Price per night from

$172

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: Pets allowed, Children's pool

1 of 2 filters match

Price per night from

$476

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Pets allowed, Children's pool

1 of 2 filters match

Price per night from

$205

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Pets allowed, 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: Pets allowed, Children's pool

1 of 2 filters match

Price per night from

$114

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Children's pool

1 of 2 filters match

Price per night from

$172

#7 Loft Apartment in Historic District Downtown Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$305

Downtown Sarasota Historic Burns Court Adorable Bungalow

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$295

Sunset Suite

St. Pete Beach studio

  • Studio
  • 1 bathroom
  • sleeps 1

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$172

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$234

One Bedroom in Historic Burns Square District downtown

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$315

Charming Private Studio in Historic Downtown Area

Sarasota studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$258

Jacaranda Artist Retreat

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$218

Steps to Beach+bikes VaCay getaway on PaG island

St. Pete Beach cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 9 minutes

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$197

BAY FRONT HOUSE WITH PRIVATE DOCK

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 31 minutes

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$344

Alice's Beach Bungalows Private Oasis #2

Treasure Island bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$228

Light and Airy and Private, Great Location

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$229

X Alice's Beach Bungalows 2 bdrm 500' to Beach!

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$373

Tranquil Tarpon Cottage - Giant Swim Spa

Redington Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 13

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$921

Tiny Home Camping Experience

St. Petersburg yurt

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$287

A Quiet Place to Relax

St. Petersburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$115

Fabulous Flamingo Cottage

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$161

Tropical Treasure Villa - Giant spa and steps from the beach!

Redington Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$942

Gorgeous Waterfront Apartment Steps From 100Ft Fishing Dock And Tiki.

Palmetto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$166

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 46 minutes

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$194

Tiny House Siesta - Yellow Lifeguard Stand Tiny House

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$422

Tiny House Siesta - Red Lifeguard Stand

Siesta Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$442

Tiny House Siesta - Tiny Aqua Oasis- Tiny House that sleeps 6 comfortably

Siesta Key hotel apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$444

Tiny House Siesta - Sand Dollar – A private master loft and open living space

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$447

A Beautiful Bungalow in St Pete!

St. Petersburg house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Pets allowed

1 of 2 filters match

Price per night from

$344

Viewing 38 of 297
rentals in Anna Maria Island

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