Vacation Rentals & Beach Rentals in Anna Maria

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432 beach rentals

Beachfront Paradise w/ Private Beach, Dogs Stay Free, Beach in Backyard

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$630

Gorgeous views,spectacular home!

Anna Maria house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

“Majestic Views” Our family loved our visit to Anna Maria. The house is gorgeous and spacious. My kids enjoyed the pool and eating outside. We hope to return in the near future.

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Price per night from

$630

Newly renovation bay side cottage: Sea Breeze

Anna Maria cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$354

Jacaranda Artist Retreat

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$218

"Island Oasis" A single family North end canal home with pool

Anna Maria house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$745

Serendipity Deux- Beachfront 4 Bed/heated pool/elevator

Anna Maria house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$2,290

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,260

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$630

Tripletail

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,718

Mintfish

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,145

Waves on Anna Maria

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$974

Cloud 9

Anna Maria house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$1,947

Great rentals within 20 miles that match your search

Walk to the beach and downtown

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$69

SPECIAL! $650 8/24 - 8/31. PRIME LOCATION AMI DIRECTLY ON BEACH HEATED POOL

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$287

Beautiful Island on Boca Ciega Bay & The Beach

St. Petersburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$115

Beautiful Location On Bay Side, Water View, Pool

Sarasota villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$229

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

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$344

Ocean Sands 504 Beachfront Studio Condo

Madeira Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 50 minutes

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Price per night from

$131

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$999

Boca Ciega Condo, #408, St Petersburg, Florida

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$201

Boca Ciega Condo, #107, St Petersburg, Florida

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$205

Castnetter Beach Resort 5

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$315

Castnetter Beach Resort 6

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$315

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

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$401

Treasure Island Villa - Beachfront with a pool!

Treasure Island house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$1,976

GULF COAST DESTINATION

Bradenton Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$201

Madeira Towers 601 Beach front with spectacular views

Madeira Beach apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Everything you expect and more” Without a doubt I'd stay there again, we've always stayed on Madeira Beach for the last 12 visits to Florida and this is the best condo we've stayed in, excellent value for money. Very clean and quiet , very well equipped, new carpets and new kitchen floor tiles , the caretaker was brilliant , polite and helpful , I really took to him , I had great conversations with him about fishing. The condo is positioned very well to all amenities and because all entrances needed keys you felt very secure ,, this is the place for me , when we visit again this will be the first condo I will look for availability ,,,and I guess a lot of renters have done as when I looked it's booked up to May 2017,, not surprised at all to be honest.

Responds fast! avg. 50 minutes

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Price per night from

$140

Lovely one story home on the water

Palmetto house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$458

Panoramic Ocean Views 2

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Great place to stay” I stayed in this condo last February. It is calm, bright and perfectly clean. The balcony and the view on the water are outstanding! In addition to that, Sabina is perfectly organized, answered all the question I had and made sure I was feeling perfect. I definitely recommand it!

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Price per night from

$201

Paradise Awaits on St. Pete Beach! **FULL Gulf Front** Panoramic Ocean Views!

St. Pete Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“It's the best beach in Florida!” If you want to stay at a plush yet reasonably priced condo on the water, Vistas on the Gulf is the place for you! Very clean facility with pool, hot tub, exercise room and oh what a view! The staff is great too. We've stayed one week and most recently last fall two weeks...I didn't want to go home...this was it!

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Price per night from

$458

Luxury Water Front Condo - Intercoastal Waterway

Treasure Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Exceptional” We just returned from a 4 week stay at another/similar condo in this same building, same owner. The unit was clean, comfortable, spacious and located in close proximity to everything we needed (i.e. Beach, supermarket, restaurants, shops). John (owner) was more than accomodating with helping us get online (wifi) and being flexible with our schedule. The Gulf view was great and the building was relatively quiet considering it was Spring Break month. Will definitely be returning.

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Price per night from

$240

Ultimate St Pete Beach Front Rental Condo #101

St. Pete Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Comfort and Convenience” We only stayed for 2 nights, but would not hesitate to rent here again. The location on St. Pete Beach was perfect. Even though there was temporary beach dredging going on in front of the condo this did not ruin our stay. The access to the beach was very convenient and there were less people and more room at this end, away from the larger hotels. The accomodations were just as pictured. Beautifully updated - everything clean as could be. All the conveniences were there and in working order. We look forward to the next time we can book a visit.

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Price per night from

$401

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.

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Price per night from

$476

Luxury Penthouse Condo Overlooking Beach/Gulf

Treasure Island apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Review” The place was amazing! Perfect weather and a great week! Thank you so much for the opportunity! We had the best week!

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Price per night from

$286

Sea Breeze 108 (Madeira Beach) Beautiful, Tranquil Beach Front Condo

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 33 minutes

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Price per night from

$247

AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 22 minutes

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Price per night from

$196

Anna Maria The Pink Flamingo

Holmes Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 41 minutes

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Price per night from

$458

Lifestyle on the island

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$172

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rentals in Anna Maria

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