Vacation Rentals & Beach Rentals in Anna Maria

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97 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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$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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$631

Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$743

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

FantaSea

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,489

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,260

Mintfish

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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$1,145

Waves on Anna Maria

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$976

Great rentals within 20 miles that match your search

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

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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$517

BAY FRONT HOUSE WITH PRIVATE DOCK

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 31 minutes

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$345

Alice's Beach Bungalows Private Oasis TI, FL

Treasure Island bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Short vacation” Still on our short vacation. So far everything is perfect! Susan has been very helpful with any questions and has been there anytime we had needed her. Hot tub is great! Place is super clean and efficient.

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$217

Alice's Beach Bungalows 2 bedroom

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“A perfect spot for us and for our golden retriever!” What a great place to enjoy the beauty of Treasure Island. The bungalow that we stayed in was wonderful...clean, a well stocked kitchen, beach towels, a great backyard. Susan, the owner, was also great to work with on every level. She was attentive, often checking in on us to make sure all was going great with our stay. She was also responsive to our rental needs and responded immediately if we had a question, etc.. She also embraced our golden retriever and he, too, immediately became fast friends with Susan. This bungalow is literally a block from the beach, a short walk over the bridge to John's Pass and close to grocery shopping, lots of great restaurants right on the beach, etc.. A great experience and we will definitely plan to stay at this bungalow again!

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$316

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

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$373

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

Holmes Beach villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$148

REDUCED FOR APRIL!

Madeira Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“get away” My experience was kinda shaky at first , I was given the wrong gate code to get in complex, plus there were a couple of wristbands for pool entry missing and a blind that was messed up,but was able to be fixed in about 15 minutes. Our reservations were never given to property managers at office as well, but as soon as Jennifer responded she was able to take care of that. I have been to 2 other units there and this unit is the most modern by far and is very clean,and a great spot in the complex.

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$171

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.

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$246

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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$240

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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$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

$197

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

$460

Beautiful Beachfront Condo on the FL Gulf Coast

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful family beach vacation condo” The condominium is a great place to stay. All the amenities you need to enjoy a relaxing family vacation. There is an picturesque view of the beach on the balcony and a large pool to enjoy. The location of the condo is convenient to shopping and restaurants. Carol (the owner) is always very helpful and accessible if you have any questions about your stay. We have found a new place to stay on our summer vacation and can't wait to visit again next year!

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$242

Paradise Lane- Dolphin View on the Intercoastal Water !! Boats Welcome

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$483

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 25 minutes

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Price per night from

$259

Steps to beach and bay on beautiful Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$101

Family friendly condo on the beach - Ocean Sands

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$158

Fine Waterfront Living . Steps to Beach

St. Pete Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$488

Beautiful Condo in Madeira Beach January Special

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$201

NSS Pattam, custom 84 foot traditional motor yacht downtown.

St. Petersburg yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 42 minutes

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Price per night from

$1,377

escape to paradise

Madeira Beach apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

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$207

SunWay Suites Unit 2 Plover

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$23

SunWay Suites Unit 4 Pelican

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$138

King size Bed room 7

St. Petersburg house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$345

Beach OASIS

St. Pete Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 16 minutes

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$172

231A Madeira Beach Yacht Club

Madeira Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$148

#1 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$345

#2 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$345

#5 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$345

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rentals in Anna Maria

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