Vacation Rentals & Beach Rentals in Anna Maria

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211 beach rentals

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

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Golf within 30mins drive

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Price per night from

$631

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.

Match: Golf within 30mins drive

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Price per night from

$631

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

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Golf within 30mins drive

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Price per night from

$743

Newly renovation bay side cottage: Sea Breeze

Anna Maria cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$354

Jacaranda Artist Retreat

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Golf within 30mins drive

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Price per night from

$219

Serendipity Deux- Beachfront 4 Bed/heated pool/elevator

Anna Maria house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Golf within 30mins drive

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Price per night from

$2,290

Tripletail

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Golf within 30mins drive

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Price per night from

$1,718

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Golf within 30mins drive

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Price per night from

$1,260

Mintfish

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Golf within 30mins drive

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Price per night from

$1,145

Waves on Anna Maria

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Golf within 30mins drive

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Price per night from

$976

Cloud 9

Anna Maria house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Golf within 30mins drive

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Price per night from

$1,947

Great rentals within 20 miles that match your search

Executive Waterfront Home

St. Petersburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Golf within 30mins drive

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Price per night from

$259

Newly Remodeled Spacious Loft in Sarasota!

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$295

SUNSHINE HOLIDAY

St. Petersburg manor house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Golf within 30mins drive

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Price per night from

$1,148

OCEANFRONT VIEW - PRIVACY OVERLOOKING THE GULF OF MEXICO

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Golf within 30mins drive

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Price per night from

$207

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

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Golf within 30mins drive

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Price per night from

$517

Treasure Island Beach Condo

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 45 minutes

Match: Golf within 30mins drive

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Price per night from

$155

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Golf within 30mins drive

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Price per night from

$1,001

Boca Ciega Condo, #408, St Petersburg, Florida

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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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

Match: Golf within 30mins drive

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Price per night from

$206

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

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$402

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.

Match: Golf within 30mins drive

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Price per night from

$217

BEACH FRONT, PRIVATE LARGE UPPER DECK, #5 SUNSETS IN PARROTDISE

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Great view, deck, yard, access to the beach!” We would definitely stay here again. Great view of the Gulf and sunsets. Closer to the beach than most places. Nice sized deck, yard and we really loved the smaller complex. Only negative side was entering through the bedroom and having the bathroom right next to your bed. Great having a washer and dryer though. Treasure Island is a clean place, lovely soft sand, great first time trip! Cannot wait to go back!!

Match: Golf within 30mins drive

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Price per night from

$347

Modern Studio, Designer Kitchen Walkable Downtown

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Golf within 30mins drive

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Price per night from

$132

Tara Golf & Country Club Condo

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful, peaceful location and beautiful condo.” This condo is wonderful and has everything anyone would want or need for a wonderful stay. We loved the property and the owners. It is located in a private championship golf course community and is just across the street from all the amenities. The amenities include tennis, pool, workout room, and of course golf at its best. There is a wonderful grill room and beautiful dining room facing the driving range. Very close to a hugh shopping area and enclosed mall. Very convenient to travel anywhere from here. Very nice rental in a wonderful area.

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Price per night from

$144

1 Bedroom Madeira Beach Cottage

Madeira Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$155

St Pete Beach Paradise

St. Pete Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$123

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!

Match: Golf within 30mins drive

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Price per night from

$316

Alice's Beach Bungalows Private Oasis #2

Treasure Island bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$229

River Strand Luxury Condo-Tennis & Golf Community

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Golf within 30mins drive

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Price per night from

$86

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

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Golf within 30mins drive

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Price per night from

$373

NW Bradenton Exectitive Home

Bradenton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Golf within 30mins drive

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Price per night from

$493

Lido Sunshine M

Lido Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$183

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

Holmes Beach villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Golf within 30mins drive

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Price per night from

$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.

Match: Golf within 30mins drive

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Price per night from

$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.

Match: Golf within 30mins drive

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Price per night from

$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.

Match: Golf within 30mins drive

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Price per night from

$240

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

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 33 minutes

Match: Golf within 30mins drive

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Price per night from

$247

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