Vacation Rentals & Beach Rentals in Anna Maria

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187 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

$635

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

$635

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

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$746

Newly renovation bay side cottage: Sea Breeze

Anna Maria cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$357

Jacaranda Artist Retreat

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$220

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

$2,299

Tripletail

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,724

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,265

Mintfish

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,150

Waves on Anna Maria

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$981

Cloud 9

Anna Maria house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$1,954

Great rentals within 20 miles that match your search

Fine Waterfront Living . Steps to Beach

St. Pete Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$491

SUNSHINE HOLIDAY

St. Petersburg manor house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$1,154

OCEANFRONT VIEW - PRIVACY OVERLOOKING THE GULF OF MEXICO

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$208

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

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$520

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

$289

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

$347

Boca Ciega Condo, #408, St Petersburg, Florida

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$202

Boca Ciega Condo, #107, St Petersburg, Florida

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$207

Perfecto's Retreat Unit #1

St. Petersburg cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$345

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$433

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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Price per night from

$218

ADORABLE BEACH CONDO!!! GREAT RATES!!! FABULOUS SUNSETS ON ST. PETE BEACH!!!

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$138

River Strand Golf and Country Club Resort

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$231

Modern Studio, Designer Kitchen Walkable Downtown

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$133

Land's End: Gulf-front Luxury, WIFI, HDTV

Treasure Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$396

Pass-A-Grille Beach House

St. Pete Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$220

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

$145

John's Pass-Time Beach Front Cottage

Madeira Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$289

St Pete Beach Paradise

St. Pete Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$124

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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Price per night from

$318

Alice's Beach Bungalows Private Oasis #2

Treasure Island bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$230

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

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Loved it” Quiet but close to what ever you want. The beach is just across the road, one restaurant within walking distance, the main road to mainland is 1.2 miles away, but everything you need is on Gulf Blvd. The house and yard were well maintained. Inside was excellent shape with open floor plan that gave a sense of a large space. The kitchen was open and had about everything you would need including basic supplies like coffee, sugar, some spices, etc. We had arrived 1/2 hr early and cleaning lady was there so we went across the bridge to Johns Pass about a 1/4 mi and had a drink and came back as she was leaving to get a new microwave as it had broken when she checked it. There is a large back yard and private sitting area. The hot tub is in backyard along with a grill. The bedrooms were large with plenty of closet space. The bath room was roomy with a " sunken tub" that consisted of one step down for a seat and another step to the bottom for about 6-8 inches of water. However the shower was more that adequate. A really nice, comfortable place to stay for a few days.

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Price per night from

$375

NW Bradenton Exectitive Home

Bradenton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$495

Lido Sunshine M

Lido Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$184

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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Price per night from

$172

Runaway Bay - Bradenton Beach - Bay View Unit 193

Anna Maria Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Home away from home” This place is an incredible value. It's spacious and comfortable, and we felt right at home. Sarasota Bay is just steps from the back patio, and it's so lovely to sit outside and watch water--so many fish, dolphins, and birds right there. Everything was in good working order and clean upon our arrival. The beach is a quick walk across the street from the complex, and we spent a lot of time at the heated pool. We would love to rent this unit again! PERFECT LOCATION.

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Price per night from

$210

Family friendly condo on the beach - Ocean Sands

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$158

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rentals in Anna Maria

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