Vacation Rentals & Beach Rentals in Anna Maria Island

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32 beach rentals

5 Star - Private Pool & Dock, and Steps Away from the Beach - Fall Availability

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 24 minutes

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Price per night from

$399

Dream Lover Boat & Breakfast on Anna Maria Island

Bradenton Beach yacht

2 bedrooms / 2 bathrooms / sleeps 4

“Celebrate Birthdays & 24th Anniversary” We had a wonderful time on the Dream Lover this weekend. It was a special way to celebrate our birthdays and 24th Wedding Anniversary. We spent early mornings up on deck. The breakfasts were amazing! Love the area - so easy to walk to many restaurants, stores, and the beach. Kay and Jonathan are a wonderful couple wit such a positive and healthy outlook on life. They are a joy to spend time with. Oh and Skipper too!!! I was a wonderful weekend. Sue & Jim Hughes

Responds fast! avg. 1 hour 29 minutes

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Price per night from

$303

Treehouse Escape

Bradenton Beach house

6 bedrooms / 5 bathrooms / sleeps 18

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Price per night from

$1,029

Ohana Hale North 1 Bedroom

Holmes Beach house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 58 minutes

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Price per night from

$155

Surfside AMI, Many Amenities included!

Holmes Beach house

5 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$900

Anna Maria Island Beach Paradise

Anna Maria Island condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 48 minutes

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Price per night from

$458

The Anna Maria Island Beach Paradise 10

Anna Maria Island condo

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 48 minutes

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Price per night from

$164

Sandy Pointe #205

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$126

Great rentals within 20 miles that match your search

Beautiful Braden River Waterfront Retreat!

Bradenton house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 58 minutes

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Price per night from

$150

Fine Waterfront Living . Steps to Beach

St. Pete Beach house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$183

BBB on Marbury lane-Beach, boating, BBQ!

Longboat Key house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$286

Waterfront Villa Isla Del Sol St Petersburg FL

St. Petersburg villa

2 bedrooms / 2 bathrooms / sleeps 4

“Fantastic getaway” We stayed the month of February and had a wonderful experience. Not only was Will great to work with but the location was fabulous, the views spectacular, and the entire condo was very comfortable to stay in. So much to do or just hang at the heated pool, watching dolphins swim by, and having great conversations with other snow birds from the us and Canada. Such a fun time.

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Price per night from

$155

Oceanfront Boating and Fishing, Private dock

Terra Ceia house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 38 minutes

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Price per night from

$182

BEACHFRONT HOME 4BR/3BA**HEATED POOL&SPA*PETS OK

Treasure Island house

4 bedrooms / 3 bathrooms / sleeps 13

“Location location location” Myself and six of my friends stayed here and had a great week! The location is perfect and the swimming pool was an added bonus due to the high winds.... we grilled and that was great, we never went into the hot tub but I’m sure that would have been great as well... The beach was amazing and the sitting area just as nice.... the game room was an added bonus and the group really enjoyed that.. We would definitely come back!! Liz, thanks for all the instructions and helpful hints!!!!!

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Price per night from

$458

BAY VIEW. SUNSETS. CLOSE TO ANNA MARIA ISLAND AND IMG ACADEMY

Bradenton house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$166

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$332

Oceanfront 3 bedroom Condo on Longboat Key- Available in Summer ONLY

Longboat Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$172

Two Story Condo on the Gulf of Mexico

Longboat Key condo

4 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$539

Unit #102 Sand Cay Beach Resort Gulf Front

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$271

Unit #110 Sand Cay Beach Pool and Garden View 5 night min. 7 night in season

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$215

Unit #113 Sand Cay Beach Resort Pool and Garden View

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$215

Modern New Yacht in Paradise

St. Petersburg yacht

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$171

Unit #103 Sand Cay Beach Resort Gulf Front

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Match: Boat available

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Price per night from

$271

Palma Del Mar 311

Tierra Verde apartment

2 bedrooms / 2 bathrooms / sleeps 4

Match: Boat available

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Price per night from

$95

Beautiful Longboat Key Penthouse Unit for Rent - partial Gulf view

Longboat Key penthouse

3 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$346

NSS Pattam, custom 84 foot traditional motor yacht downtown.

St. Petersburg yacht

3 bedrooms / 3 bathrooms / sleeps 7

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Price per night from

$859

Gulf Coast Condo Minutes from Golf and Beaches

Bradenton condo

2 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$144

Cut House- Waterfront, dock, ocean access, beach

Palmetto house

3 bedrooms / 2 bathrooms / sleeps 6

“delightful” Three 60+ hockey players and their wives in search of a house close to the Ellenton Ice arena arrived here in april not knowing what to anticipate. We were delighted to find the accommodations exceptionally charming and clean. The views of the Manatee River were great and the traffic on "the Cut" was continually entertaining. The waterside amenities were superb and next time we'll rent a boat to keep at the dock. The "Naked Beach" next to the patio just off the dock might not have any surf but my tan is Just as even as can be and the proximity to the beer cooler was awesome. We recommend The Riverhouse and Blu Mangrove Grill for dining just ten minutes away. All in all the location, amenities, service, accommodations were top notch. Thanks "Cut House"!

Match: Boat available

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Price per night from

$287

GULF FRONT Studio at Beach Resort w/ Pool Tennis Spa Hot Tub & Family Activities

St. Pete Beach hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Match: Boat available

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Price per night from

$126

A sunsets and dolphins oh my! Waterfront, 3/3 dock, boat lift in deep water.

Treasure Island house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$224

EXTREME POLYNESIAN BEACH HOUSE with BOAT/ KAYAKS

Longboat Key house

6 bedrooms / 6 bathrooms / sleeps 20

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Price per night from

$802

Family & Budget Friendly Madeira Beach 2 BR- Now Booking Summer!??

Madeira Beach apartment

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$101

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