Anna Maria Island Vacation Rentals

View photos of Anna Maria Island below and be sure to Bradenton Beach (2) Holmes Beach (1) Longboat Key (2)

BedroomsSleeps
Average Daily Rate  taxes & fees not included
Property Type Amenity

Royal Palm Drive image
$665 - $1,050 /week
* seasonal rates & fees apply
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Royal Palm Drive - Boater's Paradise and Spring Training Baseball Headquarters
2 Bedrooms / 2 Baths / Sleeps 4 in Bradenton, FL

Two bedroom house on the Intercoastal Waterway


Sunkissed Longboat Key Beachfront Condo image
$178 - $287 /night
* seasonal rates & fees apply
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Sunkissed Longboat Key Beachfront Condo
1 Bedrooms / 1 Baths / Sleeps 6 in Longboat Key, FL

Beach in/Beach out Condo (Sleeps 6 - in 2 queen beds and 2 more in a queen sofa bed)


Anna Maria Island Shell Point Unit # 92 (Pets Welcome) image
$2,520 - $4,000 /month
* seasonal rates & fees apply
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Have breakfast with the dolphins. Spacious 2BR/2BA condo overlooking Anna Maria Sound.
2 Bedrooms / 2 Baths / Sleeps 4 in Holmes Beach, Florida

This extremely bright condo offers everything you could hope for in a seasonal rental property. Brilliant morning sun fills the living areas of this spacious unit. The kitchen is fully equipped and the family room features a raised seating area ideal for entertaining or watching the dolphins swam by in Anna Maria Sound.


Longboat Key - Bungalow (Pets Welcome!) image
$126 - $189 /night
* seasonal rates & fees apply
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Longboat Key - Bungalow (Pets Welcome!)
2 Bedrooms / 1 Baths / Sleeps 6 in Longboat Key, FL

Pet friendly, Unique Bungalow Canal Home on the North End of Longboat Key.


Harbor Towers Yacht & Racquet Club, Unit 203 (2 Week Minimum Stay) Siesta Key Boaters Getaway image
$312 - $967 /week
* seasonal rates & fees apply
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Harbor Towers Yacht & Racquet Club, Unit 203 (2 Week Minimum Stay) Siesta Key Boaters Getaway
2 Bedrooms / 2 Baths / Sleeps 7 in Sarasota, Florida

As you enter the Harbor Towers Yacht & Racquet Club, you'll feel welcomed to a luxurious tropical vacation by the splendid waterfall in front of the main entrance and the exquisite tropical landscaping.


Longboat Key Towers image
$5,180 - $6,720 /month
* seasonal rates & fees apply
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Spectacular Penthouse Condo.
3 Bedrooms / 2 Baths / Sleeps 6 in Longboat Key, Florida

Spectacular penthouse condo.


Pool/ Tennis Courts image
$114 - $190 /night
* seasonal rates & fees apply
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Anna Maria Island Pelican Cove - Gulf Beach and Bay Fishing
2 Bedrooms / 2 Baths / Sleeps 6 in Bradenton Beach, FL

2 Bedroom 2 Bath Unit, Sleeps 6


New for the Upcoming Winter Season - Luxury Apartment on Longboat image
$5,180 - $8,120 /month
* seasonal rates & fees apply
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New for the Upcoming Winter Season - Luxury Apartment on Longboat
2 Bedrooms / 2 Baths / Sleeps 4 in Longboat Key, Florida

A stunning selection of color and style all situated against the sparkling backdrop of the Gulf of Mexico. This 2BD/2BA residence is elevated to the 8th level above the white sands of the private Longboat Key beaches. This beach facing unit also offers views of the Longboat Key Islandside golf course, the Sarasota Bay and downtown Sarasota. The views are amazing and the residence is updated to perfection.


Balcony image
$5,180 - $6,720 /month
* seasonal rates & fees apply
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Longboat Key Players Club #401 (3 Month Minimum Stay)
3 Bedrooms / 2.5 Baths / Sleeps 6 in Longboat Key, FL

Magnificent 3 bedroom, 2.5 bath beach front condominium (3 month minimum stay)


Top balcony view of the Gulf image
$2,000 /week
* seasonal rates & fees apply
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Anna Maria Island 3 Story Beach House
3 Bedrooms / 3 Baths / Sleeps 6 in Holmes Beach, FL

Beautiful Anna Maria Island 3 Story Beach Home with Heated Pool and Hot Tub in Private Patio