Anna Maria Island Vacation Rentals

Located just off the coast of Florida, our Anna Maria Island rentals promise beautiful beaches and pristine waters that make it a paradise. Choose from the variety of water and beach activities available for never ending fun or spend your days enjoying the many shops and restaurants of this wonderful city. There is something for every kind of traveler at our Anna Maria Island vacation rentals. No matter what kind of group you are traveling with, from couples to large families, iTrip has the perfect size rental for you. Each of our Anna Maria Island rentals guarantees the highest quality amenities and accommodations including spacious floor plans, beach views, and much more. You can experience all the comforts of home and all the fun you can imagine during your stay at our Anna Maria Island vacation rentals. Research, choose, and easily begin planning your stay at any of our Anna Maria Island rentals today.

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

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 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.


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.


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


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.


Pool area image
$3,640 - $5,880 /month
* seasonal rates & fees apply
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Longboat Key Players Club #103 (3 Month Minimum Stay)
2 Bedrooms / 2.5 Baths / Sleeps 6 in Longboat Key, FL

Spacious corner unit 2 bedrooms 2.5 bathrooms (3 month minimum stay)


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)


Longboat Key - Bungalow (Pets Welcome!) image
$132 - $195 /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.


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


Extremely Tranquil Sun City Center 2 Bedroom, 2 Bath Luxury Villa & Golfer's Retreat (Pets are welcome!) - ONE MONTH MINIMUM STAY image
$525 - $770 /week
* seasonal rates & fees apply
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Extremely Tranquil Sun City Center 2 Bedroom, 2 Bath Luxury Villa & Golfer's Retreat (Pets are welcome!) - ONE MONTH MINIMUM STAY
2 Bedrooms / 2 Baths / Sleeps 6 in Sun City Center, FL

Quiet Sun City Villa...and we do mean quiet!