Anna Maria Island Condo Rentals

Reviews (42)

Hi, we’re Terry and Sandy, the caring (and hands-on) owners and managers of Anna Maria Beach Condo. We’ve been here for years, s...

Hi, we’re Terry and Sandy, the caring (and hands-on) owners and managers of Anna Maria Beach Condo. We’ve been here for years, so we know Anna Maria Island, the island’s condos, and our island’s guests. We understand you – what you need, what you want, and what you’d really like to have. With us, every stay balances the rigorous requirements of professional managers with the enthusiasm, pride and personal touches of an owner-managed rental. That means that with us, you enjoy the dual benefits of an in-the-know local combined with the professionalism and expertise of a serious company. Come on down and experience the difference for yourself.

Our family fell in love with Anna Maria Island the first time we visited in 1989. Every summer since, we’ve spent our vacations on this island, and in 1995, we bought our first condo here. Having a young family at the time meant we had to rent our condo to offset ownership costs. Thankfully, by offering luxurious accommodations at an affordable price, we were able to keep the condo booked for an average of 50 weeks a year. These steady bookings allowed us to purchase our second condo in 2013, and a third in 2014. While opening up these homes has allowed us to keep returning to the island—and even better, to a house that feels like home—we also truly enjoy offering a place to guests to discover Anna Maria Island and feel at home here, too.

We were honored when TripAdvisor and FlipKey recognized our dedication to providing a top-notch rental experience with a “Top Rental Property” award two years running. More than anything, we appreciate that positive reviews from past guests determine the award winners.

Office located in
Pickering, Canada
Listed on TripAdvisor since
May 2009
Languages spoken
English
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Rentals from Anna Maria Island Condo Rentals

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Rentals in: Bradenton Beach (15), Holmes Beach (6), Lake Toxaway (2), Anna Maria Island (1)

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1 / 63

The Anna Maria Island Beach Paradise 6

  • 2
  • 6
  • Min stay varies

$150

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1 / 63

Beach Palms 2A

  • 2
  • 6
  • Min stay varies

$115

Details

1 / 62

The Anna Maria Island Beach Paradise 5

  • 2
  • 6
  • Min stay varies

$150

Details

1 / 57

The Anna Maria Island Beach Paradise 10

  • Studio
  • 3
  • 7 nights min

$125

Details

1 / 41

The Anna Maria Island Beach Sands 101

  • 2
  • 6
  • Min stay varies

$140

Details

1 / 51

The Anna Maria Island Beach View 209

  • 2
  • 6
  • Min stay varies

$115

Details

1 / 63

The Anna Maria Island Beach Palms 6B

  • 2
  • 6
  • Min stay varies

$115

Details

1 / 37

The Anna Maria Island Beach Sands 201

  • 2
  • 6
  • Min stay varies

$140

Details

1 / 50

The Anna Maria Island Beach Castle

  • 2
  • 6
  • Min stay varies

$140

Details

1 / 68

The Anna Maria Island Beach Palace

  • 4
  • 8
  • 7 nights min

$326

Details

1 / 69

The Anna Maria Island Beach Palms 5B

  • 2
  • 6
  • Min stay varies

$115

Details

1 / 79

Anna Maria Island Beach Sands

  • 2
  • 5
  • Min stay varies

$140

Details

1 / 74

Anna Maria Island Retreat

  • 2
  • 6
  • Min stay varies

$140

Details

1 / 69

The Anna Maria Island Beach Castaway 1

  • 2
  • 6
  • Min stay varies

$135

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1 / 35

North Carolina Mountain Condo

  • 2
  • 6
  • 7 nights min

$125

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1 / 56

North Carolina Mountain Retreat

  • 1
  • 4
  • 7 nights min

$125

Details

1 / 72

Absolute Anna Maria

  • 2
  • 5
  • Min stay varies

$140

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1 / 57

The Anna Maria Island Beach Sands 203

  • 2
  • 4
  • Min stay varies

$140

Details

1 / 61

The Anna Maria Island Beach Breeze

  • 2
  • 6
  • Min stay varies

$157

Details

1 / 45

The Anna Maria Island Beach Retreat

  • 2
  • 6
  • Min stay varies

$135

Details

1 / 64

The Anna Maria Island Beach Castaway 2

  • 2
  • 6
  • Min stay varies

$135

Details

1 / 51

The Anna Maria Island Beach Palms 2B

  • 2
  • 6
  • Min stay varies

$115

Details

1 / 59

The Anna Maria Island Beach View 207

  • 2
  • 6
  • Min stay varies

$115

Details

1 / 69

The Anna Maria Island Beach Palms 7A

  • 2
  • 6
  • Min stay varies

$108

Details