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25 Seaside Court $630.00 - $1,635.00 per week

  • Quick Facts:
    City: Holmes Beach
    Pets Allowed: Yes
    Pool:None
    • 2Bedrooms:
    • 2.0Bath:
    • 4Sleeps:
    • Property Rating:
  • Description:

    Coastal and cozy vacation villa. (2) Bedrooms, (2) Bathrooms, accommodates up to (4) guests. 1 Queen, 2 Twins. Highspeed internet, pets welcome with fee, bay front location with boat access, not far from the beach. 

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North Beach Village Unit 27 $780.00 - $1,750.00 per week

  • Quick Facts:
    City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, Community
    • 3Bedrooms:
    • 2.5Bath:
    • 8Sleeps:
    • Property Rating:
  • Description:

    Refresh, renew, and relax among lush landscaping for privacy at this vacation condo. (3) Bedroom, (2.5) Bath, accommodates (8) people: 2 Queens, 2 Twins, 1 Queen Sleeper Sofa.  Community heated pool, free wireless internet, sorry no pets, less than two blocks to the beach access.

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Summer Breeze at 313 61st St $1,575.00 - $3,360.00 per week

  • Quick Facts:
    City: Holmes Beach
    Pets Allowed: Yes,Dogs under 25lbs
    Pool:Yes, heated waterfal
    • 4Bedrooms:
    • 3.5Bath:
    • 10Sleeps:
    • Property Rating:
  • Description:

    Summer Breeze is located at 313 61st on Beautiful Anna Maria Island in the small city of Holmes Beach. This upscale single family vacation rental offers the vacationer in

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La Casa Leann $1,715.00 - $3,675.00 per week

  • Quick Facts:
    City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, Heated w/Spa
    • 3Bedrooms:
    • 2.5Bath:
    • 6Sleeps:
    • Property Rating:
  • Description:

    Some of the most popular vacation rentals on Anna Maria Island can be found at La Casa Costeria. And the reason is blissfully simple – because they’re the crème de la crème. (3) Bedroom, (2.5) Bathroom, accommodates up to (6) people: 1 King, 1 Queen, 2 Twin, 1 Air Mattress. Heated pool with spa, free wireless, sorry no pets allowed, gulf front location.

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Sweet Retreat Cottage-748 NoSh $1,505.00 - $3,087.00 per week

  • Quick Facts:
    City: Anna Maria
    Pets Allowed: No
    Pool:Yes, heated
    • 3Bedrooms:
    • 2.0Bath:
    • 8Sleeps:
    • Property Rating:
  • Description:

    Enjoy a vacation of seaside serenity at this indulgent vacation cottage in Anna Maria City. (3) Bedrooms, (2) Bath, accommodates up to (8) people: 1 King, 1 Queen, 2 Twins, 1 Sleeper Sofa. Private heated pool, free wireless, sorry no pets allowed, less than two blocks to the beach. Beach access is right across the street.

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5200 Gulf Dr Unit 401S $0.00 - $1,414.00 per week

  • Quick Facts:
    City: Holmes Beach
    Pets Allowed: No
    Pool:Community,heated
    • 2Bedrooms:
    • 2.0Bath:
    • 4Sleeps:
    • Property Rating:
  • Description:

    A magical sunset oasis.  (2) Bedroom, (2) Bath, accommodates up to (4) people; 2 Kings, free wireless internet, community heated pool, DIRECT beach front condo.

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Sandy Pants - 133 White Ave $935.00 - $2,249.00 per week

  • Quick Facts:
    City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, Heated
    • 2Bedrooms:
    • 1.5Bath:
    • 5Sleeps:
    • Property Rating:
  • Description:

    Remodel January 2015! Be the first to see all the new decor, appliances, etc. 

    The only thing that makes a week in paradise better is if you're spending it in the sort of laid back luxury found at this vacation rental called Sandy Pants. (2) Bedroom, (1.5) Bathroom, accommodates up to (5) people; 1 King, 1 Twin, 1 Double, 1 Sleeper Sofa. Private heated pool, free wireless, sorry no pets allowed, one block to the beach.

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Paradise Found-5802 DePalmas $1,186.00 - $2,498.00 per week

  • Quick Facts:
    City: Holmes Beach
    Pets Allowed: No
    Pool:Yes
    • 3Bedrooms:
    • 3.0Bath:
    • 6Sleeps:
    • Property Rating:
  • Description:

    Sweet dreams and soothing, tropical decor at this peaceful vacation rental home. (3) Bedroom, (3) Bathroom, accommodates up to (6) people: 1 King, 1 Queen, 2 Twins. Heated pool, Free wireless, sorry no pets allowed, less than two blocks from the beach.

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Little Miss Magic-116 81st St $1,260.00 - $2,625.00 per week

  • Quick Facts:
    City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, heated
    • 3Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Property Rating:
  • Description:

    Brand NEW, charming and cute vacation oasis.  (3) Bedrooms, (2) Bath, accommodates up to (6) people: 2 Queens, 2 Twins.  Private, heated pool, free wireless internet, sorry no pets allowed, only a few houses to the beach.

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Holly Hideaway-730 Holly Road $966.00 - $2,204.00 per week

  • Quick Facts:
    City: Anna Maria
    Pets Allowed: Yes dogs under 25lbs
    Pool:Yes, heated
    • 2Bedrooms:
    • 2.0Bath:
    • 4Sleeps:
    • Property Rating:
  • Description:

    With a breezy wooden patio outside, a cozy brick fireplace inside, and Florida gulf coast style throughout, you'll never want to spend a holiday on Anna Maria Island anywhere else. (2) Bedrooms, (2) Bathroom, accommodates up to (4) people: 1 King, 1 Queen, 1 Double Sleeper sofa.  Private heated pool, free wireless, pets are welcome (dogs only, up to 25lbs) with fee.

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Office Locations{ Island Real Estate } 6101 Marina Drive, Holmes Beach, FL 34217 | 419 Pine Ave., Anna Maria, FL 34216

Guest Testimonials

Great location, house was perfect for 8 adults, and an infant. Really nice area to relax in for a week, took advantage of...

-Gary Rae

Owner Testimonials

My wife and I have used Island Real Estate as our property managers since we purchased our second home at 744 North Shore...

-John