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Mangrove Cottage-105 Mangrove $938.00 - $2,514.00 per week

  • Quick Facts:
    City: Anna Maria
    Pets Allowed: Yes
    Pool:Yes, Heated,Chlorine
    • 2Bedrooms:
    • 2.0Bath:
    • 5Sleeps:
    • Property Rating:
  • Description:

    Charming and quaint "old Florida" style vacation cottage. (2) Bedrooms, (2) Bath, accommodates up to (5) people: 1 King, 2 Twin, 1 Trundle. Private heated pool, free wireless, pets welcome with fee, only a couple houses to the beach access.

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Fountainhead 5 $602.00 - $1,540.00 per week

  • Quick Facts:
    City: Holmes Beach
    Pets Allowed: Yes
    Pool:Yes, Heated
    • 2Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Property Rating:
  • Description:

    Coastal, clean and bright centrally located seasonal vacation condo. (2) Bedroom, (2) Bath, accommodates (6) people: 1 Queen, 2 Twins, 1 Sleeper sofa. Shared heated pool, free wireless internet, pets are welcome with fee, less than two blocks to the beach.

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Sugar Plum Hideaway West $1,400.00 - $2,500.00 per week

  • Quick Facts:
    City: Anna Maria
    Pets Allowed: Yes, under 25 lbs
    Pool:Yes,heated shared
    • 3Bedrooms:
    • 2.0Bath:
    • 8Sleeps:
    • Property Rating:
  • Description:

    Quaint “Sugar Plum Hideaway West” 114 Mangrove, Anna Maria. Offers (3) Bedrooms, (2) Bath and, up to (8) guests: 2 King, 2 Twin, 1 Queen Sleeper sofa. Short walk to the beach. Shared heated pool. Convenient location near shopping, restaurants and free trolley stop. Outdoor shower, Pet friendly to dogs up to 25 pounds, flat screen televisions, wireless internet, and cute décor will have you relaxed in paradise. 

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

  • Quick Facts:
    City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, Heated w/spa
    • 3Bedrooms:
    • 3.0Bath:
    • 8Sleeps:
    • 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, (3) Bathroom, accommodates up to (8) 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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Blue Wave Villas-207E 75th St $1,166.00 - $2,070.00 per week

  • Quick Facts:
    City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, elec&solar
    • 2Bedrooms:
    • 1.0Bath:
    • 4Sleeps:
    • Property Rating:
  • Description:

    Cozy, comfortable, but above all classy vacation duplex. (2) Bedrooms, (1) Bath, accommodates up to (4) people: 1 King, 2 Twin. Private heated pool, free wireless, sorry no pets allowed, less than two blocks to the beach.

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Tiffany Place 213 $865.00 - $1,495.00 per week

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

    Don't miss a single sunset from your balcony at this gulf front vacation condo in Holmes Beach called Tiffany Place.  (2) Bedroom, (2) Bath, accomodates up to (4) people: 1 King, 2 Twin. Heated pool, free wireless, sorry no pets allowed.

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Water's Edge 103 North $900.00 - $1,820.00 per week

  • Quick Facts:
    City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, heated
    • 2Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Property Rating:
  • Description:

    If you're looking for a charming vacation rental to spend your next visit to Anna Maria Island, you might just be looking for something in the Water's Edge condominium complex. (2) Bedroom, (2) Bath, accomodates to (6) people: 1 Queen, 2 Twin, 1 Sleeper Sofa. Heated pool, free wireless, sorry no pets allowed, gulf front location. 

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Palm Isle 3204 $700.00 - $1,533.00 per week

  • Quick Facts:
    City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, Heated
    • 2Bedrooms:
    • 1.0Bath:
    • 6Sleeps:
    • Property Rating:
  • Description:

    **Fantastic Value - Flexible Arrival Dates - Last Minute Discounts**

    Captivating and cute cottage-style ground level condos perfect for your relaxing island getaway. (2) Bedroom, (1) Bathroom, accommodates up to (6) people: 1 Queen, Set of short bunk beds, 1 Sleeper Sofa. Heated pool, free wireless, sorry no pets allowed, across the road from the beach access.

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7001 B Holmes Blvd $1,100.00 - $2,185.00 per week

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

    Relaxing raised vacation home, 7001 B Holmes Boulevard located in wonderful Holmes Beach. Offers (3) Bedrooms, (2) Bath and, up to (8) guests: 1King, 1 Queen, 2 Twin, 1 Queen Sleeper sofa. Short walk to the beach and southbound free trolley stop. Enjoy premium linen service, dish washer, heated private pool, canal side views, washer/dryer, driveway parking and wireless internet.

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Gulf Breeze-203E 69th St $2,068.00 - $7,498.00 per week

  • Quick Facts:
    City: Holmes Beach
    Pets Allowed: Yes
    Pool:Yes-Htdw/Spa&Tiki
    • 6Bedrooms:
    • 4.5Bath:
    • 16Sleeps:
    • Property Rating:
  • Description:

    You'll never forget the views from this luxury vacation rental - a sweeping vista of the Gulf of Mexico and its shimmering quartz sand beaches. It will be love at first sunset! (6) Bedrooms, (4.5) Bath, accommodates up to (16) people: 4 King, 2 Twins, 1 Full and 2 Sleeper Sofas. Private heated pool with spa, free wireless, pet friendly with fee, less than two blocks to the beach.

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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

Three years ago, I listed my first rental property with Island Real Estate, since then I have listed an additional three...

-Brian View Property