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Misty Beach-5802 Imperiore Ave $1,050.00 - $2,532.00 per week

  • City: Holmes Beach
    Pets Allowed: Yes under 25lbs
    Pool:Yes, Heated
    BBQ/Grill: Yes
    SQFT Under A/C: Approx 1020 sqft
    Turn Day: Any
    • 2Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Gold
Description:

Bright and beachy island home for a peaceful island getaway. (2) Bedroom, (2) Bathroom, accommodates up to (6) people: 1 King, 1 Queen, 1 Full sleeper sofa. Private heated pool, free wireless, pet friendly (up to 25lbs) with fee, less than two blocks to the beach.  

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Island Pearl - 204 76th St $1,687.00 - $3,250.00 per week

Special

Island Pearl - 20% off when staying 4/20/2017 - 5/6/2017

Special Eligible When Booking From 03/10/2017 to 04/29/2017
Save 20%

Relax at Island Pearl on Anna Maria Island for one week arriving on April 29th, 2017, and save 20% off of the rental fee!

Only valid on new reservations, doesn’t stack with other discounts, select vacation homes may be exempt, subject to manager approval and black out dates.

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes heated & spa
    BBQ/Grill: Yes
    SQFT Under A/C: 2,300
    Turn Day: Saturday
    • 4Bedrooms:
    • 4.0Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
Description:

Beautiful light, bright and beachy relaxing seasonal rental. (4) Bedroom, (4) Bathroom, accommodates up to (8) people: 2 Kings, 1 Queen, 2 Twins. Private heated pool with spa, free wireless, sorry no pets allowed, less than two blocks to the beach.

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411 63rd St $800.00 - $1,300.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:None
    BBQ/Grill: Yes
    SQFT Under A/C: 1,000
    Turn Day: Any
    • 2Bedrooms:
    • 2.0Bath:
    • 4Sleeps:
    • Guest Rating:
    • Property Rating: Silver
Description:

Light and bright vacation villa with community boat ramp available for an idyllic holiday getaway. (2) Bedroom, (2) Bath, accommodates up to (4) people: 1 King, 2 Twin. Free wireless internet, sorry no pets allowed.

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Living The Dream 703 So Bay $2,949.00 - $4,000.00 per week

Special

Living The Dream - 25% off when staying the week of 4/15/2017

Special Eligible When Booking From 03/23/2017 to 04/15/2017
Save 25%

Relax at Living the Dream for 7 days starting on April 15th, 2017 and get 25% off of your rental fee!

Only valid on new reservations, doesn’t stack with other discounts, select vacation homes may be exempt, subject to manager approval and black out dates.

  • City: Anna Maria
    Pets Allowed: No
    Pool:Yes, heated
    BBQ/Grill: Yes
    SQFT Under A/C: 2,366
    Turn Day: Saturday
    • 4Bedrooms:
    • 3.0Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
Description:

Gorgeous canal front vacation home with immaculate decor. (4) Bedroom, (3) Bath, accommodates (8) people: 2 Kings, 2 XL Twins, 2 Twins. Private heated pool, boat access, free wireless internet, sorry no pets, across the street from the bay beach access.

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Playa Casanas Family $1,897.00 - $3,297.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:No
    BBQ/Grill: Yes
    SQFT Under A/C: Approx. 1230
    Turn Day: Saturday
    • 4Bedrooms:
    • 2.0Bath:
    • 8Sleeps:
    • Guest Rating:
      No Guest Rating Available
    • Property Rating: Gold
Description:

Perfect for multifamily vacations, rent one or both sides of this vacation rental duplex directly on the sparkling white, quartz sands of Holmes Beach, FL. (4) Bedroom, (2) Bathroom, accommodates up to (8 - 10) people: 2 Queen, 4 Twins, 2 Sleeper Sofa. Free wireless, sorry no pets allowed, gulf front location.

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Tortuga-212 81st St $1,350.00 - $2,500.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, heated
    BBQ/Grill: Yes
    SQFT Under A/C: 1,200
    Turn Day: Any
    • 3Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Gold
Description:

Slow down and get yourself on island time with a week at this ground level duplex in Holmes Beach, FL. (3) Bedrooms, (2) Bathrooms, accomodates up to (6) guests. 2 King, 2 Twins. Private heated pool, free wireless, sorry no pets allowed.  Note, this property has a Friday-Friday schedule.  Please call our office if you would like to request an exception.

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La Casa O'Bar $1,960.00 - $4,000.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, Heated w/Spa
    BBQ/Grill: Yes
    SQFT Under A/C: Approx 2012 sqft
    Turn Day: Saturday
    • 3Bedrooms:
    • 2.5Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
Description:

Stunning gulf front vacation rental “La Casa O’Bar” 7308 Gulf Drive Holmes Beach. (3) Bedroom (2.5) Bathroom rooms up to (6): 1 king bed, 2 queen bed, 2 twin bed. Gorgeous views from open balcony. Heated community pool, spa and BBQ grills. Washer/dryer, dishwasher, wireless internet, wet bar, 2 parking spaces, elevator, premium linen service. Jacuzzi tub master suite. 

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Dolphin - 706 Rose B $950.00 - $1,650.00 per week

  • City: Anna Maria
    Pets Allowed: Yes <25lbs dogs
    Pool:Yes,shared heat& spa
    BBQ/Grill: Yes
    SQFT Under A/C: 625
    Turn Day: Any
    • 2Bedrooms:
    • 1.0Bath:
    • 4Sleeps:
    • Guest Rating:
      No Guest Rating Available
    • Property Rating: Bronze
Description:
Quaint duplex located on a quiet street on the north end of beautiful Anna Maria Island. (2) Bedroom, (1) Bath, accommodates (4) people: 1 Queen, 1 Twin, 1 Queen Sleeper. Shared heated pool and spa, free wireless internet, pets are welcome with fee, less than two blocks to the beach.
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7001 A Holmes Blvd $1,425.00 - $2,500.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, heated
    BBQ/Grill: Yes
    SQFT Under A/C: 1,300
    Turn Day: Any
    • 3Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Gold
Description:

Gorgeous duplex style Anna Maria Island vacation rental 7001 A, Holmes Boulevard in Holmes Beach. Rooms (6) guests in (3) bedrooms and (2) bathrooms: 1 king bed, 1 queen bed, 2 twin beds and queen sleeper sofa. Walk to beach and trolley. Lake side location. Heated pool/spa. Wireless internet, park 2 vehicles, washer/dryer, dishwasher, premium linen service flat screen televisions, propane barbeque.

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Blue Waters-230 Willow $2,800.00 - $6,000.00 per week

  • City: Anna Maria
    Pets Allowed: No
    Pool:Yes, heated + spa
    BBQ/Grill: Yes
    SQFT Under A/C: 3,234
    Turn Day: Any
    • 4Bedrooms:
    • 4.0Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
Description:

Enjoy Blue Waters, a gorgeous luxury Mediterranean-style villa in peaceful surroundings. (4) Bedroom, (4) Bath, accommodates (8) people: 1 King, 2 Queens, 2 Twins. Fabulous outdoor & indoor living areas, gourmet kitchen, private office, heated swimming pool with spa, private dock and boat lift, full size billiards table and large screen outdoor TV are just a few of the highlights. Minutes from beach & Pine Avenue.

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Guest Testimonials

"We would book from Island Real Estate again." 

...

-Michael D View Property

Owner Testimonials

Island Real Estate is outstanding to work with - from Marianne who we've known for about 8 years and wouldn't work...

-Peggy