Luxury Villas Vacation Rentals

Every Island Real Estate vacation rental home is perfect in our eye, but this selection of 5-Star rated luxury homes offer up the absolute best Anna Maria Island experience.

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LaMadeira 305 64th Unit A $1,500.00 - $3,040.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, heated
    BBQ/Grill: Yes
    Remote Entry Lock: Not Available
    SQFT Under A/C: 1,610
    Turn Day: Any
    • 3Bedrooms:
    • 3.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
Description:

Luxury vacation rental “LaMedeira” 305 64th St Unit A on Holmes Beach. Offering (3) bedroom, (3) Bathrooms: 1 King bed 2 Queen bed. Luxurious bathrooms and décor. Short walk to Gulf Beaches and free trolley stops. Enjoy Private heated pool, wireless internet, stainless appliances, premium linens, washer/dryer, and covered outdoor balconies. 

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Grande Haven-804 No Shore Dr $3,050.00 - $8,400.00 per week

  • City: Anna Maria
    Pets Allowed: Yes, under 50lbs
    Pool:Yes, heated and spa
    BBQ/Grill: Yes
    Remote Entry Lock: Available
    SQFT Under A/C: 5,512
    Turn Day: Saturday
    • 6Bedrooms:
    • 3.0Bath:
    • 16Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
Description:

Glamorous vacation rental “Grande Haven” located at 804 North Shore Drive, Anna Maria. Accommodates (16) guests (6) bedrooms (3) bathrooms: 3 king beds, 2 queen beds, 2 sets of bunks and 1 queen sleeper sofa. Pet friendly up to 50 pounds. Across the street from Gulf Beaches. Heated pool and spa. Six parking spaces, washer/dryer, dishwasher, premium linens. Elevator. Nearby marina for boat access. 

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Fun In The Sun - 302 62nd St $1,200.00 - $2,250.00 per week

  • City: Holmes Beach
    Pets Allowed: Yes, dogs under 25lb
    Pool:Yes, Heated
    BBQ/Grill: Yes
    Remote Entry Lock: Available
    SQFT Under A/C: Approx 1800 sqft
    Turn Day: Saturday
    • 3Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
Description:

Memorable and magical tropical island home with beautiful pool oasis. (3) Bedrooms, (2) Bath, accommodates up to (6) people: 1 King, 1 Queen, 2 Twins. Private heated pool, free wireless, dogs under 25lbs are welcome with pet fee.

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SeaShell-Sunsets-105 78th $4,200.00 - $5,250.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes heated & spa Remote Entry Lock: Available
    SQFT Under A/C: 3,000
    Turn Day: Saturday
    • 4Bedrooms:
    • 4.5Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
Description:

 Gorgeous gulf view home "Seashell Sunsets" 105 78th Street in Holmes Beach. (4) Bedroom, (4.5) Bathroom, accomodates up to (8) people: 2 King, 4 Twin Beds, 2 Trundle. Private heated pool with spa, wireless internet, elevator, washer/dryer, roof top balcony, dishwasher. Just steps to the gulf. 

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Coral Reef - 215 64th St $2,047.00 - $4,750.00 per week

  • City: Holmes Beach
    Pets Allowed: Yes
    Pool:Yes, Heated
    BBQ/Grill: Yes
    Remote Entry Lock: Available
    SQFT Under A/C: Approx 2690 sqft
    Turn Day: Any
    • 5Bedrooms:
    • 3.5Bath:
    • 10Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
Description:

Spacious, private vacation home that offers peeks of the gulf and backyard tiki bar. (5) Bedroom, (3.5) Bath, accommodates up to (10) people: 2 King, 1 Queen, 2 Twin, 1 Sleeper Sofa. Private heated pool, free wireless, pet friendly (with deposit), less than two blocks to the beach.

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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
    Remote Entry Lock: Not Available
    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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Honey Beach House 103 50th St $1,750.00 - $3,150.00 per week

  • City: Holmes Beach
    Pets Allowed: Yes, dogs under 25lb
    Pool:No
    BBQ/Grill: Yes
    Remote Entry Lock: Available
    SQFT Under A/C: 2,718
    Turn Day: Any
    • 3Bedrooms:
    • 3.5Bath:
    • 7Sleeps:
    • Guest Rating:
      No Guest Rating Available
    • Property Rating: Gold
Description:

Welcome to Honey Beach House located at 103 50th Street Holmes Beach on beautiful Anna Maria Island. A lot of time, love, and taste have gone into this Gulf front vacation home. (3) Bedroom, (3.5) Bathroom, accommodates up to (7) people: 2 King, 1 Double w/ twin over, 1 Trundle & double sleeper sofa. Dogs welcome under 25lbs.

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Pineapple Cottage 407 Spring $1,750.00 - $4,250.00 per week

  • City: Anna Maria
    Pets Allowed: Dogs 25lbs
    Pool:Yes, heated & spa
    BBQ/Grill: Yes
    Remote Entry Lock: Not Available
    SQFT Under A/C: 1,500
    Turn Day: Any
    • 4Bedrooms:
    • 3.0Bath:
    • 8Sleeps:
    • Guest Rating:
      No Guest Rating Available
    • Property Rating: Platinum
Description:

Experience the laid back luxury vacation you deserve when you stay at "Pineapple Cottage" located at 407 Spring Ave, Anna Maria, Florida. This lively Anna Maria Island ground level vacation rental is well-appointed with everything for the perfect tropical island getaway.

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Wine Down 2907 Ave F $4,999.00 - $13,000.00 per week

Special

Wine Down - 45% off when arriving 4/29 - 5/6/2017

Special Eligible When Booking From 03/13/2017 to 05/06/2017
Save 30%

Arrive at one of our premier gulf front properties, Wine Down, from April 29th, 2017 through May 6th, 2017 and get 45% off of your rental fee when staying for week long stays!

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
    Remote Entry Lock: Available
    SQFT Under A/C: 2,300
    Turn Day: Any
    • 4Bedrooms:
    • 4.5Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
Description:

Stunning luxury direct gulf front vacation rental, “Wine Down” located at 2907 Avenue F in Holmes Beach. Sleeps (8) guests with (4) Bedroom (4.5) bathroom: 3 king beds, 1 queen bed, 1 queen sleeper sofa. Gorgeous balcony views of the gulf, heated pool/spa, bbq grill, wireless internet, flat screen tv’s, washer/dryer, dishwasher.

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

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, Heated w/spa
    BBQ/Grill: Yes
    Remote Entry Lock: Not Available
    SQFT Under A/C: Approx 2136 sqft
    Turn Day: Saturday
    • 3Bedrooms:
    • 3.0Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
Description:

Luxury condominium “La Casa Poulos” located on direct beach front at 7318 Gulf Drive, Holmes Beach. Rooms (8) guests with (3) bedrooms (3) bathroom: 1 king bed, 1 queen bed, 2 twin bed, 1 full sleeper sofa, 1 air mattress. Community heated pool and spa. Washer/Dryer, elevator, 2 parking spaces, wireless internet, dishwasher, wet bar. Open balcony overlooking pool area.

 

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