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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Coral Escape - 132 50th St $2,400.00 - $7,250.00 per week

Special

Coral Reef - 20% off 2/18/2017 - 3/11/2017

02/18/2017 to 03/11/2017
Save 20%

Stay at Coral Escape for 7 days anytime from February 18th, 2017 through March 11th, 2017 and get20% 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 including the weeks of Easter, 4th of July, Thanksgiving and most major holidays.

Coral Escape - 25% off for April 2017

04/01/2017 to 04/30/2017
Save 25%

Relax in paradise at Coral Escape arriving anytime in April 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: Holmes Beach
    Pets Allowed: Yes >50lbs
    Pool:Yes - Heated
    BBQ/Grill: Yes
    SQFT Under A/C: Over 3000 sqft
    Turn Day: Saturday
    • 6Bedrooms:
    • 4.0Bath:
    • 12Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    Luxurious custom built multi-level tropical oasis and pool paradise. (6) Bedroom, (4) Bath, accommodates up to (12) people: 3 Kings, 2 Queens, 1 Bunk Bed, 1 Sleeper Sofa. Private heated pool, free wireless, sorry no pets, less than a block to the beach.

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Vista Grande 1 - Sul Mare $3,143.00 - $5,243.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, Heated
    BBQ/Grill: Yes
    SQFT Under A/C: Approx 2594 sqft
    Turn Day: Any
    • 3Bedrooms:
    • 3.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    Nothing but Gulf Front decadence is waiting at Sul Mare, this luxury holiday rental for the most discriminating of vacationers. (3) Bedroom, (3) Bath, accomodates to (6) people: 1 King, 1 Queen, 2 Twin. Heated pool, free wireless, sorry no pets, gulf front location. 

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3 Oars 528 75th Street $2,000.00 - $3,500.00 per week

  • City: Holmes Beach
    Pets Allowed: Yes, dogs <25lbs
    Pool:Yes, heated w/spa
    BBQ/Grill: Yes
    SQFT Under A/C: 3,700
    Turn Day: Any
    • 4Bedrooms:
    • 4.0Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    Luxury canal front Anna Maria Island vacation rental home “3 Oars” located at 528 75th Street in Holmes Beach. (4) Bedroom (4) Bathroom, Sleeps (8): 2 King beds, 1 queen bed and 2 twin beds. Gorgeous Bimini Bay Canal front dock fitting boats up to 36 feet. Dogs up to 25 pounds welcome. Elevator, high end fully equipped kitchen, wireless internet, washer/dryer, 2 garage parking plus driveway, heated pool/spa, covered patio.

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Marina Walk 396 unit 102 $1,600.00 - $2,500.00 per week

Special

Marina Walk 396 Unit 102 - 25% off through April 2017

01/10/2017 to 04/30/2017
Save 25%

Spend a week at Marina Walk 396 Unit 102 anytime now through the end of april 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 including the weeks of Easter, 4th of July, Thanksgiving and most major holidays.

  • City: Bradenton
    Pets Allowed: No
    Pool:Yes, heated comm
    BBQ/Grill: Yes
    SQFT Under A/C: 1,650
    Turn Day: Any
    • 3Bedrooms:
    • 3.0Bath:
    • 6Sleeps:
    • Guest Rating:
      No Guest Rating Available
    • Property Rating: Platinum
  • Description:

    WELCOME TO AWARD WINNING WATERFRONT RESORT LIVING ON FLORIDA'S LAST PRIVATE ISLAND Introducing Marina Walk - New Waterfront Resort Condos Overlooking the sparkling waters of Anna Maria Sound just moments from Anna Maria Island, Harbour Isle proudly introduces our newest addition of waterfront Resort Homes, Marina

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Casa Varadero-619 Gladstone $2,350.00 - $3,250.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:No, but large spa
    BBQ/Grill: Yes
    SQFT Under A/C: 2,200
    Turn Day: Any
    • 4Bedrooms:
    • 3.0Bath:
    • 8Sleeps:
    • Guest Rating:
      No Guest Rating Available
    • Property Rating: Platinum
  • Description:

    Quiet, gorgeous upscale location in Key Royale perfect for a delightful holiday getaway. (4) Bedroom, (3) Bath, accommodates up to (8) people: 2 Kings, 2 Queens.  Heated spa, free wireless internet, sorry no pets, canal access for boat lovers.

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Banyan Breeze - 122 White Ave $2,397.00 - $7,718.00 per week

  • City: Anna Maria
    Pets Allowed: No
    Pool:Yes, heated
    BBQ/Grill: Yes
    SQFT Under A/C: 2,400
    Turn Day: Any
    • 5Bedrooms:
    • 4.0Bath:
    • 12Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    Casually luxurious “Banyan Breeze” 122 White Avenue in the city of Anna Maria. Accommodates (12) guest with (5) bedrooms and (4) bathrooms: 2 king beds, 1 queen bed, two twin beds and double twin bunk with twin trundle. Six homes down the street from gulf beaches. Walk to free trolley stops, dining and shopping. Wireless internet, USB ports, premium linens, flat screen television, elevator, washer/dryer, dishwasher. Heated pool with waterfall feature and outdoor shower. Fabulous outdoor entertaining space and balconies.

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Island Oasis - 111 81st St $2,400.00 - $7,250.00 per week

Special

Island Oasis - 25% off for April 2017

04/01/2017 to 04/30/2017
Save 25%

Relax in paradise at Island Oasis arriving anytime in April 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: Holmes Beach
    Pets Allowed: Yes,considers <25lb
    Pool:Yes heated and spa
    BBQ/Grill: Yes
    SQFT Under A/C: 3,000
    Turn Day: Saturday
    • 5Bedrooms:
    • 3.5Bath:
    • 10Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    Casual Holmes Beach vacation rental just a short walk to the beach. “Island Oasis” 111 81st Street. (5) bedroom (3.5) bath, Sleeps (10): 4 king bed, 2 twin sleeper sofas, 1 queen sleeper sofa. Washer/dryer, dishwasher, wireless internet, 5 parking spaces. Heated pool and spa gorgeous backyard, propane grill. Short walk to the beach.

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