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 Reef - 215 64th St $2,047.00 - $4,542.00 per week

Special

Summer Special - 20% off

08/29/2016 to 09/30/2016
Save 20%

Stay for less this summer at this Vacation Rental Property!

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: Holmes Beach
    Pets Allowed: Yes
    Pool:Yes, Heated
    BBQ/Grill: Yes
    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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A Villa de la Playa-3603A 4th $1,750.00 - $2,882.00 per week

  • City: Holmes Beach
    Pets Allowed: Yes (no cats)
    Pool:Yes, Heated w/Spa
    BBQ/Grill: Yes
    SQFT Under A/C: Approx 2376 sqft
    Turn Day: Saturday
    • 3Bedrooms:
    • 3.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    SPECIAL 10% DISCOUNT ON ALL BOOKINGS MADE WITHIN 45 DAYS OF ARRIVAL

    The whole family can get away from it all on the top floor of this condo building located less than two blocks from the Gulf of Mexico beaches. (3) Bedroom, (3) Bath, accomodates to (6) people: 1 King, 2 Queen. Private heated pool, free wireless, pet friendly (dogs only, with deposit), less than two blocks to the beach.

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Coral Escape - 132 50th St $2,535.00 - $8,489.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes - Heated
    BBQ/Grill: Yes
    SQFT Under A/C: Over 3000 sqft
    Turn Day: Saturday
    • 6Bedrooms:
    • 4.0Bath:
    • 14Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    Luxurious custom built multi-level tropical oasis and pool paradise. (6) Bedroom, (4.5) Bath, accommodates up to (14) 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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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
    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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Blue Bayou 229 Chilson Ave $1,680.00 - $2,625.00 per week

  • City: Anna Maria
    Pets Allowed: No
    Pool:Yes, heated w/spa
    BBQ/Grill: Yes
    SQFT Under A/C: 1,550
    Turn Day: Any
    • 3Bedrooms:
    • 3.0Bath:
    • 6Sleeps:
    • Guest Rating:
      No Guest Rating Available
    • Property Rating: Platinum
  • Description:

    New Ground level rental "Blue Bayou" 229 Chilson Avenue in Anna Maria. (3) Bedroom (3) Bathroom (Sleeps 6): 1 king bed, 1 queen and 2 twins. Canal front with 16 foot dock. Walk to the beach and free trolley stops. Washer/dryer, dishwasher, wireless internet. Heated pool and spa. Outdoor propane grill. Park 3 vehicles. 

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My Sisters Beach House $3,124.00 - $7,172.00 per week

  • City: Anna Maria
    Pets Allowed: No
    Pool:Yes, heated and spa
    BBQ/Grill: Yes
    SQFT Under A/C: 5,700
    Turn Day: Saturday
    • 5Bedrooms:
    • 3.5Bath:
    • 10Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    Luxury Canal Front vacation rental “My Sister’s Beach House” 520 Bayview Place in Anna Maria. Sleeps (10) guests with (5) Bedrooms and (3.5) bathrooms: 4 king beds, 2 twin beds, 1 queen sleeper sofa and one twin sleeper sofa. Elevator, boat access, walk to beach, gorgeous open balconies, heated pool and spa, 6 parking spaces, washer/dryer, dishwasher.

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La Casa Denton $1,960.00 - $3,920.00 per week

Special

La Casa Denton - 10% off and 2 bike rentals when staying anytime in 2016

09/07/2016 to 12/24/2016
Save 10%

Book your Anna Maria Island vacation at La Casa Denton arriving anytime now through the end of the year and you'll not only get 10% off, but 2 free adult bike rentals as well!

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: Holmes Beach
    Pets Allowed: No
    Pool:Yes, Heated w/Spa
    BBQ/Grill: Yes
    SQFT Under A/C: Approx 1952 sqft
    Turn Day: Saturday
    • 3Bedrooms:
    • 2.5Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    Stylish luxury vacation rental condo “La Casa Denton” located at 7306 Gulf Drive in Holmes Beach. (3) Bedroom (2.5) bathroom sleeps (6):1 king bed, 1 queen bed, 2 twin beds. Direct gulf front property on powder sand beaches. Washer/dryer, wireless internet, fire place, wet bar, 2 parking spaces, dishwasher, elevator, open balcony, community BBQ grill and heated pool/spa.

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Beach Pearl 212 Archer Way $1,680.00 - $2,625.00 per week

  • City: Anna Maria
    Pets Allowed: No
    Pool:Yes,heated & spa
    BBQ/Grill: Yes
    SQFT Under A/C: 1,350
    Turn Day: Any
    • 3Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Guest Rating:
      No Guest Rating Available
    • Property Rating: Platinum
  • Description:

    Stylish home updated to feel brand new! “Beach Pearl” 212 Archer Way in the city of Anna Maria. Sleeps (6) guests with (3) bedrooms and (2) bathrooms: 2 queen beds and 2 twin beds. Walk to beach and free trolley stops. Washer/Dryer, dishwasher, heated pool and spa with waterfall feature, 3 parking spaces, propane barbeque grill. Beautiful backyard with open pool patio and outdoor shower.

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619 Rose - Dream Maker $2,520.00 - $3,199.00 per week

  • City: Anna Maria
    Pets Allowed: No
    Pool:Yes, Heated salt
    BBQ/Grill: Yes
    SQFT Under A/C: Approx 2100 sqft
    Turn Day: Saturday
    • 3Bedrooms:
    • 3.5Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    Everything about this Bean Point area home is special, from the unique architecture and design, the one of a kind "egg lights" over the dining table, porcelain tile floors, chef's kitchen, vaulted ceilings with elegant overhead palm fans and a very unique floor plan offer the perfect balance between privacy and comfort. (3) Bedroom, (3) Bath, accommodates up to (6) people: 2 Queens and 2 Twins. Free wireless internet, private heated pool, sorry no pets allowed, less than two blocks to the beach.

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Beachy Blue-129 52nd ST $2,397.00 - $5,500.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, heated and spa
    BBQ/Grill: Yes
    SQFT Under A/C: 2,400
    Turn Day: Any
    • 4Bedrooms:
    • 4.0Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    Luxurious “Beachy Blue” 129 52nd St Holmes Beach. (3) Bedrooms, (3) Bath, accommodates up to (8) guests: 1 King, 2 Queens, 1 Full, and 2 Twins. Short walk to gulf beaches, restaurants, shopping and free trolley stop. Premium linen service, wireless internet, private heated pool and spa, washer, dryer, dishwasher, 2 car garage and driveway parking.

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