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Stay connected to friends and family, jump on Netflix or post your vacation photos to Facebook at these vacation rental homes.

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Heavenly Holly-721 Holly Road $1,350.00 - $2,315.00 per week

  • City: Anna Maria
    Pets Allowed: Yes, under 50lbs
    Pool:Yes, heated + tub
    BBQ/Grill: Yes
    SQFT Under A/C: 2,000
    Turn Day: Any
    • 3Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Silver
  • Description:

    Whimsical canal front home located in historic Anna Maria. (3) Bedroom, (2) Bath, accommodates (6) people: 1 King, 1 Queen, 2 Twins. Private heated pool and soaking tub (hot tub without bubbles), pets are welcome with fee, free wilreless internet, boat access, less than two blocks to the beach.

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Palm Isle 3209 $950.00 - $1,750.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, Heated
    BBQ/Grill: Yes
    SQFT Under A/C: Approx 1399 sqft
    Turn Day: Any
    • 2Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • Description:

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

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Turtle Cove West $800.00 - $1,450.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, Heated/Shared
    BBQ/Grill: Yes
    SQFT Under A/C: Approx. 800
    Turn Day: Any
    • 2Bedrooms:
    • 1.0Bath:
    • 4Sleeps:
    • Guest Rating:
    • Property Rating: Silver
  • Description:

    Both sides of this charming vacation duplex are decorated in a palette of warm tropical colors and Old Florida style in Holmes Beach, FL. (2) Bedroom, (1) Bath, accomodates to (4) people: 1 Queen, 2 Twin. Heated pool, free wireless, sorry no pets allowed, less than two blocks to the beach. 

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Sandy's Getaway-122 Peppertree $950.00 - $2,199.00 per week

Special

Stay Longer, Pay Less - Get 4 weeks for the price of 3 in January 2017!

12/31/2016 to 01/07/2017
Save 25%

Stay longer, pay less! Book 4 weeks for the price of 3 when staying at this property in January 2017! Only want to stay for 3 weeks? Give us a call at 877-778-6066 to get the same discount!

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

  • City: Anna Maria
    Pets Allowed: Yes, dogs only
    Pool:No
    BBQ/Grill: Yes
    SQFT Under A/C: 1200
    Turn Day: Any
    • 3Bedrooms:
    • 2.0Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Bronze
  • Description:

    Enjoy the leisurely pace of "Old Florida" with a week of holiday at this charming vacation home. (3) Bedroom, (2) Bathroom, accommodates up to (8) people: 2 Queens, 1 Twin, 1 Trundle Bed, 2 Sleeper Sofa. Free wireless, pets are welcome (dogs only please) with fee, one block to the beach.

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Fountain Head 2 $602.00 - $1,272.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Community,heated
    BBQ/Grill: Yes
    SQFT Under A/C: 900
    Turn Day: Any
    • 2Bedrooms:
    • 2.0Bath:
    • 4Sleeps:
    • Guest Rating:
      No Guest Rating Available
    • Property Rating: Bronze
  • Description:

    Coastal, clean and bright centrally located seasonal vacation condo. (2) Bedroom, (2) Bath, accommodates (4) people: 1 Queen, 2 Twins. Shared heated pool, free wireless internet, sorry no pets, less than two blocks to the beach.

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Casa Sierra - 205 A 36th ST $800.00 - $1,650.00 per week

  • City: Holmes Beach
    Pets Allowed: Yes, dogs < 50lbs
    Pool:Yes, heated shared
    BBQ/Grill: Yes
    SQFT Under A/C: 750
    Turn Day: Any
    • 2Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • Description:

    Just a two minute walk to the beach! Casa Sierra 205 A 36th Street in Holmes Beach. Sleeps (6), (2) Bedroom (2) Bathroom: 1 king bed, 2 twin beds and queen sleeper sofa. Community heated pool. Walk to trolley, shopping, dining. Wireless internet, dishwasher, free community washer/dryer, 2 parking spaces, dogs up to 50 pounds welcome.

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7001 A Holmes Blvd $1,400.00 - $2,185.00 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:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • Description:

    Gorgeous duplex style Anna Maria Island vacation rental 7001 A, Holmes Boulevard in Holmes Beach. Rooms (8) 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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Starfish Beach Unit 1 $900.00 - $1,650.00 per week

  • City: Holmes Beach
    Pets Allowed: Yes
    Pool:Yes, Heated
    BBQ/Grill: Yes
    SQFT Under A/C: Approx 722 sqft
    Turn Day: Saturday
    • 2Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • Description:

    Kingfisher Cottage at Starfish Beach isn’t just a place to stay – it’s your means to a truly tranquil state of mind. (2) Bedroom, (2) Bathroom, accomodates up to (6) people: 2 Queen, 1 Sleeper Sofa. Heated pool, free wireless, pet friendly (with deposit)
     

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Sea Song 103 Seagrape Lane $2,750.00 - $4,255.00 per week

  • City: Anna Maria
    Pets Allowed: No
    Pool:No
    BBQ/Grill: Yes
    SQFT Under A/C: 1221
    Turn Day: Saturday
    • 2Bedrooms:
    • 1.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • Description:

    Vintage vacation cottage tucked under the shade of sea grapes and directly on the Gulf of Mexico. Fully updated, and all new everything! "Sea Song" 103 Sea Grape Lane in Anna Maria. (2) Bedroom, (1) Bathroom, accomodates up to (6) people: 2 Kings, 1 Queen Sleeper Sofa. Washer/dryer, dishwasher, private sundeck, 2 parking spaces. 

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Palm Isle 3201 $900.00 - $1,650.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, Heated
    BBQ/Grill: Yes
    SQFT Under A/C: Approx 1048 sqft
    Turn Day: Any
    • 2Bedrooms:
    • 2.0Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • 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, (2) Bathroom, accommodates up to (8) people: 1 King, 1 Queen, 1 Sleeper Sofa, 1 Air Mattress. Heated pool, free wireless, sorry no pets allowed, across the road from the beach access.

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