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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:
    • 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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Sundance-744 North Shore Dr $1,680.00 - $3,297.00 per week

  • City: Anna Maria
    Pets Allowed: No
    Pool:Yes, Heated
    BBQ/Grill: Yes
    SQFT Under A/C: Approx. 1500 sqft
    Turn Day: Saturday
    • 3Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • Description:

    No flips flops required to walk to the beach from this luxury vacation home in Anna Maria City, FL. (3) Bedroom, (2) Bath, accomodates up to (6) people: 2 King, 2 Twin. Private heated pool, free wireless, sorry no pets allowed, across the road from the beach.

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Island Livin' 516 68th ST $1,600.00 - $2,100.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes,caged & heated
    BBQ/Grill: Yes
    SQFT Under A/C: 2,100
    Turn Day: Any
    • 4Bedrooms:
    • 4.0Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • Description:

    Fun and luxurious Canal front Holmes Beach vacation rental 516 68th Street in Bay Palms(sleeps 8) in (4) bedroom (4) bathroom: 1 king bed, 1 queen bed, twin twins, twin trundle bed. Walk to gulf beach, shopping, dining, free trolley. Close to Key Royale Golf Course. Pet friendly, 4 parking spots, wireless internet, heated pool and caged lanai, boat access and dock, washer/dryer, dishwasher.

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Gulf Place 14 6700 Gulf Dr $1,347.00 - $2,468.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Comm, heated
    BBQ/Grill: Yes
    SQFT Under A/C: 1,513
    Turn Day: Any
    • 3Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • Description:

    Calming direct beach front condo “Gulf Place” unit 14 at 6700 Gulf Drive in Holmes Beach. Accommodates (6) guests with (3) Bedroom and (2) Bathrooms: 1 King bed, 1 Queen bed, 2 Twin beds. Heated community pool and tennis court. Screened lanai with grill. Short walk to free trolley stop, shopping and dining. Assigned parking, premium linens, washer/dryer, dish washer. 

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Casa Bonita-230 Oak Avenue $2,200.00 - $5,653.00 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: No
    Pool:Yes, heated & spa
    BBQ/Grill: Yes
    SQFT Under A/C: 3,600
    Turn Day: Any
    • 4Bedrooms:
    • 4.0Bath:
    • 8Sleeps:
    • Guest Rating:
      No Guest Rating Available
    • Property Rating: Platinum
  • Description:

    Experience very upscale living in Casa Bonita; a BRAND NEW single family home in our rental program. (4) Bedroom, (4) Bath, accommodates up to (8) people: 3 Kings, a double and a twin, 1 Queen Sleeper Sofa. Heated pool and hot tub, "5 Star Platinum", Elevator, less than two blocks to the beach, free wireless internet, sorry no pets please.

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Ariel's By The Sea 203E 75th $1,350.00 - $2,185.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, heated
    BBQ/Grill: Yes
    SQFT Under A/C: 1554
    Turn Day: Any
    • 3Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Guest Rating:
      No Guest Rating Available
    • Property Rating: Gold
  • Description:

    Comfortably luxurious vacation rental “Ariel’s By the Sea” located at 203 E 75th Street in Holmes Beach. Offering (3) bedrooms and (2) full bathrooms with 1 king bed, 1 Queen bed, and 2 twin beds. Short walk to Gulf Beaches and free Trolley stop. Private heated pool, wireless internet, outdoor grill, premium linens, dish washer, and washer/dryer.

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Le Paradis 727 Jacaranda $1,475.00 - $3,175.00 per week

  • City: Anna Maria
    Pets Allowed: Yes, Dogs < 50lbs.
    Pool:Yes, heated
    BBQ/Grill: Yes
    SQFT Under A/C: 2,150
    Turn Day: Any
    • 3Bedrooms:
    • 2.5Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • Description:

    Airy and charming Anna Maria rental “Le Paradis” 727 Jacaranda Road. (3) Bedroom, (2.5) Bath (Sleeps 6): 1 king bed, 2 queen bed. Heated pool, short walk to beach. Wireless internet, dishwasher, washer/dryer, basketball and ping pong. Wrap around screened balcony. Pets up to 50 pounds with pet fee. Park 4 vehicles.

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North Beach Village Unit 55 $910.00 - $1,650.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, Community
    BBQ/Grill: Yes
    SQFT Under A/C: Approx 1536 sqft
    Turn Day: Any
    • 3Bedrooms:
    • 2.5Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Silver
  • Description:

    Comfortable and relaxing Holmes Beach vacation rental  “North Beach Village” 6250 Holmes Boulevard unit 55. Sleeps (6) in (3) bedroom (2.5)bathroom: 2 queen beds, 2 twin beds. Community heated pool, walk to gulf beach, wireless internet, washer/dryer, dishwasher. Screened lanai and three open air decks. Parking for three vehicles.

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610 Hampshire Lane $1,600.00 - $2,100.00 per week

  • City: Holmes Beach
    Pets Allowed: Yes, dogs, 25lbs
    Pool:Yes, heated & spa
    BBQ/Grill: Yes
    SQFT Under A/C: 2,500
    Turn Day: Any
    • 4Bedrooms:
    • 3.5Bath:
    • 10Sleeps:
    • Guest Rating:
      No Guest Rating Available
    • Property Rating: Gold
  • Description:

    Canal front home with designer flair. 610 Hampshire Lane in Holmes Beach on the Key Royale golf course. (4) Bedroom (3.5) Bath (Sleeps 10): 2 king bed, 2 queen bed and 1 queen sleeper sofa. Heated pool and spa overlooking canal and outdoor bar. 40 foot boat dock. Washer/dryer, dishwasher, wireless internet, 4 parking spaces. Dogs up to 25 pounds welcome.

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AMI Beach Home 201 69th Street $2,000.00 - $3,634.00 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: Holmes Beach
    Pets Allowed: No
    Pool:Yes, heated & spa
    BBQ/Grill: Yes
    SQFT Under A/C: 2,000
    Turn Day: Saturday
    • 4Bedrooms:
    • 3.5Bath:
    • 8Sleeps:
    • Guest Rating:
      No Guest Rating Available
    • Property Rating: Platinum
  • Description:

    Visit AMI Beach Home, a marvelous custom-built ground floor vacation rental home just a few steps from the powder soft beaches of the Gulf of Mexico. 4 spacious Bedrooms, 3.5 Bathrooms, accommodates up to 8 people, 3 King beds, 2 Twin beds, 1 Queen sleeper sofa in living room.

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Guest Testimonials

"Thanks for the wonderful stay!!!" 

...

-Kimberly K View Property

Owner Testimonials

My wife and I have used Island Real Estate as our property managers since we purchased our second home at 744 North Shore...

-John View Property