Pool Paradise Vacation Rentals

These vacation rental homes feature one of a kind pools. Waterfalls, in pool hot tubs, swim up bars and more.

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Blue Lagoon 2 - Sand Dollar $900.00 - $1,700.00 per week

  • City: Holmes Beach
    Pets Allowed: Yes
    Pool:Yes, Heated
    BBQ/Grill: Yes
    SQFT Under A/C: Approx 1148 sqft
    Turn Day: Any
    • 2Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Silver
  • Description:

    Beautiful, bright and beachy holiday rental cottage. (2) Bedrooms, (2) Bathrooms, accommodates up to (6) people: 1 King, 1 Queen, 1 Sleeper Sofa. Shared heated large lagoon-style pool, free wireless, pets welcome with fee, less than two blocks to the beach.

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Bermuda Bay Club 26 - 1437 $1,225.00 - $2,513.00 per week

  • City: Bradenton Beach
    Pets Allowed: No
    Pool:Yes, community. Spa
    BBQ/Grill: Yes
    SQFT Under A/C: 1,500
    Turn Day: Saturday
    • 3Bedrooms:
    • 2.5Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Silver
  • Description:

    Excellent beach getaway for your island sojourn. (3) Bedroom, (2.5) Bath, accommodates (6) people: 2 Queens, 2 Twins. Heated pool with spa, free wireless, sorry no pets allowed, less than one block from the beach.

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Grande Haven-804 No Shore Dr. $3,003.00 - $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:
    • 12Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    Glamorous vacation rental “Grande Haven” located at 804 North Shore Drive, Anna Maria. Accommodates (12) 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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Salt Shack at 3705 Gulf Dr A $1,596.00 - $2,625.00 per week

  • City: Holmes Beach
    Pets Allowed: Yes, dogs under 50lb
    Pool:Yes, heated
    BBQ/Grill: Yes
    SQFT Under A/C: 1,452
    Turn Day: Any
    • 3Bedrooms:
    • 2.0Bath:
    • 7Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • Description:

    Adorable Holmes Beach vacation rental “Salt Shack” accommodates (7) guests in (3) bedroom (2) bathroom ground level duplex with 1 king bed, 1 queen bed, 2 twin beds and full roll-away. Within walking distance of gulf beaches, free trolley stop, dining, and shopping. Heated pool paradise. Propane grill, wireless internet, washer/dryer, dishwasher, premium linen service.  

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Blue Lagoon 3 - Egret $900.00 - $1,700.00 per week

  • City: Holmes Beach
    Pets Allowed: Yes
    Pool:Yes, Heated
    BBQ/Grill: Yes
    SQFT Under A/C: Approx 910 sqft
    Turn Day: Any
    • 2Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Silver
  • Description:

    Charming, light and bright cottage for your perfect island getaway. (2) Bedrooms, (2) Bathrooms, accommodates up to (6) people: 1 Queen, 2 Twins, 1 Sleeper Sofa. Shared heated large lagoon-style pool, free wireless, pets welcome with fee, less than two blocks to the beach.

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306 B 56th St $1,425.00 - $2,185.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, Heated
    BBQ/Grill: Yes
    SQFT Under A/C: Approx. 2000
    Turn Day: Any
    • 3Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • Description:

    Coastal and beachy multi-level home with a serene and relaxing pool oasis. (3) Bedrooms, (2) Bath, accommodates up to (6) people: 1 King, 1 Queen, and 2 Twins. Private heated pool, free wireless internet, sorry no pets allowed, less than two blocks to the beach.

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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:
      No Guest Rating Available
    • 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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HoneyWood House 243 Willow $1,750.00 - $3,153.00 per week

  • City: Anna Maria
    Pets Allowed: No
    Pool:Yes,heated & spa
    BBQ/Grill: Yes
    SQFT Under A/C: 2,400
    Turn Day: Any
    • 3Bedrooms:
    • 4.0Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • Description:

    Relaxing canal front Anna Maria vacation rental “Honeywood House” 243 Willow Avenue. (3) Bedroom (4) bath, Sleeps (8): 3 king bed, 1 twin with trundle. Heated pool/spa and large screened lanai. Walk to beach, shopping, dining, free trolley. Dishwasher, premium linens, washer/dryer, wireless internet, 4 parking spaces. Boat access 28 feet/12 feet.

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Tina's Piece of Paradise $1,475.00 - $3,175.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, heated
    BBQ/Grill: Yes
    SQFT Under A/C: Approx. 1750
    Turn Day: Any
    • 4Bedrooms:
    • 3.0Bath:
    • 14Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • Description:

    Perfect for entertaining, “Tina’s Piece of Paradise” located at 407 80th Street in Holmes Beach. (4) Bedroom (4) Bathroom, Sleeps (6). Short walk to beach, heated pool. Wireless internet, washer/dryer, dishwasher. Park 3 cars walk to free trolley.

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