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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Pineapple Cottage 407 Spring $1,750.00 - $4,000.00 per week

  • City: Anna Maria
    Pets Allowed: Dogs 25lbs
    Pool:Yes, heated & spa
    BBQ/Grill: Yes
    SQFT Under A/C: 1,500
    Turn Day: Any
    • 4Bedrooms:
    • 3.0Bath:
    • 8Sleeps:
    • Guest Rating:
      No Guest Rating Available
    • Property Rating: Platinum
  • Description:

    Experience the laid back luxury vacation you deserve when you stay at "Pineapple Cottage" located at 407 Spring Ave, Anna Maria, Florida. This lively Anna Maria Island ground level vacation rental is well-appointed with everything for the perfect tropical island getaway.

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Starfish 6804 B Marina Dr $1,500.00 - $2,600.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, heated
    BBQ/Grill: Yes
    SQFT Under A/C: 2,425
    Turn Day: Any
    • 3Bedrooms:
    • 3.5Bath:
    • 6Sleeps:
    • Guest Rating:
      No Guest Rating Available
    • Property Rating: Gold
  • Description:

    “Starfish” 6804 Marina Drive in Holmes Beach. (3) Bedroom (3.5) Baths (Sleeps 6): 1 king and 2 queen beds. Heated pool with waterfall and backyard tiki. Washer/Dryer, dishwasher, wireless internet premium linens. Elevator. Wet bar in master suite. Parking for three vehicles.

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L'Plage 6420 Gulf Dr Unit 3 $2,100.00 - $4,250.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, heated and spa
    SQFT Under A/C: 2,500
    Turn Day: Any
    • 3Bedrooms:
    • 3.0Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • Description:

    Gorgeous Holmes Beach condo L’Plage 6432 Gulf Drive unit 3. (Sleeps 8) with (3) bedroom (3) bathroom: 1 king bed, 1 queen bed, 2 twins beds and queen sleeper sofa. Located on gulf front, heated pool/spa, open balcony with view. Walk to free trolley stop. Wireless internet, dishwasher, washer/dryer, 2 covered parking spaces.

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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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SeaShell-Sunsets-105 78th $4,200.00 - $5,250.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes heated & spa
    SQFT Under A/C: 3,000
    Turn Day: Saturday
    • 4Bedrooms:
    • 4.5Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

     Gorgeous gulf view home "Seashell Sunsets" 105 78th Street in Holmes Beach. (4) Bedroom, (4.5) Bathroom, accomodates up to (8) people: 2 King, 4 Twin Beds, 2 Trundle. Private heated pool with spa, wireless internet, elevator, washer/dryer, roof top balcony, dishwasher. Just steps to the gulf. 

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Anna Maria Island Club Unit18S $1,400.00 - $2,500.00 per week

  • City: Bradenton Beach
    Pets Allowed: No
    Pool:Yes, Heated w/Spa
    SQFT Under A/C: Approx 1179 sqft
    Turn Day: Any
    • 2Bedrooms:
    • 2.0Bath:
    • 4Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • Description:

    Bright, beachy and breezy direct gulf front seasonal rental. (2) Bedroom, (2) Bath, accommodates up to (4) people: 1 King, 2 Twins, 1 Sleeper sofa. Shared heated pool and spa, free wireless internet, elevator, sorry no pets.

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Tropical Oasis -208 71st St $1,246.00 - $2,205.00 per week

  • City: Holmes Beach
    Pets Allowed: Yes, under 25lbs.
    Pool:Yes, heated & spa
    BBQ/Grill: Yes
    SQFT Under A/C: 1699
    Turn Day: Any
    • 3Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Silver
  • Description:

    Well appointed single family home with a spacious layout. (3) Bed: (2) Bath: Accommodates up to (6) people: 2 Queens, 2 Twins, 1 Queen Sleeper sofa. NEW heated pool and spa, less than two blocks to the beach, free wireless internet, pets welcome with fee.

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Bermuda Bay Club 26 - 1437 $1,200.00 - $2,303.00 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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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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Anna Maria Island Club Unit40N $1,250.00 - $2,100.00 per week

  • City: Bradenton Beach
    Pets Allowed: No
    Pool:Yes, Heated w/Spa
    SQFT Under A/C: Approx 989 sqft
    Turn Day: Any
    • 2Bedrooms:
    • 2.0Bath:
    • 4Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • Description:

    Idyllic and beachy direct gulf front seasonal rental. (2) Bedroom, (2) Bath, accommodates up to (4) people: 1 King, 2 Twins. Shared heated pool and spa, free wireless internet, elevator, sorry no pets.

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