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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Vitamin Sea 114 48th ST $2,200.00 - $5,250.00 per week

Special

Vitamin Sea - 25% off for Easter Week!

Special Eligible When Booking From 03/27/2017 to 04/15/2017
Save 25%

Spend Easter week at Vitamin Sea on Anna Maria Island save 25% off of your rental fee!

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
    BBQ/Grill: Yes
    SQFT Under A/C: 2,500
    Turn Day: Any
    • 4Bedrooms:
    • 3.0Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Gold
Description:

Gorgeous Holmes Beach vacation rental “Vitamin Sea” located at 114 48th Street. Sleeps (8) guests with (4) bedrooms and (3) bathrooms: 1 king bed, 2 queen bed and 2 twin bunk beds. Heated lagoon pool and outdoor lounge, gorgeous balconies, wireless internet and flat screen televisions, elevator, washer/dryer, dishwasher, parks 4 cars.

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Long Board-131WWhite $1,200.00 - $2,000.00 per week

  • City: Holmes Beach
    Pets Allowed: Yes
    Pool:Htd Shared
    BBQ/Grill: Yes
    SQFT Under A/C: Approx 1359 sqft
    Turn Day: Any
    • 3Bedrooms:
    • 2.5Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Gold
Description:

Elegant and chic duplex ready for your tropical escape. (3) Bedrooms, (2.5) Bath, accommodates up to (6) people: 2 King,  2 Twin Bunk Beds, 1 Trundle Bed, 1 Air Mattress. Shared heated pool, free wireless, pet friendly with fee, only a few houses to the beach.

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Blue Waters-230 Willow $2,800.00 - $6,000.00 per week

  • City: Anna Maria
    Pets Allowed: No
    Pool:Yes, heated + spa
    BBQ/Grill: Yes
    SQFT Under A/C: 3,234
    Turn Day: Any
    • 4Bedrooms:
    • 4.0Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
Description:

Enjoy Blue Waters, a gorgeous luxury Mediterranean-style villa in peaceful surroundings. (4) Bedroom, (4) Bath, accommodates (8) people: 1 King, 2 Queens, 2 Twins. Fabulous outdoor & indoor living areas, gourmet kitchen, private office, heated swimming pool with spa, private dock and boat lift, full size billiards table and large screen outdoor TV are just a few of the highlights. Minutes from beach & Pine Avenue.

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Promise Kept 206 76 ST $1,400.00 - $2,250.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, heated/spa salt
    BBQ/Grill: Yes
    SQFT Under A/C: 1,200
    Turn Day: Any
    • 3Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Gold
Description:

Modern and captivating island home perfect for your holiday getaway. (3) Bedroom, (2) Bath, accommodates (6) people: 1 King, 2 Queens. Private, heated pool, free wireless internet, less than two blocks to the beach.

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Wine Down 2907 Ave F $4,999.00 - $13,000.00 per week

Special

Wine Down - 40% off when arriving April 8th, 2017

Special Eligible When Booking From 03/06/2017 to 04/08/2017
Save 40%

Arrive at one of our premier gulf front properties, Wine Down, on April 8th, 2017 and get 40% off of your rental fee when staying for the entire week!

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.

Wine Down - 30% off when arriving April 29th, 2017

Special Eligible When Booking From 03/13/2017 to 04/29/2017
Save 30%

Arrive at one of our premier gulf front properties, Wine Down, on April 29th, 2017 and get 30% off of your rental fee when staying for the entire week!

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.

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes, heated & spa
    BBQ/Grill: Yes
    SQFT Under A/C: 2,300
    Turn Day: Any
    • 4Bedrooms:
    • 4.5Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
Description:

Stunning luxury direct gulf front vacation rental, “Wine Down” located at 2907 Avenue F in Holmes Beach. Sleeps (8) guests with (4) Bedroom (4.5) bathroom: 3 king beds, 1 queen bed, 1 queen sleeper sofa. Gorgeous balcony views of the gulf, heated pool/spa, bbq grill, wireless internet, flat screen tv’s, washer/dryer, dishwasher.

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124 50th AMI Beach House $2,535.00 - $7,950.00 per week

Special

AMI Beach House - 25% off now through Easter 2017

Special Eligible When Booking From 01/23/2017 to 04/16/2017
Save 25%

Stay at AMI Beach House anytime now through Easter Day, April 16tgh 2017, and get 25% off of your rental fee!

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: 3,000
    Turn Day: Saturday
    • 6Bedrooms:
    • 4.5Bath:
    • 12Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
Description:

Glamorous, luxury-style island getaway. (6) Bedrooms, (4.5) Bath, accommodates up to (12) people: 2 King, 2 Queen, 4 Twin, 1 Sleeper Sofa. Private heated pool with spa, outdoor kitchen & life-size chess game, free wireless internet, sorry no pets allowed, less than two blocks to the beach.

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Casa Morado-147 50th St $1,575.00 - $3,395.00 per week

Special

Casa Morado - 40% off for Easter Week!

Special Eligible When Booking From 03/27/2017 to 04/15/2017
Save 40%

Best discount of the year! Book a stay at Casa Morado for Easter week, April 15th - 22nd, 2017, and get an unprecendented 40% off of your rental fee! Book today!

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.

  • City: Holmes Beach
    Pets Allowed: Yes, dogs under 25lb
    Pool:Yes, heated & spa
    BBQ/Grill: Yes
    SQFT Under A/C: 2,040
    Turn Day: Any
    • 4Bedrooms:
    • 3.5Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Gold
Description:

This gorgeous multi-level home is truly a tropical paradise. (4) Bedroom, (3.5) Bath, accommodates (8) people: 2 King, 2 Queen, with 1 Double and Twin. Private heated pool,spa, free wireless internet, less than two blocks to the beach with no main streets to cross.

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Anna Maria Island Club Unit14S $1,400.00 - $2,500.00 per week

  • City: Bradenton Beach
    Pets Allowed: No
    Pool:Yes - Heated w/Spa
    SQFT Under A/C: 1195
    Turn Day: Any
    • 2Bedrooms:
    • 2.0Bath:
    • 4Sleeps:
    • Guest Rating:
    • Property Rating: Gold
Description:

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

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Grande Haven-804 No Shore Dr $3,050.00 - $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:
    • 16Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
Description:

Glamorous vacation rental “Grande Haven” located at 804 North Shore Drive, Anna Maria. Accommodates (16) 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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Au Soleil - 717 Jacaranda Rd $1,575.00 - $3,750.00 per week

  • City: Anna Maria
    Pets Allowed: Yes, under 25lbs
    Pool:Yes,heat, spa heat
    BBQ/Grill: Yes
    SQFT Under A/C: 3,100
    Turn Day: Saturday
    • 5Bedrooms:
    • 3.0Bath:
    • 10Sleeps:
    • Guest Rating:
    • Property Rating: Gold
Description:

Spacious and elegant home idyllic for your holiday sojourn. (5) Bedroom, (3) Bath, accommodates up to (10) people: 1 King, 2 Queen, 2 Twin, 5th bedroom with Queen  Murphy Bed. Private pool with spa, free wireless, pets welcome (under 25lbs) with fee, less than a block to the beach.  

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