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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Island Pearl - 204 76th St $1,500.00 - $2,850.00 per week

  • City: Holmes Beach
    Pets Allowed: No
    Pool:Yes heated & spa
    BBQ/Grill: Yes
    SQFT Under A/C: 2,300
    Turn Day: Saturday
    • 4Bedrooms:
    • 4.0Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    Beautiful light, bright and beachy relaxing seasonal rental. (4) Bedroom, (4) Bathroom, accommodates up to (8) people: 2 Kings, 1 Queen, 2 Twins. Private heated pool with spa, free wireless, sorry no pets allowed, less than two blocks to the beach.

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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, 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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Anna Maria Island Club Unit21S $2,100.00 - $2,625.00 per week

  • City: Bradenton Beach
    Pets Allowed: No
    Pool:Yes - Heated w/Spa
    SQFT Under A/C: 1,049
    Turn Day: Any
    • 2Bedrooms:
    • 2.0Bath:
    • 4Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • Description:

    Spectacular direct gulf front condo with enviable location,on the beach with gorgeous views and breath-taking sunsets! (2) Bedroom, (2) Bath, accommodates up to (4) people: 2 Kings. Shared heated pool and spa, free wireless internet, elevator, sorry no pets.

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Time for the Sea 313 B 58th ST $1,400.00 - $2,450.00 per week

Special

Time For The Sea - 20% off last minute discount!

01/14/2017 to 01/14/2017
Save 20%

Planning a last minute vacation to Anna Maria Island? Stay for the week of January 14th, 2017 at Time for the Sea and get 20% off of your reservation!

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: 1,500
    Turn Day: Any
    • 4Bedrooms:
    • 3.0Bath:
    • 8Sleeps:
    • Guest Rating:
    • Property Rating: Gold
  • Description:

    Stylish and relaxing Holmes Beach vacation rental “Time for the Sea” located at 313 B 5th Street. (Sleeps 8) guests with (4) bedrooms and (3) bathrooms: 2 king beds, 1 queen and a twin bunk bed. Heated pool/spa, washer/dryer, dishwasher, flat screen televisions, wireless internet. Park three vehicles.

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Vista Grande 3 Penthouse $4,893.00 - $5,943.00 per week

Special

Vista Grande - 25% off on January 2017 stays at Vista Grande #1 and #3

01/16/2017 to 01/31/2017
Save 25%

Stay at Vista Grande #1 or #3 for a week during the month of January 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
    BBQ/Grill: Yes
    SQFT Under A/C: 2600
    Turn Day: Any
    • 3Bedrooms:
    • 3.0Bath:
    • 6Sleeps:
    • Guest Rating:
      No Guest Rating Available
    • Property Rating: Platinum
  • Description:

    By far the BEST direct view of the Gulf you will find on Anna Maria Island. Exclusive PENTHOUSE with floor to ceiling windows across 40’ with sweeping views of the Gulf of Mexico from the kitchen, dining and living rooms. Relax on the wrap around balcony while enjoying the sea breezes and stunning sunsets.

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306 B 56th St $1,350.00 - $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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Gulf Breeze-203E 69th St $2,400.00 - $7,416.00 per week

  • City: Holmes Beach
    Pets Allowed: Yes, dogs under 25lb
    Pool:Yes-Htdw/Spa&Tiki
    BBQ/Grill: Yes
    SQFT Under A/C: Approx 2546 sqft
    Turn Day: Saturday
    • 6Bedrooms:
    • 4.5Bath:
    • 12Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    You'll never forget the views from this luxury vacation rental - a sweeping vista of the Gulf of Mexico and its shimmering quartz sand beaches. It will be love at first sunset! (6) Bedrooms, (4.5) Bath, accommodates up to (12) people: 4 King, 1 Full/Twin bunk with twin trundle, 1 Full and 2 Sleeper Sofas. Private heated pool with spa, free wireless, pet friendly with fee, less than two blocks to the beach.

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Marina Walk 396 unit 102 $1,600.00 - $2,500.00 per week

Special

Marina Walk 396 Unit 102 - 25% off through April 2017

01/10/2017 to 04/30/2017
Save 25%

Spend a week at Marina Walk 396 Unit 102 anytime now through the end of april 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 and black out dates including the weeks of Easter, 4th of July, Thanksgiving and most major holidays.

  • City: Bradenton
    Pets Allowed: No
    Pool:Yes, heated comm
    BBQ/Grill: Yes
    SQFT Under A/C: 1,650
    Turn Day: Any
    • 3Bedrooms:
    • 3.0Bath:
    • 6Sleeps:
    • Guest Rating:
      No Guest Rating Available
    • Property Rating: Platinum
  • Description:

    WELCOME TO AWARD WINNING WATERFRONT RESORT LIVING ON FLORIDA'S LAST PRIVATE ISLAND Introducing Marina Walk - New Waterfront Resort Condos Overlooking the sparkling waters of Anna Maria Sound just moments from Anna Maria Island, Harbour Isle proudly introduces our newest addition of waterfront Resort Homes, Marina

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Almost Gulf Front-203W 69th St $2,400.00 - $7,409.00 per week

  • City: Holmes Beach
    Pets Allowed: Yes
    Pool:Yes, salt heated spa
    BBQ/Grill: Yes
    SQFT Under A/C: Approx 2546 sqft
    Turn Day: Saturday
    • 6Bedrooms:
    • 4.5Bath:
    • 12Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    A dream come true holiday oasis perfect for large families. (6) Bedrooms, (4.5) Bath, accommodates up to (12) people: 4 King, 1 Queen, 2 Twin, 2 Sleeper Sofa. Private heated salt water pool with spa, outdoor kitchen, free wireless, pet friendly with fee, less than two blocks 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