Luxury Villas Vacation Rentals

Every Island Real Estate vacation rental home is perfect in our eye, but this selection of 5-Star rated luxury homes offer up the absolute best Anna Maria Island experience.

Search Results

Map All Results

Banyan Breeze - 122 White Ave $2,044.00 - $7,718.00 per week

  • City: Anna Maria
    Pets Allowed: No
    Pool:Yes, heated
    BBQ/Grill: Yes
    SQFT Under A/C: 2,400
    Turn Day: Any
    • 5Bedrooms:
    • 4.0Bath:
    • 12Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    Casually luxurious “Banyan Breeze” 122 White Avenue in the city of Anna Maria. Accommodates (12) guest with (5) bedrooms and (4) bathrooms: 2 king beds, 1 queen bed, two twin beds and double twin bunk with twin trundle. Six homes down the street from gulf beaches. Walk to free trolley stops, dining and shopping. Wireless internet, USB ports, premium linens, flat screen television, elevator, washer/dryer, dishwasher. Heated pool with waterfall feature and outdoor shower. Fabulous outdoor entertaining space and balconies.

    Read More

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

    Read More

Coral Escape - 132 50th St $2,200.00 - $7,250.00 per week

Special

Coral Reef - 20% off 2/18/2017 - 3/11/2017

02/18/2017 to 03/11/2017
Save 20%

Stay at Coral Escape for 7 days anytime from February 18th, 2017 through March 11th, 2017 and get20% 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: Holmes Beach
    Pets Allowed: Yes >50lbs
    Pool:Yes - Heated
    BBQ/Grill: Yes
    SQFT Under A/C: Over 3000 sqft
    Turn Day: Saturday
    • 6Bedrooms:
    • 4.0Bath:
    • 12Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    Luxurious custom built multi-level tropical oasis and pool paradise. (6) Bedroom, (4.5) Bath, accommodates up to (12) people: 3 Kings, 2 Queens, 1 Bunk Bed, 1 Sleeper Sofa. Private heated pool, free wireless, sorry no pets, less than a block to the beach.

    Read More

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.

    Read More

Vista Grande 1 - Sul Mare $3,143.00 - $5,243.00 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: 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. 

    Read More

Island Oasis - 111 81st St $2,000.00 - $7,250.00 per week

  • City: Holmes Beach
    Pets Allowed: Yes,considers <25lb
    Pool:Yes heated and spa
    BBQ/Grill: Yes
    SQFT Under A/C: 3,000
    Turn Day: Saturday
    • 5Bedrooms:
    • 3.5Bath:
    • 10Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    Casual Holmes Beach vacation rental just a short walk to the beach. “Island Oasis” 111 81st Street. (5) bedroom (3.5) bath, Sleeps (10): 4 king bed, 2 twin sleeper sofas, 1 queen sleeper sofa. Washer/dryer, dishwasher, wireless internet, 5 parking spaces. Heated pool and spa gorgeous backyard, propane grill. Short walk to the beach.

    Read More

Casa Bonita-230 Oak Avenue $2,200.00 - $5,500.00 per week

  • 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.

    Read More

Beachy Villa Vista-116 45th $2,000.00 - $7,498.00 per week

  • City: Holmes Beach
    Pets Allowed: Yes
    Pool:Yes, heated & spa
    BBQ/Grill: Yes
    SQFT Under A/C: 2,200
    Turn Day: Saturday
    • 5Bedrooms:
    • 4.5Bath:
    • 10Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    Comfortable luxury vacation rental home “Beachy Villa Vista” located at 116 45th street in Holmes Beach accommodating (10) guests with (5) bedrooms and (4.5) bathrooms: 1 King bed, 2 Queen bed, 2 Twin beds, 1 Twin bunk, and 1 Queen sleeper sofa. Few houses away from Gulf Beaches! Walking distance to free trolley stops, dining and shopping. Dogs up to 25 pounds welcome. Heated pool/spa, swim up tiki, and outdoor wet bar.

    Read More

La Casa O'Bar $1,960.00 - $3,920.00 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. 

    Read More

La Casa LaMar $2,900.00 - $4,400.00 per week

Special

La Casa LaMar - 10% when staying in January 2017

01/01/2017 to 01/31/2017
Save 10%

Relax in the luxury property La Casa LaMar anytime during the month of January 2017 and save 10% 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 w/Spa
    BBQ/Grill: Yes
    SQFT Under A/C: Approx 1784 sqft
    Turn Day: Saturday
    • 3Bedrooms:
    • 2.0Bath:
    • 6Sleeps:
    • Guest Rating:
    • Property Rating: Platinum
  • Description:

    Gorgeous ground level vacation rental with spectacular direct gulf view “La Casa Lamar” is located at 7318 Gulf Drive in Holmes Beach. Accommodates (6) guests in (3) bedroom (2) bathrooms: 1 king bed, 2 twin beds, 1 sleeper sofa. Community heated pool and spa. Walk to free trolley stop. Dish washer, washer/dryer, wireless internet, dogs considered, 2 parking spaces. Sun deck and open patio.

     

     

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