top of page

Whispering Winds

Steps to the beach







Pet friendly

Whispering Winds

This custom crafted two bedroom/two bath bayside beauty is your perfect beach escape.

*Features include*

  • Balcony with Bay view!

  • Private heated pool

  • Tropical private yard, chaise loungers, outdoor dining

  • Gourmet kitchen

  • Washer and Dryer

  • 2 Queen bedrooms plus sleeper sofa

  • 2 full luxurious bathrooms

  • Steps to the beach

  • Close proximity to shops and restaurants on Pine Avenue

  • Beach chairs, umbrella and cart

Welcome to Whispering Winds. This custom designed two bedroom/two bath bayside beauty is your perfect beach escape. The idyllic location, nestled on the desirable North End of Anna Maria Island just across the street from the turquoise waters of the bay, is just the beginning of this island cottage perfection. This tropical oasis is impeccably appointed and designed for relaxation.

On the ground floor of this exquisite home you will find a grand entryway leading to the private pool and outdoor living space. Indoor/outdoor living is embodied by the poolside lounge area which features an outdoor TV and plenty of seating. Take a swim in the heated pool while enjoying the seabreeze from the gorgeous bay waters right across the street.

When you head up one flight of stairs to the main level you will feel right at home in the cozy living and dining area. No details have been overlooked; from the stainless appliances, crown molding, tongue and groove wood ceilings and warm wood-plank flooring. In the kitchen enjoy the granite countertops and breakfast bar with seating for 4. Your family will love the open concept space for gathering in the living room, with brand new sofa with chaise and comfortable wingback chairs. For additional guests, the sofa pulls out into a sleeper. On this level you will also find a luxurious full bathroom with walk-in shower and full laundry area.

The magic happens on the third floor. The bayfront balcony is the ideal relaxation spot for morning coffee, evening cocktails or any time in between. You will want to relax here often and take in the sweeping views of the beautiful Bay water while enjoying the fresh coastal air breeze. Two beautiful Queen bedrooms each have a door that opens out onto the balcony. Both bedrooms feature flat screen TVs and another full bathroom with walk-in shower rounds out the top floor.

This picturesque beach house is only steps from the bayfront beach access and an easy walk to the Rod N Reel Pier or the shops and eateries of Pine Avenue. Whether it's sunrise over the bay or sunset at nearby Bean Point, you will relish every moment of your time at Whispering Winds.

We generally require a minimum stay of 7 nights with Saturday check-in during the high season. We are more flexible in the off season so please send us a message if your dates appear unavailable. We may be able to accommodate you!

This rental is dog friendly! A fee of $150 + tax is required in advance for each dog you are bringing.


2 pets maximum unless granted an exception. Weight limit of 75 lbs maximum total for 1 pet or 120 lbs total for 2 pets.

Due to property insurance policies and liability concerns NO dangerous breeds or aggressive animals are allowed. The following breeds (purebred or crossbred) are not permitted:

  • Pit Bull

  • Akita

  • Rottweiler

  • German Shepherd

  • Siberian Husky

  • Malamute

  • Doberman Pinscher

  • Chows

  • Any Wolf-dog hybrid

  • Any other dog that has been known to have bitten anyone

Anna Maria Island is a family community and the city imposes a strict noise ordinance. Please adhere to our good neighbor policy and observe the local quiet hours between 10 pm and 8 am. No loud music is allowed during these hours along with any other noise which may disturb the neighbors.

We do not accept reservations from any guests under the age of 25. The primary guest will be required to provide proof of age and must occupy the rental home for the duration of the reservation.

This home provides off-street parking for up to 2 vehicles.

A minimum deposit of 25% of the total rental fee is due at the time of booking. If the arrival date is within 60 days, payment is due in full. For information regarding our cancellation policy, please click here.


Whispering Winds


AMENITIES (scroll through)
Basic soap
Starter toilet paper
Starter paper towels
Linens provided
Towels provided
Hair dryer
Washing machine
Clothes dryer
Iron & Board
Wireless internet
Standard coffee maker
Heated pool
Private pool
Outdoor shower
Beach chairs
Beach umbrella
Beach wagon/cart
Beach towels
Sun loungers
BBQ grill
Free parking on premises


Whispering Winds