House in Anna Maria Island, FL
6 guests · 2 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this house rental
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 lounger, 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 sea breeze 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 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.
PET POLICY:
We are 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 50 lbs per pet.
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
ADDITIONAL INFORMATION
We generally require a minimum stay 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!
Housekeeping will provide a starter supply of toilet paper, soap, and garbage bags but guests will likely need to replenish the supply during their stay.
Our cleaning fee includes a professional linen service. When you stay with us you can rest assured that you will have high quality linens such as those at a fine hotel. We also provide plenty of luxury bath and beach towels.
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 or use of the pool is allowed during these hours along with any other noise which may disturb the neighbors.
This home provides off-street parking for up to 2 vehicles.
Booking Platform Note:
For VRBO bookings, the reservation payment is processed by Beach Boutique Rentals and will appear as Beach Boutique Rentals on your credit card statement. VRBO also charges a separate service fee directly to the guest as a separate transaction.
*Features include*
* Balcony with Bay view!
* Private heated pool
* Tropical private yard, chaise lounger, 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 sea breeze 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 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.
PET POLICY:
We are 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 50 lbs per pet.
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
ADDITIONAL INFORMATION
We generally require a minimum stay 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!
Housekeeping will provide a starter supply of toilet paper, soap, and garbage bags but guests will likely need to replenish the supply during their stay.
Our cleaning fee includes a professional linen service. When you stay with us you can rest assured that you will have high quality linens such as those at a fine hotel. We also provide plenty of luxury bath and beach towels.
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 or use of the pool is allowed during these hours along with any other noise which may disturb the neighbors.
This home provides off-street parking for up to 2 vehicles.
Booking Platform Note:
For VRBO bookings, the reservation payment is processed by Beach Boutique Rentals and will appear as Beach Boutique Rentals on your credit card statement. VRBO also charges a separate service fee directly to the guest as a separate transaction.
Amenities at Whispering Winds by Beach Boutique Rentals
Non-smoking
Pets allowed
Family friendly
Map of Anna Maria Island, FL
Ratings and reviews
10 / 10Outstanding·Dec 2025
Wonderful property, very clean, great location across the street from the beach. Management was amazing with ongoing communications. Looking forward to going back!
10 / 10Outstanding·Mar 2024
Great location...property matched photos on line (very nice) and stayed true to its name Whispering Winds. Pool crew came 2 times weekly and were friendly and quick. This property does have a lot of stairs...ok for our group, but worth mentioning for anyone with mobility challenges.
10 / 10Outstanding·Sep 2023
The house and location were really all we were looking for. We loved being tucked away back towards the intercoastal and even though the house is not right on the water, you have an awesome view of the water from the balcony which we enjoyed every night. We would definitely stay again.
8 / 10Excellent·Sep 2023
The location is fantastic but the house needs an upgrade!
$$$$
Top rated by guests
9.8Outstanding
(17 Ratings)
"Wonderful property, very clean, great location across the street from the beach. Management was amazing with ongoing communications. Looking forward to going back! "
Nicole K.Don't miss out! Price and availability may change
