Whispering Winds by Beach Boutique Rentals

Top rated by guests
Private heated pool
Washer and Dryer
Luxurious bathroom
Gorgeous walk in shower
Beach access out your back door
review stars
9.7Outstanding
(21 Ratings)
"Everything was great! Will be back!"
AMANDA M.
Don't miss out! Price and availability may change
9.7 / 10
Outstanding(21 Ratings)

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
High-end valueWell priced for 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.

Amenities

Free WiFi/internet
Free Parking
Air conditioning
Pool
Non-smoking
Pets allowed
TV
Heating
Coffee/tea maker
Refrigerator
Kitchen
Balcony/Terrace
WiFi/Internet
Parking Available
Private pool access
Microwave
Dishwasher
Washing machine
Dryer
Washer/dryer
Patio
Garden
Oven
Stove
Laundry services
Shower
Outdoor Cooking
Family friendly
Ironing facilities
Towels
Linens
Hairdryer
Fire extinguisher

Map of Anna Maria Island, FL

city location on map

Ratings and reviews

9.7 / 10
Outstanding(21 Ratings)
10 / 10Outstanding·Aug 2026
Everything was great! Will be back!
10 / 10Outstanding·Jul 2026
Great space. 50 yards to the beach. Nice, easy walk to Bean Point for sunset. Supplied beach accessories and beach towels was super helpful. We will be back.
8 / 10Excellent·Jul 2026
Anna Maria is a beautiful location with amazing views of the Skyway bridge, however, if you are looking for a true beach vacation, I would look elsewhere. As a native to the area, there are far better places to go and stay that have better sand, shorelines, and are more easy to get to. The beach access point across from the home is convenient, however, that side of the island has a shoreline that maxes out around 10-12 ft until it's in someone's backyard. Any time close to high-tide makes it nearly unusable. There isn't really room to lounge and lay your things out, so most time was spent at the pool. Be prepared to deal with potential A/C issues - the location of the condenser outside one of the bedrooms has it surrounded completely so it restricts the airflow heavily. They say to not set it below a certain temp, but truly just an excuse for a cheap Goodman condenser unit and a poorly designed location for it to live. While we were there, the handler inside began leaking through the floors into the ceiling above the patio (Prior drywall patches confirm it's not the first time). The management company was prompt to respond, but as someone who has dealt with a similar issue at home, I foresee this completely ruining someone's vacation at some point.
5 / 10·Jul 2022
The property was beautiful. Have no complaints. It was in a perfect location. Easily walkable to beautiful bean point beach. And definitely close enough to downtown. The pool was a perfect size. Wouldn't hesitate to re book this property.

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FAQs

Is parking included with this house?

Yes, parking is listed as an amenity at Whispering Winds by Beach Boutique Rentals. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

Yes, a swimming pool is available for use at Whispering Winds by Beach Boutique Rentals. Enjoy the water!

Is Whispering Winds by Beach Boutique Rentals pet friendly?

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Whispering Winds by Beach Boutique Rentals?

We found 33 amenities for this rental. This includes free wifi/internet, free parking, air conditioning, pool, and non-smoking.


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