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Private Home with Pool, Outdoor Dining and Grill! Close to Beach and Pine Ave!

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Whispering Whale Retreat by Anna Maria Vacations
Outdoor Dining
Living Area
Living Area
Fully Equipped Kitchen

Reviews

9.2 out of 10
Wonderful
4 bedrooms2 bathroomsSleeps 81488 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View in a map
Anna Maria, FL
  • Place, Anna Maria Island Museum and Historical Park
    ‪4 min walk‬
  • Place, Anna Maria City Pier
    ‪5 min walk‬
  • Place, Bean Point Beach
    ‪18 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪34 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Beds

Bedroom 4

1 Single Bunk Bed

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Kitchen
Balcony

About this property

Private Home with Pool, Outdoor Dining and Grill! Close to Beach and Pine Ave!

Whispering Whale Retreat by Anna Maria Vacations
Home in Anna Maria, FL
VR16-000195

Welcome to Whispering Whale Retreat, a charming vacation home in Anna Maria that promises endless fun and relaxation! This four-bedroom, two-bathroom retreat features a sparkling private pool, expansive outdoor lounging areas, and a complete deck dining set, perfect for family fun or gatherings with friends. Located just a short walk from the beautiful beaches, this home offers the ultimate island lifestyle, blending comfort, coastal charm, and outdoor adventure.

Highlights
• 3-minute Walk to Bay
• 4 Bedroom / 2 Bath
• 1 King, 1 Queen, 2 Twin Beds, 2 Twin-over-twin Bunks
• Private heated pool
• Outdoor Deck and seating
• BBQ grill
• 10-minute Walk to Anna Maria Beach
• One Block to Pine Avenue’s shops, ice cream, restaurants, and local attractions
• Washer and dryer
• 3 Parking Spaces

Enjoy your outdoor oasis with a private heated pool, plenty of loungers, and a generous outdoor dining area for family BBQs or sunset cocktails. The lush tropical landscaping provides privacy and serenity. Spend your time poolside taking in the Florida sun, step to the bay and enjoy water adventures, or relax on the beach just a short stroll away.

Inside, the home radiates island vibes with a coastal seating area featuring two sofas and a TV, just right for relaxing or movie nights after a day in the sun. The custom kitchen boasts high-end stainless-steel appliances, a wine fridge, pots, pans, and utensils to make family meals or casual snacks. The elegant dining area includes a banquette for cozy indoor gatherings, while the large outdoor deck offers a perfect space to dine al fresco amid tropical surroundings.

Retreat to the primary bedroom, decorated with nautical accents and calming blue hues, featuring a king-sized bed, a TV, and an ensuite bathroom with a walk-in rain shower and double vanity. The second bedroom offers a queen bed, the third has two twin beds, both decorated in tropical style and equipped with TVs. The fourth bedroom features two bunk beds, ideal for kids. The hall bathroom has a shower and tub combo with a double vanity, and a laundry room with a washer and dryer adds extra convenience.

Room Details
• Primary Bedroom: King bed, ensuite bathroom
• Second Bedroom: Queen bed
• Third Bedroom: Two twin beds
• Fourth Bedroom: Two twin bunk beds
• Hall Bathroom: Shower and tub combo, double vanity

Take a short walk or bike ride to the beaches, the Anna Maria City Pier, or explore Pine Avenue’s shops and eateries for unique treats, souvenirs, and island adventures. Water lovers can spend their days fishing, kayaking, or simply relaxing in paradise.

Book Whispering Whale Retreat today and experience a beautifully curated Anna Maria Island vacation. With its prime location, luxurious outdoor amenities, and comfortable interiors, this home offers everything for a memorable island getaway. Reserve now and enjoy lifelong memories in the sand and sun!



-
This property does not allow pets.

3 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.

This home is managed by Anna Maria Vacations, an Anna Maria Island property management company.

We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age.

Please see our Anna Maria Vacations Rental Policies for full details.

Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Anna Maria

Located in Anna Maria, this holiday home is near the beach. The area's natural beauty can be seen at Anna Maria Beach and Bean Point Beach. Fish Hole Adventure Golf and H2O Watersportz are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
View more Holiday homes in Anna MariaOpens in a new window
Map
Anna Maria, FL

What's nearby

  • Anna Maria Island Museum and Historical Park - 4 min walk - 0.4 km
  • Anna Maria City Pier - 5 min walk - 0.4 km
  • Bayfront Park - 5 min walk - 0.4 km
  • Island Players - 9 min walk - 0.8 km
  • Bean Point Beach - 18 min walk - 1.6 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 48 min drive

Restaurants

  • ‪The Ugly Grouper - ‬6 min drive
  • ‪Anna Maria Island Beach Cafe - ‬9 min drive
  • ‪The Sandbar Restaurant - ‬9 min walk
  • ‪The Waterfront Restaurant - ‬3 min walk
  • ‪Ginny's & Jane E's - ‬8 min walk

Frequently asked questions

Does Private Home with Pool, Outdoor Dining and Grill! Close to Beach and Pine Ave! have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at Private Home with Pool, Outdoor Dining and Grill! Close to Beach and Pine Ave!?

As of 12 Mar, 2026, prices found for a 1-night stay for 2 adults at Private Home with Pool, Outdoor Dining and Grill! Close to Beach and Pine Ave! on 28 Apr, 2026 start from S$520, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Private Home with Pool, Outdoor Dining and Grill! Close to Beach and Pine Ave! pet-friendly?

No, pets are not allowed at this property.

How much is parking at Private Home with Pool, Outdoor Dining and Grill! Close to Beach and Pine Ave!?

On-site parking is available at the property.

What time is check-in at Private Home with Pool, Outdoor Dining and Grill! Close to Beach and Pine Ave!?

Check-in begins at 4:00 PM.

What time is check-out at Private Home with Pool, Outdoor Dining and Grill! Close to Beach and Pine Ave!?

Checkout is at 10:00 AM.

Where is Private Home with Pool, Outdoor Dining and Grill! Close to Beach and Pine Ave! located?

Situated by the sea, this holiday home is within 1 mile (2 km) of Historic Green Village, Anna Maria Beach and Bean Point Beach. Bay Boulevard Beach and Anna Maria City Pier are also within 5 minutes.

Reviews

9.2

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 20 out of 29 reviews
Rating 8 - Good. 8 out of 29 reviews
Rating 6 - Okay. 0 out of 29 reviews
Rating 4 - Poor. 0 out of 29 reviews
Rating 2 - Terrible. 1 out of 29 reviews

9.0/10

Cleanliness

9.0/10

Check-in

8.8/10

Communication

9.8/10

Location

9.6/10

Listing accuracy

Reviews

10/10 Excellent

J W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved our stay at this home. Home was clean and looked exactly like the photos. Management company was very responsive. Great location! Right in town! Easy walk into town and to the beach.
Stayed 3 nights in Dec 2025

10/10 Excellent

Arietys F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing vacations

Our stay in this property was amazing. Is was nice to stay together as a family. We really enjoyed our stay! Well recommended!
Stayed 7 nights in Jul 2025

10/10 Excellent

Mark L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Stay

Property was clean and had everything needed. Great location on Anna Maria. Plenty of room and having heated pool was great
Stayed 4 nights in Mar 2025

8/10 Good

Susan B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

Great location. Lots of places to visit and eat within walking distance
Stayed 2 nights in Oct 2023

10/10 Excellent

phoebe m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house for family vacation

Loved the sleeping arrangements and pool nicely decorated
Stayed 7 nights in Apr 2019

10/10 Excellent

Kristen B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacation

My family and I loved our stay here. The house was very close to everything. We can’t wait to come back!
Stayed 5 nights in Jul 2024

10/10 Excellent

Georgina W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Whispering whale

House was beautiful and very clean.
Stayed 5 nights in Apr 2024

10/10 Excellent

Nathan C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Family Vacation

3 kids, 13hr drive...this property was worth every moment...private pool, beautiful interior, beach toys and carts. Don’t book it too often we want to come back! ;)
Stayed 5 nights in Jul 2019

8/10 Good

Keven L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Overall house is fine. Def needs a little touch up in a handful of areas. Deck needs refinishing too. Bunk beds did not feel super sturdy. Was very clean and had plenty of blankets. In a fantastic location on the north end just a block over from pine ave and super close to beach.
Stayed 7 nights in May 2025

8/10 Good

Rosa V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Overall NOT Bad

The area was beautiful overall it was great. Few things 1st Fireplace was NOT work 2 garbage left in bathrooms 3 Pots were hard to cook in 4 as it was cold the pool should have been hotter & no indication of how to do. Mgmt company was great but communication was not good we were left waiting for Fireplace to be fixed BEFIRE our last day but no call or no show texh was nice but I should get a credit as this was the feature i booked for
Stayed 3 nights in Jan 2025

8/10 Good

Patty M.

Liked: Cleanliness, communication, location, listing accuracy
Disliked: Check-in

Not big enough for all beds

We tried hard to check in earlier than 4pm since no on had the house before us and we had been up since 4am. Another company we've gone with previously let us check in earlier. The house was nice and clean. However, had beds for 10 people/children but only 2 bathrooms, one of which is located inside the king room. Living area and sofas couldn't hold us all at once.
Stayed 5 nights in Dec 2023

10/10 Excellent

Jane K.

Liked: Cleanliness, communication, location, listing accuracy
Disliked: Check-in

Great stay for 8 yr old to 85 year old

Hard to summarize: great space for just. Hanging out , enjoying nice meals in the cozy nook, watch tv (ROKU),the pool was nice and warm and everyone really enjoyed it and the shaded area was super nice. So close to everything down on Pine (the main hub with restaurants and sand beaches at either end of the short street ). location is the best and the house is so nicely appointed with everything anyone would want to cook and relax. plenty of towels for pool and daily use...nice linens. ***You really need to make sure that you have large numerals for the house incase someone comes in late! ***AND even more importantly: lights on on the house and inside if someone is coming in late at night!! A big negative for me coming in from the airport driving in a strange neighborhood with no lights at 9:30 and a very dark night! Other than that we really enjoyed our stay.
Stayed 6 nights in Mar 2025

10/10 Excellent

Christopher R.

Liked: Cleanliness, communication, location, listing accuracy

Great island experience

This place was beautiful, very clean, and comfortable. We were 4 adults and 2 kids and it was a great experience for all. Only complaint was the communication for checking from property management. Reached out at 12 to follow up on if we can have an earlier checkin. Was told the room was finishing up from being cleaned and we would be notified when it is. Never heard anything from them after that and at 430 had to call from the property to find out how to be let on because we had still not received the final information. Outside of that the experience was great and I would strongly recommend this property
Stayed 2 nights in Jul 2023

8/10 Good

Diane J B.

Liked: Check-in, communication, location

Somewhat disappointing

Ant problem, 2 tv’s weren’t working, outside deck and stairs need work or replacement. Outside front door was filthy. Disappointed there were NO pool toys or cleaning products to help keep the place clean for 5 weeks. Inside the home was lovely however.
Stayed 35 nights in Feb 2020

10/10 Excellent

Ben M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Easy to access, clean and very comfortable home. The pool was a great bonus. My only feedback is to add outdoor lighting by the pool so it can be used after sunset. Great stay!
Stayed 3 nights in Feb 2026

10/10 Excellent

Pallas K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place in perfect location

Had a great weekend with the family!
Stayed 3 nights in Aug 2022

2/10 Terrible

john c.

Liked: Check-in, listing accuracy
Disliked: Cleanliness, communication

Incredible miscues

Submitted formal complaint without any response. Washing machine did not work all week. It was reported immediately and never fixed/replaced. Propane tank to home ran out of gas, were without hot water and the use of the stove for 24 hours.
Stayed 7 nights in Apr 2022

10/10 Excellent

Tami S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

We were happy to find this place so last minute. The house was clean, roomy and met all our needs. The location was close to the pier and all the small shops on Pine. We rented bikes around the corner because most of the bikes from the house had flat tires (no pump). A few other things we wish the house came with were coffee filters, laundry detergent and better hand soap but all these things were available for purchase at the local shop on Pine.
Stayed 5 nights in Jan 2022

10/10 Excellent

Melissa K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome house

This house was in perfect location to walk to both the bay and beach! Lots of space. Nicely decorated. Great outdoor space. Lots of beach chairs/bike/beach toys/etc to use.
Stayed 4 nights in Jan 2022

10/10 Excellent

Juan R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Birthday getaway

Loved the location of the property. Everything was clean at at arrival. The outside lighting was not working but they came out the next day to fix.
Stayed 4 nights in Jan 2022

8/10 Good

Megan B.

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

Nice house needs some upkeep!

Great house! Pool light could have been fixed. Asked multiple times (3) actually. Basic up keeping . Deck needs redone. Spare bedroom shower needs better drainage. Outdoor shower needs handle for use.
Stayed 7 nights in Jul 2021

10/10 Excellent

Marnie W.

Liked: Cleanliness, check-in, location, listing accuracy

Great retreat for a family of five

We loved the house, it was so clean and well kept. The only downside was the pool was dirty and the pool area not well kept up. We did, however, have a wonderful week!
Stayed 7 nights in Apr 2021

10/10 Excellent

Kala S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great

Awsome stay great location lots of things to do! Will be back!!
Stayed 5 nights in Oct 2020

10/10 Excellent

Leimys R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family gathering

Loved the space it was enough for everyone in my family and we are 10. The property was clean, spacious, it had everything we needed for cooking. The pool needs a little update but we still enjoyed it. We had a wonderful time.
Stayed 5 nights in Aug 2020

10/10 Excellent

Paul P.

Liked: Check-in, communication, location, listing accuracy

Whispering Whale

We very much enjoyed our stay at Whispering Whale and have already reserved the house for next year. The only suggestions we would have for this property is to have access to the garage and since the main entrance and exit is at the rear of this raised living area house there is no escape route in the event of a fire from the master bedroom which is situated at the front of the house. We would suggest that this should be addressed by making a portable window escape ladder available.
Stayed 20 nights in Jan 2020

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