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Upscale waterfront home, private pool, beautiful views!

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Private Pool
Paradise On Pine - Dock
Canal Front Home
Front Exterior with Landscaping
Private Pool Area

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
4 bedrooms3+ bathroomsSleeps 10

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi

Explore the area

View in a map
Anna Maria, FL
  • Place, Anna Maria Island Museum and Historical Park
    ‪1 min walk‬
  • Place, Bradenton Beach
    ‪6 min walk‬
  • Place, Anna Maria City Pier
    ‪8 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪34 min drive‬

Rooms & beds

4 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

2 Single Bunk Beds

3 bathrooms, 1 half bathroom

Bathroom 1

Bathroom 2

Bathroom 3

Half Bath 1

Spaces

Deck or patio
Kitchen
Balcony

About this property

Upscale waterfront home, private pool, beautiful views!

Paradise on Pine by AMI Locals
VR20-000052

Welcome to Paradise on Pine, a spectacular four bedroom, three and a half bath waterfront vacation home located in the heart of Anna Maria Island. Featuring a private pool, boat dock, and elevator access, this home offers the perfect blend of island luxury and laid-back charm. Just a 10-minute walk to the beach and steps from Pine Avenue’s boutiques and restaurants, this modern retreat is designed for families and friends seeking the ultimate coastal escape.

Highlights
• Waterfront home with private dock
• 10-minute walk to the beach
• 4 Bedrooms / 3.5 Bathrooms
• Private Pool
• Elevator Access
• Tesla Universal Wall Connector (both NACS and J1772 compatible)
• Dog Friendly (with approval and fee)
• Outdoor Dining and BBQ Grill
• 4 Parking Spaces
• Near Pine Avenue shops and restaurants

Your private backyard oasis awaits, complete with a sparkling pool, covered patio, and canal views. Lounge under the Florida sun, grill fresh seafood, or dine outdoors as boats drift by. The private dock accommodates vessels up to 35 feet, making it perfect for fishing, kayaking, or launching a paddleboard adventure through the bay. For guests driving electric vehicles, a Tesla Universal Wall Connector is available; both NACS and J1772 compatible, delivering up to 48 Amps. This advanced charger accommodates all North American EVs, offering convenient and eco-friendly charging during your stay. With its modern amenities and tropical surroundings, Paradise on Pine blends cutting-edge convenience with timeless island beauty.

Inside, Paradise on Pine offers an open, airy floor plan framed by floor-to-ceiling windows overlooking the water. The living room features plush sofas and a large flat-screen TV, perfect for movie nights or planning the next day’s adventures. The fully equipped kitchen includes stainless steel appliances, quartz countertops, and a large island for meal prep and casual dining. Gather at the dining table for family meals or step out to the outdoor dining area to enjoy a sunset dinner with canal views.

The primary suite is a peaceful retreat featuring a king bed, private balcony, and an ensuite bathroom with dual vanities, a walk-in shower, and a standalone soaking tub. The second bedroom also offers a king bed and private ensuite bathroom with a walk-in shower. A third king bedroom and a bunk room with two twin-over-twin bunks share a modern hallway bathroom with a walk-in shower. Each bedroom is designed with comfort and style in mind, creating a tranquil haven after a day of island adventures.

Room Details
-Primary Bedroom, 3rd Floor: King bed, private balcony, ensuite bathroom with walk-in shower, double vanity, and soaking tub
-Second Bedroom, 2nd Floor: King bed, ensuite bathroom with walk-in shower
-Third Bedroom, 3rd Floor: King bed, shares hallway bathroom with walk-in shower
-Fourth Bedroom, 3rd Floor: Two twin-over-twin bunk beds, shares hallway bathroom with walk-in shower

Guests can easily hop on the Anna Maria Island trolley, which stops nearby; just south of Bayfront Park and north of local restaurants and shops. This home is dog friendly (with approval and fee) and features an elevator for added convenience. Spend your days exploring the island by bike, taking a sunset cruise, or booking a dolphin tour; the best of Anna Maria Island is right at your doorstep.

With its private dock, pool, and prime location near the beach and Pine Avenue, Paradise on Pine by AMI Locals captures the heart of Anna Maria Island living. Perfect for families, friends, and boaters alike, this home combines elegance, comfort, and the spirit of coastal adventure.
Book your stay today with AMI Locals and start making unforgettable memories at Paradise on Pine!

-
With host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our AMI Locals Rental Policies for full details.

Please see our AMI Locals Rental Policies for full details.

Christmas decorations provided unless requested otherwise in the month of December.

This home is managed by AMI Locals, 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 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

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 on the waterfront. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Looking to enjoy an event or a game while in town? See what's happening at LECOM Park or IMG Bollettieri Tennis Academy. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with horse riding and ecotours nearby.
Map
Anna Maria, FL

What's nearby

  • Anna Maria Island Museum and Historical Park - 1 min walk - 0.0 km
  • Island Players - 5 min walk - 0.4 km
  • Bradenton Beach - 6 min walk - 0.6 km
  • Anna Maria City Pier - 8 min walk - 0.7 km
  • Bean Point Beach - 17 min walk - 1.5 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 47 min drive

Restaurants

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

Frequently asked questions

Does Upscale waterfront home, private pool, beautiful views! have a pool?

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

How much does it cost to stay at Upscale waterfront home, private pool, beautiful views!?

As of 8 May, 2026, prices found for a 1-night stay for 2 adults at Upscale waterfront home, private pool, beautiful views! on 27 Sept, 2026 start from S$986, 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 Upscale waterfront home, private pool, beautiful views! pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Upscale waterfront home, private pool, beautiful views!?

On-site parking is available at the property.

What time is check-in at Upscale waterfront home, private pool, beautiful views!?

Check-in begins at 4:00 PM.

What time is check-out at Upscale waterfront home, private pool, beautiful views!?

Checkout is at 10:00 AM.

Where is Upscale waterfront home, private pool, beautiful views! located?

Situated on the waterfront, this holiday home is within a 10-minute walk of Anna Maria Island Museum and Historical Park and Bradenton Beach. Bean Point Beach and Anna Maria Beach are also within 1 mile (2 km).

Reviews

10

Exceptional

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. 38 out of 38 reviews
Rating 8 - Good. 0 out of 38 reviews
Rating 6 - Okay. 0 out of 38 reviews
Rating 4 - Poor. 0 out of 38 reviews
Rating 2 - Terrible. 0 out of 38 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Al K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location was excellent. Walked to the beach and plenty of shops and restaurants within walking distance as well.Pool used constantly by our grandkids and some adults.
Stayed 7 nights in Apr 2026
Verified

10/10 Excellent

Laura A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home & great location!
Stayed 3 nights in Feb 2026
Response from VrboOwner on 16 Feb, 2026
Thank you so much, Laura! We’re thrilled you loved Paradise on Pine by AMI Locals—that beautiful home paired with such an unbeatable location really is the best of island living. We’d love to have you back for more sunshine, strolls on Pine, and fun anytime!
Verified

10/10 Excellent

Lana S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was exactly as it was described and photographed. The location is a perfect mix of shops, restaurants, sunrise and sunsets. All questions and requests were answered quickly with great communication.
Stayed 4 nights in Mar 2026
Response from VrboOwner on 12 Mar, 2026
So glad it lived up to what you saw online, Lana! Paradise on Pine by is really in one of those sweet island spots—easy walks to shops and restaurants, plus those beautiful sunrise and sunset moments nearby. Happy to hear our AMI Locals team kept communication quick and easy along the way. Thanks for staying with us—we’d love to welcome you back anytime!
Verified

10/10 Excellent

Ellen J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay at Paradise on Pine immensely! The house was beautiful and in the most perfect location. Felt private with the canal in the backyard but also right in the middle of quaint Pine Avenue where there are the most amazing shops and restaurants. Also, the owners included NYE decorations and had other details that really made it feel so special! Thank you AMI Locals for a wonderful week!
Stayed 5 nights in Dec 2025
Response from VrboOwner on 6 Jan, 2026
Thank you, Ellen, for your wonderful review about your stay at Paradise on Pine! It’s fantastic to hear that you enjoyed your time and found the house beautiful and perfectly located. The privacy of the canal paired with the charm of Pine Avenue makes for a truly special experience. We’re thrilled that the NYE decorations and thoughtful details added to your stay! Your gratitude means a lot to us, and we can’t wait to welcome you back for another amazing getaway with AMI Locals!
Verified

10/10 Excellent

Katherine S.

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

Great stay

Property is a great house and location! Highly recommend. Will return.
Stayed 4 nights in May 2025
Response from VrboOwner on 28 May, 2025
We are glad to hear the house was great! And we have to agree this is a great location, we highly appreciate your review and look forward to hosting you again in the near future!
Verified

10/10 Excellent

Elizabeth E.

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

Second time to stay here. Always a pleasure

Recommend!! location is fantastic, pool, boat dock, close to everything.
Stayed 4 nights in Apr 2024
Response from VrboOwner on 13 May, 2024
Elizabeth, thank you for choosing to stay with us again! We're delighted to hear that you had another enjoyable experience and that our property continues to meet your expectations. We appreciate your recommendation and are thrilled that you find the location fantastic, along with the amenities like the pool and boat dock. If you ever find yourself back in the area for a third visit or need assistance with anything else, please don't hesitate to reach out.
Verified

10/10 Excellent

Doug C.

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

Amazing getaway

Great property in a location that gives you access to an abundance of restaurants and activities
Stayed 7 nights in Dec 2023
Response from VrboOwner on 3 Jan, 2024
Thank you for taking the time to share your experience, Doug. We are glad you enjoyed your stay and hope to welcome you back soon!
Verified

10/10 Excellent

Jennifer H.

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

Very cute and comfortable

Great house, location, well appointed. We really loved it. The kayaks and paddle boards were really fun. Manatees in the back yard were amazing.
Stayed 4 nights in May 2025
Response from VrboOwner on 15 May, 2025
Thank you for choosing us for your recent stay! Every review and every star you give us makes a huge difference to our success. If you enjoyed your stay, we'd love your 5-star review! We hope to host you again in the future!
Verified

10/10 Excellent

Melaney D.

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

Beautiful Home

This property was amazing. It was beautiful, had plenty of parking, clean, the view great, and the pool was perfect. Highly recommend staying here!
Stayed 1 night in May 2020
Verified

10/10 Excellent

Kim R.

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

Wonderful

Beautiful property, great location. Look forward to renting again!
Stayed 7 nights in Mar 2024
Response from VrboOwner on 20 Mar, 2024
Kim, thank you for your kind words! We're thrilled to hear that you found the property beautiful and enjoyed its great location. We're excited at the prospect of hosting you again in the future! If there's anything specific you'd like for your next stay, please let us know, and we'll do our best to accommodate you.
Verified

10/10 Excellent

Jen V.

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

Anna Maria Getaway

We had an excellent and relaxing time on the island. The house was great and plenty of privacy and space for the 2 of us! We will definitely stay here again on our next trip to Anna Maria!
Stayed 4 nights in Apr 2023
Response from VrboOwner on 1 Jun, 2023
Thank you for allowing us to host you, Jen. We are thrilled you enjoyed your stay and hope to welcome you back again soon!
Verified

10/10 Excellent

Mark D.

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

Wonderful

This is an amazing house…. The best location, lovely interior, well looked after, well equipped, great pool area too.
Stayed 8 nights in Nov 2024
Response from VrboOwner on 10 Dec, 2024
Thank you for your kind words! We're so glad to hear that you enjoyed the house, its location, and the pool area. It’s wonderful to know that you found the interior to be lovely and the property well-equipped and well-maintained. We truly appreciate your feedback and hope to welcome you back for another amazing stay in the future!
Verified

10/10 Excellent

Robert M.

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

Highly recommend Paradise in Pine!

Great house, accommodated 9 of us without worry of having enough space. Location is perfect, walking distance to restaurants, and other businesses. Will return to this house next vacation!!
Stayed 5 nights in Jul 2020
Response from VrboOwner on 9 Jul, 2021
Robert, we loved being your tropical home away from home while here. We hope to see you all again on your next adventure to the island.
Verified

10/10 Excellent

Joann B.

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

Paradise is an understatement!

Incredible home, wonderful location and outstanding amenities! We have a wonderful time and made excellent use of the kayaks, the pool, the beaches in close proximity and the beautiful, luxurious home! Thank you so much!
Stayed 4 nights in Apr 2025
Response from VrboOwner on 1 May, 2025
Thank you so much for your kind review! We're delighted to hear that you had a wonderful time during your stay and were able to fully enjoy all the amenities our home has to offer. Thank you again for your wonderful feedback!
Verified

10/10 Excellent

Alana L.

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

Birthday fun

Easy to rent property Loved the canal Nice place
Stayed 4 nights in Sep 2022
Response from VrboOwner on 23 Sept, 2022
Thank you for allowing us to host you, Alana!
Verified

10/10 Excellent

D Martin P.

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

One of our BEST yet!

This home on the water was perfect for us! Beautiful home, beautiful pool, beautiful view, ready access to all the places we visit on the north end of the island, where we prefer to stay. We had an absolutely wonderful time.
Stayed 12 nights in Sep 2023
Verified

10/10 Excellent

amanda w.

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

Trip of a Lifetime

This place was just a described and was absolutely beautiful. Loved the location to all the local shops and yet in the back you had the privacy and relaxation of the pool and the canal. We will definitely be back:)
Stayed 4 nights in May 2023
Response from VrboOwner on 16 Jun, 2023
Thank you for taking the time to share your wonderful experience with us, Amanda. We are glad you enjoyed the home, pool, canal, and convenient location. You were terrific guests, and we look forward to hosting you again!
Verified

10/10 Excellent

Sharon S.

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

My Birthday

Location was perfect for walking to shops and restaurants. You can see sunrises and sunsets, it was great! King size comfy beds for all adults! Would definitely recommend this home.
Stayed 3 nights in Oct 2023
Response from VrboOwner on 25 Oct, 2023
Thank you for taking the time to share your wonderful experience, Sharon. We are glad you enjoyed your stay and hope to welcome you back soon!
Verified

10/10 Excellent

Sarah D.

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

Perfect Location

My family and I had a wonderful stay at this beautiful house which is located right in the hustle bustle of Pine St. If you like walking across the street for a treat, drink or to pick up food, and easily walking to tons of shopping, you'll love this amazing house. I know we did!
Stayed 7 nights in Mar 2024
Verified

10/10 Excellent

David G.

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

Wonderful location and home

We had a wonderful time In this great home It’s conveniently located close to beach and fishing and ice cream. And restaurants. The house is nicely decorated with a nice kitchen. Good for families. Very comfortable. We look forward to returning.
Stayed 4 nights in Nov 2021
Response from VrboOwner on 15 Dec, 2021
David, thank you for your recent stay at Paradise on Pine. Great to here your stay was awesome and the home was a great fit for everyone. We welcome you back anytime, as you were wonderful guests to host.
Verified

10/10 Excellent

Janet S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything you could ever think of needing is provided. We absolutely loved staying here. This house is located in one of the best spots on Pine Ave. We walked to both ends of the street and enjoyed eating at the Waterfront (my favorite was the micro green salad and gluten free bun - ordered twice), at the other end is delicious Sandbar (blackened grouper was excellent). We shopped and ate all along Pine Ave. Good thing the post office was on Pine. I shipped all kinds of apparel back home. It is the best location. Check out Gulf Drive for restaurants as well. Being on the canal was awesome and the beach on both sides is right there. Now let me tell you about this gorgeous house. Luxurious is the best way to describe it; the most comfortable master suite I have ever rented, two bay garage, kayakes, bikes, beach towels, games, etc. The kitchen is COMPLETELY supplied with anything you could want. Absolutely wonderful. We’ll be back.
Stayed 5 nights in Jan 2026
Response from VrboOwner on 9 Feb, 2026
This truly made our day—thank you, Janet! We’re so happy you loved Paradise on Pine by AMI Locals and soaked up everything that spot has to offer, from Pine Ave strolls and incredible dining to canal views and beach days on both sides. It sounds like you fully embraced island life, and we’re thrilled the home’s luxury touches and amenities made it extra special. We can’t wait to welcome you back for another unforgettable stay!
Verified

10/10 Excellent

Laurene G.

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

Wonderful Family Vacation

We had a great stay with our kids and grandma and aunts and uncles. Walking distance to everything which was ideal for having guests of varying ages. Plenty of space in the very clean house. Very large master bedroom with space for my husband and I and two small children. Would love to come back!
Stayed 5 nights in Mar 2024
Response from VrboOwner on 26 Mar, 2024
Laurene, thank you for your wonderful feedback! We're thrilled to hear that you had a great stay with your family and guests. It's fantastic that our property's walking distance to everything was ideal for guests of varying ages, and we're delighted to hear that there was plenty of space for everyone to enjoy. We're glad to hear that the master bedroom was spacious enough for you, your husband, and your two small children. It's wonderful that you would love to come back, and we would be honored to welcome you again!
Verified

10/10 Excellent

ronald c.

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

Perfect spot

The house had everything you could need and was very roomy and put together very well if i could make one suggestion but not a bad one is to down size the plates and cooking items to open up some room for groceries in the cabinets we will definitely be back thanks for a great family vacation at your home
Stayed 7 nights in Jul 2023
Response from VrboOwner on 23 Aug, 2023
Thank you for allowing us to host you, Ronald. We are glad you enjoyed your stay. We appreciate your feedback about the cooking items and will be sure to pass this on to our team. You were terrific guests, and we hope to welcome you back soon!
Verified

10/10 Excellent

Nicholas M.

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

$ well spent

Great location with short walk to beach and pier. Plenty of room for 4 Adults & 5 children in our group. Pool was small but wonderful . Trolly was easy to use and convenient. Would definitely repeat this trip.
Stayed 5 nights in Jan 2023
Response from VrboOwner on 26 Jan, 2023
Nicholas, thank you for taking the time to share your experience with us. We are glad you enjoyed the home, pool, and location. We hope to host you again sometime soon!
Verified

10/10 Excellent

Julia H.

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

Excellent accommodations

Beautiful home with many amenities. House had life jackets, paddle boards, kayaks, beach chairs and beach towels. Enjoyed the pool and fished/crabbed right off the dock on the canal. Very clean home and looked just like what you see online. The only downside was we wish we could have stayed longer!
Stayed 6 nights in Sep 2024
Response from VrboOwner on 17 Sept, 2024
Thank you so much for your lovely review! We’re thrilled to hear that you enjoyed the many amenities, from the life jackets and paddle boards to the pool and dock activities. It’s great to know that the home met your expectations and that you had a fantastic time. We’d love to have you stay longer next time, so we’ll look forward to your next visit! Thanks again for choosing us and for sharing your experience.

About the host

Hosted by AMI Locals

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