Enjoy island life--surfer chic bungalow, private beach path, kayak - property

Enjoy island life--surfer chic bungalow, private beach path, kayak

  • 3 Beds
  • 2.0 Baths
  • 6 Guests
  • 1500 SF

Enjoy island life--surfer chic bungalow, private beach path, kayak

House in Anna Maria

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  • From: $300 per night
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Property Details

Enjoy island life--surfer chic bungalow, private beach path, kayak, grill, and dog friendly too. The perfect getaway!

On the North end of Anna Maria, this well appointed home sleeps 6 and has everything for a fun, laid-back family vacation, couples' getaway or friends' trip. There are two queen bedrooms and a full bath on the first floor. Upstairs is the main living area with plenty of comfy seating. A fully equipped kitchen has a separate coffee bar that includes a Keurig and a drip coffee maker. The dining area and outdoor deck have partial water views. There's also a second full bath and a king bedroom. A spiral staircase goes between floors inside and there are outside stairs off of the deck. This home comes equipped with a full size washer and dryer, wi-fi, TV's in each room, gas grill and beach essentials. This home is carpet and rug free, it is tile throughout.

Head down the private beach path and you are steps from the Rod and Reel pier to your right and Bean Point, where the Gulf meets the Bay, on your left. Kayak out to spot dolphins that like to hang out at the pier in the afternoon. The Anna Maria City Pier and Pine Ave is .6 mile away. That's where you can catch the free island trolley to take you around the island. There are local shops and restaurants along Pine Ave. This is the absolute perfect place to relax and recharge.

It's your vacation so there's no worries about late arrivals. We offer a keyless entry system so you can easily open and lock your door without having to be concerned with keys while you're out on the beach or enjoying the island.

Combine this home with Pirates Bay (VRBO #9119495) (a separate pool home on the property) for a 5 bedroom family retreat with space to spread out and plenty of opportunities to make lasting memories. Please note that the two properties are not connected and do not share amenities or space. This property does not have a pool but is steps from the beach. It is available for Saturday to Saturday rentals meaning arrivals and departures are on Saturdays.

Our nearest Airport is Sarasota Bradenton International Airport (SRQ). It's about 30 minutes away. Another popular choice is Tampa International Airport (TPA) which is about an hour away.

Our calendar is always updated in real time. If it shows available, it is. If we have a cancellation, it will show as available immediately. We do not accept payments via Zelle, PayPal, Facebook or Venmo. In order to give our fantastic cleaners time with their families we are closed for arrivals and departures on Holidays, such as New Years Day, Mother's Day, Memorial Day, Father's Day, July 4th, Labor Day, Thanksgiving Day, Christmas Eve and Christmas Day.

Professionally managed by Portfolio Vacations on Anna Maria Island, Florida

Sleeping Arrangements

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed



  • Bay
  • Health Beauty Spa
  • Marina
  • Museums
  • Parks

Cleaning Protocols

  • All towels and bedding washed in hot water that’s at least 60ºC/140ºF
  • Contactless check-in and checkout is available
  • Disinfectant is used when cleaning the property
  • Enhanced cleaning practices are used
  • High-touch surfaces cleaned with disinfectant (like countertops, light switches, handles, and faucets)


  • Books
  • Games
  • Satellite / Cable
  • Television


  • Air Conditioning
  • Central Heat
  • Clothes Dryer
  • Hair Dryer
  • Heating
  • Internet - Hi Speed
  • Internet - Wifi
  • Iron and Board
  • Linens Provided
  • Living Room
  • Parking
  • Towels Provided
  • Washing Machine


  • Dining Table
  • Free wifi
  • Smart TV


  • Coffee Maker
  • Cookware
  • Dining Area
  • Dining Room
  • Dining Spices
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster


  • Antiquing
  • Bird Watching
  • Boating
  • Eco Tourism
  • Horseback Riding
  • Outlet Shopping
  • Shopping
  • Water Sports
  • Wildlife Viewing


  • Hospital
  • Laundromat


  • Beach
  • Near Ocean
  • Ocean View
  • Town
  • Village
  • Water View


  • Balcony
  • Deck/Patio
  • Gas Grill
  • Kayak

Regional standard for sanitation practice

  • Regional standard for sanitation - Not Sure


  • Carbon Monoxide Detector
  • Deadbolt Lock
  • Emergency Exit Route
  • Fire Emergency Contact
  • Fire Extinguisher
  • First Aid Kit
  • Medical Emergency Contact
  • Outdoor Lighting
  • Police Emergency Contact
  • Smoke Detector


  • Biking
  • Deep Sea Fishing
  • Fishing
  • Fishing Bay
  • Fishing Fly
  • Golf Optional
  • Hiking
  • Jet Skiing
  • Kayaking
  • Parasailing
  • Pier Fishing
  • Sailing
  • Scuba or Snorkeling
  • Snorkeling
  • Swimming
  • Tennis


  • Family
  • Romantic



871 N Shore Drive
Anna Maria, Florida


Cancellation Policy

CANCELLATION: Cancellations must be received in writing and are subject to the following terms: Cancellations more than 90 days prior to arrival will receive a refund, less $100 plus 6% of the deposit. Cancellations made 60 days prior to arrival, will receive a refund of 50% of the full reservation amount. For cancellations made less than 60 days of arrival, no refund will be offered unless Portfolio is able to re-book the canceled dates at the same rate. Trip Cancellation insurance is offered and recommended.

Deposit Policy

At the time of booking, 25% of the total rental amount is due. This is your deposit on the total cost of the reservation. For reservations made within 90 days of arrival, the full payment is due at the time of booking. Final payments are due 90 days prior to arrival. Final payments will be processed automatically with the credit card on file. If paying by check, final payment not received by the due date may result in cancellation of the reservation. Canceled reservations for non-payment are not entitled to any refund of deposit.

Rate varies due to seasonality and holidays. Please select your dates on our online booking calendar for an exact quote.

7 Guest Reviews

5 star


4 star


3 star


2 star


1 star


"Great Vacation"

by Suzanne


What a great vacation. The property was as described in the listing. Location is perfect. Makeover of the property was stylish. Garage has everything you need for the beach! It is a great place to stay and close to everything. Dips for ice cream Waterfront restaurant, Sandbar restaurant, the ugly grouper restaurant, and island ocean star restaurant are great for dinner. The social for pizza, gRub Tropical for BBQ, Ginny & Jane E’s for breakfast or lunch are all some of our favorites! If you have access to a boat or can rent one - I recommend Passage Key. It is directly across from Bean point and has a peninsula that is fun to play on. The island is actually a bird sanctuary!

"Great communication"

by Lisa


Great communication and very responsive. Great location right on the beach and plenty to do. Will definitely be back.

"First stay on Anna Maria Island"

by JW


Pirates lookout is the perfect bungalow for your relaxing vacation. We thoroughly enjoyed our stay in this beautiful and comfortable place. The property manager was so nice, easy to contact and quick to respond. We had some delay upon arrival so she left a light on for us since we were arriving so late. Everything was as it appeared in the photos. Definitely a new favorite spot for us and we look forward to returning!

"Great home in a great location!"

by Timothy S.


Had a great time, even though the weather was a bit cold, the house and location we're great!

"Great beach stay!"

by Jennifer P


We enjoyed our stay at the house. The living space is comfortable for relaxing and the bedrooms were comfy for sleeping. The house is just behind a house right on the beach and you have easy access out to the beach. We appreciated the toys and beach chairs and even took the kayak out for a spin. Thank you for a nice visit.

"Fun in the sun"

by Jennifer R.


Loved our stay! Great location to everything we needed. Golf cart was a wonderful bonus. Can’t wait to come back.


by Marcie C


Perfect beach house ! Room for all of us (6 adults) . We found Anna Maria to be beautiful !

from $300 / night


Oct 9-14

Spiral staircase leading from the 2 downstairs bedrooms up to the kitchen, living area and master bedroom

Stairs leading to upper deck and the main entrance to the home. There is also an entrance from the garage.

Spiral staircase leading from the 2 downstairs bedrooms up to the kitchen, living area and master bedroom

Stairs leading to upper deck and the main entrance to the home. There is also an entrance from the garage.