Rating 5 (4)

The Cottage on Pine

$275.00 - $820.00 / night + taxes & fees

Bedroom 2 bedrooms
Bathroom 1 baths
Guests 4 guests
Pets Allowed Pets Allowed

  • Address: 411 Pine Avenue
  • Location: Anna Maria
Banner Post Storm Status:

This home experienced flooding and is undergoing a thorough professional restoration to ensure it is safe, beautifully refreshed, and newly furnished. It will be fully ready to welcome guests for an exceptional stay starting January 2025!


Location Location

Description Description

Welcome to The Cottage on Pine!
On Anna Maria Island (Anna Maria, FL)
Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.

Charming Ground-Level Beach Cottage with Heated Pool in the Heart of Anna Maria

HIGHLIGHTS:

  • Living & Dining Area: Open-concept space with comfortable seating, a flat-screen TV, and a dining area for gathering and relaxing.
  • Bedrooms:
    • 1 King Bedroom: Features a king bed, TV, French doors leading to the backyard, and ample storage with a dresser and closet.
    • 1 Twin Bedroom: Includes two twin beds, TV, dresser, and closet.
  • Outdoor Living:
    • Covered front porch with outdoor seating, perfect for enjoying coastal breezes and morning coffee.
    • Private fenced-in backyard featuring a heated pool, loungers, chairs, outdoor dining area, grill, and outdoor shower.
  • Pet-Friendly: Welcomes your furry family members with prior approval and a paid pet fee, so everyone can enjoy the island getaway!

Laundry
Washer and dryer located off the covered porch for convenience.

Kitchen:
Stove, Oven, Microwave, Refrigerator/Freezer, Coffeemaker (12 cup & Keurig), Blender, Toaster, Kitchenware

Amenities:
A/C, Heat, Cable Television, Roku, Wireless Internet, Linens, Towels, TV’s, Hair Dryers, Iron/Ironing Board

Parking
Space for 1-2 cars in the private driveway.

Please Note: 
This home is conveniently located behind another property, which also serves as our office. Rest assured, all areas designated for this property—such as the private driveway, entrance, fenced-in backyard, and pool—are completely separate and exclusively for your use, ensuring a peaceful and private stay.

Beach Gear Equipment (Provided by VayKLife Gear):
Assorted beach gear items may be onsite but not guaranteed. Every reservation now includes a credit towards personalized beach gear rental included with your stay (chairs, cart, umbrella, bikes, coolers, games, and so much more). Simply make selections prior to your stay and we will have at your home for you!

DESCRIPTION:
Your Dream Island Cottage Vacation

Experience the charm and simplicity of island living at The Cottage on Pine, a beautifully renovated beach cottage nestled in the heart of Anna Maria Island. This cozy retreat is ideal for small families, couples, or friends seeking a relaxing getaway steps away from everything Anna Maria has to offer.

Located directly on Pine Avenue, the main street of Anna Maria, this home places you within walking distance of boutique shops, delicious restaurants, and the white sandy beaches of the Gulf of Mexico. For those seeking activities, the nearby community center offers a fitness center, tennis courts, and a playground, adding even more to your vacation experience.

Step inside and discover a warm and inviting interior that blends modern comfort with timeless charm. The cottage boasts designer-inspired decor and luxurious high-end finishes. The fully equipped kitchen features premium Café appliances and everything you need to prepare meals or snacks during your stay. Relax in the living area with a flat-screen TV, or gather for meals in the dining space.

The spacious king bedroom offers French doors that open to a private deck and backyard, creating a peaceful retreat. The second bedroom, with two twin beds, is perfect for additional guests or children. Both bedrooms are thoughtfully designed to ensure comfort and relaxation.

When you’re not at the beach, unwind in the private heated pool surrounded by a lush, fenced backyard. The outdoor space includes loungers for sunbathing, a grilling area, and an outdoor shower for post-beach refreshment. The covered front porch provides a charming spot to enjoy your morning coffee or evening cocktail.

Parking is a breeze with room for 1-2 cars in the private driveway, ensuring easy access to your island hideaway.

Prime Location
Situated in the heart of Anna Maria Island, The Cottage on Pine offers unbeatable access to:

  • Pine Avenue: Just steps away, explore its boutique shops, quaint cafes, and restaurants.
  • Beaches: A short walk to the breathtaking Gulf beaches with their powdery white sand and turquoise waters.
  • Community Center: Enjoy fitness facilities, tennis courts, and a playground nearby.

Book Your Stay at The Cottage on Pine
Whether you’re strolling along Pine Avenue, lounging by the private pool, or soaking up the sun at the nearby beaches, The Cottage on Pine offers the perfect mix of location, comfort, and charm. Don’t wait—book your stay today and experience the magic of Anna Maria Island!

POLICIES:
NO SMOKING.


Pets are welcome with prior approval, provided they meet our pet policy guidelines. We allow a maximum of two pets, each weighing under 65 lbs. A pet fee applies based on the length of your stay: $100 for stays under 4 days, $200 for stays of 4-14 days, and $400 for stays of 15+ days, per pet.

Guest Requirements:
Registered guests must be at least 25 years of age, provide a copy of a valid ID, and be present throughout the entire stay.

Occupancy Limits:
The standard occupancy is two persons per standard bedroom. For additional occupants beyond this limit, a fee of $25 per person, per night, will be charged, up to the maximum allowable occupancy, if applicable.

Quiet Hours:
Quiet hours are from 10:00 PM to 8:00 AM. As this property is located in a residential area, we ask that you respect our neighbors by maintaining a reasonable noise level both during the day and at night. Excessive or unreasonable noise may disrupt the peaceful enjoyment of the neighborhood and is not permitted.

Reservation Policies:
Reservations are typically for 7-night stays, Saturday to Saturday. However, we offer flexible stays with varying minimum night requirements and non-Saturday check-ins and check-outs during most of the year, except for holidays and peak weeks. Please inquire before booking to confirm availability, as changes cannot always be accommodated after booking.

Cleaning and Safety:
All homes, including linens and towels, are cleaned, sanitized, and inspected between guest stays according to industry standards. A starter set of basic amenities, linens, towels, and bedding is provided upon check-in, based on home occupancy. Daily housekeeping and linen services are not included but are available upon request for an additional fee. For stays of 28 days or longer, a mid-stay clean is required and must be scheduled and paid for by the guest.

This home participates in our Professional Linen Program, ensuring high-quality linens and towels are professionally laundered at a commercial facility between each guest's stay. Please note that extra sets are not stored in the home.

Golf Cart Rentals:
Explore the island with ease! After booking, reserve a golf cart through our sister company, Once Upon A Beach Carts, and enjoy an exclusive discount available only to our vacation rental guests.

Baby Equipment Rentals:
Baby equipment is not provided at the home for safety and sanitation purposes. However, we partner with local companies that offer rental services for baby items, including convenient pick-up and drop-off options. Details will be provided at the time of booking, or you may inquire directly for more information.

Pool and Spa (if any):
The pool is heated year-round at no extra charge for guest convenience, with temperatures maintained between 82-85°F to ensure proper chemical balance and cleanliness. Pool heaters and filters do not operate during quiet hours (10:00 PM to 8:00 AM) per local noise ordinances. Please note that cooler ambient temperatures, especially with a 20°F or greater difference between air and water temperatures, may impact the pool heater’s effectiveness.

Guests are required to read and follow all posted rules, safety information, and operating instructions.

Property Security and Safety:
This home may be equipped with exterior cameras, such as Ring or Nest, positioned to monitor the front door, driveways, pool equipment, and entry/exit areas of the backyard. These cameras are installed solely to enhance property security, monitor deliveries, and ensure occupancy limits are met. Cameras are not angled toward areas where privacy is expected or assumed.

PAYMENTS:

  • 50% of total amount due must be made at time of reservation request to confirm reservation.
  • 50% of total amount due must be paid on or before 60 days prior to check-in date.
  • Full amount due must be made at time of booking if check in date is within next 60 days.

CANCELLATION POLICY:
Please review the details of our Cancellation Policy page or Terms & Conditions at booking.  We encourage you to review as OUR POLICIES HAVE CHANGED as of NOVEMBER 18, 2024.

For Reservations of 20 Days or Less:
Cancellations More Than 60 Days Before Arrival:

  • If you cancel all or part of your reservation more than 60 days before your scheduled arrival date, you will receive a refund of your full deposit, minus the non-refundable booking administration (processing) fee that was originally assessed.

Cancellations 60 Days or Less Before Arrival:

  • If you cancel all or part of your reservation 60 days or less before your scheduled arrival date, refunds will only be issued for the base rental rate and applicable taxes for nights we are able to rebook, minus the non-refundable booking administration (processing) fee.
  • Please note: While we make every effort to rebook the property and issue refunds, we cannot guarantee that the property will be re-rented at the same rate or for the same number of nights originally reserved. For any nights that the property cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in a loss of revenue, no refunds or price adjustments will be provided.

For Reservations of 21 Days or More:
Cancellations More Than 180 Days Before Arrival:

  • If you cancel all or part of your reservation more than 180 days before your scheduled arrival date, you will receive a full refund of your deposit, minus the non-refundable booking administration (processing) fee that was originally assessed.

Cancellations 180 to 90 Days Before Arrival:

  • If you cancel all or part of your reservation between 180 and 90 days prior to arrival, you will receive a refund equal to 25% of the base rental rate and applicable taxes, minus the non-refundable booking administration (processing) fee.

Cancellations 90 Days or Less Before Arrival:

  • If you cancel all or part of your reservation 90 days or less before your scheduled arrival date, refunds will only be issued for the base rental rate and applicable taxes for nights we are able to rebook, minus the non-refundable booking administration (processing) fee.
  • Please note: While we make every effort to rebook the property and issue refunds, we cannot guarantee that the property will be re-rented at the same rate or for the same number of nights originally reserved. For any nights that the property cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in a loss of revenue, no refunds or price adjustments will be provided.

Important Cancellation Policy Information:
The Manager is not responsible for providing refunds due to circumstances beyond their control, including but not limited to travel disruptions, guest travel restrictions, changes in work or school schedules, or similar issues. Additionally, conditions such as weather, tropical storms, hurricane threats, environmental factors (e.g., red tide), construction, water quality, or beach conditions cannot be guaranteed.

Submitting a Cancellation Request:

  • All cancellation requests must be initiated by the Registered Guest who booked the reservation.
  • Requests must be submitted either through the website where the booking was made or in writing via email.
  • Cancellation requests will not be accepted via phone, text, or from any party member other than the Registered Guest.

These policies are in place to ensure clear communication and a smooth process for all guests.

Travel Insurance:

  • We continue to offer our U.S. Citizen guests (with the exception of residents of NY and HI) the option of purchasing CSA Travel Insurance directly through us. We strongly encourage all guests to purchase Travel Insurance to protect their vacation investment in the event of any unforeseen circumstances.
  • Please note that refunds or credits are not provided for COVID-19-related cancellations, weather, or beach conditions that fall outside of our stated cancellation policy. Additionally, please be aware that hurricane season spans June 1st through November 30th, and Travel Insurance can help safeguard your plans during this period.

In the event the reservation dates fall within a mandatory island evacuation, unforeseen unavailability of the reserved home, the unavailability of a comparable alternative home, or an inability for vacation rentals to operate due to an executive order, the guest will receive a full refund of the base rental rate, applicable fees (excluding the booking administration fee), and all applicable taxes without penalty.

If you have any questions about the cancellation policy or Travel Insurance, please don’t hesitate to reach out for clarification.

Max Occupancy: 4
Max Cars: 2
City of Anna Maria: N/A

The information provided online, though deemed accurate is not guaranteed. It is subject to errors, omissions, change of price or withdrawal without notice.


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Swipe Swipe for Availability

Amenities 139 Amenities
Accommodations
  • House Cleaning Optional
  • Other Services Concierge
  • Wifi
Amenities
  • Bed Linens
  • Cable/satellite TV
  • Dryer
  • Hair Dryer
  • Hangers
  • Heating
  • Internet
  • Internet Access
  • Iron
  • Iron Board
  • Linens
  • Linens provided
  • Living Room
  • Parking
  • Private Entrance
  • Safety Card
  • Self Check-In
  • Smartlock
  • Towels
  • Towels provided
  • TV
  • Washer
Attractions
  • Bay
  • Botanical Garden
  • Coin Laundry
  • Health Beauty Spa
  • Marina
  • Museums
  • Playground
  • Theme Parks
  • Water Parks
  • Zoo
Car
  • Not Necessary
Changeover/Arrival Day
  • 24Hr Check-In
Cleanliness
  • All towels and bedding washed in hot water that's at least 60ºC
  • Cleaning Disinfection
  • Enhanced Cleaning Practices
  • High-touch surfaces cleaned with disinfectant
  • Self Check In / Check Out
Emergency
  • Emergency Exit Route
  • Emergency Fire Contact
  • Emergency Medical Contact
  • Emergency Police Contact
Entertainment
  • DVD player
  • Laptop Friendly
  • Satellite or Cable
  • Television
Household
  • Newly Listed
Kitchen and Dining
  • BBQ
  • Coffee Maker
  • Cooking Basics
  • Dining Area
  • Dining table
  • Dishes Utensils
  • Dishwasher
  • Freezer
  • Fridge
  • Kettle
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Wine glasses
Leisure
  • Antiquing
  • Bird Watching
  • Boating
  • Bowling
  • Eco Tourism
  • Gambling
  • Horse riding nearby
  • Horseback Riding
  • Miniature Golf
  • Outlet Shopping
  • Shopping
  • Water Sports
  • Wildlife Viewing
Local Features
  • ATM Bank
  • Fitness Center
  • Groceries
  • Hospital
  • Laundromat
Location Types
  • Beach
Outdoor
  • Beach Access
  • Garden Or Backyard
  • Grill
  • Outdoor seating
  • Patio
  • Private yard
Pool/Spa
  • Heated Outdoor Pool Private
  • Heated Pool
  • Private Pool
Purchaseable Amenities
  • Concierge - Equipment Rentals by Fun & More Rentals
Safety Features
  • Carbon Monoxide Detector
  • Deadbolt Lock
  • Fire Extinguisher
  • First Aid Kit
  • Outdoor Lighting
  • Smoke Detector
Sports and Adventure
  • Basketball Court
  • Deepsea Fishing
  • Fishing
  • Fishing Bay
  • Fishing Fly
  • Fishing nearby
  • Fishing Surf
  • Golf
  • Golf course within 30 min drive
  • Jet Skiing
  • Parasailing
  • Pier Fishing
  • Sailing
  • Scuba or Snorkeling
  • Skiing Water
  • Snorkeling
  • Snorkeling / Diving
  • Surfing
  • Swimming
  • Tennis
  • Tennis courts nearby
  • Tubing Water
  • Watersports nearby
  • Wind Surfing
Suitability
  • Air Conditioning
  • Central heating
  • Children Welcome
  • Free Parking
  • Hot Water
  • Minimum Age Limit
  • Pets allowed
  • Pets Considered
  • Single Level Home
  • Smoking Not Allowed
Themes
  • Family
  • Luxury

Reviews Rating 5 (4) Reviews
Rating 5
Perfect AMI Home
This was our first time coming to AMI, and we could not have chosen a more perfect location to spend it. The cottage was just the right size for our family of 4 (our boys are 5 and 7). It was well-appointed, decorated beautifully, and had everything we needed for the week. We also rented a golf cart from Once Upon A Beach and would definitely recommend it! We went to Bean Point and the access at White Avenue most days, and the golf cart made the trip much more manageable! We had a tiny issue the first night upon arrival, but a quick text to Mike and it was resolved within 10 minutes. We will definitely book again!
Anonymous U from White Pine, TN - Posted: 3/23/2024
Rating 5
The Cottage on Pine - formally Pineapple Cottage
Stayed for 6 nights for our nephew’s wedding. The Pineapple cottage was great. Very clean, nice pool, very quiet even though it’s on a busy street. Able to walk to the beach and the city pier. Lots of food options nearby. The gas grille was very clean and there is a nice covered table outside. Very nice small property. Hope to be back. Had a beach buggy and chairs.
Mike W - Posted: 6/19/2023
Rating 5
The Cottage on Pine - formally Pineapple Cottage
We vacationed at Anna Maria Island (AMI) and stayed at "Pineapple Cottage" by Once Upon A Beach. The beach cottage was cozy, exceptionaly clean, and the interior woodwork was absolutely lovely! The private partially shaded inground pool was perfect for a refreashing afternoon swim and lighted during the evening. There was plenty of outdoor seating areas including a covered and shaded dining area. The location on Pine Ave was within walking distance of many local shops, eating establishments, Two Scoops Ice Cream (which has the best ice cream on the island), and the island pier. The owners of Once Upon A Beach are very attentive to their occupant's needs and add "special touches" such as a welcome gift bag. The cottage was stocked with everything we needed for a beach day such as chairs, umbrella, and even a wagon to carry them. We will definately be back to the tranquil and relaxing AMI. I highly recommend staying at one of Once Upon A Beach's lovely homes!
Celine P - Posted: 6/19/2023
Rating 5
The Cottage on Pine - formally Pineapple Cottage
We have been coming to AMI for over 10 years now this is by far my favorite place to stay ! Very clean and cozy ! Finally a place with comfortable beds !!! Perfect location this made our trip top shelf staying here ! Coming back in May ! Love the Pineapple Cottage !!!
Kimberly S - Posted: 6/19/2023
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Want to know specifics? Ask anything about this specific property that you would like to know...

Example: "Is the balcony screened in?" or "Is there a toaster oven?"

Hello! We are a family of 5, we have three kiddos. Is the max occupancy 4 or do you allow 5? Thank you! Heidi

Heidi S - Posted: 04/08/2024

Answer:

Thank you for your inquiry. Please note that the maximum occupancy of our homes must not exceed the number listed in the property details. However, children aged 2 and under are not included in this guest count. If you have any further questions, feel free to reach out—we’re here to help!

Hi there, just wondering if Cottage on Pine has courtesy bicycles? We’re staying there in a few weeks and just wanted to know if we need to make arrangements ahead of time. Thanks!

Kelly C - Posted: 05/18/2024

Answer:

Guests with reservations at any Once Upon A Beach property will receive a credit towards beach gear rentals, which includes bicycles! The credit amount varies by nightly rate and can be found when entering your Reservation ID into the VayKLife Portal. After reserving your home, you'll receive an email from VayKLife to select your gear via the Once Upon A Beach customized beach gear website. If you exceed the credit limit, additional items can be added at discounted rates. Your gear will be delivered to your rental property on the day you arrive and picked up on the day you depart, ensuring a stress-free vacation experience.

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