Pineapple Cottage

neighborhood of Holmes Beach
  • Sleeps 4
  • 2 Bedrooms
  • 1 Bathrooms
  • Pets Allowed


Welcome to Pineapple Cottage!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Ground Level Updated Beach Cottage in Heart of Anna Maria - HOME IS BEING RENOVATED AUGUST-OCTOBER 2022 INCLUDING NEW KITCHEN, BATH, FURNITURE, AND OUTDOOR AREA IMPROVEMENTS. UPDATED PHOTOS TO COME ONCE COMPLETED.2 Bed (sleeps 4), 1 Bath with Heated Pool directly on Pine Avenue. Short walk to Piers, Shops, and Gulf Side BeachesHIGHLIGHTS:- Kitchen, Dining Area, Living w/ TV- 1 King Bedroom w/ TV- 2 Twins (can be converted into King with advance notice)- Hall Full Bath- Covered Front Porch w/ Outdoor Seating- Private Pool & Fenced in BackyardKitchen:Stove, Oven, Micr...

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  • Beach Chairs
  • Beach Towels
  • Porch / Veranda
  • Satellite / Cable
  • TV
  • Air Conditioning
  • Basic Soaps
  • Bed Linens Provided
  • Dryer
  • Hair Dryer
  • Heating
  • Iron & Board
  • Toilet Paper
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Internet
  • Living Room
  • Paper Towels
  • Parking
  • Blender
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Grill
  • Kettle
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Heated Pool
  • Outdoor Pool
  • Private Pool
  • Budget Friendly
  • Children welcome
  • Activities / Restaurants Guide
  • Beach Umbrellas
  • Cooking Utensils
  • Courtyard
  • Dining Area
  • Freezer
  • Keyless Entry System

Location Info


Nightly rates range from $200.00 to $600.00



Check-In Time : Flexible
Check-Out Time : Flexible
  • Pet(s) Allowed
  • Suitable for Children

General Policies

POLICIES: Pets are accepted with prior approval only if they meet our pet policy guidelines, max of 2, NO SMOKING. Registered Guest must provide copy of ID, be at least 25 years of age and be present throughout entire stay. Standard occupancy is 2 persons per every standard bedroom, an additional occupant fee of $25 per person/per night will be assessed for each occupant over this up to max occupancy, if applicable. Quiet Hours 10p-8a. 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. Reservations are typically taken for 7-night Saturday...

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House Rules

CLEANING AND SAFETY All our homes and linens are cleaned, sanitized, and inspected between each guest per industry standards. A starter set of basic amenities, linens, towels, and bedding are provided at the beginning of your stay per home occupancy. Daily housekeeping or linen services are not included in your stay. Additional cleaning and laundry services are available by request mid-stay at an additional charge. Additional mid-stay cleans are required to be scheduled and paid for by guests at an additional cost every 21 days. Disinfectant fogging service add-on is available by request prior to your arrival for added peace of mind. Please inquire about pricing. This home participates in our Professional Linen Program. This ensures ...

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Terms & Conditions


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

Cancellation Policy

CANCELLATION POLICY: The manager is not responsible for providing refunds due to circumstances beyond the Manager's control like travel disruptions, guest travel restrictions, work, and school scheduling changes, etc. Weather, tropical storms, hurricane threats, and environmental conditions like red tide, construction, water, or beach conditions cannot be guaranteed. All cancellation requests must be initiated by Registered Guests through the website in which they booked and/or be in writing via email. Cancellation requests will not be accepted via phone, text, or by a member of the party other than the main Registered Guest. PENALTY-FREE 100% REFUND for Reservations Greater than 60 Days From Arrival: If canceling an entire or port...

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(Based on 1 reviews)
- 04/01/2022 -

Nice property but be prepared for Anna Maria island

"The home was clean and great for a family of 4. It is right on Pine street if that is what you are looking for. One of the things I was not prepared for is how difficult it was to get food! There are very few restaurants offering seating. For the most part, all restaurants are walk up to the window wait in a long line to get your food and bring it home to eat it. I was not prepared for that. We ended up driving off the island to dinner on our 2 nights there. Just not what I was expecting. But if you are okay with this then this cottage is a great place to stay."

Host Reply
We enjoyed having you at Pineapple Cottage, Robyn! Thank you for staying with us and choosing Once Upon A Beach! We'd love to host you all again in the future!
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