House in Anna Maria Island, FL
4 guests · 2 bedrooms · 1 bath
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this house rental
Welcome to The Cottage on Pine!
On Anna Maria Island (Anna Maria, FL)
The Space
Step inside The Cottage on Pine and feel the ease of island life take hold. Gentle natural light, soft coastal hues, and thoughtfully curated details create an atmosphere that feels both uplifting and serene. Located directly on Pine Avenue, this home offers the best of both worlds — walkable access to shops and cafés, and a peaceful retreat just beyond the gate.
Perfect for: Couples, small families, or friends seeking peaceful simplicity, walkable charm, and restorative island living.
Highlights
- Located on charming Pine Avenue, steps to boutiques, cafés, and beaches
- Private fenced backyard with heated pool, loungers, dining area
- Pet-friendly with prior approval and paid pet fee (up to two pets under 65 lbs)
- Open-concept living and dining area for gathering and connection
- Covered front porch perfect for morning coffee or evening reflection
- Professionally designed interiors blending modern comfort with coastal charm
Interior
- Living Area: Bright and welcoming with comfortable seating, Roku-equipped TV, and soft natural lighting that makes every moment feel unhurried.
- Dining Area: A table set for shared meals and conversation, perfectly placed between the living room and kitchen.
Bedrooms
- King Bedroom: Features a king bed, TV, dresser, and French doors leading directly to the backyard and pool.
- Twin Bedroom: Two twin beds, TV, and ample storage — ideal for children or additional guests.
- Bathroom: Full bath with modern finishes, plush towels, and thoughtfully chosen amenities.
Each space reflects a sense of quiet care, from the crisp linens to the coastal textures and natural light that fills the home.
Layout Overview
Single-Level Living:
- Open-concept kitchen, dining, and living area
- One king bedroom and one twin bedroom
- Full bath
- Front porch and private fenced backyard with pool
This layout makes the home easily accessible for all ages and perfect for those who prefer simplicity and flow.
Outdoor Living
Step into your own private sanctuary.
The fenced backyard features a heated pool, loungers for sunbathing, and a shaded dining area for enjoying meals al fresco. An outdoor shower offers the perfect rinse after a beach day, while the grill invites slow, easy evenings spent under the island sky.
At the front, a covered porch with comfortable seating provides another peaceful perch — the ideal spot to enjoy Pine Avenue's morning quiet or an evening breeze with your favorite drink in hand.
Kitchen & Dining
The kitchen blends charm and functionality, with premium Café appliances and everything you need to prepare fresh meals or quick snacks.
- Stove, oven, and microwave
- Refrigerator and freezer
- 12-cup coffeemaker, Keurig, blender, and toaster
- Fully stocked kitchenware for cooking and serving
Whether you're creating a full breakfast before a beach day or reheating leftovers from one of Pine Avenue's local eateries, this space makes it easy to feel at home.
Additional Amenities
- Washer and dryer (off covered porch)
- A/C and heat for year-round comfort
- Cable TV and wireless internet
- Hair dryer, iron, and ironing board
- Professionally laundered linens and towels
- Beach gear rental credit for items like chairs, umbrellas, and bikes
Parking
- Private driveway with space for 1–2 vehicles.
- Please note: The home is located behind another property that serves as our Once Upon A Beach office. All areas designated for guest use — including the private driveway, entrance, fenced backyard, and pool — are completely separate and exclusively yours, ensuring peace and privacy.
Write your vacation story at The Cottage on Pine — where calm meets connection, and every moment feels like coming home.
Policies
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.
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.
Booking & Fee Policy
Include all guests and pets in your reservation request for accurate pricing. Additional fees apply for extra occupancy (over 2 guests per bedroom) or undeclared pets.
Optional Services (subject to approval)
Early check-in/late departure, elevator access, and mid-stay cleaning for stays of 28+ days. Fees for approved add-ons are collected after booking.
Reservations & Guest Requirements
Most stays are 7 nights, Saturday–Saturday, though flexible dates may be available outside peak/holiday weeks—confirm before booking, as changes are not always possible afterward. Guests must be 25+, provide valid ID, and remain for the full stay. Standard occupancy is 2 per bedroom; extra guests are $25/person/night up to the maximum allowed.
Quiet Hours
10 PM–8 AM. Maintain reasonable noise at all times to respect neighbors; excessive noise is not permitted.
Cleaning & Linens
Home is professionally cleaned and sanitized between stays. Starter amenities provided; daily service available for a fee. Stays of 28+ days require a mid-stay clean. Linens/towels are commercially laundered through our Professional Linen Program; no extra sets stored onsite.
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.
Pool
Pool heated year-round to 82–85°F; heating may be affected by cooler weather. Guests may not adjust equipment; violations may result in fines or damages.
Property Security
Exterior cameras may monitor entries, driveways, pool equipment, and backyard access for security, deliveries, and occupancy compliance. Cameras do not face private areas.
Payments & Cancellation Policy
Policies updated October 6, 2025 — see full Terms & Conditions for details.
Payment Schedule
Deposit
- Reservations up to 20 days: 50% of total amount due at time of booking.
Remaining Balance
- Reservations up to 20 days: Remaining 50% due 30 days prior to check-in.
Cancellation Policy
For Reservations of 20 Days or Less
- More than 30 days before arrival: Full refund of deposit (including taxes) minus non-refundable booking administration fee.
- 14–29 days before arrival: Refund of 50% of total rental, fees, and taxes, minus non-refundable booking administration fee.
- Less than 14 days before arrival: Refunds only for base rental rate, fees, and taxes for nights we are able to rebook, minus non-refundable booking administration fee.
- Please note: While we make every effort to rebook, we cannot guarantee the same rate or number of nights. For any nights that cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in lost revenue, no refunds or price adjustments will be made.
Travel Insurance
CSA Travel Insurance is available to U.S. guests (except NY and HI residents) and is strongly encouraged to protect your trip from unforeseen events. No refunds are given for COVID-19, weather, or beach conditions outside our cancellation policy. Hurricane season runs June 1–Nov 30; insurance can safeguard your plans. In the event of a mandatory evacuation, home unavailability, or government order halting vacation rentals, guests receive a full refund of base rate, applicable fees (minus booking fee), and taxes.
Additional Terms
No refunds for events beyond our control (weather, red tide, travel issues, etc.). Cancellation requests must be submitted in writing by the registered guest—phone/text not accepted.
Max Occupancy: 4 | Max cars: 2
Information deemed reliable but not guaranteed; subject to change or withdrawal without notice.
On Anna Maria Island (Anna Maria, FL)
The Space
Step inside The Cottage on Pine and feel the ease of island life take hold. Gentle natural light, soft coastal hues, and thoughtfully curated details create an atmosphere that feels both uplifting and serene. Located directly on Pine Avenue, this home offers the best of both worlds — walkable access to shops and cafés, and a peaceful retreat just beyond the gate.
Perfect for: Couples, small families, or friends seeking peaceful simplicity, walkable charm, and restorative island living.
Highlights
- Located on charming Pine Avenue, steps to boutiques, cafés, and beaches
- Private fenced backyard with heated pool, loungers, dining area
- Pet-friendly with prior approval and paid pet fee (up to two pets under 65 lbs)
- Open-concept living and dining area for gathering and connection
- Covered front porch perfect for morning coffee or evening reflection
- Professionally designed interiors blending modern comfort with coastal charm
Interior
- Living Area: Bright and welcoming with comfortable seating, Roku-equipped TV, and soft natural lighting that makes every moment feel unhurried.
- Dining Area: A table set for shared meals and conversation, perfectly placed between the living room and kitchen.
Bedrooms
- King Bedroom: Features a king bed, TV, dresser, and French doors leading directly to the backyard and pool.
- Twin Bedroom: Two twin beds, TV, and ample storage — ideal for children or additional guests.
- Bathroom: Full bath with modern finishes, plush towels, and thoughtfully chosen amenities.
Each space reflects a sense of quiet care, from the crisp linens to the coastal textures and natural light that fills the home.
Layout Overview
Single-Level Living:
- Open-concept kitchen, dining, and living area
- One king bedroom and one twin bedroom
- Full bath
- Front porch and private fenced backyard with pool
This layout makes the home easily accessible for all ages and perfect for those who prefer simplicity and flow.
Outdoor Living
Step into your own private sanctuary.
The fenced backyard features a heated pool, loungers for sunbathing, and a shaded dining area for enjoying meals al fresco. An outdoor shower offers the perfect rinse after a beach day, while the grill invites slow, easy evenings spent under the island sky.
At the front, a covered porch with comfortable seating provides another peaceful perch — the ideal spot to enjoy Pine Avenue's morning quiet or an evening breeze with your favorite drink in hand.
Kitchen & Dining
The kitchen blends charm and functionality, with premium Café appliances and everything you need to prepare fresh meals or quick snacks.
- Stove, oven, and microwave
- Refrigerator and freezer
- 12-cup coffeemaker, Keurig, blender, and toaster
- Fully stocked kitchenware for cooking and serving
Whether you're creating a full breakfast before a beach day or reheating leftovers from one of Pine Avenue's local eateries, this space makes it easy to feel at home.
Additional Amenities
- Washer and dryer (off covered porch)
- A/C and heat for year-round comfort
- Cable TV and wireless internet
- Hair dryer, iron, and ironing board
- Professionally laundered linens and towels
- Beach gear rental credit for items like chairs, umbrellas, and bikes
Parking
- Private driveway with space for 1–2 vehicles.
- Please note: The home is located behind another property that serves as our Once Upon A Beach office. All areas designated for guest use — including the private driveway, entrance, fenced backyard, and pool — are completely separate and exclusively yours, ensuring peace and privacy.
Write your vacation story at The Cottage on Pine — where calm meets connection, and every moment feels like coming home.
Policies
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.
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.
Booking & Fee Policy
Include all guests and pets in your reservation request for accurate pricing. Additional fees apply for extra occupancy (over 2 guests per bedroom) or undeclared pets.
Optional Services (subject to approval)
Early check-in/late departure, elevator access, and mid-stay cleaning for stays of 28+ days. Fees for approved add-ons are collected after booking.
Reservations & Guest Requirements
Most stays are 7 nights, Saturday–Saturday, though flexible dates may be available outside peak/holiday weeks—confirm before booking, as changes are not always possible afterward. Guests must be 25+, provide valid ID, and remain for the full stay. Standard occupancy is 2 per bedroom; extra guests are $25/person/night up to the maximum allowed.
Quiet Hours
10 PM–8 AM. Maintain reasonable noise at all times to respect neighbors; excessive noise is not permitted.
Cleaning & Linens
Home is professionally cleaned and sanitized between stays. Starter amenities provided; daily service available for a fee. Stays of 28+ days require a mid-stay clean. Linens/towels are commercially laundered through our Professional Linen Program; no extra sets stored onsite.
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.
Pool
Pool heated year-round to 82–85°F; heating may be affected by cooler weather. Guests may not adjust equipment; violations may result in fines or damages.
Property Security
Exterior cameras may monitor entries, driveways, pool equipment, and backyard access for security, deliveries, and occupancy compliance. Cameras do not face private areas.
Payments & Cancellation Policy
Policies updated October 6, 2025 — see full Terms & Conditions for details.
Payment Schedule
Deposit
- Reservations up to 20 days: 50% of total amount due at time of booking.
Remaining Balance
- Reservations up to 20 days: Remaining 50% due 30 days prior to check-in.
Cancellation Policy
For Reservations of 20 Days or Less
- More than 30 days before arrival: Full refund of deposit (including taxes) minus non-refundable booking administration fee.
- 14–29 days before arrival: Refund of 50% of total rental, fees, and taxes, minus non-refundable booking administration fee.
- Less than 14 days before arrival: Refunds only for base rental rate, fees, and taxes for nights we are able to rebook, minus non-refundable booking administration fee.
- Please note: While we make every effort to rebook, we cannot guarantee the same rate or number of nights. For any nights that cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in lost revenue, no refunds or price adjustments will be made.
Travel Insurance
CSA Travel Insurance is available to U.S. guests (except NY and HI residents) and is strongly encouraged to protect your trip from unforeseen events. No refunds are given for COVID-19, weather, or beach conditions outside our cancellation policy. Hurricane season runs June 1–Nov 30; insurance can safeguard your plans. In the event of a mandatory evacuation, home unavailability, or government order halting vacation rentals, guests receive a full refund of base rate, applicable fees (minus booking fee), and taxes.
Additional Terms
No refunds for events beyond our control (weather, red tide, travel issues, etc.). Cancellation requests must be submitted in writing by the registered guest—phone/text not accepted.
Max Occupancy: 4 | Max cars: 2
Information deemed reliable but not guaranteed; subject to change or withdrawal without notice.
Amenities at The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in Heart of AMI
Non-smoking
Pets allowed
Family friendly
Map of Anna Maria Island, FL
Ratings and reviews
10 / 10Outstanding·Apr 2026
This cottage is so clean and comfortable. Plenty of room - front porch, living area and backyard. It is right in the middle of Pine Ave - surrounded by shops and restaurants. The beds were comfortable, huge TV, pool is great and backyard is completely private. We loved The Cottage on pine and will definitely be back.
Thank you so much for this thoughtful review. We are so glad to hear how much you enjoyed your stay at The Cottage on Pine.
It is one of those special homes where everything just comes together. The location right in the heart of Pine Avenue, the comfort of the beds, the spacious indoor and outdoor areas, and that private backyard with the pool really make it easy to settle in and relax.
We truly appreciate you highlighting the cleanliness and comfort as well. That is something our team takes a lot of pride in, and it means a lot to hear it reflected in your experience.
We would absolutely love to host you again when you are ready to return. Your spot on Pine will be waiting.
10 / 10Outstanding·Apr 2026
All you need everything with in short walks. Shops, stores, beach and pool in the back yard. The right size place for a family of 4. The rental credit for beach supplies was perfect. The cart fit everything from chairs, umbrella and bags. Was easy to pull the few blocks to the beach.
10 / 10Outstanding·Apr 2026
We had a great stay! Perfect accommodations and great backyard.
10 / 10Outstanding·Mar 2026
Beautiful 2-bed, 1-bath home on Pine in Anna Maria. The Cottage on Pine is gorgeous inside and out, with a small yard complete with a putting green and a pool. Once Upon A Beach takes great care of this property, ensuring guests have everything they need for a fun and relaxing stay. And, you can't beat the location on Pine - walking distance to the beach, general store, local restaurants, etc. Highly recommend this cute home for a couple or even a couple with 2 children.
Thank you so much for this thoughtful and detailed review!
We're so happy you enjoyed The Cottage on Pine and everything it has to offer, from the putting green and pool to the walkable Pine Avenue location. It means a lot to hear that the home and experience came together for a fun and relaxing stay.
We truly appreciate your recommendation and would love to welcome you back again soon!
$$$$
Top rated by guests
9.8Outstanding
(34 Ratings)
"This cottage is so clean and comfortable. Plenty of room - front porch, living area and backyard. It is right in the middle of Pine Ave - surrounded by shops and restaurants. The beds were comfortable..."
Marlene H.Don't miss out! Price and availability may change
