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The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in Heart of AMI

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Pool
Living area
Living area
Living area
Dining

Reviews

9.8 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 41142 sq ft

Popular amenities

  • Parking available
  • Dryer
  • Pet-friendly
  • Washer
  • Pool
  • Air conditioning

Explore the area

View in a map
Anna Maria, FL
  • Anna Maria City Pier
    ‪6 min walk‬
  • Anna Maria Beach
    ‪20 min walk‬
  • Bean Point Beach
    ‪2 min drive‬
  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪40 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 King Bed

Bedroom 2

2 Single Beds

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Kitchen
Dining area

About this property

The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in Heart of AMI

Welcome to The Cottage on Pine!
On Anna Maria Island (Anna Maria, FL)

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 Dryer, 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
A credit for beach gear rental (chairs, cart, umbrella, bikes, coolers, games, etc.) is included with your stay. Select items before arrival and they'll be delivered to the home. Credit amount varies by home size and length of stay. Some gear may be onsite but is not guaranteed.

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.

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.

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 & Spa
Pool heated year-round to 82–85°F; heating may be affected by cooler weather. Heaters/filters off during quiet hours (10 PM–8 AM). Spa, if available, is part of the pool, seasonal, not a commercial hot tub, and may be unavailable in summer. 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 Nov 18, 2024—see full Terms & Conditions for details.

Stays 20 Days or Less
- Payments: 50% due at booking; remaining 50% due 60 days before arrival. Full payment required if booking within 60 days of check-in.
- Cancellations: Cancel >60 days before arrival for full refund minus non-refundable booking fee. Cancel ≤60 days—refunds only for rebooked nights at base rate + taxes, minus fee. Rebooking at same rate/length is not guaranteed. No refunds for non-arrivals, late arrivals, early departures, or changes causing revenue loss.

Stays 21 Days or More
- Cancel >180 days before arrival: Full refund minus fee.
- Cancel 180–90 days before arrival: 25% refund of base rate + taxes, minus fee.
- Cancel ≤90 days before arrival: Refunds only for rebooked nights, minus fee. Same rebooking limitations apply.

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.

Property manager

Once Upon a Beach Vacation Rentals
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning

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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

Check-out instructions

The host requires you to complete the following before checking out:
Load and start the dishwasher
Strip any used beds, gather used towels and store extra beds
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights, lock the doors and return the keys
VayKLife Beach Gear: Please ensure that all rented items from VayKLife are returned to their original delivery location outdoors. Do not pull items inside.
Failure to complete these may result in a negative review from the host.

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, a first aid kit and a deadlock

About the area

Anna Maria

Located in Anna Maria, this holiday home is near theme parks and near the beach. The area's natural beauty can be seen at Bean Point Beach and Anna Maria Beach. Fish Hole Adventure Golf and H2O Watersportz are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Anna Maria, FL

What's nearby

  • Anna Maria Island Museum and Historical Park - 3 min walk - 0.3 km
  • Anna Maria City Pier - 6 min walk - 0.6 km
  • Bradenton Beach - 8 min walk - 0.7 km
  • Anna Maria Beach - 20 min walk - 1.7 km
  • Bean Point Beach - 2 min drive - 1.1 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 33 min drive

Restaurants

  • ‪The Sandbar Restaurant - ‬8 min walk
  • ‪Hurricane Hanks - ‬7 min drive
  • ‪The Waterfront Restaurant - ‬6 min walk
  • ‪Ginny's & Jane E's - ‬7 min walk
  • ‪Harry's Grill - ‬7 min walk

Frequently asked questions

Is The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in Heart of AMI pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in Heart of AMI?

Check-in begins at 4:00 PM.

What time is check-out at The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in Heart of AMI?

Checkout is at 10:00 AM.

Where is The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in Heart of AMI located?

Situated by the sea, this holiday home is within a 15-minute walk of Anna Maria Island Museum and Historical Park and Bean Point Beach. Historic Green Village and Anna Maria City Pier are also within 5 minutes.

Reviews

9.8

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. 16 out of 19 reviews
Rating 8 - Good. 3 out of 19 reviews
Rating 6 - Okay. 0 out of 19 reviews
Rating 4 - Poor. 0 out of 19 reviews
Rating 2 - Terrible. 0 out of 19 reviews

9.8/10

Cleanliness

9.8/10

Check-in

10/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Verified traveller

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

Great place to stay!

My family (wife and 2 kids) and I really enjoyed this place it was just the right size for us. Located in a great area close to both the bay and the beach plus some shops. Would come back and stay here again anytime.
Stayed 5 nights in May 2025

10/10 Excellent

Jana D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Property was very well maintained and newly updated. Everything was provided for an excellent experience.
Stayed 8 nights in Jun 2025

10/10 Excellent

Delilah A.

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

Lovely Little Home on AMI

This beautiful home was a perfect fit for our family, including our 18 and 16-year-old children, offering ample space for everyone. A fantastic bonus was the small pool in the backyard, providing a refreshing alternative when we wanted a break from the beach. Although the house is located on Pine Street, which is a lively area with coffee shops and boutiques, its position set back behind the main office ensures a surprisingly quiet and peaceful stay. While being on a busy street could be seen as a potential drawback, the tranquility of the house itself and its overall charm are not diminished.
Stayed 3 nights in Apr 2025

10/10 Excellent

Verified traveller

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

Cottage on Pine

Great location and we enjoyed it tremendously
Stayed 5 nights in Jul 2023

10/10 Excellent

Jonathan L.

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

Fantastic Stay

Everything was fantastic. Great property and close to the beach. The process of checking in and out was a breeze and any questions I had were answered immediately. Would recommend anyone to stay here.
Stayed 15 nights in May 2024

10/10 Excellent

tony t.

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

Great location.

Great property for a smaller group. Close to restaurants, shopping, and beach. Private backyard and nice pool area.
Stayed 7 nights in Nov 2022

8/10 Good

Emily L.

Liked: Cleanliness, check-in, communication, location

Location, location, location

Wish we could have stayed longer. Always enjoy our time in AMI.
Stayed 2 nights in Aug 2023

10/10 Excellent

Cindy E., Keywest Florida/Flemington Nj

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

Nice Getaway

The cottage had everything we needed for our short trip. We'll be sure to come back soon!!
Stayed 4 nights in Jul 2022

10/10 Excellent

Verified traveller

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

Cutest Cottage.

Super cute cottage with the best location. Close to great restaurants and shops. Loved the pool in the back. It was perfect for us 3! We will be back for sure!
Stayed 4 nights in May 2022

10/10 Excellent

Malka R.

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

Great location

This property was nicely renovated. It was the perfect size for us (a couple and two dogs). The backyard was adorable and the pool was beautiful. We also appreciated that the back area was completely fenced in. The location was convenient to all of the restaurants and shops on Pine Ave and we were able to walk everywhere. We would definitely stay here again.
Stayed 3 nights in Jan 2024

10/10 Excellent

Laura Z.

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

Great rental for our family of four!

We had a wonderful stay at this cottage property! Perfect location to walk to the beach, restaurants and shops. Easy access for fishing, paddle boarding etc. Nice pool to cool off in and pet friendly. Checks all the boxes for small family. Also parking was perfect for our car with jet ski trailer and golf cart! We hope to be back.
Stayed 4 nights in Jul 2022

10/10 Excellent

Megan p.

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

Great cottage

Had a great stay in the heart of AMI. The cottage was adorable and clean. Great pool and renovation in the back yard. Property management was easily available with anything we needed. Definitely would come back. Thanks!!!
Stayed 3 nights in Mar 2023

10/10 Excellent

Erin G.

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

Clean and great location

The house was the perfect size for our small family. It had everything we needed. Beautifully decorated and very clean! Beds were comfy! Pool area was wonderful! Management company was very attentive and easy to communicate with. Wish the AC could have gone a little lower to cool us off a bit more, but it didn’t bother us too much. We would definitely to go back to this house again!
Stayed 2 nights in Jul 2023

10/10 Excellent

Heather D., Westerly RI

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

Quick get away

The space was perfect for our family of 3. We had our Moke to get around which was fun. I was concerned with being right in the middle of town there might be a lot of noise but,, there was none. I would recommend this space for a couple or a small family. The only negative I could say is the outside shower and back yard could use some TLC.
Stayed 5 nights in May 2022

10/10 Excellent

Kristen W.

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

Weekend Away

Perfect weekend getaway for my family of three. Amazing location right on Pine Ave. Within walking distance of local restaurants / shops and a short drive to the beach. Despite being on a main road the space was quite and felt very private. The cottage was very clean. My son’s favorite part was the newly installed 3 hole putting green in the backyard. We explored most of the island by renting a golf cart (which I was able to reserve when booking this property). The golf cart was on property when we arrived and provided a fun way to tour the island. Overall a fun weekend with my family.
Stayed 2 nights in Mar 2023

8/10 Good

robyn k.

Liked: Cleanliness, check-in, communication, listing accuracy
Disliked: Location

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.
Stayed 3 nights in Apr 2022

8/10 Good

Alexandra C.

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

Wonderful Cottage, Great Location

We stumbled upon this cottage while planning a girls trip of four to Anna Maria Island and were immediately sold on the decor and layout of the cottage on Pine (who doesn’t love a pink kitchen?!). Bonus points for the private pool in the back, complete with outdoor shower, putting green and a few little lizard friends roaming around! The space was ideal for our long weekend, conveniently located to shops, restaurants and at a mid-point of the island with easy access to either side of beaches. We opted to rent a cart from Once Upon a Beach and it was already parked in our driveway upon arrival. The amenities of the home were good for what we needed. All the necessities for a beach day were provided (chairs, noodles/floats, umbrella) which was much appreciated! However, the four of us quickly ran through the 4 bath towels provided and there weren’t additional pillows/sheets/blankets should one of us choose to sleep on the couch/had there been a child along for the trip (listing says sleeps 4 adults and up to 2 children, we did not have any with us). Lastly, while we probably chose the hottest week to visit Florida, and we expected some heat, the AC struggled to get down below 75 every night which was uncomfortable. There was a box fan provided with the house so we did utilize that to assist with the air flow. Overall, this cottage was the ideal spot for us on the trip and would highly recommend it to future travelers.
Stayed 4 nights in Aug 2023

10/10 Excellent

Pamela M.

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

Heaven on Earth

This cottage is tucked away on one of the most iconic streets in Anna Maria, so close enough to walk to restaurants, shops, gulf & pier. It's so cozy I'd stay again in a heartbeat
Stayed 28 nights in Mar 2025

10/10 Excellent

Josh C.

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

Perfect location…

Location location location. Short walk to the Bay or Gulf (5 minutes tops) as well as AMIs go to eateries. The cottage is all a family of 4 needs for a stay on AMI. We live in a fairly large home so the smaller size of the cottage brought us closer together. If I had to be really critical I would say the backyard could use some more shade, perhaps a small tiki hut with shade for 4 chairs or something of that nature. I mention this because the pool water was hot. Again I’m being very critical here but honest. Also, if you are out at night the artificial turf seems to attract mosquitoes so use bug spray if you decide to lounge in the back lawn in the evenings. Aside from that, we would certainly stay here again.
Stayed 6 nights in Jul 2023

About the host

Hosted by Once Upon a Beach Vacation Rentals

Host profile image
A world-class island getaway deserves a premier vacation rental experience. At Once Upon A Beach, we invite you to immerse yourself in laid-back luxury, where every detail is designed to make your stay unforgettable. From the moment you book until the day you depart, our local, dedicated team delivers exceptional service, ensuring your vacation is seamless, stress-free, and unforgettable.

Whether you're seeking a romantic retreat for two in a charming beach-chic cottage or gathering the whole family in a sprawling luxury home, you'll arrive to find a meticulously maintained property with unique, thoughtful amenities and concierge-style insider tips to help you live like a local. Each home is just steps from Anna Maria Island's sugar-soft white sand and the sparkling, gin-clear waters that make our slice of paradise famous.

As a boutique luxury vacation rental and property management company, Once Upon A Beach offers an intimate, personalized experience rooted in five-star care and meticulous attention to detail. We specialize in creating the perfect balance of comfort, style, and authentic island charm in one of the most picturesque beach towns in the world—the place we proudly call home.

Write the next chapter of your vacation story with us, and create cherished memories on Anna Maria Island that will last a lifetime.

Languages:

English

Premier Host

They consistently provide great experiences for their guests