House - Rating 5 (6)

Jackie's Cottage


Bedroom 4 bedrooms
Bathroom 3 baths
Guests 8 guests
Pets Not Allowed Pets Not Allowed

  • Address: 209 N Harbor Dr
  • Location: Holmes Beach
  • Type: House

Location Location

Description Description
Jackie’s Cottage by Anna Maria Island Accommodations
209 N Harbor Dr, Holmes Beach, FL, 34217
VRC18-000190

Welcome to Jackie’s Cottage, a stunning one level canal front home with a private wet dock and dry dock, now showcasing recently updated interiors with modern furnishings and coastal decor. Just a block and a half from the pristine Gulf beaches, this four bedroom, three bath vacation escape offers a serene water-centric retreat. You'll enjoy breathtaking water views, direct access to the boat slip for water adventures, and a location close to the trolley stop for exploring all of Anna Maria Island’s scenic seven miles.

Highlights
• Canal front home
• 5-minute Walk to the beach
• 4 Bedroom / 3 Bath
• 2 Kings, 1 Queen, 2 Twin beds
• Private heated pool
• BBQ grill and water views
• In-unit washer and dryer
• One block from the nearest free Anna Maria Island trolley stops
• Near Marina Drive for local shops, restaurants and more
• 3 car parking

Relax in your tropical backyard oasis and find yourself swimming in the private pool, surrounded by comfortable loungers, or docking your boat on the spacious slip with room for two jet skis. The outdoor dining area with a BBQ grill and lush landscaping creates the perfect setting for relaxing dinners and viewing sunsets. Water toys, fishing gear, and rentals are just steps away for endless water fun or unwind with a book in the waterfront serenity.

Step inside this beautifully upgraded home and enjoy a fresh, modern design. The main living area features large windows framing spectacular water views, plush seating with a TV, and a stylish, updated kitchen with a farm sink, sleek countertops, and stainless-steel appliances. The kitchen offers a bar with seating for casual meals, while the adjacent dining area with a large water-facing table is perfect for family gatherings or entertaining friends in a tropical setting, making every meal a special occasion.

Retreat to the primary bedroom, which boasts a king bed, a TV, and exclusive access to the water-facing patio. The luxurious ensuite features a walk-in shower and ample closet space. The second bedroom, with a king bed, TV, and water views, shares a hall bathroom with a walk-in shower. The third bedroom offers two twin beds with nautical decor, and the fourth bedroom features a queen bed, TV, and plenty of space for restful sleep. The hall bathroom has a combined shower and tub, and a washer and dryer provide convenience for all guests.

Room Details
• Primary Bedroom: King bed, ensuite bathroom
• Second Bedroom: King bed, shared ensuite bathroom
• Third Bedroom: Two twin beds
• Fourth Bedroom: Queen bed

Book Jackie’s Cottage today and indulge in the ultimate water-front lifestyle on Anna Maria Island. With recent interiors, stunning water views, a private dock, and proximity to beaches, shops, and dining, this home is your ideal retreat for relaxation and adventure.

Reserve now and start creating lifelong memories in this perfect island escape!


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DISCLAIMER: Depth of the canals and channels vary depending on tides, weather, and other circumstances beyond our control. At times this can result in a water level that is too low to support watercraft. It is the responsibility of the guest to review forecasts and make alternate arrangements for watercraft as necessary.

No pets are allowed in this home.

*Please note: 3 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.

This home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company.

We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age.

Please see our Anna Maria Island Accommodations Rental Policies for full details.

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.

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Bedding Bedding
Bedroom 1
1 King

Attached Bathroom

Bedroom 2
1 King

Attached Bathroom

Bedroom 3
2 Twin

Attached Bathroom

Bedroom 4
1 Queen


Amenities 72 Amenities
Essentials
  • Air Conditioning
  • Beach Chairs Provided
  • Beach Towels Included
  • Bed Linens
  • Dryer
  • Free Wifi
  • Ground Floor Property
  • Hair Dryer
  • Heating
  • Hospital Close By
  • Hot Water
  • Iron and Ironing Board
  • Long Term Stays Allowed
  • No Pets Allowed
  • Private Entrance
  • Towels
  • Washer
  • Wifi
Exterior
  • BBQ Area
  • BBQ Grill
  • Boat Dock
  • Fishing Dock
  • Heated Pool
  • Outdoor Dining Area
  • Outdoor Seating
  • Outdoor TV
  • Patio
  • Private Pool
  • Sun Loungers
Fun and Entertainment
  • Smart TV
  • TV
  • TV with Cable
Home Safety
  • Carbon Monoxide Detector
  • Contactless Check-In
  • Deadbolt Lock
  • Fire Extinguisher
  • Keyless Lock
  • Outdoor Lighting
  • Smoke Detector
Interior
  • Bathtub
  • Ceiling Fans
  • Clothes Hangers
  • Clothing Storage
  • Full Kitchen
  • Living Room
Kitchen
  • Baking Sheet
  • BBQ Utensils
  • Blender
  • Coffee Maker
  • Dining table
  • Dishes and Utensils
  • Dishwasher
  • Freezer
  • Hot Water Kettle
  • Kitchen Island
  • Microwave
  • Oven
  • Pots and Pans
  • Refrigerator
  • Stove
  • Toaster
  • Wine Glasses
Location
  • Anna Maria Island
  • Beach Access Nearby
  • Canal Front
  • Holmes Beach
  • Less than a 5-minute walk to the beach
  • Residential Street
  • Walking Distance to Beach
  • Water Front
  • Water View
Parking
  • Three (3) Parking Spaces

Reviews Rating 5 (6) Reviews
Rating 5
Accommodating and great spot. Will be back.
Ryan - Posted: 1/3/2026
Thank you, Ryan! We’re so happy you enjoyed the location of Jackie's Cottage. We can’t wait to welcome you back for your next visit with Anna Maria Island Accommodations!
Prime Vacations staff
Rating 5
Wonderful Trip
This house was wonderful, even better than the pictures in person. It was immaculately clean with very comfortable beds. Our family of six had plenty of room to spread out. The neighborhood was quiet but just a few minutes’ walk to the beach, restaurants, and the grocery store. The home was well-stocked with basic necessities and we cooked most of our meals at home. The canal out back and the pool were highlights for our family. We saw so much wildlife from the backyard including herons and egrets landing just feet away, fish jumping all day, and even a manatee right off the dock. Our kids caught starfish and shrimp by hand from the dock and spent many hours fishing. Our family swam in the pool most days, ate almost every meal at the backyard table, and spent many hours reading in the beautiful backyard or hanging out on the docks. The hosts were clear, informative, and quick to respond. They were very accommodating and helpful with an adjustment we requested for one of our kids with disabilities. This was our third stay on Anna Maria and by far the nicest home we’ve stayed in. Highly recommended!
Sarah P. - Posted: 3/5/2024
Sarah, thank you for your glowing review! We're thrilled to hear that your stay at our property exceeded your expectations and that you found it even better than the pictures. It's fantastic that the house was immaculately clean and provided comfortable beds for your family of six. We're delighted that the neighborhood was quiet yet conveniently located near the beach, restaurants, and grocery store, allowing you to enjoy all that Anna Maria has to offer. It sounds like you made the most of the backyard amenities, from the canal and pool to the wildlife sightings and fishing opportunities. We're glad to hear that our team was responsive, accommodating, and helpful. Your kind words mean a lot to us, and we're honored to have provided you with the nicest home you've stayed in on Anna Maria Island. Thank you for highly recommending our property, and we hope to have the pleasure of welcoming you back for another memorable stay in the future! If there's anything we can do to make your next visit even better, please don't hesitate to let us know.
Prime Vacations staff
Rating 5
Great place
Beautiful property, excellent location, short walk to beach, pool was great and larger than the pictures, fishing off the dock was a huge plus and enjoyed by the kids. All around great place. Only negative was the internet which was a little spotty - but didn't mind since we were on vacation! Definitely recommend and would stay again. Perfect size for our family of 4 and enough room for a 2nd family of 4.
Corey G. - Posted: 1/25/2021
Corey, Thank you for your review on Jackie's Cottage. It makes us so happy hearing that you enjoyed the home and the wonderful dock it has to offer. We apologize that the internet was not consistent during your stay, and for future reference, please let us know while you are here about connectivity issues! We would be glad to assist in any way we can. We can't wait to have you back soon on AMI!
Prime Vacations staff
Rating 5
Perfect location!
Love the house and location! We had an issue with the pool heater not working so it was a too chilly to swim. They sent someone out twice but finally got it working mid week of our stay. Overall a great place and we enjoyed it! Love the kitchen and layout of the home.
Amber M. - Posted: 12/16/2019
We greatly appreciate your taking the time to send your feedback about Jackie’s Cottage. We’re truly sorry you had a couple of days with a cool pool but are glad to know that you were able to enjoy it for the rest of your stay. The home was just recently remodeled and we’re thrilled that you liked it. We hope you visit Anna Maria Island again.
Prime Vacations staff
Rating 5
Everything was great.
We were slightly concerned with cleanliness due to prior reviews but everything was wonderful, and immaculate. Kitchen was very well stocked with everything we needed or could have wanted, pool was clean and the perfect temperature. Dock was perfect for our boat, as well as set up for kayaking and paddle boarding. We did rent those they were not included but the kayak company delivered and picked up right to the house. Walking distance to the beach and trolley stop was very close. The house was incredibly roomy and very comfortable for us. We had 7 in our party. We visited in April and the manatees stole the show. There were so many and right out the back canal. Had a great time, thank you for everything. We will be back again.
Anita B. - Posted: 5/9/2019
Thank you so much for letting us know that you enjoyed your stay at Jackies Cottage. Our team is thrilled that you enjoyed the amenities and that the home was clean and well stocked. The home is in the process of major renovations and we'd love to have you stat with us again for another great vacation!
Prime Vacations staff
Rating 5
Great spot
We arrived to the house being very dirty with the last people's bedding cast all over the floors. One phone call and they had a crew there in minutes to clean the whole house. The home was great with pool being much larger than in the pics. Beds were comfortable with a great set up for kids. Dock was perfect for the boat. Only challenge is the cleaning crew seems to whioe every condiment or anything useful from the shelves. You must stock everything. Overall great home and fun stay!
Scott G. - Posted: 4/21/2019
Thank you for letting us know about your stay with us at Jackie's Cottage. We sincerely apologize regarding the cleaning not being completed by the time you checked in and appreciate you giving us the opportunity to get the home ready for your stay. We are thrilled that the beds were comfortable as this is important to us. Since indigestible items can be tempered with, the cleaners are instructed to remove everything prior to the next guest checking in. Thank you again for taking your time to let us know about your stay, we hope to have you stay with us again for your future island getaways!
Prime Vacations staff
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