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Jackie's Cottage Vacation Rental With Heated Pool and Dock

Home Rental in Holmes Beach Florida

Canalfront home in Anna Maria, FL with a private wet dock and dry dock, heated pool, and updated interiors; a vacation rental place to stay near Gulf beaches, Marina Drive shops, and the island trolley.

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Anna Maria Island Accommodations
Connect directly with the local vacation rental manager.
Rates from
$515 / night
Additional fees may apply
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Rental overview

Why You'll Love This Rental

Jackie’s Cottage is a four-bedroom, three-bath canal-front home in Holmes Beach, Florida, sleeping up to eight guests in 1,625 square feet. Set on the waterfront with water views, it pairs a private wet dock and dry dock with a private heated pool, making it well suited to travelers planning time on the water. The home is also near a beach and is located one block from a free Anna Maria Island trolley stop.

Inside, the layout is single level with a main living area oriented to the water, plus a full kitchen with an island and dining table. Sleeping arrangements include two king beds, one queen bed, and two twin beds. The primary bedroom has an ensuite bath and patio access; additional bathrooms include walk-in showers and a shower/tub combination. Practical features include in-unit washer/dryer, keyless entry, WiFi, air conditioning, and three parking spaces. Outdoor amenities include a patio with seating, an outdoor dining area, sun loungers, a grill, and beach chairs provided. No pets are allowed.

Good fit for
Boaters Fishing trips Long-term stays
Canal-front setting Waterfront home with canal views and a private wet dock and dry dock.
Private heated pool On-site private heated pool with sun loungers and outdoor seating.
Sleeps eight Four bedrooms sleep up to 8 with 2 kings, 1 queen, and 2 twins.
One-level layout Single-level home with a full kitchen, dining table, and living room.
Three-car parking Parking is limited to a maximum of three cars at the home.
At a glance

Property Highlights

Waterfront - ViewLocation Setting
Near a BeachBeach Access
4 BedroomsBedrooms
3 Full BathroomsBathrooms
Sleeps 8Guest Capacity
1625 sq. ft.Living Space
Pool (Private)Pool
Internet AccessInternet
TelevisionTelevision
YesAir Conditioning
YesWasher / Dryer
Location & nearby Explore the Area

Jackie’s Cottage is in Holmes Beach, Florida, on Anna Maria Island, set canal-front on a residential street with water views. The home is near a beach and is one block from the nearest free Anna Maria Island trolley stops, providing an option for getting around the island without driving. The setting supports water activities such as boating and fishing, with a private dock on site. Parking at the property is limited to three vehicles.

Plan your stay

Rates & Availability (USD)

Rates from
$515 per night
7-day minimum stay
Check current rates & availability

Live booking details are maintained by Anna Maria Island Accommodations.

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Availability Calendar

Use the calendar as a guide, then confirm current availability directly with the manager.

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About this rental

About This Rental

Jackie’s Cottage is a one-level, canal-front vacation home in Holmes Beach on Anna Maria Island. With four bedrooms and three full bathrooms, it accommodates up to eight guests and offers a water-focused setting with waterfront views. A private wet dock and dry dock support boating plans, while a private heated pool adds an on-site option for swimming and downtime. The home is also near a beach and is one block from the nearest free Anna Maria Island trolley stops.

The main living space is designed around the view, with large windows, seating, and a TV. The kitchen is fully equipped and includes major appliances and essentials such as a refrigerator, stove, oven, microwave, dishwasher, toaster, coffee maker, blender, cookware, dishes and utensils, and wine glasses. A kitchen island provides additional prep and gathering space, and the dining table offers a dedicated spot for meals.

Bedroom configuration is 2 king beds, 1 queen bed, and 2 twin beds. The primary bedroom includes a king bed, TV, an ensuite bathroom, and access to a water-facing patio. A second king bedroom has water views and uses a nearby hall bathroom with a walk-in shower. The twin bedroom and the queen bedroom (with TV) provide additional sleeping options; another hall bathroom includes a combined shower and tub.

Outdoor features include a patio with outdoor seating, an outdoor dining area, sun loungers, outdoor lighting, and a grill. For convenience during longer stays, the home includes a washer/dryer, towels and linens, heating, smoke and carbon monoxide detectors, a fire extinguisher, and a private entrance. Parking is limited to three cars, and pets are not permitted.

Jackie’s Cottage by Anna Maria Island Accommodations
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.
Before you book

Vacation Rental Policies

Check In

4:00 PM

Check Out

10:00 AM

Things to enjoy

Activities and Special Interests

This property provides access to the following activities and special interests:

Fishing
Golfing
Family Vacations
Boating
Canoeing
Fly Fishing
Kayaking
Beach
Deep Sea Fishing
Ocean
Surfing
Scuba Diving
Wind Surfing

Other Activities and Special Interests

Museums Nearby
Boating Nearby
Local Eco Tourism Nearby
Horseback Riding Nearby
Outlet Shopping Nearby
Wildlife Viewing Nearby
Fitness Center Nearby
Laundromat Close By
Tennis Court Nearby
Basketball Court Nearby
Hiking Nearby
Jet Skiing Nearby
Parasailing Nearby
Sailing Nearby
Snorkeling Nearby
Surfing Nearby
Swimming Nearby
Water Sports Nearby
Health Beauty Spa Nearby
Marina Nearby
Shopping Nearby
Bird Watching Nearby
Kayaking Nearby
What's included

Property Amenities

Property Features

Towels/Linens
Coffee Maker
Hair Dryer
Full Kitchen
Microwave
Oven
Refrigerator
Stove
Toaster
Blender
Ceiling Fan(s)
Freezer

Featured Amenities

Dishwasher
Television
Internet Access
Air Conditioning
Grill
Washer/Dryer
Pool (Private)

Outdoor

Boat Dock

Other Property Amenities

Holmes Beach
Anna Maria Island
Dishes and Utensils
Fire Extinguisher
Living Room
Clothes Hangers
Hot Water
Long Term Stays Allowed
Private Entrance
Smoke Detector
Hospital Close By
Residential Street
Heating
Carbon Monoxide Detector
Deadbolt Lock
Pots and Pans
Contactless Check-In
Pack 'n Play
Iron and Ironing Board
Patio
Ground Floor Property
Kitchen Island
Dining Table
Three (3) Parking Spaces
Bathtub
Canal Front
Keyless Lock
Outdoor Seating
Water Front
Clothing Storage
Wine Glasses
Baking Sheet
Hot Water Kettle
Outdoor Dining Area
Sun Loungers
Beach Chairs Provided
Outdoor Lighting
Helpful details

Frequently Asked Questions

Jackie's Cottage is located in Holmes Beach, Florida.

Jackie's Cottage accommodates up to 8 guests.

4 Bedrooms and 3 Full Bathrooms.

The listed beach access for Jackie's Cottage is Near a Beach.

Yes. The property lists Pool (Private).

The property lists a 7-night minimum stay.
Local management

Professionally Managed By

Anna Maria Island Accommodations View Manager Profile

Questions about this rental?

Connect directly with Anna Maria Island Accommodations for current rates, availability, and local assistance.

Contact Reservations and Guest Services Anna Maria Island Accommodations
Daytime Phone
Property reference
#192104 · Jackie's Cottage
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