Book Direct. Book Local. Discover professionally managed vacation rentals from trusted local experts.
Find your vacation rental
Search destinations, vacation rentals, or local property managers

Dockside Paradise: Charming 2-Bedroom Anna Maria Island Rental House

Home Rental in Anna Maria Florida

Perfect vacation retreat in the form of 'Dockside Paradise', our 2-bedroom Anna Maria Island rental house in the beautiful locale of Anna Maria, FL.

Book Direct
SeaBreeze Vacation
Connect directly with the local vacation rental manager.
Rates from
$276 / night
Additional fees may apply
Book Direct
Rental overview

Why You'll Love This Rental

Dockside Paradise is a 2-bedroom, 2-bath waterfront home in Anna Maria, Florida, set on a canal with water views and near a beach. With 1,440 square feet and sleeping for up to 6 guests, it stands out for its private deep-water dock, a private pool with a waterfall, and a screened-in lanai designed for easy indoor-outdoor time. A golf cart is included, and parking is provided for up to 2 vehicles.

The home has an open living, kitchen, and dining layout, plus a den that adds extra sleeping space with a twin daybed and trundle. Both bedrooms feature king beds; the primary suite includes pool access and an ensuite bathroom, and the second bedroom is near another full bath. Practical amenities include WiFi, washer/dryer, air conditioning, and a fully equipped kitchen with dishwasher and standard appliances. Outdoor features include seating, an outdoor shower, and a gas grill with propane included, along with beach chairs, a beach wagon, and a beach umbrella.

Good fit for
Boating Fishing Honeymoon
Private pool waterfall Private pool includes a waterfall feature and a screened-in lanai.
Deep-water dock Canal-front setting with a private deep-water dock for boating and fishing.
Golf cart included Complimentary golf cart is included; drivers must be 21+ with required documentation.
King bedrooms Two bedrooms each feature a king bed; primary suite has pool access and ensuite bath.
Den with trundle Den adds a twin daybed with trundle for extra sleeping space.
At a glance

Property Highlights

Waterfront - ViewLocation Setting
Near a BeachBeach Access
2 BedroomsBedrooms
2 Full BathroomsBathrooms
Sleeps 6Guest Capacity
1440 sq. ft.Living Space
Pool (Private)Pool
Internet AccessInternet
TelevisionTelevision
YesAir Conditioning
YesWasher / Dryer
Location & nearby Explore the Area

Located in Anna Maria, Florida, Dockside Paradise is a waterfront canal-front home with water views and near a beach. The property includes a private deep-water dock on Bimini Bay and is in a residential area with city quiet hours from 10 p.m. to 7 a.m. A golf cart is included for getting around locally, and the home provides parking for up to two vehicles.

Plan your stay

Rates & Availability (USD)

Rates from
$276 per night
Check current rates & availability

Live booking details are maintained by SeaBreeze Vacation.

Check Availability

Availability Calendar

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

Available Booked
Season Nightly Weekly Monthly
Aug - Dec 2026
Aug 01, 2026 - Nov 20, 2026
$276 n/a n/a
Thanksgiving 2026
Nov 21, 2026 - Nov 27, 2026
$322 n/a n/a
Aug - Dec 2026
Nov 28, 2026 - Dec 18, 2026
$276 n/a n/a
Christmas 26
Dec 19, 2026 - Dec 25, 2026
$391 n/a n/a
New Year 26
Dec 26, 2026 - Jan 01, 2027
$460 n/a n/a
Jan 2027
Jan 02, 2027 - Jan 29, 2027
$338 n/a n/a
Feb 2027
Jan 30, 2027 - Feb 26, 2027
$434 n/a n/a
Spring Break 2027
Feb 27, 2027 - Mar 19, 2027
$583 n/a n/a
Easter 2027
Mar 20, 2027 - Apr 02, 2027
$659 n/a n/a
Post Easter 27
Apr 03, 2027 - Apr 16, 2027
$583 n/a n/a
Spring 2027
Apr 17, 2027 - May 28, 2027
$299 n/a n/a
Summer 2027
May 29, 2027 - Jul 02, 2027
$415 n/a n/a
4 July 2027
Jul 03, 2027 - Jul 09, 2027
$450 n/a n/a
Summer 2027
Jul 10, 2027 - Jul 30, 2027
$415 n/a n/a
End of Summer 2027
Jul 31, 2027 - Aug 13, 2027
$322 n/a n/a
Aug / Sept & Nov / Dec 2027
Aug 14, 2027 - Oct 01, 2027
$276 n/a n/a
October 2027
Oct 02, 2027 - Oct 29, 2027
$322 n/a n/a
Aug / Sept & Nov / Dec 2027
Oct 30, 2027 - Nov 19, 2027
$276 n/a n/a
Thanksgiving 2027
Nov 20, 2027 - Nov 26, 2027
$322 n/a n/a
Aug / Sept & Nov / Dec 2027
Nov 27, 2027 - Dec 17, 2027
$276 n/a n/a
Christmas 2027
Dec 18, 2027 - Dec 24, 2027
$391 n/a n/a
New Year 2027
Dec 25, 2027 - Jan 07, 2028
$460 n/a n/a
Jan 2028
Jan 08, 2028 - Feb 04, 2028
$338 n/a n/a
Feb 2028
Feb 05, 2028 - Mar 03, 2028
$434 n/a n/a
Spring Break 2028
Mar 04, 2028 - Apr 14, 2028
$583 n/a n/a
Easter 2028
Apr 15, 2028 - Apr 21, 2028
$659 n/a n/a
Spring 2028
Apr 22, 2028 - May 26, 2028
$299 n/a n/a
Summer 2028
May 27, 2028 - Jun 30, 2028
$415 n/a n/a
4th July 2028
Jul 01, 2028 - Jul 07, 2028
$450 n/a n/a
Summer 2028
Jul 08, 2028 - Jul 28, 2028
$415 n/a n/a
End of Summer 2028
Jul 29, 2028 - Aug 11, 2028
$322 n/a n/a
Aug / Sept & Nov / Dec 2028
Aug 12, 2028 - Sep 29, 2028
$276 n/a n/a
October 2028
Sep 30, 2028 - Nov 03, 2028
$322 n/a n/a
Aug / Sept & Nov / Dec 2028
Nov 04, 2028 - Nov 17, 2028
$276 n/a n/a
Thanksgiving 2028
Nov 18, 2028 - Nov 24, 2028
$322 n/a n/a
Aug / Sept & Nov / Dec 2028
Nov 25, 2028 - Dec 22, 2028
$276 n/a n/a
Christmas 2028
Dec 23, 2028 - Dec 29, 2028
$391 n/a n/a
New Year 2027
Dec 30, 2028 - Jan 05, 2029
$460 n/a n/a
About this rental

About This Rental

Dockside Paradise is a canal-front home in Anna Maria on Florida’s South Gulf Coast, offering water views and accommodations for up to 6 guests. The property includes 2 bedrooms and 2 full bathrooms across 1,440 square feet, with a focus on outdoor living and time on the water. A complimentary golf cart is included for local transportation, and the home provides parking for up to 2 vehicles.

Outdoor amenities center around the private pool with a waterfall and a screened-in lanai. The canal setting includes a private deep-water dock, supporting boating and fishing directly from the property. Additional exterior conveniences include outdoor seating, an outdoor shower, and a gas grill (propane included).

Inside, the home is arranged with an open living area connected to the kitchen and dining space. The kitchen is equipped with major appliances and essentials such as a refrigerator, stove, oven, microwave, dishwasher, coffee maker, toaster, blender, and dishes/utensils. Everyday comforts include air conditioning, ceiling fans, internet access, television, and a washer/dryer.

Sleeping is split between two king bedrooms, plus a den with a twin daybed and trundle to increase flexibility for different group setups. Linens and towels are provided, and the home includes beach-use items such as beach chairs, a beach wagon, and a beach umbrella. Quiet hours in the City of Anna Maria are 10 p.m. to 7 a.m., and maximum occupancy is 6 guests.

A few things that make Dockside Paradise special:
  • Concierge Collection Property
  • Golf cart included!
  • Anna Maria on Anna Maria Island - Short 4 min walk to Pine Ave
  • Pool with waterfall 
  • Screened in lanai, private deep-water dock
  • Outdoor seating & shower
  • Gas grill (propane included)
  • Professional Linen Service
  • Complimentary WiFi
  • Beach chairs, beach wagon, & beach umbrella
  • Parking for 2 vehicles
Dockside Paradise is a beautifully updated two-bedroom, two-bathroom canal-front home designed for relaxed coastal living. Ideal for couples and small families, this home features a private pool with a waterfall, a screened lanai, and a deep-water dock on Bimini Bay.

The outdoor space is a private oasis where you can swim, lounge, and enjoy peaceful canal views as boats pass by. With a private dock for boating and fishing, plus a poolside grill and outdoor shower, it’s perfect for soaking up the island lifestyle.

Inside, Dockside Paradise offers a bright, beach-inspired design with a modern open layout. The comfortable living area flows into a fully-equipped kitchen and dining space, creating an easy indoor-outdoor living experience.

The primary bedroom includes a king bed, pool access, and an ensuite bathroom, while the second bedroom also features a king bed and nearby full bath. A cozy den with a twin daybed and trundle provides extra sleeping space, and guests will love the short walk to the beach and easy access to the island trolley.

To make exploring the island even easier, a complimentary golf cart is included with every stay, giving you convenient access to Anna Maria’s pristine beaches, local restaurants, and charming shops.

Dockside Paradise is rated in the Elite tier of the SeaBreeze Property Rating System. This system ranks each home based on quality, design, furnishings, and guest-focused amenities. Elite properties provide a high level of luxury with stylish décor, upgraded furnishings, modern appliances, and beautiful outdoor spaces that often include heated pools or spas. Dockside Paradise offers an elevated vacation experience with impressive comfort and thoughtful attention to detail.

Property Cancellation Policy - SeaBreeze Vacation has spent a great deal of time and effort into formulating a cancellation policy for you. SeaBreeze Vacation has the most flexible cancellation policy on the Island. You are allowed to cancel your reservation up to 14 days prior to check-in to receive a refund. Additional terms and conditions apply.

Golf Cart Terms & Conditions - All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance. The golf cart $25 fee is per golf cart, not per driver. This cost covers the extra insurance required.

With all SeaBreeze Vacation properties, we think of the little things to make your vacation special. Included to get you started are the following:
  • Per Guest: 1 Bath Towel, 1 Hand Towel, 1 Washcloth, 1 Pool/Beach Towel
  • Per Full Bathroom: 2 Rolls of Toilet Paper, Hand Soap, Shower Products Set (including trial size shampoo, conditioner, shower gel, and body lotion), Cosmetic Cloth, Bath Mat
  • Per Kitchen: 2 Rolls of Paper Towels, Hand Soap, Dish Soap, Sponge, Dishwasher Pods (x4), Laundry Detergent Pods (x4), All-Purpose Disinfectant, Microfiber Cloth, 2 Kitchen Towels
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.

City of Anna Maria
Max Occupancy: 6 Guests | Max Vehicles: 2
Quiet Hours: 10 p.m. - 7 a.m.  - please respect our island community
Min stay requirements vary by city ordinance and are often 3 nights. Please contact our office with any questions.
Things to enjoy

Activities and Special Interests

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

Biking
Fishing
Scuba Diving
Kayaking
Golfing
Beach
Horseback Riding
Boating
Family Vacations
Spa
Honeymoon
Canoeing
Fly Fishing
Deep Sea Fishing
Ocean
Surfing
Wind Surfing
What's included

Property Amenities

Featured Amenities

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

Property Features

Towels/Linens
Hair Dryer
Ceiling Fan(s)
Refrigerator
Coffee Maker
Microwave
Dishes/Utensils
Stove
Toaster
Oven
Freezer
Blender
Parking
Garage
Phone
Iron / Ironing Board
Balcony

Suitability

Children Welcome
Helpful details

Frequently Asked Questions

Dockside Paradise is located in Anna Maria, Florida.

Dockside Paradise accommodates up to 6 guests.

2 Bedrooms and 2 Full Bathrooms.

The listed beach access for Dockside Paradise is Near a Beach.

Yes. The property lists Pool (Private).

Dockside Paradise is professionally managed by SeaBreeze Vacation.
Local management

Professionally Managed By

SeaBreeze Vacation
In business since 2011
View Manager Profile

Questions about this rental?

Connect directly with SeaBreeze Vacation for current rates, availability, and local assistance.

Contact Guest Services Team at SeaBreeze Vacation
Daytime Phone Evening Phone
Property reference
#185802 · Dockside Paradise
Keep exploring

Similar Rentals from Seabreeze Vacation

More rentals from the same manager, prioritized by location, property type, size, and setting.